Why I went back to a tech job after trying to leave twice

There's a version of this story that ends with me successfully outside tech — doing something meaningful and fulfilling, having finally figured out what I actually wanted. I thought that was the story I was writing, both times.

It turned out I was writing a different one. I left tech twice, and both times I came back. And the thing I want to say — clearly, not as a consolation or a caveat — is that coming back was not the failure I spent a long time treating it as.

The first time I left

I left the first time after six years as a software engineer, the last two of them at a company that had gradually made me miserable in ways I couldn't resolve from inside. I'd been thinking about leaving for three years before I did it. By the time I actually handed in my notice, I had a plan: take three months, work out what I actually wanted, move into something different. The plan was vague in the way that most plans are at the thinking-about-it stage, before the reality of it arrives.

The three months became five. The clarity I'd expected to find in the space of not working arrived in fragments rather than as a complete picture. I did some freelance work — three small engagements at rates I later understood to be too low — and started a project that interested me without knowing what it was building toward. The savings were there. The runway was intact. And yet I couldn't quite land on what came next.

What I landed on, in month seven, was a job offer from a company I'd been connected to through a former colleague. Not a different career. Not the meaningful alternative I'd been searching for. A senior engineering role at a growth-stage company with better compensation than I'd left, more interesting problems than I'd had in a while, and a team that sounded, genuinely, like people I'd enjoy working with.

I took it. And then spent approximately six months feeling like I'd failed at leaving.

What that return taught me — eventually

The feelings of failure faded slowly and unevenly. They weren't completely gone by the end of the first year back. What replaced them, gradually, was a clearer understanding of what I'd actually learned in the gap — and why "going back to tech" wasn't the same as "going back to the situation I'd left."

The company was different. The work was more interesting. But the substantive change wasn't really in the role. It was in what I brought to it. I'd spent seven months outside the structure of employment, working out how to manage my time without external scaffolding, developing a clearer sense of what I needed from work and what I was prepared to accept. I also, less comfortably, had learned some things about myself that I hadn't been honest about before: that I liked the intellectual texture of engineering more than I'd admitted while I was resenting everything attached to it. That some of what had made me miserable was fixable by changing jobs rather than changing careers. That I'd been conflating "I don't want to do this specific job, at this specific company, in these specific conditions" with "I don't want to be in tech" — a conflation that felt true and wasn't quite accurate.

I stayed at the new company for two years. I set limits I hadn't set before and they mostly held. I was, in measurable ways, less miserable than I'd been before I left. I was also — and this took longer to admit — not doing the thing I'd left to find.

The second time I left

The second departure was quieter than the first. Less charged with urgency and narrative — I wasn't fleeing anything, and I wasn't chasing a clear vision either. I'd reached a point at the new company where I knew I'd taken from the role what there was to take, and where the inertia of continuing had started to feel less like stability and more like postponement.

I left for a different reason than the first time. The first time, I was trying to escape something. The second time, I was trying something specific: a six-month engagement with a small company building tools in a domain I was genuinely interested in, with a founder I'd known for years and trusted. Not a startup-at-all-costs situation. A deliberate experiment with a defined timeframe and a clear enough hypothesis to evaluate at the end.

What happened over those six months is a story of its own. The short version: the work was genuinely interesting. The company was earlier and smaller than matched what I needed from a working environment. The founder and I worked well together and both concluded, by month five, that my skills were better suited to a later stage than where they were building. I left on good terms, with a clear read on what the experiment had answered and what it hadn't.

And then I went back to a tech job. For the second time.

The second return — and what was different about it

The difference between the first return and the second was in how I felt about it. The first return arrived with a prolonged background guilt — the sense of having not quite managed the transition I was supposed to make, of having chosen the path of least resistance when something braver had been available. The second return arrived with something more like relief, and then — once I settled into the role — something that felt genuinely like choice.

I had left twice. I had tried two different versions of what "outside tech" might look like for me. What I concluded, after both experiments, was not that I'd failed to find the exit — it was that I'd been looking for an exit from the wrong thing. I'd been trying to leave tech when what I actually needed to leave was a particular relationship to the work: the always-on availability, the environments that rewarded total absorption, the sense that my value was determined entirely by output rate. Those were things I needed to change. The field itself wasn't the problem.

That distinction looks obvious written down. What I can tell you is that it took two genuine attempts to understand it clearly, and that the attempts were necessary. Not because I couldn't have reasoned my way to the conclusion in the abstract, but because living through the attempts gave me something that reasoning alone doesn't produce: I no longer wonder if I'm in the wrong place because I haven't tried hard enough to leave. I've tried. I know what's out there for me at this point in my life. I chose to come back. That's a different relationship to the same job title — and the difference is real, even if it's not visible from the outside.

Who this is for — and who it isn't

I want to be careful not to turn this into an argument for staying in tech when it's genuinely damaging you. If the conditions are structurally toxic — if you're burnt out in ways that haven't improved across multiple roles, if the environment is affecting your health in sustained and documented ways, if you've looked carefully and there's no version of tech work that doesn't reproduce the same problems — then returning is not what I'm describing. Those are real situations and they warrant a real exit.

What I'm describing is something more specific: the experience of discovering, through the process of trying to leave, that your relationship to the work is more complicated than "I want out." That there are things about the work itself you value — the problem-solving, the building, the collaboration with smart people on hard things — and things about specific environments you don't. And that "stay" and "leave" don't fully capture the actual question, which is more nuanced than either binary suggests.

Some people leave tech and build exactly the life they were looking for, and that's the right outcome for them. Some people leave, find something essential about themselves in the process, and choose to return with a different relationship to the work and clearer conditions for what they will and won't accept. Both are legitimate. Both can be the right conclusion from the same starting point of knowing that something needed to change.

The fact that you tried to leave and didn't permanently land somewhere else isn't a verdict on your willingness or your imagination. It might mean you found something out about what you actually need. That's not a small thing, even when the story it produces is harder to tell at a dinner party than the cleaner version.

If you're considering a first departure and trying to work out what's actually driving it, the five-question framework is a useful diagnostic before you give notice. The guide to knowing when enough is enough addresses the harder version of the question — how to tell the difference between a genuinely bad situation and one that's just difficult. And if you've already left once and are wondering what to make of returning, the one year after leaving Google account is honest about how the story looks twelve months on, including the parts that didn't go the expected way.