Five signals it's getting late, and how to go on your own terms

Dana is a composite, not a member or a client. She is 49, a senior vice president, eleven years at the same company, and it is 6:40 on a Thursday evening. The resignation letter in her drafts folder is fourteen months old.

She has reasons. The transformation she is running is a year from done. The CEO who hired her retired, and the new one has not formed a view of her yet. Her equity vests in March. Her mother is unwell. Every one of the reasons is real.

This afternoon the new CEO announced the reorganization. Her peer, who joined four years ago, gets the expanded division. Dana keeps her title and gets a line in the memo thanking her for "steady leadership."

What she stands to lose

If she stays, she gets another year of "not yet," a smaller chair in a bigger room, and a boss who has now told her, in the politest possible way, what he thinks. If she goes, she gives up the March vesting, a title she worked a decade for, and the story she has been telling herself, which is that one more year will make the difference.

What she notices, sitting there, is that the recruiters stopped calling two years ago. Not because she lost value. Because she said no three times, politely, and they took her at her word.

The turn

The question was never whether to leave. It was when she stopped being someone who could. Her market value was highest in the year she turned down the first call, and it has been quietly declining since, while her reasons to stay piled up on top of it.

Nobody tells you this part. The risk of leaving is loud and specific: a lost bonus, an awkward conversation, a title you have to earn again. The risk of staying is quiet and compound. It arrives as a résumé that reads like one company's history, a network that forgot your name, and a memo that thanks you for steady leadership.

Why this is not just Dana

Deloitte's 2025 survey of 7,500 women found that only 5% plan to stay with their current employer more than five years. In the year Lean In and McKinsey named the "Great Breakup," two women directors were leaving for every one promoted. The women leaving are not the ones who failed. They are the ones who finally did the math.

Three things to take from it

Know the signals that it is getting late. Recruiters have stopped calling. You describe your job in the past tense. Your "one more year" has a sequel. The sponsor who hired you is gone. The new org chart was drawn without you in the room.

Keep your exit value warm even when you are happy. One outside conversation a quarter costs an hour and keeps your name in circulation, so that when the call matters, it comes.

Leave from strength. The best time to go is the quarter after a win, when you are leaving a story, not the quarter after a snub, when you are leaving a wound. Vesting dates are real, but they are a number. A decade is not.

Dana's letter is still in the drafts folder. Yours does not have to be.