I spent a long time thinking I had a consistency problem.

I couldn’t keep a streak going for longer than a few weeks. Some people can do the same thing every day for a year. I’ve just never been one of them.

I’d start the habit tracker. Get excited about the new routine. Make it to day 12 or 17 or, if I was feeling particularly disciplined, somewhere in the twenties.

Then I’d miss a day.

And somehow one missed day became evidence that the whole thing wasn’t working.

What I didn’t notice for a long time was that I was actually pretty good at trying things.

Nine of them, on and off, over the two or three years before I eventually left.

Some mornings, I’d sit with tea and a diary before the 9 to 5 started.

Not because it was productive, but because it was the one part of the day nobody else had scheduled.

Some experiments lasted a month.

Some lasted a week.

Some disappeared completely, then came back months later in a different shape.

I cold-messaged business owners for coffee with no pitch prepared.

I tested tools I didn’t understand yet.

I broke things inside free trials on purpose.

I followed ideas that sounded slightly ridiculous when I tried to explain them to someone else.

If I’d tried to track any of this as a habit, I probably would have quit by week three.

But I wasn’t really trying to build habits.

I was collecting evidence.

That distinction changed the way I thought about my life.

A habit tracker asks: Did you do the thing today?

An experiment asks: What did the thing tell you?

Those are very different questions.

A habit tracker treats a missed day as a break in the chain.

An experiment treats it as information.

Maybe I was tired.

Maybe I hated the thing.

Maybe the timing was wrong.

Maybe I liked the idea of it more than I liked actually doing it.

None of those answers is particularly dramatic.

They’re also useful.

And over time, the small pieces of information started adding up.

None of the nine experiments looked like much written down.

Ten minutes with a journal doesn’t look like a career pivot.

One coffee with a stranger doesn’t look like a new professional network.

Breaking a tool during a free trial doesn’t look like the beginning of a different kind of work.

But that was never really the point.

I wasn’t trying to prove, in advance, that any of these things would become my next life.

I was trying to find out what happened when I gave them a little room to exist.

Some things became useful.

Some didn’t.

Some surprised me.

Some confirmed things I already suspected but hadn’t wanted to admit.

And a few kept pulling me back.

That became much more interesting to me than whether I could maintain a perfect streak.

Because when you’re trying to figure out what comes next, I don’t think you always need more discipline.

Sometimes you need more evidence.

You can spend months trying to decide whether you’d like a different kind of work, a different routine, a different creative practice, a different way of spending your time.

Or you can run a small experiment and see.

Not commit.

Not quit your job.

Not announce your reinvention to everyone you know. Just try the thing for long enough to learn something about yourself.

That’s what eventually became the Independent Life Experiment.

Being obsessed with designing digital products and tools, I naturally approached this as something that could be designed to.

I built the full version as a 30-day experiment because I wanted enough time to collect real evidence, but a short enough window that it didn’t require me to make a life-changing decision first.

Thirty days won’t tell you everything.

It might, however, tell you more than one particularly good Tuesday.

THE INDEPENDENT LIFE EXPERIMENT · TOOL Nº 03

I turned the framework into a 14-page companion workbook you can actually run.

It takes you through three phases of the experiment, gives you a work page for each of the nine areas I’ve been testing, and gives you a place to record what you actually did, what happened, and what you learned.

There’s also a re-run tracker, because sometimes the first experiment isn’t the end of the question.

It’s just the first piece of evidence.

The Independent Life Experiment lives in the Reinvention Library, and it’s included for paid subscribers.

Upgrade Now

Read more

Hi, I’m Katie! Welcome to Multiple Lives Theory — a place for anyone who has ever wondered, “How many lives can I live within this lifetime?”

I write about unlived lives, identity, reinvention, and the messy process of becoming someone new. Essays from inside the transition, weekly.

Subscribe now

I told my family over FaceTime, because of distance and convenience.

That’s the detail I keep going back to. Not the decision, which I’d made weeks earlier and had been carrying around like something in a coat pocket. The screen. A life change delivered to faces in a grid, at whatever hour it happened to be where they were, with that half-second lag that makes everyone talk over each other at the start.

My friends took about four seconds. Most of them I have known since high school or university, and they backed me out of what I can only describe as loving insanity. I said I was doing it and they said good, and there were no questions attached to it.

My mother was the one I paid more attention to.

She has always been an advocate for stability. As long as there is a payslip it does not much matter who you work for, you grind it out. So when I told her, I saw her face go, slowly, the way a face goes on a screen when there is nothing else in the frame to look at.

The mouth settled first. Then she asked what I was going to do. Then, after a pause I have thought about more than the rest of the call, she said okay. As long as you know what you’re doing.

The colleagues ran on a different current altogether. Corporate stress energy, immediate and practical. What are you going to do now. Where are you going to find a job. They offered help and they meant it, and I noticed even at the time that it was a completely different question to the one my friends had not bothered asking.

Some people looked at it and saw the freedom.

Some people looked at it and saw the missing safety net.

Nobody was wrong, exactly.

What’s the right hour to say something like that, when there isn’t one anywhere?

I told my friends at somebody’s birthday, which I also hadn’t planned.

It came up the way things come up at those, in the gap between one conversation and the next, and then it was out and I was answering questions about my future whilst somebody was cutting a cake.

Neither of those was a moment I chose. I think that’s probably normal and I hadn’t expected it. You rehearse the announcement and then it turns up sideways.

Everyone’s case was good

Here’s the part that made it hard, and it isn’t the part I thought would be hard.

Nobody was wrong.

How was I meant to argue with people who were right?

My family were hesitant, and the hesitance came from care. They want my career to be secure. They want to know I’ll be okay. That’s the entire content of it, and when I take out how it landed on me at the time, I have real trouble finding anything in there to object to.

My friends asked what’s next. What’s your future going to look like. What will you be doing. Different people, different stakes, and all of them fair questions to put to someone who has just put down a thing that was working.

And underneath all of it was the same argument, which I would make myself if I were sitting on their side of the screen. Security. Building a future. Family. And the plain fact that we do need money to fuel a life, that capital is what buys the version of it you actually want, and that walking away from a reliable source of it is not a small move.

I didn’t have a counterargument. I still don’t have a good one. I had a feeling, and a feeling holds up badly against a well-constructed case about your own future.

Fine is the hardest thing to leave

The leaving stories we get handed all come with a villain in them.

A boss. A culture. A moment where somebody said the unforgivable thing and you walked out.

Those stories are satisfying because they do the justifying for you.

You never have to explain the leaving, the story explains it.

I didn’t have one of those. I had a job that was, by every measure anybody around me was using, good.

What was I supposed to submit as evidence?

So leaving it needed a justification I couldn’t produce on demand.

Every conversation turned into a small hearing where I was expected to present evidence, and the only evidence I had was that I’d stopped wanting it, which isn’t admissible anywhere.

What I was actually chasing

I’d got everything I set out to get. The career. The business that worked.

The title in tech that made people’s eyebrows move when I said it.

What I hadn’t clocked until much later is how much of the getting was driven by FOMO.

Not ambition exactly, and not a plan either.

Just a persistent low-grade worry about being left behind, and a habit of reaching for whatever the next visible thing was so the worry would go quiet for a bit.

Which it did.

And then I’d arrive, and the feeling on arrival was never satisfaction. It was what’s next.

Was any of that actually mine, or had I just been running from something?

I’m coming into my early thirties now and I’d like the second half of my working life to have more in it than the first.

More surface area, is how I keep saying it to myself. More exposure to opportunity, to experiences, to joy, to being somewhere I’ve never been and being bad at it for a while.

You can’t build that out of not wanting to be left behind. Or I couldn’t.

Surveillance, and then not

For a long time I heard all of those questions as surveillance.

What’s next felt like an audit.

What will you be doing felt like somebody checking whether I’d made a mistake yet so they could file it away.

I’d go into those conversations with a defence already prepared and come out depleted, having spent an evening proving something to people who weren’t actually prosecuting me.

Were they ever actually asking, or was I answering a question nobody had put?

I don’t hear it that way anymore.

Same questions. Same people.

What changed is me, and I’m suspicious of how tidy that sounds, so let me be specific about what actually shifted.

Somewhere in the last few months of working for myself I stopped needing them to agree.

Not in a triumphant way. It was more that arguing turned out to be expensive, and there’s only so much of that particular energy in a day.

And spending it debating someone who loves me and is worried about me started to feel like a bad allocation.

They were caring. They were always caring. It just arrived in the shape of a question, and I’d been reading the shape instead of the thing inside it.

I don’t have a test for this

I don’t want to make that sound like a technique, because when I try to use it as one it stops working.

There are still days I walk in with the defence prepared.

There are conversations where I can hear the care perfectly well and get annoyed by it anyway, because being cared about and being doubted can arrive in identical sentences and I don’t always have the patience to sort them.

And I suspect if the money stopped working, if the numbers went bad for a few months, I’d hear surveillance again immediately.

Whatever generosity I’m describing here is at least partly funded by things going okay.

Is that patience, or is it just what having enough money in the account looks like?

Share The Multiple Lives Theory

So I don’t have a test for when fine stops being enough.

I was half hoping one would turn up whilst I wrote this and it hasn’t.

What I’ve got is smaller than a test.

The case for staying was good, and it stayed good the whole way through, and I left anyway.

Those two things sat next to each other for months before I did anything about it, and they’re still sitting next to each other now.

What was the good case somebody made for you staying, and what did you say back? If this landed, send it to somebody who is trying to explain a decision that doesn’t have a villain in it.

More from Multiple Lives Theory:

• You can grieve a life you never chose

• ‘How’s the business going’ is never about the business

• The five-year plan is dead. The questions haven’t caught up.

✍️ New here?

Multiple Lives Theory is for anyone in the in-between — when the life you’ve built no longer quite fits, but the next one hasn’t taken shape yet.

I publish Thursdays and Sundays. Both are free.

Paid members get the Reinvention Library — a growing collection of decision maps, workbooks, Notion dashboards, and practical frameworks for making sense of what comes next.

The essays are where I explore the questions. The Library is where we start turning them into experiments.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie! Welcome to Multiple Lives Theory — a place for anyone who has ever wondered, “How many lives can I live within this lifetime?” Multiple Lives Theory helps you make sense of the in-between, rethink the idea that you have to live one prescribed life, and experiment with what comes next.

I write about unlived lives, identity, reinvention, and the messy process of becoming someone new. Essays from inside the transition, weekly.

Subscribe now

The realization didn’t arrive all at once. There was no single afternoon, no dramatic pause on a street corner to anchor the story to. There was just the walking…

There’s just a stretch of about six months where I’d get out and go, and somewhere in there the same question would arrive. What am I actually doing?

It never turned up at my desk. At my desk I was fine, or I was busy, which I’d more or less stopped being able to tell apart. It seemed to need the conditions. No deliverables, no notifications, nobody to be responsive for. Not journaling either, because journaling is still a task with a page to fill. Just me and a footpath and forty minutes, and the thought would come up louder than I’d ever let it get indoors.

And every time it came up, I answered it with a list.

It’s a good job.

I’m getting paid.

It’s secure.

It’s a salary I can’t argue with.

There are promotions along the way.

I’m making an impact.

I’m working with worldwide markets….

What was I meant to do with a list where every line on it was true?

I could run that whole list in about four seconds.

I’d run it, and the question would go quiet for a while, and I took the quiet as proof the list had worked. I think what was probably happening is that the list was correct and it still wasn’t an answer, and it took me a long time to notice those are two different things.

And the part I still can’t get around is that every item on that list is true. I’d probably still say most of it if somebody asked me now, which is maybe why it took as long as it did, because there was nothing in the list to argue with and I kept taking that to mean there was nothing to argue with.

What the six months actually looked like

There’d been a restructure. I stayed through it, and then I stayed after it, and then I kept staying for about six months whilst the question got louder on the walks and stayed quiet everywhere else.

Was I waiting for it to get worse? I think I might have been.

At the same time I was running an e-commerce business at night and training for a marathon.

I’ve typed that sentence a few times now and it keeps coming out sounding like a brag, which isn’t what I mean by it. It’s just what was in the calendar. The job, the business, the training, and forty minutes somewhere in there where the whole arrangement would come apart a bit and then more or less reassemble itself by the time I got home.

The commute did the same job. I was working from home a lot by then, so going in had turned into an event rather than a default, and the trains and the metros gave me the same conditions the footpath did. Nothing to produce. Nobody expecting a response for half an hour. And there it was again.

Misery needs a reason, or it comes looking for you

What I understood much later, and only in hindsight, is that misery with a reason attached is almost manageable.

You can point at the thing. You can say it out loud at dinner and watch somebody nod. You can decide whether to fix it or leave it, and either way you’re doing something about it.

What was I going to complain about, exactly?

Misery with nothing to point at won’t give you any of that. There’s no incident, no villain, no line in a contract you could show someone. So it just sits there next to you, and after a while, probably longer than I’d want to put in writing, you stop looking for what’s wrong with the job and start looking for what’s wrong with you.

Is that the bit nobody warns you about, or did everybody else already know?

That’s the actual damage, I think.

Not the job but the slow arrival at the idea that you must be the faulty part, because everything else checks out.

The thing about my brain I still don’t have language for

I don’t know why I dragged it out.

I’ve got a few theories and I don’t fully believe any of them. One is that I’m a millennial and we were trained fairly thoroughly to stay, to be grateful, to treat a secure job as something you don’t put down without a better one already in your hand.

