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.

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.

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.

If you enjoyed this episode, please take a moment to rate, follow, and share The Big Four Oh Podcast. It helps others find the show—and who knows, it might help someone else feel a little less alone in their own midlife transition.

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What if slowing down isn’t a setback, but a turning point? In this episode, Stephanie explores how midlife often presses pause on our hustle-filled lives - and what looks at first like a punishment is usually an invitation. Through powerful stories from past guests and her own experience, she unpacks how stillness can help us reconnect with what really matters—and why our worth was never meant to be measured by productivity. If you’ve been feeling the pull to step off the hamster wheel (or if life has already pushed you off), this episode offers the clarity, compassion, and company you didn’t know you needed.

In this episode, Stephanie explores the hard-earned wisdom that comes when midlife forces us to slow down. Whether through burnout, illness, or emotional exhaustion, many of us hit a moment where hustle stops working, and stillness becomes not just necessary, but enlightening. Drawing from past guest stories and her own experience, Stephanie reflects on how slowing down can shift our relationship with productivity, identity, and self-worth. Midlife, it turns out, might just be the invitation we need to listen more closely to the voice within—and discover a gentler, more honest way of being.

In this episode, you'll hear:

• Why hustle is so deeply ingrained for many of us—and how it eventually starts to break down
• The breaking points that forced past guests like Anna Brooke, Tina Bakehouse, and Jennifer Arthurton to stop pushing
• How quiet moments revealed surprising truths for Stephanie Rose and Steve Vincent
• The disorientation (and gift) of realizing you don’t really know yourself
• The difference between judgment and discernment—and why it matters
• How slowing down opens space to reconnect with long-lost parts of ourselves
• Stephanie’s personal journey toward redefining productivity on her own term

Slowing down isn’t the end of ambition—it’s the beginning of wisdom. In the stillness, we stop performing life and start living inside it. Whether midlife has already forced your pause or you’re just beginning to question the pace, this episode is a gentle reminder that your inner voice is worth listening to—and it’s probably not asking you to hustle.

If this episode resonated with you, please take a moment to rate, follow, and share The Big Four Oh with a friend. It might be just the nudge they need today.

Download Stephanie’s guide to the Ick to diagnose whether you or someone you love is suffering from this insidious midlife malaise. www.thebigfouroh.com/ick

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When Anna Brooke heard a mysterious voice say “burlesque dancer” during a meditation, she had no idea it would lead to a full-blown metamorphosis. Known on stage as the Reverend Legs Malone, Anna built a dazzling career that lit her up—until her body forced her to stop. In this deeply human episode, she opens up about listening to intuition, navigating grief, and learning to slow down. From the thrill of the spotlight to the quiet power of discernment, Anna’s story is a bold invitation to shed the shoulds and embrace joy on your own terms.

Anna Brooke is an author, speaker, and healing arts practitioner dedicated to helping people reconnect with their hearts and core creative spark. She is the author of the award-winning book Stripped Down: How Burlesque Led Me Home and co-author of WRITE! Your Guide to Revealing the Writer Within. She is also known as Rev. Legs Malone, a burlesque performer, show producer, educator and advocate who has been featured in Page Six, Buzzfeed, and Huffington Post. She has taught her transformational workshops nationally and internationally since 2010.

What happens when you finally listen to the quiet voice inside you—and it says “burlesque dancer”? Anna Brooke’s story is a masterclass in trusting your gut, embracing your weird, and healing from the burnout that comes from doing all the “right” things.

From her early days of internal tug-of-war between what she wanted and what others expected, to becoming Rev. Legs Malone on the stages of New York City, Anna shares how stepping fully into joy changed everything. When a back injury at 39 forced her to slow down, she began a deeper journey—this time into the healing arts, entrepreneurship, and the hard-won clarity of her 40s.

Episode Highlights:

• How Anna navigated a lifelong conflict between doing what she wanted and what she “should” do
• The serendipitous moment when intuition told her to become a burlesque dancer—and how she listened
• Creating and evolving the on-stage persona of Rev. Legs Malone
• The toll of hustle culture on her physical health, and the injury that forced a complete lifestyle shift
• Finding strength through slowing down, healing, and learning to trust herself
• Letting go of the “shoulds” and learning to follow discernment over judgment
• Why self-expression and joy are powerful tools for personal transformation

Anna’s story reminds us that our bodies don’t lie, joy is a radical act, and that sometimes the most powerful transformations come from sitting still long enough to hear ourselves. If you’ve ever felt pulled in too many directions or wondered what it might look like to trust your intuition, this conversation will inspire you to take the next right step—for you.

If you enjoyed this episode, please rate, follow, and share The Big Four Oh Podcast. Your support helps us reach more people navigating life’s beautiful, bumpy middle!

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