This is a story about a woman who has been preparing to quit her job for six years, the letter she has been writing the entire time, and what the letter has become.

The woman — I will call her Iris, because that is the name she has chosen for herself in this piece, and because she said, when I asked her why she chose it, “It sounded like the name of someone who would actually leave” — is forty-one. She works for a mid-sized consulting firm in Boston. She has been there for twelve years. She is a senior manager. She has, in the past six years, been promoted twice.

She has, in those same six years, been updating her resignation letter.

The letter

The first draft of the letter was written on a Tuesday morning in October of 2019. Iris was, at that point, thirty-five. She had just been passed over for a promotion she had been promised eighteen months earlier. She came home that night, opened her laptop, and wrote what she now considers the first version of the letter.

The first version, she has told me, was “honestly not very good.” It was angry. It was three paragraphs long. It used the word “frankly” twice. It ended with the sentence: “I deserve better than this.” She did not send it.

She saved it in the drafts folder of her personal Gmail account.

She came back to the letter the following week. She had calmed down. She rewrote it. The second version was shorter, more measured, more professional. It thanked her colleagues. It thanked the firm. It said that she had decided to pursue other opportunities. It included, for the first time, a sentence she would later describe as the heart of the letter: “I have learned a great deal here. I am leaving because the things I have learned no longer require me to stay.”

She did not send the second version either.

The discipline

What happened next is the part of the story that I have spent the most time thinking about.

Iris did not send the letter. She did not, however, delete it. She instead returned to it, on average, every two to three weeks, for six years. Sometimes she made small edits — softening a phrase, removing a redundancy. Sometimes she made larger edits — restructuring entire paragraphs, replacing the closing line, updating the tenure number. (The letter, in its most recent revision, refers to her twelve years at the firm. The earliest version referred to her six years. The number has been changed, by my count, six times.)

She has updated the letter, in total, forty-seven times.

She has not sent it.

I asked her, in our first conversation, why.

She said: “Because the letter is the point.”

I said: “What does that mean.”

She said: “I will tell you, but I would like to think about it for a few days first.”

A small interlude

I want to pause here, because I think the story will be clearer if I tell you what Iris does for a living, and what kind of person she is, and why the letter has become what it has become.

Iris is, by every account I have been given, very good at her job. She manages a team of nine. Her clients trust her. Her firm, by all measurable signals, would be in significant trouble if she actually left. She is paid well. She has stock options that have, in the last two years, become quietly substantial. She has, by most metrics that the modern American economy uses to indicate that a person is succeeding, succeeded.

She is also, she has told me, “tired in a way I cannot explain to anyone who is not also tired in that way.”

The letter, she has come to believe, is what allows her to keep working.

The realization

In our second conversation, Iris told me that she had figured out what to say.

She said: “The letter is a kind of permission slip. I do not send it because I do not want to leave. I want to want to leave. The letter is the thing I have built that proves I could leave if I wanted to. As long as the letter exists, I am a person who has not given up. As long as I have not sent the letter, I have not, in fact, left. Both of these things are useful to me. They cancel each other out in a way I find restful.”

I said: “That is a very specific feeling.”

She said: “I know.”

She said: “I think a lot of people have it. They just haven’t given it a name.”

The forty-seven versions

Iris allowed me to read all forty-seven versions of the letter. I have, with her permission, picked three to share. I am not reproducing the letters in full — Iris asked me not to — but I will summarize.

VERSION 7 (April 2020). Written during the early pandemic. The tone is exhausted. The letter mentions, for the first time, “the events of recent months” and includes a sentence about how Iris has been thinking about “what work is for.” She did not send it. She has told me she came closer to sending it than at any other point.

VERSION 23 (November 2022). Written after Iris’s mother was diagnosed with a chronic condition. The tone is suddenly soft. The letter mentions, for the first time, “the people who depend on me outside of this office.” It is the first version that does not include the closing line about learning. It is the only version that does not.

VERSION 41 (March 2025). Written after Iris’s second promotion. The tone is, of all things, grateful. The letter mentions the colleagues who advocated for her. It thanks her boss by name. It is, Iris has told me, “the version I am least afraid of.” She added: “Which I think probably means I will not send it.”

The most recent version

The current version of the letter — version 47 — was written three weeks ago, on a Sunday morning, while Iris was making coffee. She has not, since updating it, opened the file.

I asked her if I could read it.

She let me.

The letter is now one page long. It is dated for “the day I send it.” It does not specify when that day is. It thanks the firm. It thanks her colleagues. It thanks her boss. It includes, near the end, a sentence I had not seen in earlier versions: “I have written this letter many times, and many things have changed in the time it has taken me to send it, and I am not entirely sure why I am sending it now. I am sending it because I am tired of writing it.”

She has not sent the letter.

She told me, when I asked, that she is not sure she ever will.

She told me, in the same breath, that she would not delete it.

What this is

I have asked several people I trust to read this piece in draft, and almost all of them have told me, in various ways, that they have something similar. A letter they have written and not sent. A list of grievances they refine but never deliver. A resume they update annually but never submit. A breakup speech they have rehearsed for a relationship they have not ended. A decision they have made — clearly, definitively, again and again — and not acted on.

It is, I think, one of the small private rituals of modern adult life. The decision we keep making. The decision we never quite make.

(For an earlier piece on related territory — the gap between the decision and the doing — see the Wattalife story about the man who broke up with his AI and was not sure, afterward, whether anything had ended.)

Iris asked me, in our final conversation, whether she came across in this piece as someone trapped or someone free.

I said: “I think you come across as someone who has figured out how to live with both at the same time.”

She said: “That sounds about right.”

She paused.

She said: “I am going to go open the letter.”

—

Margot Hale is the editor of Wattalife. She has, in the course of reporting this story, located three letters in her own drafts folder that she has not sent. She is not going to send them. She is, however, going to keep them.