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A few weeks ago in a hotel room bathroom, my left big toenail fell off. I mean, I gave it a little nudge, as I had been expecting it to come off for a while, and I was leaving the next morning on a weeklong sea kayaking trip, and I thought it would be better to get it taken care of beforehand.

On said sea kayaking trip, I would be wearing water shoes instead of sandals. I made the switch before a raft trip in 2020, when I looked down at my toenails, hammered by a few hard years of running long distances, and said to myself, “No one else needs to look at these, especially not when they might have recently eaten, and would prefer not to vomit up all that food they worked so hard to masticate and partially digest.” So I got myself a pair of water shoes and hid my little gross toe caps from view, and have worn said water shoes on all river, lake, and ocean activities since then.

I have run lots of miles on roads and mountain trails since 2015, when I ran my first ultramarathon. I’ve done a few mountain 100-mile races, a couple 100Ks, and a bunch of shorter distance ultras, in addition to lots and lots of other miles up and down steep trails. Despite all of that time pounding the shit out of my feet, I managed to retain all of my toenails for almost seven years, until the incident in the hotel bathroom a few weeks ago.

When that big toenail came off, I thought, “So this is what it’s like,” and also, “Am I finally an ultrarunner now?” Because sure, I’ve gotten belt buckles and medals at the end of a race, but I felt like I was missing out on something. It just seemed like every other trail/ultrarunner had fewer than ten toenails—even when I asked on Twitter the other day:

I felt like I was doing something wrong. Should I work on running faster downhill? Run more miles? Steeper trails? Wear tighter shoes? What was the password to get into this secret, and also disgusting, club? Was I deeply flawed in some way, or did I have some sort of talent?

When I was in third grade, either my brother or I came home from the Scholastic Book Fair with a trade paperback copy of the 1987 edition of The Guinness Book of World Records. I spent so much time with that book that I can now close my eyes and see the font for “Longest Mustache” or “Most Conquests of the English Channel.” But the image that is forever burned into my brain is that of Shridhar Chillal, the Indian man who dedicated his life to growing the world’s longest fingernails, holding his left hand out to the side, showing his two-foot-long winding fingernails and his circular thumbnail. At that time, his fingernails totaled 143 inches in length.

Not long ago, I decided to google Shridhar Chillal, to see what he’d been up to for the past 35 years. Well, I learned, he grew his fingernails for a total of 66 years, until 2018, when they totaled 358.1 inches, and he cut them off for a Guinness video—or, actually, someone else using a Dremel tool with a grinding wheel cut them off. I could not watch the entire video of the manicure because fingernails that have been growing for 66 years are surprisingly (to me) tubular, which makes them look more like—actually, you know what, they’re fucking gross, and I felt like watching more than a few seconds of the video would give me nightmares, but if you want to watch it, like 10 million other people have, it’s [TRIGGER WARNING] .

In the 1987 edition of The Guinness Book of World Records, there is no entry for “Longest Toenails,” but if you search the Guinness World Records site for “toenails” today, the first result details that Louise Hollis of Compton . The second search result is “Fewest toenails possessed by elephant,” and the sixth result is “Most consecutive days to run an ultra marathon distance (female)” because the world record holder, Katie Spotz, who ran ultras on 11 consecutive days in 2021, mentioned losing her toenails.

The first time I can remember hearing of the phenomenon of ultrarunners losing toenails was in 2007, when I read about Jan Ryerse making [TRIGGER WARNING] , and also some friends’ toenails. This was long after Marshall Ulrich had all of his toenails removed in 1992 to deal with chronic issues from his high running mileage, and , “I like to think that I’ve got a reputation as an ultrarunner. But … I’d say an equal number of people know me as the guy with no toenails.”

Ask runners and they’ll tell you that you lose toenails from wearing shoes that are too tight, wearing shoes that are too loose, wearing shoes that are too narrow, accidentally impacting a rock or other hard object with a toenail, having a middle toe that’s longer than other toes, friction from a toenail rubbing on a tight shoe (possibly because of swelling), or just having toenails that aren’t trimmed down far enough. Podiatrist that toenails experience microtraumas from the toes hitting the toe box of the shoe when you’re striding and your foot is behind you, as the other foot is hitting the ground, and high mileage running basically equals a lot of cumulative microtraumas. “Runners can experience discolored nails, which is a collection of blood beneath the nail plate (subungual hematoma) as a result of microtrauma to the toe against the ‘shoe box,’” Rothschild said. Then the blood gets between the nail plate and the nail bed, and eventually the nail falls off. And then a few months later, it grows back.

But lots of miles doesn’t automatically result in losing all your toenails. At the end of the highest-mileage year I’ve ever had (in which I ran 26.2 miles 52 times), my toenails were intact—not necessarily what you might call attractive, but intact. I continued to wonder why I hadn’t lost a single one, and I kind of started to feel like I was being left out of some weird club.

Finally, last fall, after six years of running trail ultramarathons, I started training for The Rut, Montana’s steep-as-hell 50K. I did some steep runs, and after one with 5,600 feet of climbing in 11 miles, I noticed a little blood under my big toenails. Then after the race, a little more. A few months later, I could see the nail separating from the bed, and a few months after that, I could see that a toenail growing underneath was pushing the old one out. A few months later, the old toenail came off.

I don’t know what I was expecting, but the now-visible replacement toenail on my left big toe was not a pristine, shiny new-looking thing. It looks like it wants to be a toenail someday, like a little kid wearing an adult’s suit, the jacket all but falling off to one side. I mean, I don’t exactly talk shit to it, like “You call yourself a toenail? Ha!” but I kind of wonder if it will ever fill the shoes—ahem, toe-sock compartment—of the old one.

Brendan Leonard’s new book, Have Fun Out There or Not: The Semi-Rad Running Essays, .