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The first thought that entered my head when my employer commandeered my body for two months of endurance running—the first dribble from the cloud of dread forming above me—was Oh, man, my poor nipples.

I vividly remember slews of joggers crossing the finish line during Run to the Farside on a rainy San Francisco morning. It was the early 1990s. One man came in with bright blood streaked down his soaked white T-shirt. It was then, when I was just a wee pup, that my mother explained to me the chafed-nipple effect.

I was horrified. I’d gone to the finish line to score some free swag only to meet face-to-nipple with wet, bloodied zombie runners. Ever since that moment, running, to me, has been a foreign and frightening endeavor.

As if that wasn’t bad enough, when I told my coworker Jon that I'd been selected for long-distance trail running—like a tribute in the Hunger Games—the first thing he said to me was, “Right on, dude. Let me know if you need help taping your nipples.”

Wonderful.

Eight weeks later, I've logged more than 180 miles, gobbled fistfuls of après-run hamburgers, and re-awakened a 15-year-dormant knee condition. (. It sucks.) I even ran 12 miles (almost) straight, and my nipples, I'm happy to report, are fully intact. But does all of that make me a hero?

When I set out on this journey, my colleagues and I debated what, exactly, I’d have to do to officially overcome zero status in trail running. Running differs from most sports in that you can do it anywhere, anytime, with little to no gear. And unless you suffer from a debilitating physical setback, progress is dictated more by willpower than skill.

Our other newly minted heroes had skill-based goals. Matt had to haul himself up a 5.8 route on top rope; Scott trained specifically to scoot down a blue run.

But nearly everyone can run. So would running fast make me a hero? Maybe. But I’m a newbie—an off-road newbie at that—so I wasn’t going for speed just yet. Would covering a certain distance make me a hero? Probably not. Anyone with enough grit can run really, really far. Ultrarunner Scott Jurek and I are doing essentially the same thing, he just does it longer.

Finally, we figured it out. As most runners have told me, running is a lifestyle. To become a hero, I’d have to like running.

So back in early January, my main concern—apart from preserving my virgin nipples—was getting my mind in the game. For the sake of pretending I was on-track to become a hero, I conjured an alter ego for myself—one who doesn’t hate running or suck at it.

“Blackbird?” said my coach, associate editor Meaghen Brown, when I told her about my run-happy other self. “That’s just stupid.” (Meaghen, by the way, is a nationally-ranked ultrarunner of most miraculous origin. Apparently, five years ago she discovered—practically on accident—that she could crank out 30-mile runs on a whim.)

It was the morning after my first trail run. Because Meaghen told me to, I’d run up a system of icy trails that crisscrosses a sprawling park in the hills above Santa Fe.

The earliest I could get there was after work on a 30-degree, pitch-black evening in January. I selected what appeared on the trail map to be a simple circuit, then clicked on my headlamp, gloved up, and headed into the frozen wilderness.

Partway through, I glanced at the fancy GPS watch Meaghen had handed me earlier that day. The watch said I’d slogged just under two miles in about 20 minutes. Sometime around then, I decided I relate to fictitious figures like Superman more than flesh-and-blood freaks like Meaghen. I formed Blackbird’s call-sign while lost in mid-bonk delirium.

As Blackbird, I pushed through nearly three more miles that first night for a grand total of 4.84. Maybe that’s farther than you’d expect from a true zero. But I was under orders to record at least four miles, and when you’re under that kind of peer pressure to perform (I’ll say it: Meaghen can be intimidating) and half-mad from oxygen deprivation, putting one foot in front of the other is about the only thing you can do.

I returned to find the parking lot at the trailhead empty. Apparently I was the only person foolish enough to clomp around in the snow. And my body was begging for a cheeseburger. Without pausing to stretch or even catch my breath, I dove into my car, phoned in a desperate takeout order, sped to the burger shop, then beelined it home and gorged.

I’d say that whole ordeal pretty much sums up my two-month relationship with running. There were moments of pain—deep-tissue aches developed in strange places on long runs that stayed around for weeks. There were a few revelations—fleece-lined running tights was a big one. There were mornings when I awoke with strange urges to lace up the shoes and go further—dig deeper—than the day before. There were Zen-like moments of mind-body-soul numbness. And there was a lot of boredom. Try standing still on the sidewalk for an hour and a half watching traffic. Running is a lot like that.

I no longer fear running, but I don’t love it either. I probably don’t suck quite as much as I first did, not because I’ve learned a new skill so much as exercised my resolve. I will say, as someone who enjoys a challenge, that it’s hard to pass up the opportunity to find out how much ground you can cover when the running shoes are staring at you from across the room each day. I still haven’t found out, and I’m still running. Does that mean I've achieved hero status?

The second thing I did after that first run—after phoning in the burger order—was text my co-worker, Jon: “Remind me tomorrow to ask you about my nipples.”

How to Not Hate Running

1. Like Born to Run author Chris McDougall says: Go easy, light, and smooth before you worry about moving fast. Endurance and intensity aren’t the same thing. You can go for a long time and cover some real distance if you take it easy.
2. Try running in different types of shoes. I’ve run in cheap basketball high-tops with flat soles because the heel and ankle support feels amazing.
3. Keep your back straight. It makes me feel slower, but also more in control.
4. If you’re running in cold, dry weather, put on Chapstick. This was a revelation for me.
5. Find new places to run but get familiar with a specific circuit. Switching up the terrain helped keep my interest. But getting to know a spot inside and out (La Tierra, I own you) helped me measure my improvement more easily.
6. Bring something interesting to listen to. Music doesn’t really do it for me on a long run. The podcast Serial got me through some long, dark, cold miles. If you’re like me and your brow sweat somehow works its way into your ear and causes your earbuds to lose their stick, think about investing in buds with an ear brace, like any of these..
7. Go for gear with thumbholes. On long runs, sometimes my hands would get itchy (They’re probably not used to being away from a keyboard for more than an hour). I’d hook my thumbs into the sleeves of my running jacket and it helped stabilize my hands. Weird trick, but it worked.
8. Find people who like running and talk to them about it. The first week I started, I read Born to Run for inspiration during those long trail miles. Luckily, I also work in an office where half the people run regularly. They answered a lot of stupid questions and smiled through my misguided bragging.
9. Try jogging at random times. I’d jog home from the office sometimes (it takes five minutes), or start jogging in boots during a weekend hike. It’s a reminder that running is something you can do anywhere, anytime, for free, for pleasure. It doesn’t always need to be a task measured in steps, miles, minutes or ounces of sweat.