The resignation letter I couldn't write

By Juan · December 15, 2025 #personal#career

I quit a job in 2022 that I should have quit in 2021. Possibly 2020.

I’m writing this because the most-reacted-to category on Surbias is career, and inside career the most-reacted-to subset is “I stayed too long.” I’m one of the people in that data. Here’s what staying too long actually looked like, in case you’re in the middle of it.

The first attempt

The first time I tried to write the resignation letter was June 2021. I’d just had a meeting that crystallized something I’d been ignoring for months: my work was being slowly redirected toward a thing I didn’t believe in, by people who knew I didn’t believe in it, because they didn’t have anyone else.

I opened a Google Doc. I wrote: “I am resigning effective two weeks from today.” Then I sat there for an hour.

I closed the doc without writing anything else and went back to work.

What kept me there

Reading this back later, the reasons looked stupid. In the moment they were real and they were heavy:

I’d told everyone I loved this job. I’d been talking about it as the best job I’d ever had for over a year. Quitting felt like admitting I’d been wrong publicly. My identity outside work was partly built on enthusiasm for it.
I didn’t have a next thing. No offer, no plan, no concrete idea. Just a vague sense that I needed to leave. The advice I’d absorbed was “always have something lined up” and not having one felt like proof I wasn’t ready.
The financial cliff was real. I had savings for maybe four months. Four months sounds like plenty when you’re not staring down it; from inside, it looks like a number that gets smaller every day with no income coming in.
I liked specific people. I told myself I’d be “abandoning” them. The team I worked closest with was good. Quitting felt like a betrayal of them, separately from the company.
I was scared I was the problem. Maybe the work was fine and I was burnt out. Maybe I’d take a break and feel the same way at the next place. Maybe I was the common factor.

Each of these is rational individually. Together they paralyzed me for almost a year.

The seven other attempts

Between June 2021 and March 2022 I tried to write the letter eight more times. Sometimes after a particularly bad meeting. Once after a vacation, when the gap between how I felt on Monday morning vs. the previous Friday was so wide it felt diagnostic. Once after a friend asked me, very gently, why I sounded like a different person than I had a year ago.

Each time I’d open the doc, write the first sentence, and then talk myself out of finishing it. I had a list of reasons; the list got longer over the year, not shorter, because every month I stayed was another month it would feel embarrassing to leave.

This is the trap the most-reacted-to stories on Surbias describe. Each additional month invested makes leaving feel more expensive, when actually it makes staying more expensive — because the months you’ve already spent are already gone.

I knew about sunk cost. I’d written about sunk cost. I lectured friends about sunk cost. None of that knowledge moved me an inch when the cost was mine.

What actually moved me

Two things, in close succession.

The first was a 2 a.m. anxiety attack on a Tuesday in February. Nothing happened that day in particular. The body just got tired of waiting for the brain to figure it out and ran the alarm itself. Lying on the bathroom floor, the resignation letter was suddenly the easy thing and continuing was the hard thing.

The second was that, by complete chance, a friend offered me a small consulting project the same week. Nothing big — three months, decent rate, lower than my salary but enough to extend my runway from four months to seven. Concrete dollars in a calendar.

That was enough. The vague “I should leave” became “I will leave on Friday and start the project Monday.” I wrote the letter that night. It took eleven minutes.

What I’d tell the person I was

You won’t believe me if I tell you the cost of staying is higher than the cost of leaving. You can read that sentence a hundred times and it won’t move you. So I’ll tell you something else.

The thing you’re waiting for is not going to come. You’re waiting for clarity, an offer, a sign, the perfect timing. You’re waiting for the moment when leaving feels obviously right. That moment is a fiction. It will never feel obvious from inside the job. It will only ever feel obvious in retrospect.

What will get you out is not certainty. It’s something concrete enough to make leaving the practical move — a number on a calendar, a deadline you make for yourself, a friend who says “do it.” Anything that converts the decision from “should I leave eventually” to “I’m leaving on this date.”

If you’re sitting with a half-written resignation letter, the date is the thing. Pick one. Not “the right time.” A specific Friday. The rest is logistics.

— Juan