Controversial career advice

Contrarian ideas to help you think about your career

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(This is a guest essay!)

The internet is full of career advice. Some good, some bad. The problem? Have you noticed?

A lot of it sounds the same.

It’s at least partially because of the internet bubbles I occupy (send me your hot takes! hi@nextplay.so). But you would think that the internet (and social networks) could do a better job of enabling a diversity of opinions about what you should do with your life to come to light.

I tried to do perhaps the next best thing. Which is to create a list of controversial/not super popular career advice that you may benefit from reading.

They are just opinions. They may be wrong or missing nuance. But I think…at the very least…I hope…they will get you to pause for a moment and think.

It’s rather obvious but I think the power of ideas and influence cannot be understated. You’d maybe be surprised by the number of people I meet, who are years into their careers, who tell me they feel as if they’ve just awoken from a sort of hypnosis: they’ve been living their whole life asleep simply following what’s popular in the moment instead of thinking for themselves.

The problem with just following the hot trend of the time is that you’ll always feel as if you’re playing catch up. One step behind the action. Often full of regret. Thinking for yourself allows you to carve your own path, and build your own trail forward (that others can of course join).

That’s why I think it’s worthwhile to at minimum question the status quo. Popular advice can certainly contain useful nuggets. But accepting it blindly can take you to weird places. One day you’re the naive optimistic college grad. A decade later, you’ve bounced between a bunch of now failed startups taking a lower salary because you were fine taking the “do whatever it takes role” because you thought “you were joining a Rocketship!”

Nonetheless, really do hope these ideas and questions are useful. Let me know what you think (and if they made you think!) — hi@nextplay.so.

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Controversial career advice

WARNING: THESE ARE JUST IDEAS. MAKE SURE YOU QUESTION THEM AND THINK FOR YOURSELF.

#1 - Don’t follow your passion.

I often hear people tell young people to follow their passion. I can remember the advice ringing in my years: “JUST FOLLOW YOUR PASSION!!” (Says the older person who has worked a few decades in some boring corporate job)

To which I ask, what is a passion? People talk about passions as if they are this sort of thing you are born with, but the reality I find is that passions can be developed over time.

I know plenty of people who have spent years “chasing their passion” only to realize that they could have been passionate about lots of topics. They thought they were doing the right thing because when they were 18 they felt like they were maybe interested in history. But years later, they are asking themselves: “why did I spend all this time reading about history when I was not actually that COMMIT MY WHOLE LIFE TO IT interested in it?”

I am not sure the Collison Brothers (the founders of Stripe) were born passionate about Payments APIs. They probably liked solving problems. Especially hard valuable ones that could be important. But this idea that they were born passionate about international finance law feels unlikely.

Sometimes you have to try loads of things to figure out what you’re good and what you like doing. The sooner you model this as a sort of rigid unchanging thing, the harder time you’ll have adapting in the world. That’s not to say you can’t have interests. And you can explore things you are interested in. But recognize there are levels of interests - maybe you’re interested in working with particular types of customers or solving certain sets of technical problems or collaborating with particular types of people. You can be passionate about any of those dimensions, it doesn’t have to be this holy unifying thing to uncover.

The reality is that working at a startup has many aspects. You could work at a startup aligned to your passion of “music” - but end up spending all your time in spreadsheets. Is that still following your passion?

Also, people tend to discriminate around the quality of your passion. Saving the forests? Great passion. Making money? Meh BAD PASSION. I don’t really think so. I think trying to make a lot of money, especially while you’re young, is a totally viable strategy. There are certainly drawbacks (maybe the job is extra boring or maybe you have to work long hours or maybe you are doing something bad for the world) but making money is a totally valid optimization.

#2 - Don’t ask for advice.

When you are figuring out what to do, it’s tempting to think that asking people for advice, especially accomplished people, is really useful.

Sometimes it is. Sometimes it’s useful to hear what people did with their lives or maybe what they would do in your situation. Sometimes this sparks new ideas.

But sometimes. And by sometimes I mean more often than you would think. Sometimes it leads to tons of wasted time.

A lot of advice is bad. A lot of people underestimate the impact of receiving advice. They think of themselves as good filters. People who can sort through the good and bad advice and figure out which to apply to them.

But if you’re in a state of openness, and you’re looking for what’s next and you’re really open to being influenced by new ideas, I think it’s so so easy to fall into a trap of more or less blindly accepting bad advice.

Why? Well I think it’s just hard to figure out what is good advice in the first place. And so you start labeling something as “good advice” versus “bad advice,” but in reality you have not even defined what makes something good versus bad. You end up confused and inconsistent with yourself.

This can go much further than people think. Ask founders of big companies. Why did you do this thing? They may think they thought about it for themselves, but in reality they outsourced a lot of the thinking to some advice they read in a book or saw on X. Outsourcing isn’t inherently bad, and relying on others isn’t inherently bad, but most advice is not universally true. It depends, is the reality. It depends on the specifics of your situation.