Another is that I didn’t trust my own read on it, because I’d never really had to, because up until then, the things I was good at and the things I was meant to be doing had happened to be the same things.

There’s a third one and I’m still working out how to say it. My brain has never done well with one lane…

It goes wide, it wants a few things running at once, and it gets restless in a way that reads as distraction from the outside and feels like oxygen from the inside.

I spent a long time treating that as a fault to manage. I’m not sure anymore that it is one. I’m also not sure it explains anything, and I’d rather say that than pretend I’ve landed it.

Some people don’t need any of this. They get a feeling, they trust it, they go.

I’ve met them. But I’m not one of them, and I don’t think it says anything good about me that I had to go most of the way to the bottom of something before I’d believe my own read on it.

Do you have to feel it in your body first, or do some people just know?

Share

The restructure came and went and I stayed.

I’d like to say that I knew, on those walks, and was quietly building towards something.

I don’t think that’s true.

I think I knew there was a question, and I kept answering it with the list, and the list kept working for about four days at a time.

Was I hoping somebody would come along and decide it for me?

What I had at the end of those six months wasn’t a decision.

It was just a growing suspicion that the quiet after the list had never actually been agreement.

If a job has ever looked right on paper and felt wrong anyway, what was the list you used to answer yourself with?

If this landed, send it to somebody who is doing well on paper and can’t explain why that isn’t the same as doing well.

More from Multiple Lives Theory:

• The relief you’re not allowed to feel when the job ends

• How I knew it was actually time to leave (not the signs. the signal.)

• Nobody warns you that reinvention is boring

✍️ New here?

Multiple Lives Theory is for anyone in the in-between — when the life you’ve built no longer quite fits, but the next one hasn’t taken shape yet.

I publish Thursdays and Sundays. Both are free.

Paid members get the Reinvention Library — a growing collection of decision maps, workbooks, Notion dashboards, and practical frameworks for making sense of what comes next.

The essays are where I explore the questions. The Library is where we start turning them into experiments.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, weekly.

Subscribe now

A hundred days today, which I only noticed because of a calendar reminder I set in May and forgot about.

Today is day one hundred.

Nobody is going to mention it, which is completely fine, and which is also the thing I want to write about.

When I announced it, people were lovely. Messages, comments, a couple of phone calls from people who don’t phone. Genuinely warm, all of it, and I reread some of them for longer than I would like to admit in writing.

That lasted about two days. Then everybody went back to their own lives, correctly, and I got on with mine. The distance between those two experiences is most of what I have learned in three months.

The support arrives on the wrong day

A decision is easy to see. It happens on one day, it gets announced, it has a shape, and there is an obvious thing to say about it. Good luck. So brave. Well done you.

The work afterwards is invisible. It is slow, it is incremental, there is no moment in it, and there is nothing for anyone to react to. Nobody is going to message you on day fifty-two, because nothing happened on day fifty-two, and the only person who knows that is you.

So all of the encouragement lands in one place, and it is the wrong place.

You get all of the encouragement on the day you need none of it, and none of it on the days you would have used it.

On day one you are running on adrenaline and certainty and a slightly manic sense of having finally done the thing. You could not need less support.

By day forty you are neither of those things, and there is nobody there, because forty is not a number anybody marks.

Everything nobody claps for

Here is a partial list, from the last hundred days.

• Sending the invoice.

• Following up on the invoice.

• Following up on the invoice again, with a different subject line, trying to sound relaxed about it.

• Going through social media engagement

• Rewriting the same page four times and publishing the second version.

• Saying no to work I could have done, for money I could have used.

• Reading a contract properly, all of it, including the part at the end.

• Starting on a new creative brief.

• Auditing my week

• Working out the tax thing. Then working out the other tax thing.

• A whole day where nothing happened and I sat there anyway.

• Not checking whether anyone from the old place had noticed.

• Checking my inbox.

• Getting to Friday with no measurable outcome except that I hadn’t stopped.

• Deciding, somewhere around day forty-one, not to go back, and telling nobody I had been considering it.

None of that is a milestone. All of it is part of the job.

The part I didn’t expect to mind

I thought I left for autonomy, and I did.

I would make the same call again tomorrow. What I hadn’t understood is how much of the old job was other people watching me do it.

Not praise. I was never especially fussed about praise. Just witnesses. Somebody who knew roughly what I had worked on that week.

A person who would notice if I disappeared for a day, and might send a message about it.

The ambient sense of being observed doing something, which I found irritating at the time and apparently was also using as a scaffold.

I got rid of all of that deliberately and then missed it, which is an embarrassing thing to write down. I have rewritten this paragraph four times trying to make it sound less needy. It still sounds needy. I’m leaving it in.

Although I want to be careful here, because this is very close to complaining about something I asked for. I chose this. The version before it was worse and I have not forgotten how that felt.

And I’m not sure I trust the feeling entirely. Some of wanting witnesses is just wanting a manager. Which is a strange thing to miss and not obviously a healthy one.

There is a version of this where I am describing a genuine structural problem with working alone, and a version where I am describing a habit I have not finished breaking.

What I can’t tell yet is whether it eases once the work gets bigger?

Or whether this is simply what working for yourself is and everybody who does it stops mentioning it after the first year.

What I’d put in the announcement post

Definitely not advice. But if I could go back and add two lines to the day one version of this, it would be these.

The applause is for the decision, and the decision was the easy part.

Budget for doing the hard part with nobody watching, because that is the actual arrangement and it starts on day three.

And find the smallest possible way to have your week witnessed by somebody.

A friend who asks on Fridays, a group chat, a standing coffee, anything with a person in it.

Not accountability. I have never got on with accountability, it turns your own week into homework and somebody else into a supervisor.

I mean something much smaller than that. Just that the week gets said out loud to another person before it disappears, so that it existed somewhere other than inside my own head.

Day one hundred looks like a Sunday. I’ll do some admin, I’ll finish this, I’ll send it, and tomorrow will look a lot like today.

The one thing that has changed is that some of the week gets written down now, and it goes out to a couple of thousand inboxes, which is not the same as a colleague noticing and turns out to be close enough to do the job.

I don’t know what day two hundred looks like. Probably like this.

If you are somewhere in your own hundred and nobody is clapping, that isn’t a sign it is going badly. It is what it looks like from the inside.

That is the whole finding, and it isn’t much of one, but it is the true one and I would have liked somebody to tell me on day forty.

-Katie

What day are you on, and what’s the thing nobody clapped for?

If this landed, send it to somebody who is somewhere in their own hundred days.

More from Multiple Lives Theory:

• Nobody warns you that reinvention is boring

• How I stacked 4 income streams to replace a salary

• The hardest part of a nonlinear career isn’t building it. It’s explaining it.

Share

🌱 New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, weekly.

Subscribe now

A practical one today. This is the essay I needed about four years ago and could not find anywhere.

There’s a specific kind of afternoon where you open your CV, look at a date range, and start doing small arithmetic to make it disappear.

You round a finish date up. You round a start date down. You switch months to years so the shape is less obvious. You consider whether the two months of contract work in the middle technically count, and decide that they do.

I’ve done all of it. Multiple times.

Once for eleven months and once for a stretch of about two years where things were genuinely happening, just nothing I could name in the way the document wanted me to name it.

I wrote a while back about the reflex to justify all of this out loud. This is the written version of the same problem and it is harder, because the document has no tone.

You don’t get a second sentence. You don’t get to read the room and adjust.

Whatever is on the page is the whole of what you said. There is no tone of voice in a date range. Nobody reads a CV and hears you.

The gap is the only real thing on the page

Look at a CV for a second and notice the whole shape of it.

Job title, company, dates, three bullets.

Job title, company, dates, three bullets.

Job title, company, dates, three bullets.

Every one of those lines is a category. Thousands of people could fill them in more or less identically, and quite a few of them are applying for the same thing you are.

The gap is the only line that is specifically yours.

It is also the only thing on the page a stranger will actually ask you about.

Nobody has ever opened an interview by asking about your third bullet point.

The gap is the only unstandardised thing on your CV, and you are using it to store an apology.

Why hiding it doesn’t work

The eye goes to dates. It is the first thing anyone scans and the easiest thing to check, and it takes about four seconds.

So the gap is going to be found. That was never actually in question. The only thing you control is whether it gets found with a name on it or without one.

And this is the part I think people get wrong.

An unnamed gap does not read as neutral. The document has no way of expressing choice. It cannot distinguish two years you decided on from two years that happened to you, because both of them look like the same empty space between two dates.

So the reader supplies something. They are not being unkind — they are filling in a blank, and the thing people reach for is whatever is most common.

The risk with leaving it blank is that a reader picks an explanation for you.

Which means the silence you thought was safest is the only option on the page that is actively working against you.

Three things, and none of them is a reason

A gap turns into an entry when it has three things in it, and not one of them is a reason.

The first is a name.

Something specific, and ideally not career break, because career break is only another category and it tells a reader nothing they had not already guessed from the empty space.

The second is dates, laid out exactly like every other line on the page.

This is the part people skip and it does more work than the wording does. A line that looks like the other lines gets read like the other lines, and most of that happens before anyone has consciously taken in a single word.

The third is a verb. Something you did, rather than something you learned or something you became. Built, studied, ran, cared for, travelled, recovered, wrote. A verb is a fact. Learned and became are claims, and a claim invites the follow-up question in a way a fact does not.

None of that is a justification, which is the whole point. You are not making a case for the gap, you are giving it contents. It ends up shorter than the version you had, and it closes the subject instead of opening it.

Although this is much easier to write than to do

I’m aware I have made this sound more tidy than it actually is.

The hard part was never the wording. It’s that naming the gap requires you to have decided what it was, and most gaps are still unresolved at the moment you have to write them down. Mine was.

I was three months out of the thing and had no real idea yet whether it had been a breakdown or the best decision I ever made, and there is no verb that covers both.

So you end up naming it before you know. Which feels dishonest and mostly isn’t, because a CV was never a confession.

It is a summary written for a stranger who has ninety seconds, and summaries are allowed to be provisional.

Though I notice that is quite a convenient thing for me to believe, and I did arrive at it about ten minutes after I needed it to be true.

What actually changes

You stop editing to remove evidence and start editing to add information. Same set of facts, completely different document, and it takes about twenty minutes.

The other thing that shifts is what happens in the room afterwards. An unnamed gap is the conversation you are braced for the entire time, sitting there in the middle of the page, waiting.

A named one is the fourth item down. Sometimes it gets a question and the question is curious rather than sceptical, which is a different experience entirely and I did not believe it until it happened.

I haven’t opened mine in a long time. I don’t need it for anything at the moment, and there is a version on my hard drive where two years are compressed into a phrase I picked one afternoon when I was tired and wanted to be finished.

I know roughly what I would write now. What I’m less sure about is whether today’s version would be any truer, or whether I would name the same two years differently depending on the week I was having.

That doesn’t seem like a reason to leave it blank. It might be a reason to stop treating the document as though it is supposed to be permanent.

-Katie

What’s the gap on yours, and what have you been calling it?

If this landed, send it to somebody who is about to update theirs.

More from Multiple Lives Theory:

• The hardest part of a nonlinear career isn’t building it. It’s explaining it.

• The over-explaining audit: what to stop justifying about your career

• Your CV is lying about you (it’s designed to)

Share

🌱 New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, weekly.

Upgrade

This is the first of my series called Sessions, which is a name I have only recently settled on for something I have been making for a while.

A Session is an essay with a working part attached. The essay is what I think about something. The working part is the thing I actually use, and in this case it is a prompt you can run on your own list by the end of the afternoon.

I wanted to start here because it is the least flattering thing I know about my own working life and also the most useful so far.

The folder of ideas that came with me

It is not really a folder.

It is a few folders, some domains I have kept renewing for reasons I could not defend, three podcast episodes sitting on my hard drive, and a handful of things still live on the web that I have not looked at in years.

I call it the folder because that is easier than saying I have started a lot of things and finished a few.

When I stopped having a salary, I assumed some of this would sort itself out. The unfinished projects had stalled because I was tired, I thought, or because there were only so many hours after work.

Once the hours were mine, I assumed the half-built things would either get finished or stop mattering.

That is not what happened.

I left, the folder came with me, and within four months I had added to it.

Here is the actual list, which I had never written down in one place before and would rather not have.

• 2018. A travel blog. Tips, itineraries, the whole thing.

• 2019. Journal printables, sold online, alongside self-taught coding tips on an Instagram account called Katie Kodes, now deactivated.

• 2020. WordPress, Shopify and Squarespace templates, still floating somewhere on the web.

• 2021. A podcast. Three episodes recorded, none published.

• 2022. A domain for a career coaching thing. Bought it, never built it.

• 2023. A Notion template pack. Dashboards and tools for career changers.

• 2024. Online zines about tea and coffee, because I wanted to bring the beverage thing into the world somehow.

• 2025. An Etsy and Gumroad store selling digital marketing tools and AI prompt packs for small businesses.

• 2026. SEO audits and website templates.

Nine, give or take, depending on whether you count the things that never got past a domain name.

I am not going to pretend that list is fine. Some of it is abandonment. There were months when I started something new mainly to avoid finishing something old.

Most of them are dead and should stay dead

I want to say this early because the tidy version of this essay would not.

The comforting story is that every abandoned thing taught you something and that the skills carry forward.

Some of that is true.

Plenty of what I stopped doing, I stopped because it was not good, because I was the wrong person for it, or because I only wanted it in the way you want something at eleven at night.

The travel blog is dead.

The podcast is dead, three episodes into a medium I did not enjoy.

The coaching domain expired without a single page on it.

