Join the other curious and interested readers of my Sunday letters. Sign up
Enjoy this piece? Get more like it every Sunday.Sign up

How to Get to the Life You Want Without Being a Superhero.

In the Fall of 2014, I sold everything I owned, bought a one-way ticket to Thailand, and got on the plane.

Before that, I worked a pretty normal job in Portland, OR. You’ve heard stories like this before, and the narratives all go pretty similarly: one day, I said, screw it, and I just jumped. Those people are inspiring as hell, but if you’re a normal person like me, not relatable. They’re superheroes. They jumped.

Except I’m not a superhero. I didn’t jump. Maybe it’s that I’m chicken. Maybe it’s that I haven’t actually done anything all that bold. But most likely, it’s that I’ve figured out a little secret on how to get yourself from the life you have to the one you want. The bold one. The unfettered what-if one.

That secret?

Take actions that make you a little bit scared.

Eleanor Roosevelt famously said “Do one thing every day that scares you.” It’s great advice. But it’s also terrifying, and non-specific. What one thing? How scary? Should there be snakes? I hate snakes!

Mark Manson beautifully argues that the key is to realize that your emotions aren’t real, that you will survive them, and that your actions are what really shape your life. It too, is brilliant advice. But if you’re driven by your heart, like me, that argument, beautiful as it is, never makes it past your heart into action.

But here I am, living in Thailand, picking the language up on the fly, and loving it. Somehow, I’ve done it. How did I do it?

These three simple steps.

One: Pick Your Mountain.

Take some time, reflect, and pick your mountain. That far off dream life. The career change. The bucket list. The thing you’ve always wanted to do. Whatever that big “if” is. (If you don’t have a big “if”, seriously consider the possibility that you’re already living your dream life, and just enjoy it.)

Once you have it, write it on a piece of paper. Take up the whole page.

Stick it on your wall.

Two: Ask How, Not If.

Now that you have your mountain, switch the question from if I could do ____ to how can I get to ____. Move your brain from dream-mode to problem-solving mode. What are the actual things you’d need to do to get from here to there? This will dull some of the romance. That’s ok. When you get there, the romance (and a whole lot more) will be there, waiting.

If this doesn’t come easily, it pick an arbitrary date in the future that you’ll be on your mountain. Then, think of that as a true thing that happened, and backtrack. How did you get there? What sorts of things did you need to do?

However, don’t worry about a plan or making a list. All you need to do is switch your frame of thinking. When you think about your mountain from here on, you’re not asking if. You’re asking how.

Three: Take Actions That Make You a Little Bit Scared.

On a regular schedule, once a week, once a day - whatever you will actually do, commit a block of time to take one action with the following characteristics:

  1. It scares you a little,
  2. It is small and absolutely achievable,
  3. It tangibly moves you toward your goal.

Importantly, your action should be completely self-contained. It doesn’t commit you to anything in the future, and it is completely separate from your big mountain. It’s its own thing.

Tomorrow, you can totally decide that the whole mountain is a terrible idea and walk away. But today, you commit to doing that one totally achievable, slightly scary thing.

Here’s an example.

I wanted to learn Parkour, but was way too scared to actually go do it. I was in my 30’s, not coordinated, and hopelessly unhip. Have you seen those videos? Those kids are buff and crazy and can fly!

But despite my terror and unhipness, I was honestly interested. So I tried the little-bit-scared technique. The first day, my action was to get online and look up if anywhere nearby offered lessons. I didn’t have to go to any classes or talk to anybody or anything. I just had to see if classes existed. I could do that. I did.

The next day, my action was to schedule a class. I wasn’t committing to go to the class, just schedule it. I could do scheduling. I did.

When class day rolled around, my action was to show up to the start of that one class. I could leave five minutes in and never come back, no problem. I wasn’t committing to anything more than showing up for the start. I could do that. I did.

Four months later, Parkour training was a 2 or 3 times a week part of my life, I loved it, I’d made friends there, and I could scale an eight foot wall and jump-roll off a six-footer. And on the way there, though I’d been a little bit scared, I’d never really been terrified.

Seem like magic or too simple to actually work? It’s not. It’s actually science.

How it works.

Tackling a challenge this way does something really neat: it uses your brain’s habit-forming mechanisms for your benefit. When you’re taking a small risk, your brain kicks in all those fight-or-flight chemicals. When you succeed, you get the rush of all the dopaminey feel good chemicals. What you’re doing, day after day, is training your brain that taking small risks is pleasurable. And once you’ve got a good groove going, your brain will start prompting you on its own. It’ll have a craving. It’ll say, “heeey, isn’t it about time we took another little risk on that dream life?”

The little bit scared is the absolute key, and it’s an emotion you can rely on to guide you toward your goal. If you feel a little bit scared, you can trust you’re actually moving in the direction of that big scary/awesome thing. But you never have to look it right in the eye. It never gets a chance to eat you. You just get up, take your little risk, succeed, and walk away.

Day after day, your little risks and little actions will add up. And before you’ve even realized what’s happened, you’ll find yourself standing on top of your mountain. You won’t have ever been terrified, and you won’t have ever jumped. It’s uncanny.

That's the secret.

That's how I got on the plane to Thailand. By the time I walked down the ramp, I’d been taking little-bit-scared actions for months, eating away at Move to another country. When flight day came, my day’s little-bit-scared action was to walk onto the plane. And it did feel a little bit scary - but also like every day before it. I could totally handle it.

That’s how you get the life you want without being a superhero. Those three steps. The little-bit-scared. Give it a shot.

The only thing you risk is feeling a little bit scared. You can totally handle that.

p.s. Since I wrote this, I've actually built a full course, based on the principles in this essay. It's called the Two-Year Life Plan Masterclass. If you dug this essay, you might want to check it out :)

Nah, I hate curiousity.