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.
