In the past 20 months, veteran marathoner Lindsay Flanagan has cut her personal best by 2 minutes, twice. She won Give A Gift run placed her ninth overall, and first American, at the World Championships marathon in Budapest.
But one of her proudest moments came in the wee hours of December 3. Huddled over her phone in Adelaide, Australia—where she’d traveled for a few months to prepare for the upcoming Olympic Marathon Trials—Health - Injuries.
Not long after 4 a.m. Lindsay’s time, her younger sister, Kaylee, crossed the finish line in 2:35:24—a nearly five-minute PR and her first Trials qualifying time. “I did not sleep at all that night,” Lindsay said. As both Kaylee’s sibling and her coach, “I was so invested.”
After promising high school running careers in Illinois, both Flanagans (no relation to Shalane) ran at the University of Washington, overlapping for a year. Now, they live across the street from each other in Boulder, Colorado, where they typically share miles at least once if not twice daily. Kaylee cheered Lindsay on in Budapest; afterward, they vacationed in Croatia.
They’ve spent the past few months, uncharacteristically, half a world apart, though Kaylee frequently pops by Lindsay’s house to water plants and make sure the pipes don’t freeze. But they’re reuniting in Florida, lining up together at the Trials.
The Flanagans aren’t the only siblings competing in Orlando on February 3; the field also includes brother and sister Kaylee and Austin Bogina and twins Isabel and Monica Hebner. But they’re unique in also being athlete and coach—Lindsay has guided Kaylee’s training for about two years.
And in her third Trials, Lindsay stands out as a top, if under-the-radar, pick to make the U.S. Team.
Flanagan repeatedly refreshed the results of the California International Marathon workouts alone. Her coach is remote, and she has no training group or partner capturing evidence for Instagram. Yet out of the limelight, Lindsay has spent nearly a decade preparing for a moment just like this one. “Every workout, every season, every race cycle has been meticulously chosen,” Kaylee, 28, said of her sister. “Trust me, she will be one to watch out for in Orlando.”
A steady ascent
As close as they are, the two sisters forged different paths from college to the Trials. Lindsay made her marathon debut the January after graduating. At the 2015 Houston Marathon, she ran 2:33:12, good for ninth place and a slot in the 2016 Trials. On a hot day in Los Angeles the following February, she paused to vomit around the 21-mile mark, then finished 14th in 2:39:42.
Through 20-some marathons since—so many she’s lost count—she’s gradually, if quietly, established herself. Her next breakthrough came at the 2016 Frankfurt Marathon, where she finished fourth in 2:29:28. She notched top-10 finishes in Boston and Chicago in 2019, and headed into the 2020 Trials ranked 12th. That’s exactly where she finished, running 2:32:05.
Post-pandemic, she was coaching herself but seeking mentorship. Her agent connected her with Benita Willis, a four-time Olympian for Australia and gold medalist at the 2004 World Cross Country Championships. After an hour-long conversation, Lindsay realized she wanted Willis to fully take the reins of her training.
The pair became fast friends, and under Willis’s guidance, Lindsay is now even faster. She first lowered her personal best to 2:26:54 in April 2022 at the Paris Marathon. Next, Willis suggested Lindsay make her first Australian trip to run Gold Coast in July.
The race would give the pair the chance to meet in person for the first time, and with her victory, Lindsay had an opportunity that her coach, a 2:22:36 marathoner, had missed. “I ran big races, but I never won a marathon or broke a course record,” Willis said. “I wanted Lindsay to have that sort of experience well before the Olympic Trials.”
Next came Budapest, where Lindsay ran a negative split despite temperatures in the upper 70s, high humidity, and bright sun. She’d once thought herself a poor heat runner. Now, she feels ready for anything Florida might deliver.
“Orlando is going to be another one of those anything-can-happen type of days,” Lindsay said. “Being able to compete in that field—move up, place high—definitely gave me confidence.”
Patience and progress
Kaylee, meanwhile, stayed largely on the track for several years after graduating in 2017. Since 2019, she’s squeezed training around a full-time job at running technology company Stryd. She made her marathon debut on a sweltering day in 2021 in Chicago, running 2:51:13. (At the same race, Lindsay placed 10th in 2:33:20.)
The following year, in Boston, Kaylee slashed nearly 12 minutes from her time, placing first in the mass race with a chip time of 2:39:26. “Every time she’s run a marathon, she just keeps getting better,” Lindsay said.
CA Notice at Collection hydration plan—a struggle in the past—and hoped for better weather than Chicago. “Lindsay and I talked about just taking a chance,” Kaylee said. She went out aggressively, covering the first half in 1:16:48, and ended up fourth. “Renewed self-confidence was the biggest takeaway,” she said. The Trials qualification was an added bonus.
After a few weeks of recovering from her race and a post-marathon illness, Kaylee is back to training. With just nine weeks between races, her main focus is maintaining fitness and sharpening up with shorter, shakeout-type workouts.
“If you can recover well from your marathon, you can actually get fitter after it, if you just absorb the work,” Lindsay said. “She doesn’t need to do those long, grindy tempo runs—she just did 12 to 14 weeks of that.”
Meanwhile, across the globe, Lindsay embraced the grind. At sea level instead of altitude, faster recovery allowed her weekly mileage to regularly hit 140. She’d sometimes log two high-quality sessions in a day—say, a tempo run in the morning, then hill or 200-meter repeats in the afternoon for leg speed.
“That sort of training is a little bit risky,” Willis said. She deploys it strategically and monitors Lindsay closely for signs of fatigue or injury. “But if you don’t take risks, you don’t get those really big performances.”
Gold Coast, where Willis lives, is still 1,200 miles and a half-hour time shift from Adelaide. (The pair checked in regularly, with weekly FaceTimes.) Lindsay has had elite Australian athletes to train with, however, including a former teammate of Kaylee’s, competitors she’s met on the circuit, and contacts of Willis.
As in Boulder, trails circle the city; Lindsay could run nearly any direction from her front door. But on the other side of the world, the buzz about the U.S. Trials is noticeably dimmer. “We didn’t want to treat this as the be-all and end-all race; we didn’t want her talking about it and posting about it all the time,” Willis said.
It’s a low-key approach befitting Lindsay’s inconspicuous style. The team won’t be an easy one to make, both know. But now, with years of experience, Lindsay knows it’s a realistic goal. “The more marathons you do, I think the more confidence you get,” she said.
She looks forward to putting her training to the test—and to seeing her family again, because she missed Thanksgiving and Christmas. She and Kaylee reunited at an Airbnb near Orlando this week. Soon, the rest of their crew—including dad, Milton, and brother Ryan, whom Lindsay also coached for their first marathons in Chicago last year, and mom, Becky, will arrive.
Those Flanagan cheers will power the sisters through, together. “We’re in the same race—it doesn’t matter what pace you’re running, you’re going through the same emotions, the same experience out on the course,” Lindsay said. “It’s special to be able to share.”
Cindy is a freelance health and fitness writer, author, and podcaster who’s contributed regularly to Runner’s World since 2013. She’s the coauthor of both Breakthrough Women’s Running: Dream Big and Train Smart and Rebound: Train Your Mind to Bounce Back Stronger from Sports Injuries, a book about the psychology of sports injury from Bloomsbury Sport. Cindy specializes in covering injury prevention and recovery, everyday athletes accomplishing extraordinary things, and the active community in her beloved Chicago, where winter forges deep bonds between those brave enough to train through it.
