Leave While It's Still Going Well

Almost everybody waits to be pushed. It's the worst possible condition to decide in.

Ask people why they left and you get a story that starts with something going wrong. A reorganization. A new boss. A promotion that went to somebody else. The role quietly changing into something they never signed up for.

The stories are true. But look at the pattern: the decision wasn't made on its own merits. It was triggered by an event that had less to do with the person than with their surroundings.

There's one question that settles whether you should go. I'll get to it at the end.

Waiting means deciding on your worst day

If you're waiting for a reason to leave, that reason will be something unwanted. That's what a reason is. Which means you've decided, in advance, to make the biggest decision of your working life on one of the worst days you'll have.

Nobody plans it that way. It's just what waiting means.

Deciding from there costs you three things.

First, you pick the wrong thing. When standing still has become unbearable, any motion feels like progress. You take the first idea within reach instead of the one you'd have chosen with a clear head.

Second, you leave your network behind. Years of people who know your work is the most valuable thing you carry out of a corporate career, worth considerably more than any severance package. Your first customers come from there more often than from anywhere else. People who are sorry to see you go will take your call for a decade. People who watched you leave resentful won't.

Third, you start with less. Planning an exit gives you a multiyear head start. Reacting into one means spending your first year, or longer, replacing income instead of building anything.

Whose decision is this

Think about what the trigger actually is. A reorg. A particular executive staying or moving. How the bonus pool lands this year. Whether your role drifts into something you didn't sign up for.

Every one of those is a decision made in a room you're not in, by people solving for something that has nothing to do with you. And you've made them your starting gun.

So the question isn't really when you should go. It's who gets to decide, and right now the answer is your employer. Not deliberately. You've just attached your move to events they control and you don't.

You'll describe the result as timing. It isn't timing. It's delegation.

Deciding isn't leaving

Here's what the trigger really takes from you. Deciding and leaving are two separate events, and a trigger collapses them into one afternoon. You decide and leave in the same breath, with whatever you happen to have on hand.

Pull them apart and everything changes. Decide now, while nothing's wrong. Then leave on your own schedule, with savings built, relationships intact, and your first customers already in conversation. The head start isn't luck. It's what the gap between deciding and leaving buys you.

I left when nothing was wrong

I'd come up through Accenture and worked across Microsoft, Cisco, HP and Oracle. Thirteen years, and at every one of them I was the up-and-comer, moving faster than the people around me. Nobody was pushing me out. There was no reorganization, no boss I couldn't work for, no moment I could point at afterwards and say that was when I knew.

Which made it much harder.

When it's going well there's nothing to react to, so you have to decide, and deciding is considerably harder than reacting. Everybody around you can see things are fine, so nobody backs you. And you can't explain it properly, because the honest version is that you want something different, and there's no argument attached to that.

So I left without one. I built my first company from nothing and sold it two years later.

Then back into corporate executive roles for a couple of years, doing well again. And then I did it a second time, with nothing wrong: two and a half million dollars into an acquisition. Every dollar of liquidity I had, with three kids at home aged seven, five and one.

The first two years were hard. Payroll came due whether or not the cash had come in. Clients took their time on decisions the month depended on. I'd expected all of it. That didn't make any of it easier.

Escape has a shelf life

When you're unhappy, you can't tell the difference between wanting to build something and wanting to get out. They feel identical at the time. They don't behave the same once the work gets hard.

A decision made to escape has a shelf life. The relief wears off, and then you're just making payroll, with some part of you quietly noting that this was supposed to be better than what you left. A decision made to build keeps going, because it was never propped up by the comparison in the first place.

Mine had no grievance underneath it, so there was nothing to run out. That second company ultimately sold at a valuation close to a hundred million.

The question

Stop waiting for permission from your circumstances. Nothing has to go wrong first. If you're treating a reorganization or a bad quarter or a difficult boss as the signal, you're waiting for your employer to make your decision for you, and it'll make it later and worse than you would have.

So here's the question. If your job stayed exactly as it is today, nothing better and nothing worse, for another five years, would you stay?

If the answer is yes, you're in the right place and you can stop reading essays like this one.

If the answer is no, you already have your reason, and it's a better one than anything a reorg was going to hand you. Make the decision today. Then leave on your schedule, not theirs.

Leave before you have a story about why you had to.

Until next time,

George

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