I liked this analysis of “Best Practices”:

I often hear people working on startups mention “best practices.” I have always wondered—what makes something a best practice? Who determined it was best?

YCombinator (YC) is one of the world’s most influential startup investors. They’ve seeded numerous now-public companies like Airbnb, Dropbox, Instacart, and many more.

Some of their most popular advice for founders: launch early, raise as little money as possible, and always talk to customers.

Would those count as best practices? Surely!

Sam Altman ran YC for five years. He helped create a number of those teachings. He left YC in 2019 to found OpenAI.

OpenAI did not launch any products for three years. OpenAI raised hundreds of millions of dollars before having a product. And OpenAI never really spoke with customers.

Now, OpenAI might be the fastest-growing startup in the history of the world.
So what are the best practices?

Advice beware!

#3 - You’re young you have plenty of time.

Do you?

I mean in some ways you do.

But I think some young people interpret this advice as they should just waste their younger years or procrastinate doing this thing they’ve always wanted to do.

Here’s a little insider secret (from someone who has lived a bit): it’s not like you’re magically going to have more time in the future.

What’s more likely is that you’re only going to get busier. Maybe you’ll get a family. Buy land. Own assets. Be tied down more. And as you get older, you’ll probably just get more tired and more sick and more injured. Not that life sucks. It’s great! There’s just stuff going on.

So if you want to…fly to New Zealand or run an Ironman or start a company or make a million dollars or do whatever…why not start now?

What are you waiting for? Really, what are you waiting for?

Lots of people make up all these excuses. I need to go to this school first or I need to do this job first or whatever. I think a lot of those excuses are pretty bad. Bad meaning they do not need to exist and do not actually lead to better outcomes.

You can do better. And you can do it now!

I think you should aim to do the best possible thing that you can think of…right now. It does not matter that you’re young. You do not have plenty of time. Life is long. Yes. But it often surely does not feel like it. Go and make the most of it.

#4 - You should not work at a startup.

Really? This is good advice?

I just think people should think before they sign up to work at a startup. If for some reason you think it is, I’ll be the first to tell you: Working at a startup is not all glamour. In fact, it’s quite mundane most of the time. Spreadsheets. Calls. Coding. Etc. Doing actual work.

If you want to do that, then great. I personally really like that stuff. And I like startups.

But they are not for everyone. I think only recently, in the past decade or so, startups have become really popular. They are now very much in the mainstream media. I think it’s led to a lot of people starting and joining companies that do not actually like working at a startup and would be better served elsewhere. I do not mean to gatekeep; everyone who wants to work at a startup really should. And everyone who is even a little bit interested in exploring also probably should.

But that does not mean it’s a great fit for everyone.

I think, for example, if you are looking to make a particular amount of money let’s say in the next five to ten years, you may be better off joining e.g. Big Tech or some other industry. There’s often more money and less work to do.

There are definitely tradeoffs but you should explore those more explicitly. I think people think that just because they join a startup they’ll tick off the boxes of “high impact” and “learn a lot.”

Most startups fail. If you join a startup, chances are it will fail (hopefully not!). When you join a failing startup, it’s not that you are guaranteed to learn useful skills. In fact, it’s likely that you’ll learn a lot of bad practices that you’ll one day need to unlearn. This may also happen at a big company, but I just don’t think it’s obvious the best way to learn is just to join a startup.

I know loads of people who would have made way more money if they joined a big company out of college instead of bouncing between startups. They joined those startups thinking they’d hit it big and that they’d leave with a big impact on their customers. The reality was not the case.

#5 - You could do whatever it takes

This one is more on the positive note, because it’s how I really feel, which is that I, without even knowing you, believe in you.

I believe you could do whatever it takes. That does not mean you will of course. But it does mean you could.

And that’s a much more empowering perspective I think than what’s common.

What’s typical, I hear, is something far more rigid.

YOU CAN ONLY GET THIS JOB IF YOU HAVE 5 YEARS OF EXPERIENCE

Meh. I think you could get it with less.

YOU CAN ONLY DO THIS WORK IF YOU LIVE IN THIS CITY

Meh. I think they will make an exception for you if you can prove your ability to do a really great jobs.

I think it’s best to avoid mass market arguments. You don’t care about the averages or the expectations. You are you.

Now the question is if you will lean into that and actually be you?

Will you actually think for yourself and do the creative problem solving necessary in order to land that dream job of yours?

Will you come up with the creative cold outreach? Will you take the paycut if needed? Will you invent a new role that’ll drive value for the business?

If you really want to make it happen, just know you could.

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Enough of this rant. I’ll leave you this week with a simple ending: think for yourself. You’ll be surprised by how far it takes you.