Always Try To Do It The Hard Way

On stage in Sydney, Australia. Get tickets to see me live in Europe and Canada here.

I was coasting on fumes when he asked me the question, so I don’t think I got the answer right.

To be fair, I was 90 or so minutes into being on stage for my talk in Sydney when I was asked: “If obstacles make us better, should we seek them out (or create them for our kids)?”

Like I said, I was a little fried, so I said something like: “Life is full of obstacles already, I’m not sure we need to go around creating additional ones.”

It’s strange that I said this because I was in the middle of doing the exact opposite… and it’s Chris Williamson’s fault.

He and I were talking in Austin back in May and he told me he had just gotten back from a speaking tour. “What kind of presentation did you do? Did you have slides?” I asked, curious because I was getting ready to head out of the country for my own set of theater dates (which, by the way, ​you can get tickets for my next stops in Europe and Canada here​) and Chris had spoken at some of the same venues I was going to be at.

“It was just me and a microphone,” he said.

This struck me because most of the talks I do—usually at conferences or to companies or to sports teams or soldiers—are not that way. You’re expected to have a slide deck that walks the audience through what you’re talking about. This extra work can really help drive your points home, but it’s also a bit of a safety net because you never forget where you’re at and you always have something behind you to keep the audience’s attention.

In any case, I’ve been doing this so long, it’s what I’m used to. It’s what I’m comfortable with. I know that the material works and I know I have it down.

Which is precisely why when I heard Chris say he was doing it alone with a mic, I thought, I want to try it that way.

Because it seemed harder and different.

General Sherman, the great military strategist and Civil War hero once wrote in a letter to his friend that he had an “old rule never to return by the road I had come.” Meaning, he favored blazing new trails to retracing his steps, picking the more difficult journey over the easy and familiar.

This is a great rule for life.

In ​Meditations​, Marcus Aurelius writes about holding the reins in his non-dominant hand as both an exercise to practice and a metaphor for doing the difficult thing. He wanted to get good at doing things both ways, at developing the ability to thrive in any and all situations. Naturally, we’re more confident where we are dominant. But the problem is you become progressively weaker in the hands or the areas that you neglect through this favoring.

I felt like I’d gotten comfortable with one way of speaking. Why not change it up?

Well, one reason is that to fail in front of 2,000 people in Sydney would have been pretty mortifying. But that reason was also pretty motivating!

Epictetus said when a challenge is put in front of you, think of yourself as an athlete getting paired with a tough competitor or a sparring partner. You want to be Olympic-class? “This is going to take some sweat to accomplish,” he said.

It took a lot of preparation–much more so than if I had done what I normally do. It also meant settling a lot of nerves. But these are features, not bugs of picking the harder path.

The point is: If it’s easy, you’re not growing.

Not everything that’s hard is good of course, but almost everything good (and worth it) is hard.

Think about all the things you’re good at. There was a time when you weren’t good at them, right? When they were hard. But you chose to work at it despite that initial difficulty. Even though it was frustrating, even though you had to fight the urge to quit, you saw a glimpse of goodness, you clawed out a bit of progress, you felt a glimmer of confidence, and you chose to keep at it. To keep pushing. And you grew from the fight against the resistance.

Even more, you found something on the other side of it all—a you that you realized you didn’t entirely know and had possibly never met. You learned something incredibly valuable about yourself: you’re capable of more than you know.

This is why the Stoics urge us to fight our tendency toward complacency. We have to keep pushing, adapting, shaking things up. We have to seek out challenges. Because would we know anything about ourselves if we never did?

I don’t just mean in big ways, but in small ways, too. Every day, you stand at little crossroads—decisions about how to do things and what things to do. Should you walk the 15 minutes to your meeting or take an Uber? Should you pick up the phone and have that difficult conversation or leave it to an email? Can you choose to do kick turns in the pool instead of push off? Can you choose to pick up a journal instead of your phone first thing in the morning?

As you weigh these competing options, always lean towards the hard one. Don’t be that person that Seneca talks about, the one who skates through life without being tested and challenged, who deprives oneself of opportunities to grow and improve.

Jump into the colder water. Have that tough conversation. Use the weaker part of your game. Take ownership where you can. Choose the more difficult option. Seek out the challenge. Lean into it.

Iron sharpens iron, after all. Resistance builds muscle.

Sparring partners make us Olympic class.

You’ll be better for it—not only for the improvement that comes from the challenge itself but for the willpower you are developing by choosing that option on purpose.

So, to revise my response to the question I was asked in Sydney:

Life is full of obstacles already, but if you want to be more adept at overcoming them, you should always try to do it the hard way.

It wasn’t until I was off-stage, coming down from the rush of trying something new in front of that many people, that I could fully understand that.

And now…I’m on to figuring out how I can challenge myself in November on these other dates. ​See you there​!