I left a $180k engineering job to become a writer — here's year one

I want to be careful not to make this sound heroic. There was no single moment of clarity, no walk in the woods where I decided my authentic self needed to write. What actually happened is that I spent three years writing engineering documentation, internal proposals, and post-mortems at a pace that felt increasingly pointless — and simultaneously spent the hour before work every morning on a newsletter I'd started for no strategic reason, that had somehow accumulated 3,000 readers, that I was genuinely excited about in a way I hadn't been excited about anything at work in longer than I could clearly remember.

The decision to leave happened slowly and then very fast, the way most decisions like this do.

What the job actually was

I want to set this scene accurately, because "I left a $180k engineering job" can mean a lot of different things and the specifics matter.

I was a senior software engineer at a Series C SaaS company. The $180k was base; with equity and bonus it was closer to $215k in my last full year. The work was not terrible. I was on a distributed team across four time zones, good at the work, and my performance reviews were consistently strong. By any external measure, things were going well.

I was also completely checked out. Not dramatically — there was no single moment where the mask fell. More like a slow dimming. I still wrote clean code. I still showed up to standups. But I had stopped caring about the outcome in a way that was difficult to explain to anyone who hadn't experienced it. The work felt like a performance I was giving rather than something I was genuinely doing.

The newsletter was different. Writing that felt like something that was mine. I could feel the difference, which sounds imprecise but is accurate. The hour before work was the only part of my day where I was completely present, with no awareness of how I was being perceived or what the sprint velocity looked like.

How the decision actually happened

I'd been writing the newsletter for two and a half years when I picked up a freelance content project from a startup — a short series of articles about a space I knew well. It paid $4,000. I did it in three weekends. The money was almost beside the point; the fact that something I'd written had generated income from someone other than an employer was not.

After that I started quietly building: pitching to publications, taking on occasional freelance work, growing the subscriber count, trying to understand whether writing could actually support itself or whether it was just a hobby with occasional upside. Eight months later I sat down with a spreadsheet and tried to do the maths honestly. What would I need to make this work? What did I have saved? How long could I survive without income from the job? What was the realistic trajectory of freelance writing income in year one?

The answer was uncomfortable but legible. I had fourteen months of runway. The freelance writing market was real but slow-building. If I was serious about doing this, I needed to leave soon enough to build momentum before the runway ran out.

I handed in my notice in September. My manager looked surprised. I was a little surprised too.

Year one: what actually happened

The numbers, honestly

I'm showing these because I spent months trying to find honest accounts of what writing income actually looks like in year one and found almost nothing useful. Most "I quit my tech job to write" stories either omit the numbers entirely or feature a book deal or viral article that isn't representative of a normal trajectory.

$68k is below what I needed. I used runway to make up the gap. That's what runway is for.

What I got wrong

I thought the writing itself would be the hard part. It wasn't. The hard part was client acquisition — pitching, following up, handling rejection, building relationships, pricing myself correctly, navigating contracts. The writing was relatively straightforward. The business of writing was not, and nothing in my previous career had prepared me for it.

I underestimated how much I'd miss external structure. Not the meetings — god, not the meetings — but the scaffolding that a job provides. A reason to be at my desk. Colleagues to be accountable to. Milestones that weren't self-imposed. I spent the first six weeks building artificial structure and it helped considerably more than I expected. A simple rule: mornings are for writing, afternoons are for everything else. The simplicity of it sounds obvious and was not obvious until I'd spent three weeks drifting.

I thought I was leaving tech. I was not. My clients are mostly technology companies. My newsletter audience is mostly people in or adjacent to the industry. What I'd actually done was reposition myself from inside tech to writing about and for tech — which turned out to be a far more viable path than writing for general audiences. The expertise I'd accumulated wasn't a thing I'd left behind. It was the thing that made me worth hiring.

Where I am now

I'm writing this eighteen months out. Income is at about 55% of what I used to make in total compensation. The equity I walked away from has appreciated, though I don't know by how much and I've made a deliberate decision not to calculate it too precisely.

I don't particularly regret it. But I also don't want to oversell the romance of the decision. There are days when the uncertainty is real and the freedom is mostly theoretical. There are weeks when the work is routine, the clients are difficult, and I think about the clean certainty of a salary with something that isn't quite longing but isn't nothing either.

What I don't think about is going back. Not because I'm certain this is right — I'm genuinely not certain about much — but because the version of me that was dimming slowly in those meetings is not the version I want to keep feeding.

If you're at the beginning of thinking about something like this, the career pivot track on the Start Here page has more on the financial planning side and what other people's first years have actually looked like, including the parts that most accounts leave out.