I left a job I liked. Not a dramatic exit, no burnout story, nothing to expose. Good team, fair pay, work I was decent at. I still think it was the right decision, and it took me the better part of a year to make, so these are the notes I wish somebody had handed me at the start of that year.
Comfortable is a real thing to give up
Advice about changing jobs is mostly written for people who are miserable, which makes it useless when you are not. Leaving something good has a different cost: you are trading a known quantity for a described one, and the description is written by people who are trying to hire you.
Take that seriously rather than talking yourself out of it. Being clear about what you are giving up is what stops you romanticising the next thing.
The signal that mattered
What eventually decided it was not the work, it was the shape of my learning. Two years in, my hardest problems were social: convincing, coordinating, waiting. Useful skills, and I was glad to get better at them. But I had stopped being confused by anything technical, and being confused is how I know I am somewhere I can still grow.
That is a personal measure, not a universal one. Plenty of people are happiest exactly where the technical confusion ends. Worth knowing which person you are before borrowing my reasoning.
What I checked before deciding
- Whether the thing I wanted was actually elsewhere, or just elsewhere in the same building. I asked internally first. The answer was honest, and it was no.
- What specifically I would be learning in the first six months of the new thing, in the words of somebody already doing it.
- How long I could go without income if the new thing ended badly, calculated properly rather than felt.
- Whether I was moving toward something or away from one particular person. Away rarely survives the first hard month.
The month before is the worst part
Between deciding and telling anybody there is a stretch that feels dishonest. You sit in meetings planning work you will not be there for. My only useful advice is to make it short. Once you have decided, the kind thing for everybody is to say so and hand over properly.
Leave the work better than it was the day you announced. Write the document nobody asked for. It costs a week, and it is most of what people remember about you.
Nobody remembers your best quarter. They remember what the last two weeks were like.
Six months later
The parts I expected to miss, I did not. The part I did miss was small and specific: knowing, without checking, who to ask. That takes a year to rebuild anywhere, and it is the real cost of moving. Not money, not title, not the work itself. Context.
Still worth it. But that is the number to put in the calculation.
Written by
Ari Bennett
Software engineer and writer
I build web software for a living and write about the parts that are hard to search for: the trade-offs, the dead ends, and the small habits that make a codebase pleasant to come back to a year later. A decade in, I still keep a paper notebook next to the keyboard.
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