I was out for a run last week, counting my steps like always.

One. Two. Three. Four.

It was cold, about to rain, but nice enough to get in a few miles.

Get to that tree. No the next. Catch that guy. You’ve got this.

I rounded the curve next to the golf course in Lincoln Park, just hitting my stride, when I came down on the side of my foot and sharply rolled my ankle.

I winced in pain and collapsed on the side of the path. I’ve rolled my ankle before but this was worse. The run was over and I hobbled a mile back home, my foot throbbing with every step.

Another setback.

See, the past couple of years have been all about getting back on my feet. Custom orthotics, physical therapy, special shoes, and so on.

I’ve been a runner most of my life but a few injuries here and there have left me discouraged and stagnant.

This year was supposed to be different.

But then I rolled my ankle and over the weekend I’d wondered if I might have ruined my chances at getting back to marathon pace this year.

Another freakin’ setback.

I’ve had a lot of setbacks over the course of my career. Both big and little things that made me put stuff on hold or go a different direction.

I’ve had so many setbacks.

I moved to Los Angeles after I graduated and slept on couches for a while. I only had $500 to my name and worked tirelessly to find gigs and get my name out there. I’d take the bus two hours to a show then back again several days a week, just to afford my tiny room and a few groceries to get by. After a year, I had made progress with gigs and gotten better - but I was still broke.

Our first year living in Chicago was miserable. My wife and I spent all of our savings just to afford our first apartment. We maxed out a credit card just so I could travel to gigs. I even got in a car wreck and totaled our car. It was rough.

I self-represented myself for a few years, convinced I would meet an agent who would want to work with me. And I did! An agency offered me a spot and promised me big things. Two years later, I had no gigs to show for it and the agency went bankrupt. I was back where I started.

I’ve had so many attempts at weekly shows in Chicago. (Including my current show MIND READER running right now in Lincoln Park.) This will be my seventh year doing a long-running show in the city. I’ve had venues close in the middle of a run, producers not hold up their end of the bargain, and shows have to close due to unforeseen circumstances. It often felt like the shows would come to a screeching halt, without any warning.

So many setbacks.

But you know what’s great?

Looking back I don’t view any of those moments as “setbacks” because every one of them ended up leading to something better.

Failing in L.A. didn’t mean giving up. It gave me the focus I needed to know how I could make this a success. I realized I didn’t want to sleep on couches forever but that I had what it takes to get gigs and be successful. I just knew it would take time. So I took a step back to reassess, get better, and make a plan.

The first year in Chicago might have been a disaster but it led to a year-long job doing my show at Disney World. When I totaled the car, we made a stupid decision to put the insurance money towards a new camera. My wife taught herself to take photos so we could promote the show. It worked. And now she’s opening her own photography studio in Chicago.

Having a failed experience with an agent made me realize to never rely on someone else. I had a fantasy in my mind that an agent meant I had “made it” and would suddenly be successful. But that’s simply not true. If anything, getting an agent just means you have to work even harder, only on different things. I found out that no one can work as hard on my behalf as I can. I’ll get back to you if that ever changes.

And my experiments with weekly shows has culminated in a current run right now. Every run has gotten better. Every performance was been an education. This year will be my longest run yet and hopefully we’ll keep it going for a while this time.

And as for my ankle…it’s luckily not a fracture. Just a sprain. My doctor tells me I’ll be running again by the end of the month. It wasn’t nearly as bad as it could have been. You’d better believe I’m going to conquer the Chicago Marathon again this year.

Every single moment of disappointment has led to something better. Sometimes the better moment happened within a week. Sometimes I didn’t realize it for years. But after I got through the initial phase of being “incredibly bummed out” I got over it and made the most of it. And that has always meant that I was better off than when I started.

Another setback…so that means something great is on the way.

Being Bad

I get my best ideas when I’m running.

For the first couple miles…nothing. It takes me a while to find my groove. So I count my steps and listen to the sound of Lake Michigan crashing against the path.

And I run farther.

I watch the other runners and imagine what their morning has been like. We’re out here together, but we keep to ourselves. That’s how we like it.

And I keep going.

Then, a breakthrough. My music fades away. Everything is a blur. I’m running, but my mind is elsewhere. 

Now I’m working.

I’m mentally rehearsing or writing my next Thursday Thoughts. I’m memorizing a list or dreaming up new bits for the show. I’m more creative than I’ve ever been.

I don’t look at my phone on a run. E-mail and Twitter can wait. I turn on Do Not Disturb and nothing gets in the way.

I have to run far away from my condo to get in the right mind set. I need to leave the dull pounding of construction and traffic behind so I can free my mind. If nothing else, I need an escape from those Washington Post notification alerts, each more scary than the last, that warn of the impending deterioration of the very foundation of modern American democracy.

So I run.

Or at least I used to.

But sometime last year I woke up and I couldn’t walk. I could barely stand. It was all I could do to get moving, let alone head to the airport and fly to my next show.

I had suffered an extreme injury in both feet and I had to stop running altogether. As a result, my daily routine changed dramatically. I had to learn to work differently. It was rough.

My physical therapist broke the news to me: “Your feet aren’t really built for running.” He promised me we could change that but that it would take a long time.

He wasn’t lying.

I’ve been trying to get back out there off and on all year long. Sometimes it feels good, but most of the time it’s agonizing. I’m still in pain and my new orthotics aren’t quite right. And even worse, I lost all my progress. I’m a horrible runner now.

I miss the open air and the silent camaraderie of my fellow runners. I miss the moment when I stop counting my steps and start feeling creative.

I miss running.

In the past few days I’ve noticed some slight progress. Slowly I’m feeling more positive about my training again. Will this be the breakthrough I’ve been waiting for?

I hate being bad at something. Especially something I know I was decent at once before. But I’m learning to let go of my expectations and enjoy the process. I’m starting over but this time I’m able to approach it with more experience than I did before. I’m doing it the right way this time.

It occurred to me this week that to have a career in a creative field you must be able to be bad at many things. At least for a while.

When I was starting out onstage I had no mentor or guidebook. I just knew I wanted to be a performer. So I copied other performers, hoping I’d find my own voice somewhere in the process. 

I stole their jokes and their style and wore it like a loose glove. Eventually I dropped the jokes that didn’t fit me and made changes to the ones that did. I stopped trying to be someone else and started accentuating the things I’m good at. I was constantly aware of what was unique to me and what wasn’t.

I still am.

But slowly, my imitation has turned to emulation. But it took years of struggle to get there. I had to give myself permission to question and fail and rediscover and progress on my own terms.

And that’s what I’m trying to do with my running now. As hard as it is, I know that getting good starts with being bad.