Five signals it's getting late, and how to go on your own terms
Dana is a made-up figure drawn from several people, and does not correspond to any actual member or client of the association. She is 49, a senior vice president with eleven years at one company, and it is 6:40 on a Thursday evening. The resignation letter that still sits untouched in her drafts folder has been waiting for over a year.
She has good grounds for her choice. The transformation she leads is a year from finished. The CEO who brought her in has retired, and his successor hasn't yet made up his mind about her. Her equity vests in March. Her mother's health is failing. Each of those reasons is genuine.
On that particular afternoon, the incoming CEO unveiled the reorganization plan. The expanded division went to a colleague who had only joined the firm four years earlier. Dana kept her title, plus a sentence in the memo praising her "steady leadership."
What she risks by staying
If she stays, she gets another year of "not yet," a smaller seat in a bigger room, and a boss who has now communicated, as courteously as possible, exactly where she stands. Walking away would cost her the March vesting, the title she had worked a decade to attain, and the comforting belief she keeps rehearsing, that another year will somehow fix everything.
What strikes her, sitting at her desk, is that the recruiters stopped calling about two years ago. Not because her value dropped. She declined their offers three times, always courteously, and each time they simply took her at her word.
A turning point
Whether to leave was never the real issue at stake. The real turning point came when she quietly lost the ability to imagine leaving. Her market value peaked the year she declined the first call, and it has been slipping ever since, while the reasons to stay stacked up on top of it.
Almost no one talks openly about this part. The danger of leaving is loud and concrete: a forfeited bonus, an uncomfortable conversation, a title you'll have to rebuild. Staying carries a risk that creeps in gradually and piles up without notice. You notice it in a résumé that tells the story of a single employer, in a professional network that no longer recognizes your name, and in a memo that praises your steady hand.
Why this isn't only Dana
According to Deloitte's 2025 study of 7,500 women, only 5% expect to stay with their present employer beyond five years. Throughout the period that Lean In and McKinsey labeled the "Great Breakup," for every woman promoted to a board seat, two women directors walked away. The women walking away are rarely the ones who fell short. These are the women who were first to sit down and crunch the figures.
Three points to keep in mind as you go
Watch for the early indicators that your opportunity is narrowing. Recruiters have gone quiet. You begin describing your current role as if it has already ended. Your pledge to stay "just one more year" has been pushed back again and again. The leader who pushed for your hiring is no longer with the firm. The fresh org chart was sketched out while you weren't in the room.
Even when you feel settled, keep your alternatives ready to go. One outside conversation a quarter takes an hour and keeps your name in circulation, so that when the right call comes, you're reachable. Cincinnati's networks make this easy: the Cincinnati USA Regional Chamber, the Greater Cincinnati BPW, CREW Greater Cincinnati and the WBEC Ohio River Valley all host the kind of conversations that keep a name alive.
Depart while you still have momentum. The best time to go is the quarter after a win, when you are walking away from a success story, not the quarter after a slight, when you are walking away from a wound. Vesting dates carry weight, but at heart they are simply dates on a calendar. A decade is not a date.
Dana's unsent letter still rests in her drafts folder. Your own letter need not remain there indefinitely.