Do the hard thing

For many months—okay years!—I’ve contemplated doing a certain really “hard thing.” I circled around the hard thing. I thought about it. I talked about it. But I didn’t start.

Meanwhile, my son was deciding where to go to college.

At the time, he had diploma-threatening senioritis, a well-paying job, and a local-college acceptance in the bag.

“The path of least resistance is a terrible teacher,” I told him.

I wanted him to do a harder thing, so I was quoting from Ryan Holiday’s cult classic The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. It’s a tiny volume—full of inspiring stories—that’s loosely based on the Roman philosophy of Stoicism.

A few weeks later, I found that boy of mine in his bedroom, packing for a faraway school he’d never visited. Where he will learn Greek and read the Great Books. And be in over his head much of the time. Marcus Aurelius will be his friend.

So, with my son out of the house, I had to tackle my hard thing. An excruciatingly personal essay that I’ve sent over the transom to the Modern Love editor at the New York Times.

Next, I’m facing a book proposal, for which no agent or publisher is waiting.

Why do I bother? Because pushing through the obstacles feels good! And because doing the hard thing—getting my message into the world—isn’t just for me. It will benefit others.

So. When you’re ready to do your hard thing, here are a valuable few tips, distilled from Holiday’s book.

Prepare to act. The conditions will never be perfect, but once you get started, you’ll gain momentum. Then, just keep moving.

Follow the process. Commit to moving forward, one step at a time. Even the hardest things become manageable when we replace fear with process.

Iterate. On the path to success, we will fail. Ask yourself, What can be improved? What can be done better? If you’re too close to see what’s missing, ask friends for help.

Persist and persevere. If persistence is short-term “dogged determination,” then perseverance is the long game—a matter of will. We need them both in order to gain traction.

Think of others. When we’re personally stuck, it can help to think about how pressing forward might make things better for other people.

Obstacles are everywhere. Are they not?

Holiday wrote: We shy away from writing a book or making a film even though it’s our dream because it’s so much work. We can’t imagine how we get from here to there.

What’s your hard thing? The project that has long sat dormant in your head. The thing you can’t ignore.

I invite you to start. Today!

And let me know how it goes!