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Career Hypnosis


A lot of my friends say they are unhappy with their current job and do not know what to do about it. While I often have no idea what to tell them, I do wish I could be helpful. This short essay is an attempt at that.

Dear Friend Who Asked Me About Their Career [0],

I think you may have been hypnotized, and it is stopping you from achieving your dreams. Or, at least, from making better career decisions. Please let me explain.

It started from a young age. Parents, teachers. Then it was friends, coworkers, bosses. Everyone telling you what you can do, what you should do, what you must do with your career.

You’re a free-thinking person, of course, but some of these career ideas really are quite persuasive. Little by little, they dig their claws into your mind. You start seeing other people’s career opinions as facts. It becomes hard to separate the two. Until…eventually…HYPNOSIS.

What if those ideas are holding you back?

I suspect that much of your uncertainty, your stuck-ness, your working at a job you hate for five years, is a result of that hypnotism. And my guess is that if you want clarity, the first thing you should do is wake up. Unlearn those bad, limiting, hypnotizing ideas.

I put together a list of what I am seeing—not just in your case but with many people I have met. Hope it helps.

Remember that our writing below is a list of opinions and ideas, not a list of facts. Be wary of anyone presenting opinions as facts. If you aren’t convinced by what we say, you could even consider doing the opposite as you think about this for yourself. And of course, email us if you have any others we should add.

  • You should know what to do before starting. We did not have a giant list of essay ideas before we started this blog. Now we do. Often, new ideas only come when you give yourself a reason to have the new ideas. Don’t start the blog so you can publish your great essay ideas; start the blog so you can have the great essay ideas in the first place. Open the door.

  • Life is a marathon, not a sprint. It sounds like good advice. But the fastest marathon runners are hitting sub-5-minute miles the whole race. That’s a full-blown sprint for most people. The marathon v. sprint idea is a false dilemma: why can’t you run the marathon of life at full speed?

  • You need to be perfectly rational. This is impossible. They didn’t make Toy Story with a logic algorithm. You should probably not try to decide the path for your life with pure facts and logic, either. You can do things just because you feel like doing them. You can let emotion and feelings guide you. If you ever find yourself in a position where you have a spreadsheet open and are comparing four different job offers based on small differences in salary and equity, you may be trying too hard to be rational.

  • Money is a bad motivator, and it won’t bring you happiness. It’s true that seeing a bigger number in your bank account is (probably) not your key to long-term fulfillment. But money can be important! And having more money does, in fact, make most people happier. Not because they love sitting on their hoard like Smaug, but because money can, among other things, unlock more freedom and choice in life. So I’d be skeptical if someone tells you that "doing it for the money” is somehow a bad thing. Money can be a perfectly reasonable motivator.

  • You’d be better off not working. Would you? It’s nice to believe that your life’s problems would all be resolved if you were on a beach somewhere drinking a beer. It’s a convenient answer. The good news is that you can go try it right now. For a few hundred dollars you could be on a flight this evening! We aren’t convinced you will walk away from the experience thinking it was the solution (but if you think so, we encourage you to try). It seems that a lot of people make decisions about the direction of their careers based on the idea that they would be better off not working (see the FIRE movement as a good example). And so they end up trading years or decades doing the wrong thing only to later learn that they did it for the wrong reasons, too.

  • You need to have connections to land a (good) job. This is an excuse. What might be true is that connections can make landing a good job easier. Getting a warm intro to a company, though, is far from the only way you can stand out.

  • Try smarter, not harder. What does this really mean? In at least one sense your smartness may be baked in—it’s not like you’re going to magically double your IQ with this little piece of advice. And lots of the time, “trying smarter” can slip quickly into thinking you can compensate for laziness or inaction with cleverness. It’s a lot easier, and we would argue more effective, to simply try harder than most other people. You can’t snap your fingers and double your IQ, but you could start trying harder right now. This is true for everything from applying for a job to writing an essay.

  • Years of experience means useful wisdom. Some old people have wisdom, sure. And maybe the percentage of wise old people is higher than the percentage of wise young people. But being old does not bestow wisdom on you by default. So be careful of assigning too much value to advice just because the person who said it has been alive on this planet for longer than you have.

  • Giving up means you failed. That’s one way to frame it. But arguably, spending more time on a lost cause—after you realize it’s probably lost—is the bigger failure. Sometimes, giving up on something is the most successful decision you can make.

  • Asking other people for advice is a good idea. Talking to people can be therapeutic in its own right. But talking is not the same as seeking advice—and we’d guess that most people’s advice would have a net negative impact on your life. People tend to view solicited advice as a charitable gift that should be treated with respect, but maybe they shouldn’t. Advice is not always helpful, and it is not always easy to differentiate between good and bad advice.

  • “At least you learned”. Failing is overrated and approaching life with the ‘I’ll learn something no matter what’ may lead you to doing unsuccessful things you shouldn’t have done in the first place. Our guess is that you are probably going to learn a lot more by succeeding.

  • Avoidance is a bad thing. In certain contexts, like not replying to messages at work, avoidance is bad. But when you’re considering a career, you may find it helpful to avoid doing the things you don’t want to do. If you think your role is a bit boring and meaningless but are going to dedicate 30 years of your life to it anyway, ask yourself whether that is a great idea.

  • You need to work somewhere before you know what it’s like. Why? What if you just pretended you had the job right now? If you want to join a company as a marketer, you could design a marketing campaign for that company today, right now, for free. You could even show it to them

  • There is a linear career ladder you need to follow. The standard ladder works for some people. But you could also hit bank shots: data science for a fish farming company, then fish farming regulatory work for your government, then running a fish conservation nonprofit, then, I don’t know, running to be the governor of your state. Or you could go from brewing coffee to launching a startup. It doesn’t really matter. Don’t climb the ladder just because you feel like you have to.

  • “They are outliers, so you can’t follow their paths or advice”. Okay, and why are they outliers? What makes them great? How could you study and replicate that? It’s lazy to use someone’s greatness as an excuse for why you can’t be great, too. And it’s probably better to study the outliers as opposed to the average, at least if what you want is an above-average outcome.

  • You are supposed to be fulfilled by your job. You could make that a goal. You could also find purpose elsewhere, though, if you wanted to. There might be better ways to feel good about life.

So now you’ve read the list. Maybe you agree with some of the pieces. What now? It’s likely you won’t immediately unlearn some of these things. A new magical world of ideas and opportunity did not just open up to you after 90 seconds of reading. Unlearning takes time. You may find yourself stumbling upon excuses along the way—in fact we think that a lot of the things on the list above are common excuses.

If all of it seems rather difficult, it can help to remember that one day, you are going to die. If a dead version of you could Ghost of Christmas Past your life, do you think you’d be impressed by the fact that in your 20s you decided you weren’t compatible with someone based on the month they were born in? Do you think you’d be proud that you decided ‘I’m just not a good writer’ and never wrote that novel? Do you think you’ll pat yourself on the back for working a job you hated for 20 years? Or do you think perhaps, with a long view, all of those things would be a little bit silly?

Wake up! (...is that what hypnotists say when the show is over?)

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[0] Not to be confused with The Guy I Didn’t Invite to My Wedding.

[1] By “better” we mean more optimal for whatever trajectory you would like your life to take.