Career Cheat Codes

Three things that with make you feel like you're playing life on easy mode.

Here are a few things that, in my experience, can make you feel like you’re playing the game of your career on easy mode. They still take plenty of effort, but they make that effort go further, so you end up moving quicker than people around you who are working every bit as hard. I’ll go through them in the order of impact they’ve had on my own life, though what works for me might not be the same for you. More on that later.

I wanted to write this because most of the career advice I come across is either too generic to be much use or comes from someone trying to sell you the one thing that happened to work for them. I've had a strange enough path of my own, and enough help from people who knew better than me, to end up with a handful of things I'd be happy to pass on. I'll go through them in the order of impact they've had on my own life, though what works for me might not be the same for you. More on that later.

1. Mentorship

I’ve been very, VERY fortunate in my life to find some incredible mentors. By mentor I mean someone capable and well-meaning who is invested in you going well, who you trust enough to call when you’re stuck, and who has no real reason to help beyond wanting to. It’s no exaggeration to say that having access to people like that has changed the direction of my life.

A mentor does a few things for you that turn out to be pretty fundamental to a successful career. The first is access to what’s called tacit knowledge. This is the deeply personal sort of knowledge that only comes from experience, the thing people often mistake for intuition. You’ll have sat with someone who can look at a problem and tell you, do this and here’s what happens, do that and you’ll get this instead, while you’re left wondering how on earth they know. That’s tacit knowledge at work. It’s different from the declarative knowledge we get taught in school, the facts and frameworks you can write down and revise for an exam. The declarative kind is exactly what a machine can be trained on, while the tacit kind still lives in people’s heads, which is why finding someone who has it is such a rare and valuable shortcut.

The second thing is that mentors open doors. Age is no guarantee of experience, but youth guarantees that some people will doubt you before you’ve said anything. Nobody likes to admit it, but we are hardwired to judge a book by its cover. I can think of countless networking events where I’d start talking to someone and watch their eyes drift across the room, already hunting for the person with a bigger wallet or a more useful address book. I believe this to be a key part of why my first business ultimately failed. I had a solid logical case for what we were selling and almost no ethos, the credibility that Aristotle set alongside logic and emotion in his famous triangle of rhetoric. What a good mentor can do is stand in as a proxy for that missing credibility. When someone respected is willing to vouch for you, people lend you a trust you haven’t yet earned on your own.

What took me a while to put into words is how you get someone to agree to this weird sort of social contract. It mostly comes down to checking your ego at the door. Mentors are drawn to people who are curious and easy to teach, and the quickest way to put one off is to spend every conversation trying to prove yourself. Most people get this backwards. They walk into a room with someone they admire and try to show how much they already know, when the thing that makes an experienced person want to help is the sense that you’ll take what they give you and run with it.

The way you do this, especially when you’re young and have limited experience, is simple. Ask good questions, then shut up and listen. Let other people be the most interesting person in the room. If you play this correctly, you’ll have plenty of time to assume that role yourself later. What goes around, after all, does in fact come around.

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2. Embarrass yourself

At eighteen I made the decision to quit my plans of being an engineer and study music instead. I always hated performing, so I don’t know what possessed me to make this decision, but anyway, one of the few things I did get from my liberal arts degree is the ability to deal with cringing at myself multiple times a day. This “have a crack”, “I don’t care what people think” sort of attitude has served me countless times as my career has developed.

You can’t reason your way to a good career in your own head. There isn’t enough information in there to know what you’re good at, let alone what you’d enjoy or who would pay you for it. You get that information by doing things and seeing what comes back. Every time you put something into the world before you feel ready, you learn something about yourself or the work that you didn’t have before. I get into this more in my conversation with Anne-Laure Le Cunff , whose book Tiny Experiments is built around exactly this idea.

I’ve started plenty of things that went nowhere, including but not limited to: multiple businesses, writing that nobody read, endurance sports events, a career in engineering, a career as a musician, and a career as a marketer. The few things that did work only happened because I wasn’t afraid to keep having a go.

If you’re in your twenties and you can’t remember the last time you embarrassed yourself, you’re doing something wrong. It tends to mean you’ve built a life that protects you from embarrassment, and a life like that protects you from learning at the same time. Nobody counts the opportunities they let pass or the skills they never built because they didn’t want to risk looking daft.

It’s harder than it used to be, in some ways. Everyone walks around with the equivalent of a megaphone in their back pocket, recording everything, with algorithms on top that can turn a small failure into something a lot of people see. That very rarely happens. The good news is there’s now so much online that even if your moment does go viral, and it probably won’t, people will have forgotten by the time you’ve got your head round what happened.

3. Be careful who you listen to

Before I get into this one, I want to say: yes, I’m aware of the irony of a 25-year-old giving people advice on the internet. You should probably ignore everything I say just to be safe.

I’m also aware that point one was all about shutting up and listening to other people. The distinction is that a real-life mentor, or someone able to give you specific advice for your exact situation (and yes, sometimes those people do actually exist online), is a different thing from what I’m about to warn you about. Anyway.

If you’re an entrepreneur, a pivoter, a generalist, one of those portfolio-career types, there has never been a better time to be alive. Information is more available than it has ever been in human history. If you want to learn how to do something, almost anything, you can, and most of the time you can do it for free. That’s the good news. The catch is that the same flood of free information comes with a flood of bullshit, and the bullshit tends to be louder and more confident than the good stuff, and much better at finding you. Listen to everyone on the internet for long enough and you’ll drown in a sea of contradiction and nonsense, holding ten opinions at once and trusting none of them.

A lot of the loudest advice out there comes from people who got a result once and decided their way must be THE way. They forget how much of any outcome comes down to luck, to timing, or to the fact that there’s usually more than one way to get where you’re going. This is what’s called survivorship bias. You mostly hear from the people it worked out for, never from the ones who did the exact same thing and got nowhere. It’s the lottery winner announcing that his strategy for getting rich is... play the lottery.

Here’s where it gets a little tricky, especially if you’re younger. The people who care about you most, your parents, older colleagues, anyone who’s done well and wants the same for you, whilst well-meaning, are working from a map of the world that was drawn in a different economy. Advice that made sense when a degree guaranteed a job and a house cost a fraction of what it does now can lead you astray, and it’s harder to ignore because it comes from someone you trust, with all sorts of other relationship dynamics tangled up in it.

This is also why parents, for all their good intentions, rarely make ideal mentors, and I say that as someone who got lucky. They tick most of the boxes. They mean well, they’re invested in you doing well, you can trust them. What you can’t guarantee is capability in the specific thing you’re trying to do, and the closeness of the relationship, with all its history and unconscious bias, puts you in a poor position to judge whether their advice is any good.

This is where the first two start to pay off. A real mentor is one of the few reliable filters you have, someone whose judgement you’ve tested over time. And the only way to build your own judgement, so you can tell good advice from confident nonsense, is to go and try things and see what happens for yourself.

Everything here worked for me, with my temperament and in my circumstances. The person who gets everything from a mentor might get nothing from making a fool of themselves on a stage, so part of it is knowing yourself well enough to work out which of these matters most for you. Most career advice fails for a simple reason: it was true for the person giving it, then handed to someone built nothing like them. I’d still argue these three are fairly universal, though. Find people you can learn from, get comfortable looking stupid, and keep some discipline about who you let into your head, and you’ll be playing with an advantage almost wherever you start.