Should I Quit My Job? Three Questions Before You Decide

Whether to quit your job is the wrong question. The right one is whether you've actually seen the next thing. People who quit toward something they've verified tend to be fine. People who quit away from something they're tired of usually land somewhere new and discover they brought the problem with them.

"Don't do it"

When I told my business partner at the pest control company that I wanted to go sell solar, he said, "Dude, don't do it. You won't make any money. Stick with this four years and you'll make six figures." Then my manager gave me a list: solar takes forever to get paid, it's harder than it looks, you won't make what people say.

Both of them were being reasonable. Four years to six figures is a real offer. But neither of them had sold solar. Both of them benefited from me staying. And I'd done something they hadn't: I'd watched people sell solar and seen what hit their accounts.

I went. I doubled my income within a year.

Years later I quit a company and moved across the country for a role in Ohio. From the outside it looked insane. From the inside, I'd met the company three or four times in person and sat down with the person I'd be paired with before I said yes. That's the difference between a leap and a jump.

Three questions before you give notice

1. Have I seen it, or have I just heard it? A friend saying "you can make a lot here" is a story. Watching someone do it, seeing the numbers, meeting the people, that's evidence. If you haven't seen anything, your next step isn't quitting. It's asking to see something.
2. Does the structure make sense? Not "could this work," but "does it make sense that it works." Why is the next thing good? If the only answer is "trust me," there's no structure, just a pitch.
3. Does it fit the life I'm building? More money isn't the question. Does it get you closer to what you actually want? When those two answers differ, the second one wins.

And the one that catches most bad quits: am I running toward something, or away from something? I once left a good situation for a "come to California, I'm closing a ton" phone call. I lasted two or three weeks and made less than if I'd stayed. I was running away from a long summer, dressed up as running toward money.

If the answer is "I don't know"

Then you're not ready to quit yet, and that's fine. "I don't know" isn't a verdict. It's a to-do list. What does the next thing actually pay? Who can you talk to who's doing it? Can you try a piece of it on the side first?

Answer those, and the decision usually makes itself. For the longer version of this check, read should you trust your gut?

What the research says

People are too cautious about big changes. Economist Steven Levitt ran an unusual study: thousands of people who were stuck on a major decision, including whether to quit a job, agreed to let a coin flip nudge them. Six months later, the people the coin told to make the change were happier than the ones told to stay put. His conclusion was that people facing life-changing choices tend to err on the side of doing nothing. (Levitt, 2016; published in the Review of Economic Studies, 2021)

That doesn't mean quit on a coin flip. It means if you've done the checking and the answers hold, the risk of staying is probably bigger than you think.

This week

1. Write down what you'd be quitting toward, in one sentence. If you can't, that's your answer for now.
2. Go see it. Talk to one person doing the next thing. Ask to see the real numbers or the real day.
3. Ask the fourth question out loud to someone you trust: toward, or away?