Become An Explorer To Figure Out What You’re Good At

A lot of success advice centres around the idea of “being honest with yourself about the things you’re good at and pursuing those things relentlessly”. We’re told that all successful people can be boiled down to a paragraph that states their chosen field and the personal style that allowed them to be successful.

Picture: Mike Laptev/Shutterstock

Here are some examples:

Bill Gates: entrepreneur and philanthropist; intensely smart; workaholic, ruthlessly competitive.

Christopher Hitchens: master wordsmith and essayist; contrarian; known for his outspoken views on Athiesm and his pugnacious writing style.

Steve Jobs: entrepreneur; design and product driven; known as a hard driving dictator who won’t accept anything less than 110 per cent.

Oprah Winfrey: media mogul; revolutionised the daytime tabloid talk show; philanthropist; known for her ability to get celebrities to open up about their lives on TV.

Woody Allen: writer/director/actor; known for raucous one liners, Marx-brothers inspired slapstick comedy, portrayal of neurotic characters in romantic comedies and a prodigious output of films over his long career.

Because successful people can be described in this way, the common wisdom goes, if you can figure out what you’re good at in a similar way it will help you be successful.

In order to figure out what you’re good at, a common piece of advice is: “Be brutally honest with yourself about it.” But the problem with this advice is that for most of us younger than 22, asking ourselves “What am I good at?” returns a blank response. Most success advice doesn’t recognise this, because it’s generally written by people who have spent a lifetime figuring out the answer to that question. By contrast, even the most prodigious 20-year-olds among us probably have been working successfully for five years, if that many.

When you’re 50, asking yourself “What am I good at?” probably returns at least a few responses. But the key is that those responses were developed from experience over the last 30 years. When they were 18, things weren’t so clear. People forget that you aren’t born with an Owner’s Manual tucked under your pillow that says “You are Joe Smith. Brown hair, blue eyes, very visual, cut out to be a painter, quiet and introspective.” So telling an 18-year-old to “figure out what you’re good at” is thoroughly non-actionable. We already know that we have to be good at something in order to be successful. The question is how do we figure out what that something is?

Some people conclude that because they can’t come up with an answer to that question immediately it must mean that they’re not good at anything. But thinking like that is stupid and unproductive. More importantly, it doesn’t actually reflect the reality of the process of becoming excellent at something. The nice thing about my position is that I’m old enough to know what I’m good at (at least partially), but I’m young enough to remember not being able to answer that question at all. Given this unique angle, I thought it might be useful to get down a few thoughts on how to figure out exactly what you’re good at.

Emulate Successful People

A common first step in figuring out what you’re good at is emulating successful people.

For example, I read a few biographies of Bill Gates when I was a kid and remember reading that he used to rock back and forth in his chair whenever he was thinking hard about a problem. This was supposedly a sign of his intense mental concentration and intelligence. For weeks after I read that I would try to rock in my chair as I thought about business ideas. I used to do the same thing with writing. When I was little my mum bought me the complete collection of Sherlock Holmes stories. For months after I read it, every time I sat down to write a story it would always feature a character called “Watson” and be written in British English.

In general, all of those assumed styles and traits tend to fade after a while. Sometimes trying them on can teach us as much about who we aren’t as who we are. Some people don’t recognise this and they try to force themselves to adopt the traits and the persona of the person they most admire because they think it will make them successful. This is not a good idea. Even if you do manage to force yourself to take on someone else’s characteristics, you’ll end up being inauthentic, and it won’t allow you to be your optimal self. What worked for them might not work for you. You’re a different person, in a different situation, in a different time.

“OK,” you might say, “but if I can’t actively pick what I’m good at then what am I supposed to do?”

This is actually a tough problem, because if you can’t actively pick, it seems like the only other option is to sit back and let what you’re good at come to you on its own. This feels wrong intuitively. You can’t sit around your whole life waiting for what you’re good at to show up out of the blue and change your life. You could wait your whole life for it to happen and die before anything ever does. Now you’re stuck between a rock and a hard place. You can’t pick what you’re good at, but you can’t sit back and allow it to come to you. As it turns out though there is a third option that we haven’t yet considered.

The Explorer Mindset

The third option is what I’d like to call the Explorer Mindset. In order to illustrate it, I’ll give you a quick example.

One thing that I’m good at is blogging. To get more specific, I’m good at writing long, philosophical thought pieces about startups and entrepreneurship. Because I know that I’m good at this, I’ve developed a pretty large audience of people who read my posts on a regular basis. Traditionally, someone in my position will tell you that in order to be a successful blogger you need to decide what you’re going to write about and what unique perspective you can bring to the table. But when I started blogging I had no idea that my niche was going to be these long-form thought pieces about startups. I didn’t sit down and say “Yes, I’m going to create DanShipper.com, and this is what I’m going to post about, and this is why people are going to like it.”

And so I wouldn’t suggest that you do that either. Just because I ended up with a niche, doesn’t mean that you should pick one. Instead of actively picking one, what I did was adopt an explorer mindset. I knew I wanted to blog. Throughout high school and into university I started a bunch of blogs and wrote on them. No one ever really read them, and I was a pretty bad writer. But I kept going, because I couldn’t help but write. I just liked to do it when I was bored. Then, one day, I stumbled across Hacker News and read a few of the articles. They really resonated with a lot of things I was thinking about. Most interestingly, they all centred around the software business — the other thing that I’ve always done with my free time.

I thought to myself: “Hey I think I could write something like that.” And so I started writing about startups.

As I kept writing, I started to understand what I could talk about well and what I couldn’t. It became clear what kinds of posts I was able to write most successfully. And gradually a style and subject matter of choice materialised. Now, two years later, I can confidently tell you that I’m good at writing this type of blog post. This might seem like pretty simplistic advice: it sounds like I just sort of stumbled across something that worked and stuck with it. But I think it’s a little more nuanced than just that.

The process is almost “lean” in the sense that you want to try a lot of different things, and develop a strong feedback loop for what works for you and what doesn’t. But what’s really key is to not be discouraged by the fact that if someone asks you what you’re good at you can’t give them an answer right away. You weren’t meant to be able to do that. Figuring out the answer to that question is an organic process that unfolds over a long period of time. Expecting anything else is unrealistic: no one’s powers of introspection are so strong that they can plumb the depths of their head and find an answer immediately.

The whole thing reminds me of sailors travelling uncharted waters during the Renaissance. Just like you can’t actively decide what you’re good at, Christopher Columbus didn’t sit around in his Spanish villa, point to a map and say “This is where America is!” and then claim that he discovered the New World. Just like you can’t say “I’ll wait for what I’m good at to find me”, Christopher Columbus didn’t decide that the location of the New World would just pop into his head some day and sit around waiting for it.

Instead, what he did was get on his ship and point it in a direction that looked promising. And every day he would look out across the horizon and say to himself “Do I see land?” And eventually after doing that for enough days in a row with no result, he got up one morning and saw a shoreline in the distance. And he sailed his ship straight for it.

That’s what it’s like to figure out what you’re good at — it’s like discovering land in uncharted waters. You have to travel long distances and constantly be on the lookout for land. And, if you see land, you have to head straight for it and chart every inch of it.

How to Figure Out What You’re Good At [Dan Shipper]

Dan Shipper is a junior at the University of Pennsylvania where he majors in philosophy. He’s currently working on a startup called Firefly that does co-browsing for customer support. He can be found on Twitter at @danshipper or on his blog.