Somewhat Uncommon Career Advice
some of it is wrong, a lot of it is missing nuance.
Note: I edited this in June 2025 since there were some things I wanted to change and flesh out.
I was writing this as part of another post about selling out, and then realized it was a different thing and probably needs its own post.
This is a list of career advice that I’ve personally found useful, and which I haven’t seen in most other career advice posts. In many cases, I’m leaving the advice unjustified; you can decide for yourself whether it matches your own experiences. Some of it is probably wrong, and a lot is missing nuance.
Two common pieces of career advice:
(a) It’s important to live a balanced lifestyle—one that gives you the flexibility to meet your goals for your health, your social life, and your career, both now and in the future.
(b) If you’re a skilled person in a first-world country, you can probably afford to take bigger risks than you think. In particular, if there’s something you love, there doesn’t have to be an existing job or company you can work at in order for you to do it. You can figure out or start something on your own.
You can “just do things,” as some people say.
Some nuance on where I think people go wrong when they consider them:Often, people don’t properly apply (b) even if they feel like they’ve heard it. Like, you can’t just hear the advice and check off the box of knowing that you can “just do things.” You have to actively force yourself to really consider the advice and be able to easily step outside your comfort zone if it’s the best option. Knowing the advice is not the hard part.
But those who do make that leap of faith often don’t properly consider that
Living a balanced lifestyle is extremely important, and it is hard to do this without routines and stability.
Going off the beaten path is stressful.
Going off the beaten path is expensive.
Going off the beaten path is lonely, and there are a lot of positive-sum trades you get with normal career paths that you miss with the exotic ones. E.g., it’s harder to find good training and to build a network.
If a decision has long-term consequences, ask yourself: Would this still be a good idea in 20 years?
As an example, if you want to have a spouse and kids, ask yourself whether career decisions would still be wise if future-you has a spouse and kids.
Young people are short-sighted, and it’s easy to feel like you’re missing out if your startup-creating friend seems to have a better life than you.That said, I think people underestimate how frequently we make life-altering decisions. Your future trajectory is probably closer to a chaotic system where every event has long-term consequences than to some stable equilibrium that will revert to a default trajectory after being perturbed.
This means you should probably allow yourself to make such decisions more often.Decisions are usually reversible. Be aware of when a decision isn’t easily reversed without large costs (e.g., what college to attend, who to marry), which often means you are underestimating how long you should take to plan it out.
If someone gives you advice on something that isn’t independent of who you are, figure out why they think it’s good advice and whether those reasons apply to you. They may know more about the domain, but you know significantly more about yourself.
For example, you should be more skeptical of advice on what career to enter (which is highly personal) than advice on how to succeed within a given field (which is more transferable).Because most people haven’t tried multiple careers, many pieces of career advice, especially uncommon ones, are generalizations from n=1. To be better informed, talk to a portfolio of people doing different things. And talk to hundreds of them.
Do not be afraid to be shallow or “low status” if it’s what you care about. In particular, it’s valid to
Choose a job that pays you the most
Choose a job that makes you feel the best about yourself
Choose a job that impresses other people the most
You should also feel able to seriously consider being something like a farmer or a sailing instructor.If you plan to go into a risky, unstable career, talk to both success cases and failure cases to reduce your exposure to survivorship bias. The career will often look attractive if you only see success cases, since high risk often means the successes have better rewards.
While recruiters have some incentive to “deceive” you, they also have strong incentives to be honest with you about their company and what the role you’re applying for is. Employees who don’t like their jobs or aren’t a good fit are often also terrible employees.
Strangers who tell you not to apply for x company1 often:Don’t have strong incentives to be honest with you.
Have pretty incomplete knowledge of the given role or company.
They say this because:
They might want to see more of something from younger people — pursuing their passions or something, pursuing something altruistic, etc. — and want to nudge them in that direction.
They might just give whatever advice justifies their own career decisions.
Jane Street is a common value for x in my circles, and was kind of the inspiration behind this comment. People I’ve met who work for Jane Street seem to like it!