The Rebuy
The short answer
The Rebuy replaces the question of whether to leave with the question of whether you'd join again. If you didn't have this job today, and someone offered it to you today at its current salary, knowing everything you now know about it, would you take it? It works because it removes sunk cost, status and the fear of the exit conversation in one move, and turns a hard leaving decision into an easy buying one.
The question
Would you buy into this again, right now, knowing everything you know today?
That's it. For a job it's usually phrased with the number in it, because the number is the part people are defending. If you're on $95,000 and someone offered you this exact job at $95,000 tomorrow, with the commute you actually have and the manager you actually have, would you say yes?
Answer it out loud. People take about three seconds.
Why it works
Leaving and joining are the same decision seen from two sides, and we're much worse at one of them.
It deletes sunk cost. The four years you've already given are not an argument for the next four, but they feel like one right up until you're asked to buy fresh.
It deletes the exit conversation. A lot of people who want to leave are not weighing a career, they're avoiding one uncomfortable meeting. Buying doesn't require that meeting, so the fear stops distorting the answer.
It deletes status. The title, the company name, what your family says about it. Those matter when you're defending a position and matter much less when you're being sold one.
It makes you an outsider to your own life. That's the whole trick. You're allowed to see it clearly for the length of one question.
What to do with the answer
Clear no. You've already decided and you're negotiating with yourself about timing. The work now is a date and a first step, not more thinking.
Clear yes. Genuinely useful, and more common than people expect. Something specific is wrong and it isn't the job. Find out what, because leaving won't touch it.
A wobble. Usually the interesting one. Say the version you'd buy. "I'd take it at $95,000 if I could do it from anywhere" is not indecision, it's a spec, and it's often something you could go and ask for.
It isn't only for jobs
The same question works on a city, a course, a business, and it works uncomfortably well on a relationship. Would you choose this again, today, as it actually is rather than as it was when you chose it.
That's why it earns its place. Most decision tools handle one category. This one handles anything you're already inside.
Where it doesn't work
When you're in the middle of something. Ask it in a bad week and you'll get the bad week's answer. Redundancy, a breakup, an illness. Wait.
When the alternative doesn't exist yet. A no tells you this isn't right. It doesn't tell you what is, and it certainly doesn't tell you the next thing will be better. That's a separate piece of work.
When the honest answer is "I'd buy it, I just want a different life." Then the job was never the decision, and running this on it will keep giving you a yes while you get more frustrated.
Questions that come up
What if I don't know whether I'd rebuy?
Then say the version you would buy. "Yes at this salary if I could work remotely" or "yes if I didn't report to this person." That sentence is more useful than a yes or a no, because it names the one thing that would have to change, and quite often that thing is askable.
Isn't this just asking whether I'm happy?
No, and the difference matters. Happiness is a mood and it moves week to week. The Rebuy asks about a transaction: given the full price, would you pay it again. People answer that consistently even on days they feel fine.
Does a no mean I should quit tomorrow?
It means you've stopped choosing this and started tolerating it. What follows is a plan with a date, not a resignation letter this afternoon. Knowing the answer and acting on it well are two different jobs.
Where did this come from?
It came out of answering stay-or-go questions on the daily show, unscripted, over and over, until it turned out I was reaching for the same reframe every time. It's the thing I use most.
Last updated 3 September 2026