She Had a Week Between Tours, So She Ran an Ultramarathon

Margaret Glaspy was 17 miles into the race when she entered the pain cave.

It was always a question of when, not if, she would experience it. Her body was already jetlagged when she started, thanks to an international flight two days before. Tropical Storm Ophelia had been pummeling her with wind and rain throughout the entire race. (The message on the race’s website seems almost sadistic in hindsight: “Hopefully we are going to have a nice fall day!”) The course, which blended technical single-track trails, rolling hills, and double-wide gravel roads, could either be her best friend or hated enemy, depending on the terrain. None of it was a clear path, she realized. It was all boulders and roots — a lot of ways to fall.

But now, after around four hours of running in the Squatchayanda Trail Festival in New Jersey last month, Glaspy entered the pain cave, a visualization technique coined by ultramarathoner Courtney Dauwalter to describe how to mentally power through the part of a race where your rational, logical, craving-for-calories body is begging you to stop.

It was Glaspy’s first ultramarathon — defined as any race past the marathon distance of 26.2 miles — and consequently, her first cave. She pushed through it against her better judgment and ran 12 more miles, only stopping at 29 miles as it started to get dark. She thought about running more, but there was still an entire U.S. tour to think of.

For many people, the idea of running an ultramarathon even in the best training conditions is a mentally questionable decision. The training for a 50-miler, 100-miler or beyond can be long, grueling, monotonous, painful, and all-consuming. Tell a person you’re doing a marathon and they’ll reply, “Good for you!” Tell them you’re doing an ultra and prepare for a bemused “Why?” There’s strength work, foam rolling, speed work, mental training, stretching, more foam rolling, prep races, yoga, nutrition and hydration planning, and even more foam rolling. Ten-milers become “fun runs” compared to Saturdays, which are usually 20- to 25-milers for months on end. Social engagements are planned and cancelled. Families’ patience is tested. And sleep is the most idyllic part of the week.

It’s a big commitment for anyone. Glaspy — the California-raised, New York-based singer-songwriter, who just released her superb third album, Echo the Diamond — chose to take it on between UK and U.S. tours. “I would say I’m not a masochist,” she tells Rolling Stone at the start of her U.S. leg. “It was not some challenge of, ‘Let’s see if I can go on tour and then run as much as I can.’ It was more like, ‘I just have these few months where I can train for this the best that I can. I have this little window.’ So I just did it.”

When Glaspy’s mother, also a distance runner, was in her mid-twenties, she had run the Western States course, one of the most acclaimed and punishing ultramarathons in the country. “When I was growing up, there was always a running energy in the air,” Glaspy says. “We woke up one day and there was a poster of Jackie Joyner-Kersee on the wall. There was this tone set: ‘You will run, and it will be a part of your life.’”

Glaspy herself ran casually in her teens and twenties, attending Berklee College of Music before releasing her debut EP, Homeschool ,when she was 23 and signing to ATO Records two years later. Emotions and Math, her debut LP recorded in “only three or four days,” arrived in 2016 to critical acclaim. “I make records almost the way that jazz musicians do in the sense that it’s just like, I like to play it down and then done,” says Glaspy, who remembers Miles Davis and John Coltrane on steady rotation in her parents’ home. “I don’t really like going back and pondering about it. It just is what it is as soon as you play it.” Her sophomore album, 2020’s Devotion, found Glaspy expanding both her fanbase and palette, mixing electronic flourishes and keyboards with her candid lyrics.

But as her musical career ascended, it was only “in the last couple of years” that she had a realization: She needed to run longer. 5K races turned into half-marathons, which morphed into a desire to push herself for even longer distances. “I started to promote this new record and it just took over and I just said, ‘All right, I’m gonna do this,’” she says. “Going from 13 to 29 miles is a big jump, but in being a fan of the sport, it’s absolutely nothing.”

It raises the question: Why not go from a half-marathon to a marathon like most people?

“I didn’t really relate to marathon culture; I just couldn’t quite wrap my head around why it was fun,” she says. “It was like, go big or go home, which is usually the case with me.”

Soon she set on the idea of a 50-mile run. “It’s such a beautiful thing to do and to find an activity and a community that is completely separate from music, and just dive headfirst into it was such a treat for me,” she says. She chatted with ultramarathoner Addie Bracy, who would become one of her biggest running inspirations. “I asked her, ‘Am I crazy to try and run 50 miles?’ But she was like, ‘No, just go do it.’”

She consulted with Bracy on nutrition and gear, picking her brain on things both practical and philosophical. “It was unique to find this common connection with someone else who also is living this life as a touring rock star,” Bracy says. “She had a very healthy perspective of not necessarily forcing herself through 50 miles, but wanting to see what distance she could cover. She seemed to be really curious about what it felt like to just go try to run as far as she could.”