The tea and coffee zines still interest me, and I am fairly sure they were never a business. They were something I wanted to exist.

Those things are not lessons. They are things I did not do.

Admitting that makes the rest of the list easier to read. When every abandoned project has to mean something, you miss the ones that actually have a pattern.

I did not start nine things

This is the part I did not see until I put the list in order.

The printables in 2019, the Notion pack in 2023, and the prompt packs in 2025 are the same idea: make a small useful thing and put it somewhere people can buy it.

The WordPress, Shopify and Squarespace templates in 2020 and the website templates in 2026 are the same idea again.

The coding tips on Katie Kodes in 2019 and the SEO audits in 2026 are also related.

So I did not abandon nine unrelated projects.

I started about three things, several times each, in different clothes, and quit each version before anyone had much chance to pay me for it.

That is worse to admit and much more useful to know.

A person who abandons nine unrelated projects may have a focus problem. A person who keeps restarting the same three things has probably been circling something.

I had been reading my own list as evidence that I was flaky.

It was closer to evidence of a direction I kept refusing to commit to.

I think that is because starting again feels like ambition. Finishing feels like a verdict.

The signal is not how you felt about it

For a long time, I sorted the list by whether I had liked doing each thing.

That sounds sensible and is mostly useless.

I liked nearly all of them at the start. Enthusiasm at the beginning tells you very little.

The useful question turned out to be much duller:

Did anyone ever ask you for it without you offering first?

A compliment does not count. Neither does someone saying it is a good idea.

I mean someone coming to you and asking whether you could do that thing, make that thing, or whether it was available.

Most people have had this happen and ignored it because it arrived in a message months ago and looked like a favour.

Mine was a founder at a femtech health company asking whether I could redo their web architecture.

I treated it as a favour with a fee attached rather than information.

It did not feel like a business arriving. It felt like someone I knew needed a website, and I could do it, so I did.

That was the clue.

The useful question is which of your abandoned ideas somebody came looking for while you were busy looking elsewhere.

The four steps

1. Get the whole list out, including the embarrassing ones.

Write down the domains, courses you outlined and never recorded, things you built for one person, and projects you stopped mentioning.

The list only works if it is complete. The ones you would leave off are often the ones where somebody asked for something.

Put everything in order by year.

2. Look for the repeats before you look for the winners.

Read the list from the beginning.

Mark anything that is the same idea in different clothes. You will probably find a few clusters and some genuine one-offs.

The clusters tell you where you keep returning when nobody is making you do anything.

3. Mark every unprompted ask.

Go through each project and ask whether somebody came to you about it without you raising it first.

Be strict. Encouragement does not count. A friend saying you should do it does not count.

Someone asking whether they can have it, buy it, book it, use it, or whether you would do it again does count.

If there was an ask, write down who made it and roughly what they said.

4. Put a number on it and say it to one person.

You do not need a business plan. You need a price and one person who might pay it.

This is where a project either leaves the folder or stays there for another two years while you tell yourself you are still deciding.

So that’s the exercise. Here’s what it gave me when I ran it on my own list.

The four projects that pay me now

The four are website work, SEO audits, coaching, and digital products.

All four are on that original list.

The website work came from the templates.

The audits grew out of the coding and website work.

The digital products are the printables on their fourth attempt.

The coaching idea has been sitting in some form on the list since 2022.

None of these arrived as a perfect business idea. They kept coming back.

And more importantly, people asked for them.

I would like to tell you I recognised this at the time. I actually did not.

They sat there while I worked on things that looked more like proper businesses. I eventually returned to them because I needed the money and they were the projects on my list that somebody had actually asked me for.

That is a much less glamorous reason to make money from a passion.

It is also a more useful one.

Where this stops working

There are two places where this exercise can give you an answer you do not like.

The first is that some folders are simply graveyards.

If you find no unprompted asks anywhere on your list, that is a result. It means the things you have been building may be things you wanted to have built rather than things other people wanted to buy.

The second is that the project with an ask attached may be the one you are least proud of.

Mine is not the thing I would lead with at dinner.

There is a cost to reopening something you had quietly decided was beneath the version of yourself you were trying to build.

You should know that cost before you price it.

There is another pile I did not expect: things people keep asking for that I no longer want to do.

Demand on its own is not a reason.

Some things should stay in the folder even when people want them. The question is whether you would still be willing to do the work six months from now.

I also want to be careful about what this exercise can promise.

You may have one thing somebody once asked for. That does not make it a business.

It may be worth two weeks of attention.

It may make some money.

It may tell you something about the direction you keep returning to.

That is enough.

For me, these four projects now pay some of the bills.

It is not what I imagined I would be doing.

I still catch myself describing the work as the small thing I do on the side, which, after 12 months, is starting to sound like a lie I tell for the sake of a tidier story.

The zines are still in the folder.

I have not worked out whether that is the one honest thing on the list or just the next thing I am going to quit.

There’s one more thing, and it isn’t about the list.

I’ve used Claude for a couple of years as a lean coworker. It challenges my thinking, gives perspective, helps me sort through technical complexity. That part isn’t new.

What was new was pointing it at myself. I’d been using it on work, never on the story I tell about my work, and those turn out to be very different jobs. The prompt below is written to refuse encouragement, to reject a yes I can’t back up with a person’s name, and to quote my own dismissive phrasing back at me at the end. I had to write those rules in deliberately, because the default behaviour of every one of these tools is to agree with you warmly and let you leave feeling productive.

So the shift is smaller than it sounds. I stopped asking it to make things and started asking it to notice things. It isn’t smarter than me about my own list. It just has no investment in the story I’ve been telling about that list for nine years.

I sorted nine years of work by how I felt about each thing. It sorted by what was actually there.

The prompt is below, for paid subscribers. It’s the version I run, not a cleaned-up one. About twenty to thirty minutes and you’ll have a shortlist with a price and a date on it.

Read more

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, weekly.

Subscribe now

A slightly contrarian one today. I’d actually love to hear your perspective on this one. I’m not sure I have the answer either, but it’s been sitting with me for a while. Because maybe there isn’t a right or wrong answer here. Maybe it just depends on the life you’re building.

I have spent the last few weeks writing about burning down the thing I worked hardest to build, and my brain has not really stopped since.

Somewhere in the middle of all that, a question surfaced that I have not been able to put back down.

I’ve started asking a different question instead of the passion one, and I want to try to explain why, because it initially does not feel like the nicest question.

What could you do badly, in public, for a year, without quitting?

That’s it.

Every time I’ve run it on myself it has given me a more accurate answer than what do you love ever did, and the answers have been less flattering, which I think is the point.

Why passion keeps giving the wrong answer

Passion is measured at the ‘peak.’

When somebody asks what you love, you don’t picture the reality.

You picture the good version.

The version they ‘sold’ to you. The finished thing, the day it goes well, yourself competent and mid-flow and pleased.

Everyone does this. It isn’t dishonesty, it’s really what the question invites.

But nobody enters a skill at the peak.

You enter at the worst point on the whole curve.

You’re slow, you’re bad, the output is embarrassing, and other people can see all of it.

I am not afraid to admit, I have done this in public about 2-3 times now.

Making my career pivot when working as a receptionist, entering coding competitions and documenting about it online via my Katie Kodes instagram.

And another one is building this publication on Substack for The Multiple Lives Theory.

I honestly do not know how well it will go and if it will even go anywhere, but I know this is the lifestyle and type of craft I want to refine daily and show up for.

Passion measures the top of the curve. You only ever get to start at the bottom of it.

So, the question tests you on a day that hasn’t happened yet, and the actual test runs on all the days before it. Which is why people can be completely certain they love something and still be gone by March.

The year of being bad

Every real thing has one. Sometimes longer than a year, though a year is about the shortest honest version.

The writing nobody read, for much longer than I tell people. The early client work that was fine and wasn’t good, which is a distinction you can feel and can’t quite prove. The first ten of anything. The stretch where you can already tell what good looks like and you cannot yet do it, which is the worst part and the one that lasts.

The question was never whether you love it.

I’m starting to see the question as whether it can be seen doing it badly for long enough to stop being bad.

Getting specific

If you’ve changed direction more than once, you’ve already been a beginner several times. You know exactly what it feels like to be the worst person in the room at something everyone else finds obvious.

Which sounds like an advantage. Some of it is. But there’s a trap in it that I don’t think people with straight careers have in the same way.

You’ve got a ready explanation. When the discomfort arrives, you have a sentence waiting for it. This one isn’t right either. And that sentence is usually plausible, and occasionally it is completely correct, which is what makes it so hard to argue with at the time.

So, the pattern isn’t quitting.

The pattern is quitting at the same point each time, and having a good reason each time.

I’ve done this. I could name the point.

It is roughly the moment the thing stops being novel and starts being work I am not yet good at, and I have left three separate things within about a month of that point and explained every one of them convincingly, mostly to myself.

Why nobody uses this filter

Because it sounds like settling. It also implies unnecessary pressure to reach for the ‘perfect’ role and perfect job.

Choosing on what you can put up with, rather than on what you love, in a way feels like giving something up.

That you never had a calling. That you have got practical about something that was supposed to be a feeling.

And the answers it produces are unglamorous.

Again, mine is writing. Something I’ve been publicly mediocre at for years, then burnt out on so badly that I lost my voice and, for a while, my sense of self along with it.

I decided this year to keep doing it anyway. I resisted that answer for a long time because it didn’t feel like a decision. It felt more like a habit I just hadn’t got around to stopping.

That might be what it actually looks like from the inside. Not a pull. Just the one you didn’t stop.

Or that might be a generous story I am telling about failing to quit something.

I go back and forth on it, usually depending on how the week went.

What the question is actually measuring

This is the part that took me longest to see.

It isn’t measuring grit, and it isn’t measuring love. It’s measuring how much of your sense of yourself is riding on being good at things.

If being bad at something threatens who you think you are, you will leave early. It won’t matter how much you love it. The discomfort will find the fastest available exit and dress it up as discernment. If being bad at it doesn’t threaten anything, you’ll stay, and staying is the entire mechanism.

Which is why the honest answer is often something you were already bad at before you had anything to protect.

Things you started young. Things nobody expected you to be good at. Things that sat outside whatever you were known for, so failing at them cost you nothing socially. That’s not a coincidence, and it’s quite a useful place to go looking.

The limit, and it matters

Tolerance for being bad is not the same as aptitude, and I don’t want to be vague about that.

You can cheerfully be bad at something for a decade and remain bad at it. The question predicts persistence. It does not predict that you will get good, and it certainly does not predict that anyone will pay you. Those are three different things and running them together is how people spend eight years on something that was never going to work.

So, it’s a filter, not a forecast. It narrows the field. It doesn’t tell you what happens next.

The question isn’t what do you love.

It’s what can you be humiliated by on a Tuesday and still come back to on a Wednesday.

I have one answer and I’m not especially thrilled about it. It isn’t the most interesting thing I do. It doesn’t pay the most. It’s just the one I have been bad at for years and never quite stopped.

I still don’t know whether that counts as choosing something.

-Katie

What have you been bad at for years and never stopped?

If this landed, send it to somebody who keeps starting things.

More from Multiple Lives Theory:

• Nobody warns you that reinvention is boring

• The hardest part of a nonlinear career isn’t building it. It’s explaining it.

• The five-year plan is dead. The questions haven’t caught up.

  Share

🌱 New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, weekly.

Subscribe now

Somebody asked me last month how I make money and I gave an answer so vague that it embarrassed me on the way home.

Not because I didn’t know. I knew. I could have listed them. But I was vague because the honest answer is four things, and four things said out loud sounds like scraping by, when the actual situation is that the rent has been paid on time for a good while now.

So here it is properly, which is not something I have written down before.

The four

1. Design work

Design work for clients is the biggest, and it is mostly small startups overseas.

SaaS apps, a few e-commerce ones, education brands and fellow digital marketing brands.

Every so often a new client turns up and decides they need a stronger digital presence on the web even though they might not know what that means yet.

The other type of design work is the ongoing site builds, mostly. It is also the part I find least interesting to talk about, probably because it is the thing I was already good at before any of this started.

2. Retainer packages

Then the retainers, monthly, from partnerships I already had with brands in a few different countries.

Fixed scope. Checking the SEO content is still holding up, design updates, internal links, metadata.

Unglamorous, and it mattered more than its size suggested, because it was the first money that ever turned up without me having to go out and find it.

I had not understood, until then, how much of the exhaustion was the finding rather than the doing.

3. E-commerce stores

Online e-commerce stores, which my partner and I built together.

There were two of them, which is the part that makes this hard to say in one sentence.

The one still running is in the digital product space. Tools, website templates, UI/UX tools and components for small businesses trying to look like they know what they are doing on the web.

It grew more than I expected, mostly while I was not watching it, because the aim was to make it a passive income business.

The other one shipped actual objects, and it closed earlier this year. That is a longer story than this essay wants. I never really paid myself out of either of them, or I paid myself just enough.

The closed one is the one I keep thinking about. I did not want a future in inventory and logistics. I had pictured myself somewhere with a laptop, and when I started shipping actual objects I had not thought that far ahead.

I opened it to find out how I liked working, which is an expensive way to run that experiment, and I learned more about daily operations than I ever wanted to.

While it was a short-term business, I am glad I gave it a go, as it showed me what I do not want, and I think that is a reasonable thing for a business to have done.

It just took closing it before I would listen.

4. Writing

And the writing, which is maybe about five percent of it.

To tell you the truth, definitely the least money, my longest runway yet, and the one I would keep if somebody made me choose, which I am aware is the kind of thing people say about the thing that pays least.

