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For the past several years, New York–based runner Greg Cass has wanted to run a marathon in under 2 hours and 30 minutes. That would be outside the feasible range of most recreational runners, but with a current personal best of 2:30:44, Cass has already come tantalizingly close. He’s still in his early thirties—the prime age for most marathoners—so it’s probably only a matter of time before he gets there.

Then comes the difficult part.

“A big question that always comes my way is: How did you get started into running?” Cass, who didn’t pick up the sport until after college, told me when I interviewed him last year for an article on competitive amateur marathoners.

“But the more I’ve thought about that, the question that I think is bigger for me is: How do I get out of running? Not because I want to, but because, ultimately, if I run a 2:29, will I be satisfied with that? Or will I say, ‘That’s a good time. Should I run a 2:28?’ This journey is as long as you want it to be.”

Where does the journey end? To some extent, it’s a question all runners who care about their finishing time have to ask themselves—from the aspiring Boston qualifier to Meb Keflezighi. But there’s an argument to be made that the issue poses a particular dilemma for the likes of who occupy the no-man’s-land between earning a spot in the first corral at Boston and qualifying for the U.S. Olympic Trials. These are the people who have no plausible shot at a professional career and yet compete at a standard that requires enormous discipline and sacrifice to maintain. If you’re a pro or collegiate runner, that sacrifice is easier to justify—there’s the external pressure of keeping a sponsor or a scholarship. The sub-elite athlete, on the other hand, has to decide for him- or herself when the five a.m. 15-mile threshold runs and ascetic living are no longer worth it. However, once you’ve reached that level of commitment, chances are good that it will have become an essential part of your identity (see: of pretty much any sub-elite runner), which makes it harder to voluntarily give up.

Your identity is also conditioned by the company you keep. For Blue Benadum, a 2:23 marathoner who, at age 37, knows he’s nearing the end of his career as a competitive amateur, bidding adieu to serious training would also impact his social life, such as it is.

While achieving a new personal best can provide a sense of validation for an ostensibly thankless pursuit, it’s also unlikely to make it any easier to walk away from serious racing. If anything, the opposite is true.

“All of the people in my life right now—all of my buddies­—are the guys that I go running with at six in the morning. The problem is that you start to create this dynamic with your friends where there’s this whole expectation of: ‘What race are you going to do next?’” says Benadum, who ran the Chicago Marathon last fall (his 59th marathon) in 2:27:05.

Benadum was a dedicated surfer for ten years before he took up running at age 26, and it’s a sport that he thinks he can eventually have a more casual relationship with. Not that he wasn’t competitive with his fellow surfers, but the nature of the competition was less rigidly quantifiable—it was just about who could ride the biggest wave. In distance running, there’s always the subtle tyranny of the clock; your athletic self-worth is measured in minutes and seconds. (Benadum’s : “59 marathons run (from 3:14 to 2:23).”)

To non-runners, the way certain devotees fuss about their personal bests can seem borderline pathological. After , a sub-elite-caliber runner based in Portland, Oregon, first ran under 2:30 at last year’s Boston Marathon, he documented the occasion with Reading it, one gets a sense of the degree to which Bromka was emotionally invested in his arbitrary (and definitely nonremunerative) goal: “Since last fall when I turned my attention to Boston I’ve run for over 200 hours…And I’ve asked so much from my wife and my baby boy. Those hours were spent selfishly investing in my goal, for this day…tears running down my face.”

While achieving a new personal best can provide a sense of validation for an ostensibly thankless pursuit, it’s also unlikely to make it any easier to walk away from serious racing. If anything, the opposite is true. Earlier this year, Bromka returned to Boston to improve his marathon PB by nearly a minute. He wrote

Of course, hanging up the racing flats isn’t any easier for top amateur runners who are forced to “retire” because of injury. After running track at Ohio University in the early 1990s, had a stellar second career as a nationally competitive marathoner two decades later. In 2014, at age 42, she came within two minutes of qualifying for the Olympic Trials with a personal best of 2:46:56 in the Philadelphia Marathon—her third sub-2:48 effort of the year. Not long after that, however, Husted suffered a disc herniation in her back. She hasn’t been able to do any hard training for more than a year, and it’s looking more and more like her days as a competitive marathoner might be over. Letting go has not been an easy process.

“I don’t think anyone understands what it feels like to have been really good—one of the top runners in the state and [as a masters runner] in the nation—to go from that to not doing it anymore. It probably took me eight months [to come to terms with it]. I kept hoping that I was going to be able to work through it,” Husted says.

Even though she’s well aware that every athletic career has an expiration date, Husted regrets having to quit when she did. She still runs regularly, and the ease with which she’s able to click off eight-minute miles makes her somewhat wistful about her latent potential. “It’s frustrating because I know, cardio-wise, I could do it!”

All the same, Husted is grateful for having had the chance to experience an athletic renaissance at an age when most pro runners have already retired.

“To me, it was just a gift,” she says. “Even now, just thinking about it makes me feel very nostalgic—a little sad, a little happy—all those emotions that go along with something that just was a huge part of your life.”

Anyone who thinks that sounds like a somewhat melodramatic assessment should speak with Blue Benadum. Rather than one big debilitating injury, Benadum’s main challenge of late has been finding the desire to dedicate hundreds of hours toward a chance at incremental improvement. The realization that he doesn’t have the fire he once did has been spiritually taxing, to say the least.

“When you’re looking back, and you know what it feels like to put it on the line every year, day in and day out, year after year, when you know what that commitment is like, and you’re that person that does that, to not have it is such a weird thing,” Benadum says.

So when is it time to pull the plug on competitive racing?

“I don’t even know what the right answer is. I just know that it scares the shit out of me. It’s a tough question for me.”