Turning 40 and facing a midlife curveball

Anne Montgomery was one of the first women to anchor ESPN’s SportsCenter—but when her TV career ended abruptly at 38, she found herself broke, heartbroken, and convinced her best days were behind her. In this gripping and often funny episode, Anne shares the highs of breaking barriers in sports media and the lows of losing it all. What came next? A completely unexpected new identity that brought her more joy and meaning than she ever imagined. If you've ever faced a reinvention you didn’t ask for, Anne’s story will make you laugh, tear up, and rethink what it means to start over.

Guest Bio 

Anne Butler Montgomery has worked as a television sportscaster, newspaper and magazine writer, teacher, author, and amateur sports official. She worked for five TV stations, including ESPN where she anchored SportsCenter and finished her on-camera broadcasting career with a two-year stint as the studio host for the NBA’s Phoenix Suns. Montgomery was a freelance and/or staff reporter for six publications and has written six traditionally published novels. Montgomery taught journalism and communication skills in a Title I high school for 20 years and was an amateur sports official for four decades, a time during which she called football, baseball, ice hockey, soccer, and basketball games. Montgomery is a foster mom to three sons and a daughter. When she can, she indulges in her passions: rock collecting, scuba diving, and playing her guitar.

Turning 40 and facing a midlife curveball

Anne Montgomery broke barriers as one of the first female sportscasters in the U.S., working for five television stations—including anchoring SportsCenter at ESPN—during an era when women were barely visible in sports media. But when her contract wasn’t renewed at age 38, her career came to an abrupt halt, and she faced a painful truth: the industry thought she was too old to be on TV. What followed was a years-long identity crisis marked by debt, self-doubt, and the collapse of her marriage. And yet, as she shares in this remarkable conversation, Anne's midlife “derailment” led her to the most meaningful work—and relationships—of her life.

In this heartfelt and often hilarious episode, Anne recounts the twists and turns of a life that didn’t go as planned, but ended up exactly where she was meant to be.

Highlights from the episode:

• The moment in high school when Anne insisted on reading the sports—and never looked back
• How she trained as a referee in five sports to learn the rules and build credibility as a sportscaster
• What it was like to be the only woman in the locker room, on the sidelines, and at ESPN in the 1980s
• The brutal way she was pushed out of TV and how long it took to find her footing again
• The unexpected friendship that helped her shift perspective and stop feeling sorry for herself
• How returning to school at 42 led her to a 20-year teaching career that reshaped her identity
• The emotional story of how she became a mother—at age 55—to one of her former students

Anne Montgomery’s story is one of perseverance, reinvention, and unexpected blessings. What began as a pioneering career in sports broadcasting eventually gave way to an equally meaningful chapter as a teacher and foster mother. Her journey reminds us that losing what we thought we wanted can clear space for what’s truly meant for us—and that midlife transitions, no matter how messy, can become the catalyst for our most profound growth.

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