I should admit that I cannot give you the exact split. My partner does the maths. He is, among other things, my business partner and accountant, and I could not tell you what share of last month came from where without asking him first, which for someone writing an essay about her own income is either funny or slightly damning, and is probably both.

How they actually arrived, which is less impressive than stacked

They did not turn up together and saying ‘stacked’ makes it sound like a plan, where in reality, all this did not come planned.

The design work came first, because it was a continuation rather than a decision.

I was already doing it. The retainers came about eight months later.

The shop was already running quietly in the background by then, and had been for a while.

The writing came last and took much longer to pay anything at all, and for most of that time I would have called it a hobby if anyone had asked, which is a word I now think I was using defensively.

Somewhere around twelve months in, the four of them together made more than the salary had, though not every month since, and I think that is the more honest way to put it.

I didn’t really notice on the day. I worked it out about six weeks later, doing sums for something unrelated, and then sat there for a while feeling considerably less than I had expected to.

Why the business is still open

My high achiever side and a dash of stubbornness are part of it, and I have said that out loud before.

The rest is less flattering.

I left a salary and I felt guilty about leaving it, and the guilt turned into a rule I never wrote down, which was that there always had to be money coming in from somewhere.

The online shop is still operating behind the scenes. And closing it would mean fully trusting the other three, and I am not there yet.

What a job actually bundles

It took me a while to redesign this in my mind and make it make sense for myself in my world.

A job is not a source of income.

It is a bundle, and you do not notice because it never comes apart while you are inside one.

A job hands you money. It also hands you a title, a schedule, somewhere to be on a Tuesday, a category on every form you will ever fill in, an answer at a party, something to tell your parents, and the general assumption that you are fine.

All of it arrives in one object, automatically, and none of it is itemised.

Take the bundle apart and one item survives on its own. The money. The rest does not come with it and nothing turns up to replace it.

Paying your way and being taken seriously used to arrive together. They come apart now, and the money is the half that turns up first.

Which is a state most of us do not have a word for. Financially fine, socially unplaceable. So people reach for the nearest available word, and the nearest available word is usually struggling.

The word I went and found

Except finally I found a word that resonated while I was scrolling on Substack. Portfolio work or fractional work.

I came across it in Anna Mack’s Stack writing and then again in Nonlinear News, and something in me settled, which is the part worth admitting.

Nothing had changed. Not the money, not the week, not one of the four things. I just had a phrase that sounded like a category, and a category was the thing I had been missing. I used it on myself long before I ever used it on anybody else.

I am still not sure whether that counts as understanding something or just as being relieved.

The part I actually find hard

It is not the money. The money got sorted, roughly, and later than I would have liked.

It is that four things means four beginnings and nothing that ever finishes.

There is no promotion in this. Nobody moves you up a level. You keep four plates going, and the reward for keeping them going well is that you get to keep doing it.

Which is fine, and it is what I signed up for.

It is just not a structure anybody prepared me for, because every story we get about work has a ladder in it somewhere.

I notice I am proud of it and slightly embarrassed by it at the same time. Occasionally in the same conversation. Once, memorably, in the same sentence.

Although, I wonder whether the embarrassment is about legitimacy at all, or whether it is simpler and less flattering than that.

Some of it is just that I miss being able to answer in one word. That is not an identity crisis.

It is a small daily friction, and I think I have dressed it up as something larger because something larger is more interesting to write about, and because admitting you want the easy version of a question makes you sound lazy.

What changes when you stop waiting to feel legitimate

The more useful move, I think, is to stop treating it as a stage you are going to reach and start treating it as something that simply lags.

The money is a fact, or it is a fact my partner can find for me. Being taken seriously is an opinion held by people who are not looking very closely, and it updates slowly, if at all.

That does not make the wanting go away. I still want it.

But it does change what you do with a month where the money worked and the feeling did not, which for me is most months.

The rent got paid again this month. Four transfers, four different dates, not one of them called salary.

I still say I work in design at parties. It is true enough, it ends the question, and I have stopped feeling bad about that.

What I have not worked out is who I am waiting to hear it from. Somebody, apparently. I keep checking now and then…

-Katie

If this landed, send it to somebody whose income you could not describe in one word.

More from Multiple Lives Theory:

• The 30-something’s guide to the actual maths of starting over

• ‘How’s the business going’ is never about the business

• The hardest part of a nonlinear career isn’t building it. It’s explaining it.

Share

🌱 New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Hi, I am Katie. Welcome to Multiple Lives Theory. Essays, frameworks and tools for people who have already lived more than one working life, and are still working out the next one.

Last year I opened the same spreadsheet most evenings to look at a price, and then I closed it again without changing anything.

Not a salary, and not a rate for a big client. A price on a product that nobody had bought yet, because it had not launched.

I wanted to write about it because I have never really seen anyone describe how that feels, which is that the size of a decision has almost nothing to do with how long you end up spending on it.

Some of the longest weeks of my working life have gone on things that did not matter at all, and I suspect I am not the only one.

So this one is about the tree I built to get myself out of it. Four steps, with one test sitting in the middle that ends most of the arguing before it really gets going. And then a rule about forty eight hours, which I will be honest, I still have to talk myself into some weeks.

For a decade, this was literally my job

If the user clicks this, show them that. If the field is empty, branch left. If the error fires, catch it, explain it, offer the next step.

That was the work for about ten years. Mapping other people’s choices in advance, so that nobody using the product would ever arrive at a moment and not know where to go. And I was good at it. It is genuinely satisfying work, taking something that feels like fog and turning it into two clear paths with a sentence explaining each one.

Then I would close the laptop and spend three hours deciding whether to send an email I had already written.

It took me a long time to see those two things as related. I think I had quietly filed them in different places. One was work, and the other was just me, and it never occurred to me that the skill might be portable. It did not feel like a skill by then. It felt like something I did for money.

Overthinking arrives dressed as diligence

Overthinking never turns up loudly. That is the part that gets you. It arrives quietly, and it looks quite reasonable, cautious even, the way a person is supposed to be when something actually matters. It reads as thoroughness. It reads as taking it seriously.

And because it looks like that, nobody interrupts you. Not the people around you, who think you are being sensible. And not you either, because from where you are sitting there is no reason to stop.

So here is the test I use now, and it is not a clever one.

Diligence gives you something you did not have before. Overthinking takes what you already had and moves it around.

If hour four contains the same three facts as hour one, maybe you are not actually deciding anymore. Maybe you are just waiting for the discomfort of having decided to disappear.

The strange thing is, it usually does not disappear first. I know this, and I still catch myself waiting for it.

That was the part I misunderstood for years. From the inside, the two feel almost identical. Both involve the same looping thoughts. Both leave you exhausted. Both feel like you are doing something important.

But one is thinking something through. The other is trying to negotiate with a decision you have already made.

Upgrade To Download Tool

Read more

Hi, I’m Katie! Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Essays from inside the transition, not the other side. Thursdays and Sundays.

Subscribe now

Since starting this journey, I’ve been thinking about the part of changing your life that nobody puts in the warning, and truthfully, it isn’t the scary part.

Everyone warned me about the fear. The money, the uncertainty, the what if this doesn’t work. People were generous about it, repeatedly, and they meant well. I had a number in a spreadsheet and a rough plan for what I’d do when the number ran out.

What nobody warned me about is that most of it would be boring.

Simply put. Just boring.

There’s a difference and I did not know it until I was sitting in it.

A boring day goes like this. You get up, you make coffee, you sit down, and you have three things to do that would take about forty minutes if you did them one after the other.

You stretch them across seven hours, because there’s nothing else in the day and stopping at half past ten feels like cheating or procrastinating.

You reread your own website copy. You iterate on the design mockup. You send a follow-up. You wait. Somebody replies on Thursday. That was the week.

And you can’t really tell anyone. That’s the other half of it. Say you’re stuck on ideas and people start giving advice. Say you’re bored and it sounds like you’re complaining about the thing you asked for. And they continue to give advice.

And the other day someone asked me, “What was it like going full-time into your own business!?” They were genuinely excited for me. I thought I’d have some glorified answer to share. Like I’d finally figured life out. But after going through it, my answer was surprisingly ordinary.

I replied, “Honestly, it was pretty normal. It just felt like starting another project.”

I realized I’d built this version of it up in my head. That starting over would feel exciting all the time. That every day would come with some big breakthrough or sense of progress. But somewhere along the way, I stopped noticing the transition because it had simply become my life.

And maybe that’s the part we don’t talk about enough. The real work isn’t the highlight reel. It’s the ordinary process you wake up to and do again the next day, until one day you realize it was never supposed to feel like this extraordinary transformation.

It was just your life, changing one ordinary day at a time.

You’re just living it. That’s the part I don’t hear people talk about enough. The real work isn’t the highlight reel. It really lives in the ordinary process you wake up and do again the next day.

Why nobody wrote this down

I don’t think it’s a conspiracy of silence. I’m starting to think it’s a storytelling problem.

A decision is an event. It happens on one day. It has a before and an after and a moment in the middle, which means it fits in a paragraph, a post, a phone call to your mum. It is tellable.

The rebuild isn’t an event. It’s a process. It’s a duration. Eight months of steady, unremarkable work has no shape you can hand to somebody. Nothing in it changes fast enough to hold anyone’s attention, including your own.

So we have an enormous amount of writing about the leap and almost none about the year that follows it. Not because people are hiding it. Because there’s no way to make it interesting, and the people living through it are the least likely to have the energy to try.

What the boredom actually is

I assumed boredom meant there wasn’t enough going on.

But that wasn’t it.

There was plenty going on. Most days I had more things on the list than I could finish. There were ideas to chase, things to build, things I wanted to learn.

What had disappeared was the response in a what is considered ‘normal’ day to day system.

Think about a normal week in a job. Somebody replies to your message. A meeting happens and you say something and someone nods. A deadline arrives. Your manager says “looks good,” or says nothing, which somehow also counts. There are all these tiny moments throughout the day that tell you something is happening.

You’re moving. You’re contributing. You’re roughly where you’re supposed to be.

You don’t really notice them until they’re gone.

Because when you step away from that structure, the work doesn’t disappear with it. The list is still there. Sometimes it’s even longer.

But you do something and nothing happens. You do the next thing and nothing happens.

Nothing is going wrong either, which is the strange part. If it was failing, at least there would be something to respond to. Something to fix. Something telling you where you stood.

You didn’t get bored.

When you’re reinventing, especially when you’re building something new, those signals disappear before the new ones have had time to form. The work is still there. Sometimes there’s more of it than ever. But the response is delayed.

Which is why it doesn’t respond to the usual fixes. Working harder doesn’t create clarity. Working less doesn’t create momentum. I tried both, at some length, before I realised I wasn’t dealing with boredom at all.

And this is where people quit

Here’s the part I care about most, because it costs people the thing they wanted.

The boredom shows up somewhere around month four or five. It doesn’t announce itself as boredom. It turns up as flatness, and flatness looks a lot like evidence. Evidence that you chose wrong. That the thing you left was actually fine and you were being dramatic. That you’re not cut out for this after all.

It feels like information. It usually isn’t. It’s just what an unmetered week feels like from the inside.

Almost nobody quits during the frightening part.

They quit during the dull part, and they call it clarity.

I’ve watched three people do it in the last year, and each of them had a reasonable explanation ready. One of them was right, I think. I’m not sure about the other two, and I didn’t say anything at the time because who am I to come in and give an authoritative opinion.

Although I might be excusing myself here.

Some boredom is real information. If you’ve been bored for eleven months and nothing you change makes any difference, that might be the work rather than the transition, and no amount of reframing will fix a thing you don’t want to be doing.

I can’t always tell which one I’m in, and I’d be suspicious of anyone who says they can. The rough test I use is whether it lifts. Boredom that disappears the moment something interesting turns up is the transition. Boredom that sits there through the interesting parts as well is probably the work.

That isn’t a clean test. It requires the interesting parts to actually turn up, and sometimes they take their time.

What changes if you expect it

You stop reading it as a verdict. That’s most of the value, and it isn’t nothing.

The other thing that shifts I notice is the assumption underneath, which is that the dull stretch is an interval. The bit between the decision and the life. It isn’t.

Ordinary days were always going to be the majority, in this life and in the one before it.

The old job and the new job had them too. They just had meetings in them, and the meetings made the week feel like something was occurring.

Which means the thing worth building isn’t more excitement. It’s some way of registering a week that doesn’t depend on anybody else noticing it. I’m not going to pretend I’ve nailed that. I have a system I like for about three weeks at a time.

And there’s a version of this where the boredom is a good sign. A settled week is boring almost by definition. Nothing urgent, nothing on fire, nobody needing anything at nine at night. It might just be what stable feels like before you’re used to it. Though I notice I want that to be true, which is usually a reason to hold it loosely.

What this leaves you with

Nobody warns you about this because it doesn’t sound like a warning.

One day, reinvention becomes ordinary.

Eight months in, most of my days are admin, waiting, sending outreach emails, and work that compounds so quietly it barely feels like progress.

However, I’d choose it again tomorrow. Maybe that’s the point.

Reinvention isn’t supposed to stay exciting forever. Eventually, it starts feeling like your actual life.

And strangely, I am comfortable normalizing it and admitting it’s another day in the mundane life of.

What’s the most mundane part of your week right now, and what did you think it was going to be instead?

More from Multiple Lives Theory:

• The hardest part of a nonlinear career isnt’ building it. It’s explaining it

• The five-year plan is dead. The questions haven’t caught up.