To train as best she could on tour, Glaspy would run outside first thing in the morning (“I’m not on the clock, essentially”) or sneak in a late-night treadmill run at the hotel after the gig, gradually increasing the time on her feet. Finding two straight hours or so of time was rare. “It’s tricky to decipher what’s giving me more life right now: the music or the running,” she says. Glaspy says she “dabbled” in different training schedules but ultimately, the demands of an album release cycle reinforced the “perfect is the enemy of good” credo. What started with supplemental strength training and leg exercises morphed into, “I have time right now, I’m going for a run.”

Which brings us back to the pain cave and Courtney Dauwalter, who Glaspy calls ”the greatest runner in the world” and “a legendary human being.” It’s hard to overstate the contribution and impact Dauwalter has made both on Glaspy and the sport in general. Her model of the pain cave is hard-earned from grueling stories that might sound apocryphal, but for Dauwalter are all too real. As Deadspin wrote in 2018, “Stuff she’s carried on through includes but is not limited to: blindness that came on in the last 12 miles of a 100-mile trail race and the subsequent falls and bleeding head injury, firehose vomiting, hallucinations, toenails falling off, 96-degree heat, hail, and quads so swollen they appeared to be swallowing her kneecaps.”

Glaspy was attracted to Dauwalter’s mentality of how to push through the worst moments — both physically and mentally — of a race and how to apply that mentality, as many ultramarathoners do, to everyday life. “This mentality that when your brain might say, ‘OK, you’re done. I don’t really like this anymore’ or ’You’re not good enough.’ The deep emphasis and concentration on your mental state has changed my life, and I found it via her world. [The pain cave] just comes up for me on a daily basis.”

In the end, Glaspy cut her planned 50-mile run off after mile 29. But she loved how it felt to push herself that far. The last 12 miles she ran felt “fucking terrible but really fun,” she says — a contradictory if normal feeling for ultra runners. “There was a moment when I was talking to her where Courtney looked at me and just said, ‘I can’t wait for you to get to the pain cave. I’m so excited for you.’ … There’s so much from embarking on this path that has translated to my real life and especially being in incredibly stressful situations and having attention directed to you. It just makes it all seem like, ‘Well, whatever.’” (“Her commitment to training for an ultra while on tour is inspiring,” Dauwalter tells Rolling Stone.)

Embracing the “pain cave” mentality was key not just for the run, but for Glaspy’s main job. “I was diagnosed with ADHD a couple years ago, and it’s hard for me to sit down for that long and just do one thing,” Glaspy says. “To not be able to sit in one place for very long starts to affect the [creative] process,” says Glaspy. “I’ve found that this artistic stamina for me, in sitting in one place a little bit longer, has helped a lot.”

She adds: “Usually, I find really beautiful things in my writing process if I just stay in the chair 20 minutes longer. Once you actually make it past this disturbing time that your mind wants to tell you that you’re worthless, you can do anything, which is really inspiring.”

After months of songwriting and just “staying in the chair,” Glaspy and her band recorded Echo the Diamond in three days, with most of the first takes being used as the final cuts. (Glaspy’s partner, guitarist Julian Lage, co-produced the album.) “I wanted the experience of ultimate preparation,” she says. “You have it already before you get in and then it’s like you’re taking a photo of what you’ve already done.”

Echo the Diamond blends Glaspy’s penchant for hard-driving rock (“Act Natural,” “Get Back”) with more plaintive material (“Memories,” a devastating, personal lament about grief and loss, was recorded in one take because it was “the only take that that I could fully get through,” Glaspy said on Instagram.) Elsewhere, the sad missed connections of “Irish Goodbye” and pointed lyrics of “Female Brain” — “Your life’s an all-inclusive cruise/While I’m out here getting stiffed and screwed,” she sings — makes Glaspy one of the more relatable songwriters in recent years.

“I crave to create something that doesn’t make you want to go somewhere else but makes you a little more OK with where you are,” she says. “I get excited in creating things that feel closer to my own reality, rather than making things that feel like a glamorized version that can tempt a listener into wishing that life was different.” Glaspy points to Elliott Smith as a songwriter who “didn’t make me want to wish that my life were different. It made me be at peace like, OK, someone else is feeling something similar to me.”

As Glaspy wraps up her U.S. tour, she’s already started to research more races and is “looking for the next pocket of time when I’ll be off tour to give it another go. I’m hooked.” For her first ultramarathon, she was deeply aware that the touring lifestyle and training lifestyle can be mortal enemies. “I’ve been living on a tour bus and you’re sleeping in a coffin every night,” she says. “Everything’s just a little bit weird.”

Still, she’s ecstatic with how it turned out and where she may go from here. “I just was like, ‘Let’s have fun and see what this world is about. I need to get it out of my system,’” she says. “But I’m so glad how it all went down. I just had a big smile on my face the entire day.”