97: Lottery to Finish Line: Becoming a Marathoner in Chicago w/ Monique Sayles
My First Marathon27 Loka 2025

97: Lottery to Finish Line: Becoming a Marathoner in Chicago w/ Monique Sayles

Last fall, my mom and I ran a half marathon together in North Carolina, the first time she’d really laced up again in years. Not long after, I sent her a text about the Chicago Marathon lottery and told her to throw her name in just to see what happens. She wasn’t convinced, but she humored me. Months later, she opened her inbox to find an email that started with one word: “Congratulations.”

That moment kicked off an entirely new chapter. In this episode, we talk about her first marathon journey, from learning how to train smarter in her 50s to balancing early mornings, long runs, and a full-time job. She shares how getting sick years ago nearly ended her running for good, how she rebuilt her confidence, and what it felt like to finally cross the finish line in Chicago.

It’s a story about grit, patience, and what happens when a little lottery luck and a slightly pushy daughter change everything.

Follow along with the show:
👣 Personal IG/TikTok: @tay.says / @taysays
🎙️ Podcast IG/TikTok: @myfirstmarathonpod
📺 YouTube: @MyFirstMarathonPodcast
🌐 Website & extras: myfirstmarathon.co & myfirstmarathon.co/resources

Join my coaching waitlist! - https://docs.google.com/forms/d/1FPqUiZnVWcXaD-N14Qpcf4YL7zejJqcWEMUslPAAbw4/edit

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Jaksot(182)

150: Still Buzzing: A Same-Day Detroit Marathon Recap w/ Laren Gonzalez

150: Still Buzzing: A Same-Day Detroit Marathon Recap w/ Laren Gonzalez

When Laren Gonzalez shot me an email seeing if she could come on the show just hours after her marathon, my first thought was this person is insane (and I love that) and my second was YES!! Her runnin...

9 Marras 1h 5min

149: I Still Ran a Marathon: Redefining a Tough First 26.2 at Shamrock w/ Chris Field

149: I Still Ran a Marathon: Redefining a Tough First 26.2 at Shamrock w/ Chris Field

Chris Field spent high school playing football, where running was something he had to do rather than something he chose. That changed in 2024, when partway through a weight loss journey a friend of hi...

2 Marras 1h

32: Catching Up Before Taper! Life & Running Updates (Mini Episode)

32: Catching Up Before Taper! Life & Running Updates (Mini Episode)

I’m back with a Wednesday mini episode for the first time in a long time, and I’m catching up with you right after finishing my 20 miler for the Charlotte Marathon. I was supposed to be about eight mo...

28 Loka 16min

148: There’s Never a Perfect Time: Training for a First Marathon With Three Young Kids w/ Morgan Berry

148: There’s Never a Perfect Time: Training for a First Marathon With Three Young Kids w/ Morgan Berry

Morgan Berry spent her high school track days saying yes to whatever event her coach needed filled, but the marathon didn’t feel like hers until she watched her husband chase a Boston qualifier and fi...

26 Loka 1h 6min

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

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

Jess O’Brien became a mom at 18, and for years movement took a back seat to raising her son. Running didn’t stick the first time she tried it, but joining a CrossFit gym had built up her endurance, so...

19 Loka 56min

146: Follow Your Curiosity: 30+ Marathons, Ultras, and Chasing Sub-3 w/ Casey Cline

146: Follow Your Curiosity: 30+ Marathons, Ultras, and Chasing Sub-3 w/ Casey Cline

Casey’s running story starts with summer camping trips, where she raced anyone who would line up and tried her hardest to beat the boys. Thirty-plus marathons later, she’s a landscape architect and ru...

12 Loka 39min

145: Back Where It All Began: Running Sydney, the City That Became Home w/ Sandy Engler

145: Back Where It All Began: Running Sydney, the City That Became Home w/ Sandy Engler

When Sandy moved from Switzerland to Australia in 2020, she was quickly swept into the country's active, early-morning lifestyle, though running wasn't on her radar yet. That changed when the owner of...

5 Loka 51min

144: A Bad Race Doesn't Erase the Training: Unfinished Business w/ Steve Carrier

144: A Bad Race Doesn't Erase the Training: Unfinished Business w/ Steve Carrier

Steve Carrier spent decades lifting heavy and hated cardio for a long time. When COVID closed the gyms, he started hiking and kayaking with his wife, and after she mentioned a 5K she wanted to do, he ...

28 Syys 59min

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