• You can grieve a life you never chose

Share

🌱 New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Hi, I’m Katie. Welcome to The Multiple Lives Theory, where I write for people who have outgrown a version of a life they worked hard to build. Actionable insights and essays from inside the transition, not the other side. Thursdays and Sundays.

Subscribe now

This is the fourth time I’ve tried to write this one. And I’ve finally discovered what it was actually about.

Lately I’ve been thinking about the hardest part of building a nonlinear career, and I’ve convinced myself I don’t think it’s the building part.

Which is a strange thing to say, because I found the building process especially grueling and hard. Extremely hard.

The point where it is unexplainably hard and the only way to understand it is to go through it. But in a way, I am getting better at it.

Financially, money was unpredictable for years. There were long stretches where I couldn’t tell whether I was doing something brave or just avoiding a decision. Overtime, most of that got easier, or I got used to it, and now I’m at the stage where I am unsure there’s much difference between the two.

What hasn’t got easier is answering the four word question at a gathering. In fact it is probably the most jading question during this time of my life right now.

Once you step outside the 9-to-5, the structured career ladder, and the linear path we’ve been taught to follow, you start to see that a career is so much bigger than a job title. Building a portfolio life isn’t just about the work you do. It’s also about the many ways you create, contribute, learn, and evolve. Because there’s so much more to life than what you do for a living.

You know the question I’m talking about. Somebody asks what you do and there’s a beat before the answer, half a second, sometimes less.

In it you’re running a quick calculation. Who’s asking? How much time they’ve got? Which version should I share? Should I share a quick one-liner or just throw a simple job title at them because I honestly cannot be bothered explaining myself. Which version of this gets you both out of the conversation without it turning into a whole thing?

Then in the moment of it all, you pick one.

Perhaps not exactly the answer you wanted to give so you move on.

I did that for years and assumed it was a me problem. That my working life had got too complicated to say out loud, or that there was a sentence out there which would fix it and I simply hadn’t found it yet. If you’ve had the pause, you’ve probably had that thought too, and you’ve probably had it more than once.

I don’t think that’s it anymore. I think the question stopped working a while ago and nobody said anything.

What a job title used to do

It used to carry a great deal more than it does now.

For a long time one word told you nearly everything. Lawyer. Teacher. Electrician. Engineer. Accountant. You would hear it and you would know roughly what someone did all day, what they earned, how long they had trained, what their hours looked like, probably where they sat socially. All of that, from one word, with nothing to follow up…

Which is why the question is so short. And the answer used to be equally short.

A lot of that has come apart, and not in the most even ways either.

The pause belongs to a particular set of people. The ones running a contract, a retainer and something of their own in the same week. The ones who trained for one field, left it, and now use it sideways in another. The ones whose title is accurate on Monday and misleading by Thursday. The ones whose biggest source of income has no settled name, so they end up describing it by comparison to something else.

The question didn’t change, though. Still the same four words, still expecting the same kind of answer, still being asked at every dinner.

And the way we talk about work

And the title is only part of it. The language sitting around the title has the same problem.

First this, then that, which led to here, which is why I’m doing this now.

A line.

Nearly every question we ask each other assumes the line is already there.

How did you get into that. What’s next. Each one is asking you to draw it.

If your work has run in more than one direction, there isn’t a line. Things happened at the same time as each other. Some of it overlapped for years. Some of it only made sense later. You might have built your most useful skill during the stretch your CV calls a gap.

So when someone asks, you have two options. Both of them cost you something, and perhaps you have been alternating between them for years without ever calling it that.

You don’t have to explain or prove yourself. You can flatten it and shape it the way you want to. Pick the piece that makes the most immediate sense, say that, let them file it the way that makes sense to them. It works.

It works so well that you sometimes leave the conversation a bit annoyed at how well it worked. Then you carry on.

Or you can unfold it. Give the real answer, in order, with the connections explained. That’s the one that ends with somebody saying “wow, you’ve done a lot”, which is what people say when they stopped following a while back and want to be kind about it.

Most of us default to one or the other and have done for years without noticing which. You can usually tell by how you feel afterwards. If you flatten, you leave feeling slightly unseen. If you unfold, you leave certain you talked too much.

What the question is actually for

You’ve probably assumed there’s a third option and you just haven’t found the wording for it.

I did too. For a long time.

There isn’t one, and the reason there isn’t is the part that changed how I think about this.

When somebody asks what you do, they’re not asking to understand your working life. They’re lowkey asking where to put you. Somewhere to file you, so they can stop wondering and get on with the conversation.

The question is over the moment they have somewhere to put you. Not when you have finished explaining.

I had this moment of realization when I went to get my hair done, sitting in the hairdresser’s chair (which isn’t a dignified place to realise anything). She asked me, ‘what do you do for work’. I started answering, and somewhere in my second sentence I watched her face in the mirror go still like she was confused. Not that she was bored. But more like she was either distracted or focusing on giving me perfect even layers with my hair.

And at that point I realized it was probably just a question to feel the silence and something that we default to in front of people.

You’ve been giving a more and more accurate answer to a question that was never about accuracy.

I realized that being accurate actually works against you here, which feels unfair. The more precise you are, the longer it takes someone to understand what you do, because they have to hold more pieces in their head before they can make sense of it.

Precision starts to look like complication. Not because your work is confusing, but because you’re trying to fit something complex into a format that was only ever designed to hold something simple.

And the space never gets bigger

The part that surprised me most is that this doesn’t get easier.

You would think it would. Ten years of answering the same question ought to produce a decent answer to it, the way ten years of most things makes you better at them.

It goes the other way. Every new direction you add makes the thing you’re compressing bigger, and the space the other person holds open for your answer stays exactly the size it was when you had one job and four words.

You haven’t got worse at explaining yourself.

What you’re explaining got bigger and the space stayed the same. That’s a maths problem rather than a character problem. I find it steadying, though I notice I want it to mean more than it does.

What changes when you stop aiming for accuracy.

None of this gives you the perfect sentence. There isn’t one. Looking for it’s a good part of what has been tiring.

What it changes is what you’re aiming at, which sounds like a small distinction and isn’t one.

The short answer isn’t a lie. It’s a placement. You’ve probably been treating the four word version as a small betrayal of everything underneath it, when it’s closer to a kindness. The full account still exists. It hasn’t gone anywhere. It’s just not owed to somebody who is holding a comb.

A verb usually works better than a title. A title is a category, and if your work runs in several directions it fits categories badly. What you do to things is easier to place than what you’re, because somebody can picture an effect and has to look up a role. That’s a direction rather than a script.

And the person asking sets the format, not you.

The version for a stranger and the version for somebody who genuinely wants to know are two different things doing two different jobs.

Most of the frustration comes from trying to make one answer do both.

It just can’t. And it was never a fair thing to ask of yourself.

Which quietly changes the question you’re trying to answer. Not ‘what do I do.’ What does this person need in order to stop wondering about me.

That one has an answer, it’s usually short, and it’s different every time.

What this leaves you with

The question isn’t going anywhere. It will keep turning up, at dinners and in taxis and on the second day of every new project, meeting new people and more. That moment will always keep happening.

What you can change and redesign is how you assign meaning to that question and the response thereafter.

It’s easy to assume that struggling to answer it means something is unfinished. That you’re still in transition. That eventually your work will settle into a shape that’s easier to explain.

Sometimes it does. Often it doesn’t.

Some working lives just aren’t the kind that produce a single sentence. Mine hasn’t yet.

Maybe that’s where the real work is. Not in building something unconventional, but in finding new language for it. And learning to talk about it without shrinking it into something it isn’t.

-Katie

What’s the short version you give strangers, and what does it leave out? If this landed, send it to the person you were thinking about while you read it.

Share

More from Multiple Lives Theory

• The over-explaining audit: what to stop justifying about your career

• Your CV is lying about you (it’s designed to)

• You can grieve a life you never chose

✍️ New here?

The Multiple Lives Theory is for anyone who has outgrown a version of a life they worked hard to build. Thursdays are the personal essays. Sundays are the frameworks. Both are free.

Paid members get the Reinvention Library, which is where the tools live. Decision maps, workbooks, Notion dashboards and the step by step versions of the frameworks that appear here in outline.

Written from inside the transition, not the other side.

Upgrade

Welcome! If you’ve ever outgrown a version of your life you worked hard to build, you’re in the right place.

The Multiple Lives Theory is a weekly newsletter about reinvention, nonlinear careers, burnout, identity shifts, and the many selves we become across one lifetime.

I’m Katie: web developer, designer, digital systems thinker, writer, five career pivots in. None of them wrong. Just none of them final. I’m not writing from the other side with everything figured out. I’m writing from inside the transition.

Less hustle culture. More honest becoming.

There’s a fair bit in the archive now, so here’s where to start.

If you read one thing, read this

The Theory of Multiple Lives is the framework the whole newsletter is built on: a way of thinking for people who were never one thing. Read it alongside You don’t pivot. You add., on why “starting over” was always the wrong frame for a life like yours.

If you’re questioning the path you’re on

• How I knew it was actually time to leave — not the hundred reasons to go, the one quiet signal.

• The five-year plan is dead. The questions haven’t caught up.

• You’ve been measuring yourself on the wrong clock — borrowed timelines and inherited milestones.

• What season are you actually in — a diagnostic for naming where you are. You’re not behind.

If you’re in the middle of it: identity, grief, relief

• What happens to your identity when you remove the job title

• The relief you’re not allowed to feel when the job ends

• You can grieve the life you never chose

• The reinvention story we’re not telling — on drift, luck, and the clean narrative we install afterwards.

If you’re tired of explaining yourself

• The multi-passionate person’s guide to answering “what do you do.”

• How to explain a nonlinear career without apologizing for it

• The over-explaining audit — what to stop justifying about your career.

• “How’s the business going” is never about the business — and the answer that lands.

If you want everything and were told to niche down

• The clarity trap — why “get clear” advice fails people who want more than one thing.

• Niche down is the worst advice anyone ever gave a creative person

If you’re actually making the move

• The 30-something’s guide to the actual maths of starting over — the calculation most people never write down.

• Your CV is lying about you (it’s designed to)

• The mid-year audit for nonlinear careers

• Why your nonlinear career needs a reshape test — how to stop leaving jobs and rebuilding the same one somewhere else.

How this newsletter works

• Free subscribers get the weekly essays on reinvention, identity, ambition and modern adulthood, plus Notes and chat threads where the in-between gets talked through in real time, not just written about.

• Paid members get two slower, longer essays a month, each ending with a framework, an experiment or an exercise you can actually use — plus the Reinvention Library: decision maps, Notion dashboards, workbooks, templates, guides and mini-courses for when you’re choosing direction or making a change. Essays that stop at insight weren’t enough, so I built the tools that come after.

Say hello 👋

If you read all the way here, tell me what you’re in the middle of.

Leave a comment, reply to any email, send a direct message or find me on Notes. I put every effort to read and connect with my readers! And if something here named a thing you hadn’t been able to name, send it to the person you were thinking of while you read it.

What if we are allowed to become different people across one lifetime?

Subscribe now

🍀 Become a member and unlock every resource

Become a paid subscriber to The Multiple Lives Theory to unlock everything I’ve built for people rebuilding in the in-between — the thinking, and the tools that come after it, so you can reshape a nonlinear career, choose a direction with less flailing, and become the next version of yourself without setting fire to the one you already built:

• In-depth member essays. Deliberate thinking framed as practical teaching. Each piece ends in a specific framework, experiment or exercise, not just a feeling.

• The Reinvention Library. A curated, growing collection of decision maps, Notion dashboards, workbooks and templates designed for real-world use.

• Members-only downloads. Step-by-step guides, checklists and mini-courses that translate ideas into action, so you can move with clarity instead of confusion.

Have a look at what’s already waiting inside: The Reinvention Library.

🍀 What it costs

• Monthly — A$10 a month. Full access to the essays, the Library and every members-only download. Leave whenever you like.

• Annual — A$80 a year (about A$6.67 a month). The same access for 33% less than paying monthly, which is why most people choose this one.

• Founding Member — A$120 a year. Everything in the annual plan, plus ongoing email support for your nonlinear career shift and monthly feedback on one piece of your writing.

And staying free is a real choice, not a lesser one: the Sunday and Thursday essays and fragments in between are free forever.

Upgrade

Share

I spent two years trying to change a job before I left it.

Today’s post has been sitting with me for years.

I spent a long stretch changing jobs every few years, and every time I told myself the next one would be different. It never really was. Within about eight months I had rebuilt the same job in a new building. Same hours, same over giving, same trouble saying no on a Sunday night. Nothing was new except the logo.

I wanted to write this one because living multiple lives is not only about the leaving. It is about noticing what you keep carrying into the next one, and deciding on purpose what you are not taking with you this time.

In this post I share the Stay, Reshape, Leave framework, a test that runs on a real timeline, an approach I used for my own career changes, life events, and a key for reading the result.

Read more

Hi, I’m Katie! Welcome to The Multiple Lives Theory. This is a space for anyone rewriting the rules of modern work, embracing a nonlinear career, and actively designing a life of creative freedom outside the standard 9-5 ladder.

Subscribe now

The version of me who wanted to live abroad

This week, while building out this new version of myself, I’ve felt an older version of myself come back.

Not in a big, dramatic way. Just quietly. As if trying to share a hidden sadness that doesn’t often get spoken out loud.

It happened in the middle of my usual day-to-day, planning, ideating and drafting. Just another ordinary hour at my desk, mapping out ideas for the year ahead, writing my next essay for MLT, and there she was…quietly making her presence known, but shying away at the same time.

