Changing Jobs

Questions and model answers

1. What would make you start looking for a different job?

   Stopping learning, mostly — and I mean something specific by that, not boredom. It's the point where I could predict my whole next year: same problems, slightly bigger numbers, nothing I'd have to work out. That's usually about six months before I'd admit it. Bad management would do it faster, but honestly only if it's the kind that doesn't change. Everyone has a difficult year. What I wouldn't leave over is money on its own. I've watched people take twenty percent more to do work they described as fine, and fine turns out to be quite expensive at eight hours a day. The people I know who moved for money alone were back on the market within two years, describing the new place in the same words.

2. If a job stops working, is it better to try to fix it or to leave?

   Try once, properly, and then leave — and the word doing the work there is once. Most people either leave without asking or spend two years hinting. Asking properly means naming the actual thing and what would need to change, out loud, to someone who can change it. That conversation is uncomfortable enough that I understand why people skip it, but skipping it means you never find out whether the job was fixable or just uncomfortable to fix. The reason for the limit is that a second attempt tells you almost nothing new. If the honest version has been said and nothing moved, you've got your answer, and staying longer is mostly hoping the answer changes on its own.

3. Tell me about a time you left something before you were ready.

   I left a part-time job about two months before a project I'd built was finished. The new thing had a start date and wouldn't move it. What I hadn't expected was how much the leaving itself would cost — not the work, the handover. I spent three weeks writing down things I'd been carrying in my head for a year, and discovered most of them had never been written anywhere. Nobody had asked me to document any of it and I'd never volunteered. The person who took it over was fine, but she rebuilt about a third of it because my notes explained what I did and not why. I write things down differently now, and it's entirely because of those three weeks.

4. Do you think changing jobs frequently damages someone's career?

   Less than it used to, and I think the people who still say it does are mostly describing a labour market that stopped existing. The old objection was that you never see anything through — and that's a real risk, but it's about depth, not frequency. Someone who has finished four things in six years is not the same as someone who has started six. What I'd actually look at is whether the moves have a direction. Four jobs going somewhere reads as ambition; four jobs going nowhere reads as escape, and interviewers can usually tell which by asking why you left, one at a time. So it damages a career mostly when the person cannot explain the sequence.

The Korean translation, the expression breakdowns, the reusable frames and the common-mistake notes for these four questions are in the book. The recording and this transcript are free, here and on YouTube.