Olivia: Most people think winning is about being the toughest. But what if the secret to winning the world's most brutal marathon was actually deciding you were going to quit? Jackson: That’s a wild thought. It sounds completely backwards. Like training for a boxing match by learning how to get knocked out. Olivia: It’s the exact paradox we're unpacking today. And it’s at the very heart of Des Linden's incredible memoir, Choosing to Run. Jackson: Ah, Des Linden. She's the one who broke that massive 33-year drought for American women at the Boston Marathon in 2018, right? I remember that race—the weather was insane, like a full-on nor'easter with freezing rain and headwinds. Olivia: That’s the one. And what makes her story so compelling, and why the book got such high praise for its honesty, is that she pulls back the curtain on the brutal, unglamorous, and often ethically murky world of professional sports. This isn't just a story about running; it's about navigating a life of extreme pressure. Jackson: I’m intrigued. So where does this idea of 'quitting to win' even begin? I thought the whole mantra for elite athletes was 'never give up,' no matter what. Olivia: That’s what she thought, too. For a long time, her career was defined by that exact mindset—just pure, unadulterated grit. But it wasn't a grit she necessarily chose for herself, at least not at first.

Jackson: What do you mean, 'not one she chose'? She's a professional runner. Isn't choosing to run the entire job description? Olivia: On the surface, yes. But the book paints a really clear picture of her early motivations. It started with her father, who was incredibly demanding about sports. He instilled this relentless work ethic in her, summed up by his motto: "No shortcuts. Nothing is given, everything is earned." It was all about achievement, not necessarily enjoyment. Jackson: I can see how that would build a tough athlete. But it also sounds… exhausting. Like you’re always running to meet someone else’s expectations. Olivia: Exactly. And that carried over when she went pro and joined the Hansons-Brooks team in Michigan. Their whole training philosophy was built around something called "cumulative fatigue." Jackson: Okay, you have to break that down for me. 'Cumulative fatigue' sounds like a clinical term for 'being tired all the time.' Olivia: That’s pretty much it. The idea is to train in a perpetually tired state, running high mileage day after day, so that when you get to the final, grueling miles of a marathon, your body is already used to performing under extreme stress. It’s a philosophy that has produced some incredible runners, but it’s a brutal way to live. For years, Des just put her head down and did the work. She was tough, she was gritty, but she was running on someone else's terms. Jackson: So she’s following the formula, doing what she’s told, and it’s working, I assume? Olivia: It was. She made the 2012 Olympic team, which was a massive achievement. She was at the top of her game. And then came the moment that changed everything: the London Olympics. Jackson: The dream, right? The culmination of all that work. Olivia: The dream that turned into a nightmare. In the lead-up to the Games, she developed a nagging pain in her leg. She tried everything—physical therapy, cortisone shots—but it just got worse. An MRI showed nothing, so the pressure was on. She flew to London knowing she probably couldn't finish the race. Jackson: Oh, man. The pressure must have been immense. You have your country, your coaches, your sponsors all watching. What did she do? Olivia: She tried. She lined up at the start, but after just a couple of miles, the pain was unbearable. She had to step off the course. A DNF—Did Not Finish—at the Olympics. It was a public, humiliating failure. She later found out it was a femoral stress fracture. Her bone was breaking. Jackson: A DNF at the Olympics must have been absolutely crushing. How do you even begin to come back from that? Most people would just see it as a failure, full stop. Olivia: And she did, for a while. She was lost. But the book shows how that moment of public 'quitting' was actually the most important turning point in her career. It was the first time she truly took control. It forced her to stop running on autopilot and ask herself: Why am I doing this? Is this my dream, or someone else's? Jackson: So the failure became a catalyst for finding her own motivation. Olivia: Precisely. She started to rebuild her career, but this time on her own terms. She started to find joy in the process again. There's this fantastic part of the book where she talks about "Filthy Rich Saturdays." Jackson: 'Filthy Rich Saturdays'? That does not sound like the life of a professional runner. Olivia: It was her way of reclaiming the fun. Her agent had negotiated a contract with a $5,000 bonus for any race win. So, she and her agent would hunt down small, local races—Turkey Trots, Jingle Jogs—where she was basically guaranteed to win. She’d show up, crush the field, collect her bonus, and they’d joke about being 'filthy rich.' It was absurd, but it was hers. It was a choice. Jackson: That's hilarious. It’s like a heavyweight champion entering a local Toughman contest. But I get it. It’s about taking back control and finding the fun. Olivia: And it went beyond that. She started integrating travel and life into her training. She took a trip to Rome with her sister, running hard workouts along the Tiber River in the morning and exploring the Colosseum in the afternoon. She was proving to herself that she could be a world-class athlete without sacrificing her life. She was no longer just enduring the grind; she was choosing it, designing it, and even enjoying it. This new mindset, this new definition of resilience, is what set the stage for everything that came next.