She’s the version of me who wanted to live in Japan for a while. To teach English. To experience cultural exchange and maybe even live with host parents. To be inside someone else’s version of normal. To find out who she could be in a place she did not grow up in.

I haven’t thought about her in a long time.

Why I chose science instead

I was maybe twenty when that dream was loudest, in my second year of uni, picking out my electives as you would. I naturally excelled in science-based units, so while I enrolled in all my mandatory ones, I was inexplicably compelled to choose more science for my electives. I look back at it and wonder, why Katie?

I had peers who were doing electives in business, finance and cultural studies. I was so close to enrolling in Japanese studies, but my comfort stayed in science.

Normal, to her, looked like waking up in someone else’s language. Eating breakfast at a table that wasn’t hers.

I look back and wonder what it would be like to learn how another family lived, talked, forgave, sat in silence together. I never got past the pondering stage. A few tabs open. A program page bookmarked that I never dared to apply to. It stayed a private thing, something I told almost no one, which maybe is part of why it was so easy to let go of. I thought to myself, perhaps I was having a moment.

It’ll pass, I told myself.

The job offer that ended it

After graduation, I was head down looking for a job or continuing on to a Masters, because that was really all I knew. It felt like the natural progression in scientific academia at that stage. Not thinking about it too much, just following what I thought was right.

During my last year of university, I picked up blogging, building and designing websites on WordPress, Wix and Squarespace in my spare time. It was the only thing giving me solace in my time of confusion, turmoil and ‘what do I do with my life’ conundrums.

Then one afternoon after my medical reception shift, I had this grand epiphany, asking myself, ‘wait, what am I really doing with this Masters degree and where do I want to go with it?’

It was a brief moment of realisation that I was cruising, and I put myself in the driver’s seat. From that moment forward, I always wondered what it would be like to design for the web. I applied for any job possible, fixed up my resume and found a way to stand out. After my first full-time job offer in tech, I slowly let go of the idea that I wanted to move abroad. Almost as if that life had already passed as I discovered this new one in the world of technology, digital design and hustle culture.

I think I stopped thinking about her somewhere around that first real job offer, the one that came with a salary and a title and made the idea of teaching English abroad look like something people do before their life starts, not during it.

So while that all happened across five years, it led me to focus on striving for promotions, bringing value to the company, and jumping roles because I found out that you can double your salary by not ‘climbing the corporate ladder’ at one company.

Years later, I still think about Katie in another life, another timeline, where I’m in Japan teaching English and building a life there. It’s strange, because technically I could still do all of that now.

Nothing is stopping me. But it doesn’t feel the same. When I look back at that version of myself, the way she imagined her life, I can’t help but feel something close to a grieving sadness. Do you feel that way too?

The obstacle was never logistics

As I deeply reflect on every life decision I’ve ever made, if I’m completely honest, the obstacle isn’t logistics. It’s that I haven’t made the self-trusting decision to live the way I want.

If I had to name it precisely, it probably has to do with a mix of confidence, seeking approval, and wanting to feel accepted no matter where I went.

I look back and wonder: did I just focus on my career because it felt like I was being cheered on for it?

And I don’t know if I’m the same person who wanted it, and doing it now would mean admitting I built an entire decade around a version of success she never asked for.

A person or a possibility

The more I think about it, the more I’m not sure if I’m grieving a person or a possibility.

Would I be a different person if I’d chosen differently back then? Would my life look any different now?

A person you can picture ageing, changing, disappointing you in specific ways. A possibility just stays perfect, frozen at the exact age she was when I put her down.

Perhaps I’m not grieving the choices I made or didn’t make. Just that it didn’t happen then.

But why does it matter so much? Is it timing? What would have been the difference between living out what I wanted then, versus doing it now?

Is it because there’s a version of that life that was only available to a low-stakes twenty-year-old with nothing to lose and nothing built yet? She could have left with no ties to anything, no adult responsibilities, no reputation to protect. I can’t get that particular kind of freedom back, even if I book the same flight.

But I wonder if this is the wrong type of thinking. It feels as if I’m painting freedom as scarce.

Whose approval was I actually chasing?

It felt like a version of her was achieving things driven by what society deemed normal, or because they fit within the parameters of what would be considered ‘impressive’ enough to gain the approval of others.

If I picture a face attached to that pressure, it’s not one specific person. It feels more like a composite. The primary school teacher who awarded me the DUX and said, ‘you’re going to be a doctor.’

My favourite high school teachers who called me ‘bright and smart.’ Family who used the word ‘stable.’

A version of adulthood that got handed to me early and I never thought to question.

Underneath all this, I think there was another version of me that wanted something slower. Something with more room for myself in it. She got overridden so fast I’m not sure she ever got a name.

Studying science because she was good at it in high school and university. Trying careers in healthcare and medicine because it was a natural progression.

Pivoting into the web space only because it was her pastime outlet and the money was promising. Subscribing to tech hustle culture, where productivity and optimising were rewarded.

What a normal week actually cost

I remember sitting a science exam I’d studied weeks for, getting the mark I wanted, and feeling nothing. Not relief. Not pride. Just the quiet confirmation that I was good at doing things I didn’t actually want.

That became the pattern. A normal week during the hustle years looked like waking up before an alarm out of guilt, answering messages before I’d properly opened my eyes, measuring the day by how much I’d produced rather than how I felt inside it.

The technology world rewarded productivity above everything else and it cost me the ability to tell the difference between resting and failing.

The slow leak

Years later, after major burnout and observing everyone around me, I started to notice that this was not what I wanted anymore. Everything felt odd. The kind of odd we don’t talk about. That we worked so hard, night and day, to build a life we no longer want.

Odd looked like sitting at my desk on an ordinary Tuesday and not recognising the life around me. Constant wondering of, ‘what am I doing here? What do I really want?’

It wasn’t one single day. It was a slow leak I didn’t notice until the tank was already empty, until getting out of bed took the kind of effort that used to be reserved for hard things.

I look back and think it’s so strange. How we spent so many years, so many grueling hours, so much stress chasing everything on a checklist of things to achieve, only to realise I no longer want the life I built.

The stable paycheque that made my parents stop worrying.

The impressive title working in technology.

Running two small businesses on the side, as if it was something so glamorous.

The house.

A calendar so full it looked like proof of being important.

I remember the exact moment it cracked, sitting in my car in a parking lot before work, unable to make myself walk inside, thinking, I don’t want any of this, and being terrified because I’d spent a decade building toward it.

What’s burned down, and what hasn’t

I read a quote that stuck with me during a time when I was in a stagnant phase after burning out and years of misalignment with myself. In order to build the life that feels aligned, we must first burn down everything we know.

Day by day, I was on auto-pilot. I had a solid daily routine. Looking after my physical health was a representation of how much discipline I had.

While I was doing all the things:

• waking up at 6am

• going for my morning run

• having a solid breakfast

• gymming in the afternoon

• repeating that

I felt like I was a walking shell. As if my soul was no longer there and I was just doing it because I was programmed to.

The stagnant phase also looked like cancelled plans and unanswered messages. Putting a smile on my face and saying ‘I’m good’ each time I met people and caught up with family.

Days that blurred into each other because nothing in them needed me to be a particular version of myself. I wasn’t building. I wasn’t performing. I was just surviving each one, which at the time felt like failure and now looks a lot like the beginning of something.

That quote stayed with me for some time and is still present to this day.

Since then, the job title burned down. The idea that productivity equals worth burned down, mostly. What hasn’t burned down yet is the instinct to explain myself, to justify why I’m allowed to want something different now. I still catch myself doing it in conversations I haven’t even had yet.

With all my thoughts firing at once, I could sense it in my body. Or sense my previous self, grieving a version she wasn’t able to live.

How wild is that.

I felt it in my shoulders and my chest. It felt heavy, tight and hollow. Almost as if I’d turned into that walking shell. But this time, not walking. Just a curled-up shell.

The tightness in my chest wasn’t quite panic and wasn’t quite sadness. Somewhere in between, the way grief usually is. I was at my desk when it happened, mid-task, nothing dramatic going on around me at all, which is maybe what made it land harder. Grief doesn’t wait for a good moment. I felt homesick for a future I haven’t even lived yet.

And whilst I have my life goals to ground me, I’m feeling the grief of time, events, experiences and the ‘what ifs’ of the life I didn’t live.

It’s not like ordinary homesickness, which at least has an address. This has no place attached to it. Just a feeling of missing something I never had the chance to miss properly the first time. My current goals feel more mine than the old checklist ever did, or at least I hope they are, and not just a newer, quieter version of the same performance.

The ‘what if’ that visits most is the simplest one. What if I had gone when I was twenty, before I knew what staying would cost me?

Even though I could still live out those dreams now, moving my life to Japan, living in Copenhagen for a while, building my business overseas as a digital nomad, I still feel the grief of a life I didn’t get to live in my twenties.

Copenhagen isn’t an old dream. It’s a newer one, something that showed up after I started building this version of myself, proof maybe that the wanting never actually stopped.

It just changed shape.

Realistically, it would take very little. A decision. A date. The willingness to be a beginner again in a language and a city that owes me nothing.

Even though there’s always a chance today, the grief occupies my mind. It’s a feeling I’m unable to describe.

If I had to describe it without using a single emotion word, I’d say it feels like standing at a train platform after the train has already left, knowing another one will come, and still feeling the specific weight of having missed that one. Does that happen to you sometimes?

Even on a daily commute to work. You’re not really missing out on anything, but you missed that train, and it still lands as ‘damn, I missed it.’

I don’t know if it needs to loosen.

Maybe it’s allowed to just stay, quietly, alongside everything else I’m building.

-Katie

More from Multiple Lives Theory:

→ The multi-passionate person’s guide to answering “what do you do”: on describing a life that doesn’t fit one title

→ You don’t pivot. You add.: on why “starting over” was always the wrong frame

→ I’ve been five different people at work. None of them were wrong.: on the rooms, before I had the word for them

→ the clarity trap: on why “get clear” fails the people who want everything

Share

New here?

Multiple Lives Theory is a weekly essay on nonlinear careers, reinvention and the emotional reality of changing your life. Sundays and Thursdays.

Hi, I’m Katie! Welcome to The Multiple Lives Theory. This is a space for anyone rewriting the rules of modern work, embracing a nonlinear career, and actively designing a life of creative freedom outside the standard 9-5 ladder.

Subscribe now

You don’t owe anyone the story arc.

A few weeks ago, I caught myself doing something that I thought I would no longer do.

I was at a meetup, talking to someone I’d known for only maybe four minutes.

He asked me what I did for work. Instead of answering the question, I heard myself hesitate and say, “Oh well, it’s a bit of a long story...”

Then I launched into this whole, unnecessary explanation.

The chemistry degree. The career pivot. Why I ended up writing. The reasons behind it all.

He’d asked for a simple job title, probably with no other intention to it other than small talk. Instead, I gave him my origin story.

The funny part is... he never questioned any of it. I didn’t know him. I’ll probably never see him again. Whatever he thought of my answer had absolutely no impact on my life.

And yet I still reached for the version that made my career make sense before anyone had asked me to make it make sense.

I walked away thinking: Why do I keep doing that? Why do I always feel the need to justify and explain myself for even a stranger that will probably have no significant impact on my life?

The audit

After that moment, I immediately took it to my journal and decided to try something. For one week, I paid attention to every time I explained my career to someone. Not the facts. The extra bits. The little disclaimers that crept in before or after the actual answer.

Things like:

“It’s a bit of a long story.”

“I know it sounds random...”

“I’m still figuring it out.”

I didn’t do anything fancy to keep track. I just kept a tally in my OneNote app whenever I caught one. And a few days in, something shifted.

Once I’d started noticing them, I couldn’t stop hearing them. And that’s the point of the exercise. I realised I am not trying to become someone who never over-explains, but trying to catch myself while you’re doing it.

An explanation isn’t the same as an answer

A few days into doing this, I realised I actually had two different ways of answering the exact same question. One sounded like this:

“It’s a bit of an unconventional path. I studied chemistry, then moved into design, and now I write. It probably sounds all over the place...”

The other sounded like this:

“I run a writing business.”

Neither one is more true than the other.

The difference is that one is trying to earn the listener’s understanding. The other is simply answering the question.

I started noticing this everywhere. When I was explaining, I was waiting for the other person to look convinced before I could move on. When I was just answering, the conversation carried on naturally. Sometimes they’d ask another question. Sometimes they wouldn’t.

Either way, I didn’t feel like I’d handed them my life story to evaluate. I think that’s the shift I’m trying to make. Not from honesty to vagueness but from explanation to confidence.

If someone wants to know more, they’ll ask. And if they don’t, they already have enough.

Why we do it

I don’t actually know where this habit comes from. I just know a lot of us seem to experience it and relate.

Maybe it’s because we’ve been taught that careers are supposed to make sense on paper. That there’s a “normal” path, and anything outside of it needs an explanation. So before anyone else has the chance to question it, we do the work for them.

It took me so long to realise this.

The strange thing is, over-explaining doesn’t make us sound more credible. It usually does the opposite. It sounds like we’re trying to convince someone of something they weren’t doubting in the first place.

When I tried to work out where I learned this, I couldn’t land on one answer. Maybe it was years of filling out forms with a single box labelled Occupation. Maybe it was school, where the tidy story always got rewarded. Maybe it was a manager who looked at my CV years ago and asked, “So... what’s the story here?” in a way that made me feel like I owed one. Or maybe it’s sharing with close friends and family and feeling afraid of what they will think.

