The three questions I ask before anyone quits their job

I spent eight years in a law firm and then stopped, badly, at thirty. People book me to talk about the leaving. What they usually want is permission, and what I try to give them instead is three questions. None of them are inspiring. All of them are the ones that decided it for me.

1. How many months could you cover with nothing coming in?

Not “do you have savings”. A number, in months, assuming zero income and no change to your rent. Write it down before you read on.

Under three months, you are not planning a career change, you are planning an emergency. Three to six is enough to start something on the side, not enough to jump. Somewhere past nine months the conversation becomes real, because nine months is roughly how long it takes for the first version of the new thing to be bad, then slightly less bad.

My first freelance year, I earned about a fifth of my old salary and spent the whole of it. That was the plan working, not failing. If I had budgeted for four months I would have gone back at month five and concluded I was not cut out for it, which would have been the wrong conclusion from the right data.

2. What would have to be true in twelve months for this to have been the right call?

This is the one people struggle with, and it is the one worth the money. Most answers come back as feelings: “I’d be happier.” “I wouldn’t dread Mondays.” Those are real, and they are useless as evidence, because you cannot tell in month eleven whether you are getting there or simply having a bad November.

Push until it is checkable. Three clients who came back. One piece of work you would show a stranger. Income at forty per cent of the old number and rising rather than flat. Now you have something that can be wrong, which means you have something that can also be right.

3. Who are you doing this in front of?

Everyone has an audience in their head. A parent, an old boss, a version of yourself at twenty-two who had opinions. It is worth naming them, because a surprising number of career changes are arguments with someone who is not in the room, and those tend to end badly whichever way they go.

If the honest answer is that you want a particular person to be impressed, that is not disqualifying. It is just information you should have before you hand in a resignation letter.

What I actually tell most people

Not yet. Most of the conversations I have end with a six-month checklist rather than a resignation, and the people who come back a year later are almost always glad about it. Leaving well is mostly a question of timing, and timing is unglamorous, which is why nobody writes about it.