Olivia: And that new sense of ownership, of choosing her own path, completely changes how she approaches the biggest race of her life. Jackson: The 2018 Boston Marathon. The race in the hurricane. Olivia: The very one. And the story of that win is one of the most incredible tales of sportsmanship I've ever read. She goes into the race feeling terrible. She's been dealing with a hypothyroidism diagnosis, her training has been inconsistent, and the weather is just apocalyptic. Freezing rain, 30-mile-per-hour headwinds. By mile six, she’s already thinking of dropping out. Jackson: So her big comeback story is already falling apart just a few miles in. Olivia: It seems that way. And then, around mile 13, something happens. Her main American rival, Shalane Flanagan, who was the reigning New York City Marathon champion, says she needs to make a quick port-a-potty stop. Jackson: Wait, in the middle of the Boston Marathon? The leaders just stop? Olivia: It’s a huge risk. The pack could surge and leave you behind forever. But Des, thinking her own race is already over, turns to Shalane and says, "Hey, it’s not gonna be my day; I think I’m going to drop out soon. Let me know if you need anything." She essentially offers to be her support crew. Jackson: She offers to help her rival? In the middle of the race she's dreamed of winning her whole life? That sounds like career suicide. Was she just giving up? Olivia: That’s what it looked like. Shalane takes the pit stop, and Des slows down, waiting for her and helping her work her way back to the lead pack. It's a pure act of camaraderie. But here’s the twist. In the process of focusing on helping someone else, Des completely gets out of her own head. She stops thinking about how miserable she feels, about the wind, about the rain. She just focuses on the task: help Shalane. And a funny thing happens. She starts to feel… good. Jackson: No way. The act of giving up her race is what saves it? Olivia: It’s the ultimate paradox. By letting go of her own ambition for a moment, she finds a new rhythm. The pack starts to break apart in the brutal conditions, but Des is just steadily moving forward. Before she knows it, she's near the front. She looks up and realizes she’s in a position to win. She had to "yank herself out of her old sun-splashed dreamscape," as she puts it, and adapt to the opportunity right in front of her. Jackson: That is an unbelievable story. It feels like something out of a movie. But it also seems to fit this larger theme in the book, this idea of playing the game by a different set of rules. Olivia: It’s the perfect example. And it wasn't a one-off. Her entire career became about this. She made the strategic, and at the time unusual, decision to hire her own agent, Josh Cox, to negotiate her contracts. His mantra was, "You don’t get what you deserve, you get what you negotiate." She was taking control of her financial future, refusing to just accept what was offered. Jackson: Which I imagine could create some tension with her team, the Hansons, who were used to being the gatekeepers. Olivia: Huge tension. And it came to a head later in her career. She publicly voiced her discomfort when the Hansons signed an athlete who was associated with a coach under a doping investigation. She knew it could cost her her sponsorship, her job. But she chose to speak out. It was another moment of choosing her own ethical line, even when it was the harder, riskier path. Jackson: So whether it's helping a competitor, negotiating a contract, or speaking out on ethics, it's all part of the same pattern. She’s running her race, on and off the course, on her own terms. Olivia: Exactly. She’s not just a passenger in her career; she's the one at the steering wheel. And all of those choices—the painful DNF, the Jingle Jogs, the ethical stands, the act of camaraderie in the pouring rain—they all lead her to that final, iconic stretch on Boylston Street.

Jackson: So it all comes together in that final mile of the 2018 marathon. She's not just running against the competition or the weather; she's running with the weight and the power of all these choices she's made over the years. Olivia: Precisely. The victory isn't just about crossing the finish line first. It's the validation of a decade-long journey to find her own 'why.' The book's title, Choosing to Run, isn't about the simple act of putting on shoes in the morning. It’s about choosing your terms, choosing your ethics, and choosing your own definition of success, even when—and especially when—it's the harder path. Jackson: It’s a powerful reframe of what resilience means. It’s not just about enduring hardship. It’s about the agency you claim within that hardship. It’s the difference between being a victim of the grind and being the architect of it. Olivia: That’s it perfectly. She writes about her high school coach telling her, "One day you’re going to be in position and say, ‘Fuck it,’ and pull the trigger on one of these races." That 2018 win was her 'fuck it' moment. It was the culmination of choosing to believe in herself, on her own terms, when no one else, not even she, expected it. Jackson: It makes you wonder, in our own lives, where are we just 'grinding it out' because we feel we have to, versus where are we truly choosing our path? Olivia: That’s the question, isn't it? We'd love to hear your thoughts on that. What's a moment you chose a different path, even if it was harder? Find us and let us know. The conversation is always richer with more voices. Jackson: This is Aibrary, signing off.