Nobody sits you down and teaches you to apologise for a career that doesn’t fit neatly into a timeline. You just pick it up somewhere along the way. And once you’ve been doing it long enough, you stop hearing it.

What my own audit found

Before writing this, I tried the exercise on myself for a week. I caught eleven justifying clauses in seven days.

Nine of them were completely unprompted. Nobody looked confused. Nobody challenged me. Nobody even asked a follow-up question. I was answering objections that only existed in my own head, while the other person was probably just waiting for me to finish so we could get back to talking about literally anything else.

The last one was the interesting one. I heard myself start to say, “I know it probably sounds...”

And I stopped. The sentence ended there. Nothing happened.

He nodded, asked what kind of writing I did, and the conversation carried on. That ended up being the whole lesson for me. Most of the judgement I spend time anticipating never actually arrives.

The scripts

So here's what I've started replacing those justifying clauses with.

1. The gap year.

“I took a year out in 2023.” That’s it. Not, “I took a year out because I was burnt out and needed the break.”

The reason is yours. The fact is enough.

2. The industry change.

“I moved from research into design.” I don’t need to follow it with, “I know it sounds like a big leap...”

People usually make the connection themselves. And when they do, it feels like curiosity instead of me trying to convince them.

3. The plural answer.

“I design and I write.”

No need for extra, unnecessary disclaimer about being scattered. No apology for having more than one answer.

4. The still-figuring-it-out.

“I’m building the next thing at the moment.”

That’s true and it’s also enough.

5. The one for family.

“It’s going well.”

Short but simple. I’ve found this one surprisingly useful. Some conversations are looking for connection. Others are looking for an update. I’ve come to terms with it’s okay not to turn every family catch-up into a quarterly business review.

But what if someone actually wants the explanation?

This was the first objection my own brain came up with.

“Sure... but what about interviews?”

Or a client who’s genuinely trying to understand your background. That’s understandably different. The point isn’t to become vague. It’s to stop apologising.

If someone asks about a career gap, I can say:

“I took a year out in 2023 and I missed the work, so I came back.”

Simple and to the point.

I’ve found it’s less about what you say and more about when you say it. Answer the question that was asked.

If they want more, they’ll ask.

You don’t have to answer the follow-up before it exists.

One thing I’ve noticed is that the silence isn’t nearly as uncomfortable as I imagine it’ll be. Half the time, there isn’t another question.

The conversation just... carries on.

The part I’m still practising

I’d love to tell you I’ve stopped doing this but while I am still learning all this, I haven’t.

Last week I caught myself halfway through saying, “I know it probably seems...”

I was on a call with someone I wanted to subconsciously was trying to impress. I heard the words come out of my mouth and immediately thought, there it is again.

The funny thing is, that sentence wasn’t helping either of us. It wasn’t making me sound more trustworthy or making my work clearer.

It was just an old habit showing up. I don’t think this audit fixes that overnight.

What it does do is make the habit visible. And once you can hear yourself doing it, you get the chance to choose differently.

Not every time. But more often than before.

For me, that’s enough.

— Katie

What’s the one line about your career you always over-explain, and what would the full-stop version sound like? Reply with both. I’m collecting the all the honest before-and-afters.

More from Multiple Lives Theory:

→ Your CV is lying about you (it’s designed to): on the format that hides the person

→ The multi-passionate person’s guide to answering “what do you do”: on describing a life that doesn’t fit one title

→ how to explain a nonlinear career without apologizing for it: the earlier version of this argument

→ You don’t pivot. You add.: on why the history never needed defending

Subscribe now

New here?

Multiple Lives Theory is a weekly essay on nonlinear careers, reinvention and the emotional reality of changing your life. Free essays, Sundays and Thursdays.

Hi, I’m Katie! Welcome to The Multiple Lives Theory. This is a space for anyone rewriting the rules of modern work, embracing a nonlinear career, and actively designing a life of creative freedom outside the standard 9-5 ladder.

Subscribe now

You know that feeling when a quiet week reads like a verdict?

Nothing went wrong, exactly. You did the work. You showed up. But there is nothing to point at. No result, no visible movement, no proof. And by Sunday night a small voice has decided the quiet means something. Stalling. Slipping. Falling behind people you have never even met.

I want to name what is actually happening in that moment, because it is not failure.

It is a category error.

The destination tone

Somewhere along the way, we started expecting every chapter of a life to carry the tone of the destination.

Steady, if you have supposedly arrived. Triumphant, if you have just leapt.

So when a season shows up that is simply quiet, or slow, or unglamorous and in-between, it does not register as a season. It registers as evidence against you.

Most of the anxiety in a transition is not the transition. It is misnaming the season you are in, and then defaulting to the most alarming interpretation available. A quiet season reads as stalling. A slow one reads as failure. A season with no visible proof yet reads as proof of the opposite.

I didn’t have language for this until I built a rough map for myself: four seasons instead of a straight line.

The Season Map

I made this ‘Season Map’ during a year when almost everything in my life was moving at once: work, home, who I thought I was becoming.

I needed something steadier than my own mood to check in against.

Not stages, not a ladder.

Four seasons you move through, out of, and back into, sometimes twice in the same month. Here’s what each one actually asks of you:

• Building. Nothing visible yet. You are laying structure that will not show results for a while. The correct metric is not outcome. It is whether the structure is actually going in.

• Proving. Early signal exists. Small, unglamorous, real. The job is to gather more of it, not to have already arrived. This is the most fragile-feeling season, because the proof is real but still small enough to doubt.

Read more

Upgrade to paid

There is a line on every form that has ever tried to describe me, and it is one line long.

Occupation.

Then a blank, ruled the width of a single word. I have sat in waiting rooms and airport queues and bank offices with a pen over that line, running a quick calculation about which version of myself this particular stranger would find easiest to believe. One word. Not a paragraph. Not a list. The form has already decided that a person is something you can say in one word, and if you can’t, the problem is you.

For years I treated that hesitation as a personal failing. Other people had a word. I had three different answers depending on who was asking, and a practiced shame about all of them.

I don’t think it’s a failing anymore. I think the form is wrong.

This is the first piece I’ve ever put behind a wall, and I want it to be the one that says the actual thing, not another essay that makes you feel seen and then leaves you where it found you. This is the theory I needed at the start of my working life, when I was quietly concluding there was something wrong with me for wanting more than one.

Nobody said it to me then. So I’m saying it to you now.

The question that never stops

Start with the question we ask children. What do you want to be when you grow up.

Not what do you want to do, or make, or try. Be singular. Permanent. A noun you become and then remain.

The kid who says “astronaut and a vet and someone who draws” is gently corrected, not celebrated. Pick one, sweetheart.

We never stop being asked. The question just puts on a suit. It becomes what do you do, and then where do you see yourself in five years, and then so what’s your thing; and, if you’ve lived more than one working life, but what do you actually do though, with the little emphasis that means no, really, in one word, so I can file you.

Underneath every version of the question is one inherited belief, and I’ve started calling it the one-life assumption: the idea that a well-lived life is one thread. One calling, discovered early. One career, climbed steadily. One coherent self, the same at the end as at the beginning. Everything that doesn’t fit the thread gets a demoting name. A hobby. A phase. A distraction. A pivot, if people are being generous. A crisis, if they’re not.

I subscribed to it for years. I thought the people with one word had simply done the finding earlier than me, and the honourable thing was to keep auditioning selves until one of them turned out to be the real one and the rest could be politely retired.

Nobody told me the assumption itself might be the broken part.

The lives I actually lived

Here is my count, done honestly.

There was a version of me in a lab coat who measured things for a living and assumed she’d wear that coat until retirement.

There was the version who taught herself to build websites on her bed with a laptop after dinner, squinting at code she had no qualifications for and feeling more awake than she had all day.

There was the version with the health tech job title, fluent in a language she would have found unreadable five years earlier.

There was the version running online shops at night while holding the day job, packing orders on the living room floor at midnight, not because anyone made her, but because some part of her needed a thing that was entirely hers.

And there is this version, the one writing to you.

Every time I moved between them, someone reached for the small vocabulary. A phase. A pivot. Brave, said with a wince.

At my first startup job, I was the platform support specialist, new enough to still be thrilled by the lanyard, when the company sponsored me to attend the annual industry conference.

Afterwards the team went for drinks, and at some point the VP put a question around the circle: what would you want to do if you didn’t work here?

I was young, and I took the question at face value. “A travel writer!” I said too quickly, with too much light in my voice.

He didn’t miss. “Oh, so you want to sell fruit at an empty fruit market?”

The circle laughed. I didn’t understand the joke then, and I’m still not sure there was one, beyond a senior man reaching for the room’s laughter at the expense of its newest person. But I laughed too. I smiled, said “yeah, why not,” and shrugged it off like it was nothing.

That’s the part I still think about. Not his sentence but my appeasement. Underneath it was a truth I couldn’t yet name: I didn’t need to invent the other lives. They were already there. I had simply learned to apologise whenever one of them got noticed.

Because here is what those years actually were: they were not detours from some real career I kept failing to have. Each one was a life. Fully lived while I was in it. Real skills, real people, a real version of me who woke up and cared. I wasn’t failing to pick.

I was living several lives and calling it failure, because nobody had handed me any other word for it.

What the theory says

So here it is, plainly.

You are not one life that keeps getting interrupted.

Almost everything downstream of this comes from one distinction: the difference between a detour and a life.

A detour is measured by what it cost the main plot. A life is measured by what it built. A detour has to justify itself in every job interview.

A life doesn’t owe the interview anything. A detour ends and is written off as wasted time.

A life ends and keeps holding you up: the skills, the people, the nerve you grew in it don’t leave when the job title does.

The one-life assumption files everything you did off the main thread as a detour.

Multiple Lives Theory files it as a life. That one change of filing is the whole theory.

And it changes something deeper than language. It changes what you believe your years were for.

The job that fit like someone else’s suit

None of this would matter if the one-word world merely disapproved. But it doesn’t just disapprove. It caps you.

I once sat in a performance review where the extra things I could do were raised, gently, professionally, as a concern. Focus was the note. And the review wasn’t wrong by its own maths. The role had a shape, and I kept growing out of the shape, and there is no box on that form for grows out of shapes. I’d leave those conversations and sit in the car park doing a different kind of maths. Stay one word here. Or be several somewhere else, and pay for it.

If you’re the multi-hyphenate in the building, you already know this tax.

You’re too much for every box and somehow not enough for any of them. You’re the person they call when the problem doesn’t fit a department, and the person they overlook when the title gets handed out, because nobody knows what to call you. You’ve stood in your kitchen at 11pm googling whether it’s too late to change everything, with three real talents and no single word, slowly concluding that this is a deficiency rather than a design.

That conclusion is the one-life assumption doing its quiet work. It doesn’t fail you with a crash. It fails you with a low, persistent sense that you left parts of yourself unlived, and called it maturity.

I know, because for a stretch in my late twenties, I tried very hard to become one word. I wanted to fit myself neatly into a version of success that would be accepted by others, celebrated by others, and, maybe most importantly, prove that I had made something of myself.

I picked the one word that seemed to make the most sense and started editing out everything that didn’t fit around it.

Looking back, I’m not entirely sure why I did it. Maybe that was the Katie who wanted so badly to be seen and thought becoming one thing would finally make her visible. Sounds ridiculous…but I see it so differently now. I thought I was finding clarity. But really, I was just getting better at making myself smaller.

Start Your Multiple Lives Snapshot:

If this theory lands, take ten minutes and answer these honestly.

1. What are the lives you have already lived?

2. Which one did you call the “real” one, and which ones did you call distractions?

3. What stayed the same across all of them?

4. What did each life teach you that you would not have learned anywhere else?

5. What do people keep coming to you for, regardless of your job title?

6. What part of yourself have you been apologising for?

7. Every room of your working life opens onto one hallway. What verb is yours?

8. Which life in you is asking to be taken seriously now?

You do not need a perfect answer. You only need a truer one than the one-word version.

If you want a sharper version, try this:

• I have been calling ___ a distraction, but it was actually a life.

• The pattern I can now see is ____.

• The thing I keep doing across every version of myself is ___.

• The next life I am ready to live is ___.

That is enough to begin.

The thread underneath it all

Now the obvious objection, the one hiding inside the fruit-market joke. If you’re several lives, aren’t you just scattered? Isn’t multiple a nice word for unfinished?

It would be, if the lives had nothing in common. But they do, and it took me years to see it.

Underneath every life I’ve lived there is one thing I have never stopped doing, no matter what the job title said.

I call it the hallway, the thing that runs through every room: not what you do, but what you’re always doing.

Mine is translating.

In every life I have experienced so far — the lab, web, digital, health tech, e-commerce, design, writing — I have been the person who stands between a complicated thing and the human being trying to use it, and makes the passage easier.

I did it for data. I did it for software. I did it for customers at midnight. I’m doing it right now, for you, with your own life.

On paper, my working lives look unrelated: a CV that swears its own chapters never met. Underneath, they are the same person doing the same thing in new territory. Every one of my supposed reinventions was just the hallway reaching one more room.

You have one too. It’s usually a verb, not a noun. A way of paying attention. A problem you can’t stop solving regardless of what you’re officially paid to do. When you find it, multiplicity stops looking like a mess. It starts looking like evidence.

Five things I believe now

Not steps. There’s no order and nothing to complete. Just the beliefs this theory has left me with.

1. You’ll move before you can explain why. The impulse to change arrives long before the reason does. You’re allowed to follow it and let the explanation assemble itself later.

