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First Marathon Story: You Can’t Pour From an Empty Cup: Finding Something Just for Me w/ Jess O’Brien

Writer: Taylor Sayles
Taylor Sayles
3 days ago
3 min read
Split-screen video call with two women in home offices, one smiling into a microphone; text says Jess O'Brien.

Finding Her Back to Movement

Jess was pretty active in high school. Two weeks after graduating high school, she found out she was pregnant. She gained a lot of weight and took a long break from movement. Years later, she had just started going back to the gym when COVID shut everything down. So instead, she decided to go with a couch to 5K program. She did a Turkey Troy 5K, hated every moment of it, and thought running probably wasn't for her.


When gyms reopened, she went back to the gym for weight lifting, and found CrossFit in 2022. There was some running, but not a ton. And then, she saw there was a marathon happening on her favorite stretch of road in New Hampshire. She knew she'd never have an opportunity to run it again, and she decided to sign up and figure it out later.


Deciding to Run a Full Marathon

Jess relied on an app for training, but had no education around long distance running. She ended up running up to 16-mile long runs without fueling at all, before finally realizing that fueling her runs would make all the difference. Her next run, fueling with two gels, she felt so much more energetic. She felt ready to tackle the marathon.


The race, which was a Revel race, was mostly downhill, but she distinctly remembers one large uphill in the middle of the race. She felt strong in her fueling, didn't really feel like she hit the wall, and had tears in her eyes as she ran further than she'd ever run before. She crossed the finish line sobbing, in disbelief that she had done this crazy thing. There was a lot of emotion tied to the finish line that Jess will never forget.


The Marathons Since

After crossing the finish line of her first marathon, Jess was convinced she'd never do it again. Everything hurt, in ways she had never experienced before. But she kept thinking about it. Another marathon in the area passes right be her dad's house, was relatively flat...and she decided to sign up. It was in the fall, giving her the ability to train through the summer (which she much preferred). Race day ended up being much hotter than expected (87 degrees Fahrenheit), and the race ended up not being what she hoped.


Jess left that race wanting redemption. The rest, as they say is history. Jess has run seven marathons since then (with a redemption race!). She ran races in the pouring ran, raised $16,000 to run the Boston Marathon, and won an entry into the Sydney Marathon.


Lessons Learned

  • You can't pour from an empty cup.

  • You can do the hard thing.

  • You can't control race day conditions.

  • You are more capable than you believe that you are.


Want to hear Jess tell the story herself? Listen to the full episode now: You Can’t Pour From an Empty Cup: Finding Something Just for Me w/ Jess O’Brien— available wherever you get your podcasts.


Listen to my most recent mini episode: Survival Guide To Running Your First Marathon



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Follow along with the show:

👣 Personal IG/TikTok: @tay.says / @taysays

🎙️ Podcast IG/TikTok: @myfirstmarathonpod

📺 YouTube: @MyFirstMarathonPodcast


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