2. Leaving something doesn’t erase it. You’re permitted to stop doing a thing without pretending it never mattered.

3. The quiet parts of you are still yours. Some lives you’ll only visit in certain seasons, or with certain people. Their worth isn’t measured in hours logged.

4. When you feel scattered, look for the hallway, not another room. Coherence was never going to be a job title.

5. You’ll have to explain yourself to one-word people, and you should do it gently. You don’t need them to agree with yours. You just need to stop asking their measuring tape whether your life is long enough in a direction it was never trying to go.

The Door

Here’s what you’re actually getting. The reasoning before it’s been tidied for the caption. The numbers I’m willing to put on the record. The frameworks worked all the way through on my own life first, so you have something to run on yours, not just admire.

Not more to read. Somewhere to actually do the becoming, in progress, alongside people doing the same thing.

Why does Multiple Lives Theory need to exist?

Because the one-life assumption is still the water almost everyone is swimming in, and it is still quietly convincing good people that the most interesting thing about them, the number of lives they’ve lived, is a flaw to correct before someone notices.

Somebody has to say, out loud and on the record: keep them. All of them.

The straight line was never the achievement. The achievement is a lifetime with enough lives in it that you never run out of ways to become.

I still hesitate over that one-word line on the forms. I probably always will in some way or another…but the hesitation doesn’t feel like a stammer anymore.

Nowadays, it’s the sound of several lives, refusing to answer to one word.

— Katie

Which life of yours have you been calling a distraction, and what would change if you started calling it a life?

✍️ New here?

Multiple Lives Theory is for anyone who's outgrown a version of a life they worked hard to build. Weekly essays on reinvention, the in-between and the many selves one lifetime can hold, written from inside the transition, not the other side.

Share The Multiple Lives Theory

Hi, I’m Katie! Welcome to The Multiple Lives Theory. This is a space for anyone rewriting the rules of modern work, embracing a nonlinear career, and actively designing a life of creative freedom outside the standard 9-5 ladder.

Subscribe now

“Where do you see yourself in five years?”

I used to have an answer for this.

I don’t anymore, and for a long time I thought that was the problem. It wasn’t. The question was.

I was in an interview about eighteen months ago for a role I genuinely wanted. The interviewer asked it kindly, almost casually, the way people do when they expect the usual answer.

And I felt a very specific kind of blankness. Not because I didn’t know the answer. Because the answer I used to give no longer existed.

I gave a version of an answer. It wasn’t a lie…but it also wasn’t true.

The plan everyone was handed

Somewhere back in a career-guidance session or a first performance review, most of us were handed the same IDP tool: pick a fixed point five years out, then work backwards to today. Title, salary band, maybe a city and professional development goals in between. It’s a clean piece of engineering, a destination and a route. For a long stretch of the twentieth century it also matched how careers actually worked: one ladder, one industry, promotions on a predictable clock. The tool fit the terrain.

The terrain that changed under it

The terrain doesn’t look like that anymore, for almost anyone I know. Roles get created and dissolved inside eighteen months. Whole job categories didn’t exist five years ago and won’t exist, in their current form, five years from now.

I’ve had four distinct working identities in the time it would’ve taken to walk one five-year plan to completion, and not one of them was visible from where I started. The fixed point stopped being reachable, not because I failed to hit it, but because the ground itself kept moving underneath the mark.

The plan vs the range

Here’s the distinction I’ve landed on, and it’s the only version of the question I can answer honestly anymore. The plan is a single fixed point, named once, that you hold yourself accountable to hitting. The range is a direction — a rough bearing you keep checking and re-setting, usually on a much shorter cycle than five years.

A plan says: this exact spot, by this exact date. A range says: broadly this way, and I’ll tell you more precisely in six months once I can actually see further.

One is a promise. The other is a practice.

Think about how you’d navigate somewhere you’d never been. You used to buy the paper map before you left, trace the whole route, and commit to it — wrong turn or not, you were locked in until you pulled over and started again from scratch. Now you type in a destination and the thing recalculates every time you miss a turn, using information you couldn’t have had when you started. Nobody thinks the GPS has failed because it revised the route. We’d think it had failed if it hadn’t.

Why the question survives anyway

The five-year-plan question is still everywhere — job interviews, family dinners, the awkward pause at a reunion — because it’s easy to ask and it produces a tidy answer, whether or not the tidy answer is real. The range is a genuinely harder thing to say out loud to someone who wants a title and a number. It requires the asker to sit with more uncertainty than the question was built to hold. So we keep asking the old question and getting old-shaped answers back, and nobody updates the form, because updating it would mean admitting the terrain moved.

I’ve stopped trying to answer the fixed-point version, and started tracking a shorter, truer one instead:

• What are you paying attention to right now, not what will you have accomplished. Attention is the leading indicator. Achievement is the lagging one, and it lags by years.

• What did the last six months actually teach you about the direction, not the last five years’ plan. The range updates on a six-month clock. Five years is too slow an interval to be useful information.

• Where did you correct course without noticing you had. The corrections are usually more honest than the original plan ever was.

• What would you say no to now that you’d have said yes to two years ago. That’s the bearing shifting, in real time, more reliably than any stated goal.

• What’s the thing you’re moving toward without being able to name the destination yet. You don’t need the name. You need the direction to be true.

The honest version

I still don’t have an answer to where I’ll be in five years, and I’ve stopped treating that as a gap in my planning. What I have is a direction I trust more than I trust any fixed point I could name today, built from six-month corrections and not a single decision made once and defended for half a decade.

I don’t know if that’s a better answer. I know it’s the true one, and for now, that’s the only version I’m willing to give.

— Katie

I’m curious, what's the question people keep asking that no longer fits the life you're living?

Share the multiple lives theory

More from Multiple Lives Theory:

→ The reinvention story we’re not telling — on why moving comes before clarity

→ You’ve been measuring yourself on the wrong clock — on trading someone else’s timeline for

New here?

Multiple Lives Theory is a weekly essay on nonlinear careers, reinvention and the emotional reality of changing your life.

“So — how’s the business going?” And there’s a full second where I have to decide which answer I’m giving: the true one, the safe one, or the one that will let us get back to the roasted beans.

The question that sounds like data

On paper it’s an information request. Revenue, clients, trajectory — a business update, the kind you’d give a shareholder. That’s the shape of the sentence. But I’ve sat across enough of these dinners now to know the shape of the sentence and the shape of the actual question are two different things, and mixing them up is where the trouble starts.

What they’re actually asking

Nobody at that table wants a P&L. What they’re actually asking, underneath the business language, is: are you okay? Should we be worried about you? Did the thing you did — the leaving, the risk, the thing that made your mother go quiet for a week — did it work in the simplest, safest, most reassuring sense of the word “work?”

Information wants numbers. Reassurance wants a feeling. They ask for the first and need the second, and the mismatch is why almost every answer you give feels wrong even when it’s accurate.

Why the true answer never lands

I tried the honest version for about a year. Full picture — the good quarter, the client who ghosted, the number that’s climbing but slower than I’d like. Delivered as neutral fact, the way I’d want it delivered to me. It landed badly every time, not because the facts were bad but because a nuanced true answer doesn’t produce a feeling fast enough. By the time I got to the reassuring part, the table had already filed it under “not going well” and moved to concerned faces. The truth was too slow for the question actually being asked.

The doctor’s-office version

A friend who’s a GP told me something that reframed this for me completely: patients almost never want the full clinical picture when you ask “how are you feeling” — they want to know if they should be scared. She said the real skill of the question isn’t gathering symptoms, it’s reading which kind of answer the person in front of you actually needs first: the data, or the “you’re going to be fine.” Get the order wrong and it doesn’t matter how accurate you were.

How I actually answer now

I’ve started giving the reassurance first, deliberately, before anything else. “It’s going well — slower than I’d like some months, but well.” True, and it does the actual job the question was asking, which was never really about the spreadsheet.

Reading the table before you answer, once you notice it:

• You start translating before you’ve even swallowed. The mouth is still full and the sentence is already being rewritten for the room.

• You give the version with a shape, not the version with the truth. Shape first. Truth, if there’s room after.

• You notice who’s listening for content and who’s listening for tone. It’s rarely the same person twice, and it’s almost never who you’d guess.

• You resent the question more than the person asking it. They usually mean it kindly. The resentment is really about the mismatch, not them.

• You’ve started answering the reassurance instead of the number. Once you notice this, you can’t fully unnotice it — every “how’s it going” becomes two questions instead of one.

What I still haven’t solved

I still don’t know what to do the year the honest answer and the reassuring answer point in genuinely different directions — when it isn’t going well and there’s no shape I can give it that isn’t also a small lie. I’ve been lucky enough that this hasn’t come up yet. I think about the dinner where it will, and I don’t have a script ready for that one.

— Katie

What’s the worst version of this question you’ve ever been asked, and what did you actually say back? Reply and tell me. I’m reading the answers people gave versus the ones they wanted to give.

Share

More from Multiple Lives Theory:

→ What happens to your identity when you remove the job title — on who you are underneath the shorthand

→ The multi-passionate person’s guide to answering “what do you do” — on describing a life that doesn’t fit one title

New here?

Multiple Lives Theory is a weekly essay on nonlinear careers, reinvention and the emotional reality of changing your life. Sundays and Thursdays.

Subscribe now

Hi, I’m Katie! Welcome to The Multiple Lives Theory. This is a space for anyone rewriting the rules of modern work, embracing a nonlinear career, and actively designing a life of creative freedom outside the standard 9-5 ladder.

Subscribe now

The maths that stops you was never actually calculated

There’s a kind of maths that runs in the background of every career-change conversation, and it almost never gets written down.

It goes: I’m thirty-one. If I start something now, I won’t have real traction for two years. The people already doing this have a ten-year head start. By the time I have what they have, I’ll be forty-five.

I know this maths intimately, because I ran it, in various configurations, for about three years before I stopped. It was always available when I needed a reason to wait.

The calculation that runs in the background

What I never did, for an embarrassingly long time, was check it. I treated it as a fact about the world rather than a sum I could actually sit down and do. It hummed away, generating reasons to wait until the conditions were better, until I was more prepared, until the risk felt smaller and it never once resolved, because I never once wrote it down.

Anxiety maths vs actual maths

Anxiety maths is felt, not computed. It runs in the background, uses no real numbers, and exists mainly to justify waiting. Actual maths is written down. It uses your real figures, includes the cost of staying, and uncomfortably tends to produce a different answer.

When I finally ran the actual version, I found the anxiety calculation had three structural errors in it. Not emotional errors.

The maths was simply wrong.

Where the anxiety maths goes wrong

• The compound-interest assumption. Anxiety maths measures the gap between where you are and where someone established is now, then projects how long to “catch up.” But catching up assumes the same trajectory. The person ten years ahead is optimising within a lane; you’re still in the steep part of your own curve, where everything you learn changes how you learn. The gap is real. The projection is wrong.

• The opportunity-cost miscalculation. Anxiety maths adds up what you’d give up, salary, stability, status — but almost never subtracts what staying costs: the skill atrophy, the network you’re not building, the options quietly closing while you wait. Staying has a price too. The sum should include it.

• The “is it too late” binary. This frames the question as yes-or-no, and conceals a premise — that there’s a correct time you may have missed. But almost nothing worth doing has a correct time. It has a range. And within that range, earlier beats later, so the honest answer to “is it too late” is almost always: later than if you’d started when you first thought about it, and earlier than if you wait.

• What I actually did (the numbers)
  I’m sharing these because most people don’t, and the opacity feeds the anxiety. I had roughly seven months of living expenses saved. I had two small clients I’d been working with part-time for about four months, generating around a third of my old salary. I had a plan to reach full income replacement in twelve months, and I was wrong about the timeline altogether. It took about fifteen in total.

The gap was uncomfortable and manageable. The numbers weren’t special. They weren’t a set of circumstances that made the decision obviously sensible. They were enough (barely) to make it survivable. And survivable, it turns out, is the relevant threshold. Not safe. Not certain. Just survivable.

Share

Why nobody writes it down

Writing the maths down makes it real in both directions. It makes the risk real. The exact number of months you could last, the exact income you need to hit. But it also makes the survivability real, and the survivability, looked at with actual numbers rather than anxiety, is usually far less catastrophic than the background hum suggests.

How to run the actual maths

1. Write the number down. A vague calculation can’t resolve. A written one can.

2. Include what staying costs. Not just the salary you’d keep but the options you’d lose.

3. Find the floor: survivable, not safe. You’re not solving for certainty. You’re solving for “can I get through the gap.”

4. Treat “too late” as a premise, not a fact. Ask what correct-time it’s secretly assuming, then check whether that time exists.

5. Decide on the real number, not the feeling. They’re almost always different.

What surprised me

When I finally ran my own numbers, the thing that surprised me was how much energy I’d been spending just maintaining the anxiety version.
The vague, unexamined calculation takes constant work. It hums and never settles. Writing it down made it less consuming, even when the answer was harder than I’d hoped. A real number, however uncomfortable, has an edge.

And you can work with an edge.

— Katie

What calculation have you been running in your head that you’ve never actually written down? Reply and tell me, or if you’ve done the maths, I want to hear what it said.

Subscribe now

More from Multiple Lives Theory:

→ the reinvention story we’re not telling — on why moving comes before clarity

→ the relief you’re not allowed to feel when the job ends — on the honest feeling underneath the leap

New here?

Multiple Lives Theory is a weekly essay on nonlinear careers, reinvention and the emotional reality of changing your life. Sundays and Thursdays.

Subscribe now