What if your life doesn’t “click” at 22- and that’s actually the point?In this episode of Choose the Bear, I’m joined by beloved illustrator, author, and creative mentor Lisa Congdon to talk about reinvention, creativity, and the myth that your best years have an expiration date. We start with a little friendly “beef” over her book A Glorious Freedom: Older Women Living Extraordinary Lives (40 is not “older”!), then go deep on what the book really offers: proof that women can begin again, at 40, 50, 70, and beyond.Lisa shares her path from elementary school teacher and education nonprofit leader to becoming a full-time artist in her late 30s, plus the practical, honest stuff that makes change possible: persistence, transferable skills, learning through failure, and getting comfortable with uncomfortable feelings.We also dig into her essential guide Finding Your Artistic Voice, why “practice + failure + practice” is the only real shortcut, how to stop perfectionism from strangling your work, and what it looks like to give fear a bear hug and move forward anyway.And because this is Choose the Bear, we connect it all back to the bigger message: women living whole, joyful lives on their own terms, regardless of relationship status, parenting status, or age.In this episode, we cover:- Why the “figure it out in your 20s” timeline is a lie- Starting a new career later in life (and why it can be an advantage)- The “beginner gap” and why most people quit right before it gets good- Perfectionism vs. becoming an “imperfectionist”- How to work with fear instead of letting it run your life- Finding your voice (in art, writing, activism, life)- Using art as activism + creating change through creativity- Why women in midlife have more power, skill, and wisdomIf you loved this conversation, please like, subscribe, and share, especially with a friend who needs the reminder that it’s not too late.

Comedian, writer, and podcaster Alison Leiby joins Choose the Bear for a wide-ranging, deeply honest conversation about horror movies, feminism, abortion, friendship, and choosing a full life outside of marriage and motherhood.

Alison is best known as the co-host of the hit podcast Ruined, where she bravely (and hilariously) listens as horror movies are explained to her so she never has to watch them. She’s also the creator of the acclaimed off-Broadway solo show Oh God, a Show About Abortion, which explores abortion with humor, honesty, and zero shame, and a writer on The Marvelous Mrs. Maisel.

In this episode, we talk about:

• Why horror is one of the most feminist film genres• The “final girl,” body horror, and why women understand fear differently• How Ruined became a cultural phenomenon• Abortion stories that don’t center shame or tragedy• Why women are still punished for not wanting kids• The pressure to frame childfree women as “sad” or “incomplete”• Friendship, collaboration, and building community outside the nuclear family• Being bad at something new, and why that’s actually the point• Navigating male-dominated industries as a woman• Why women don’t owe marriage, motherhood, or explanation

This conversation is funny, smart, deeply validating, and full of moments that will make you feel seen- whether you love horror, hate horror, are childfree by choice, undecided, or just tired of women being told there’s only one acceptable way to live.

🎧 Subscribe for more conversations about single life, independence, feminism, and choosing your own path.
Because everything you are is more than enough.

Burlesque icon Dirty Martini joins Choose the Bear for a powerful, hilarious, and deeply inspiring conversation about confidence, creativity, and claiming your body on your own terms. From the Vegas stage with Dita Von Teese to intimate performances around the world, Dirty shares how burlesque became her path to visibility, artistry, and radical self-love.

We talk about:
✨ How Dirty went from being told she’d “never be a dancer” to becoming a global burlesque star
✨ Burlesque as a political act—and why stepping onstage in your body matters
✨ Body pride vs. body positivity
✨ The magic of seeing real, diverse bodies onstage
✨ Advice for beginners who feel scared, uncoordinated, or “not dancer enough”
✨ Why taking a burlesque class can transform how you see yourself
✨ Gen Z, cringe culture, and the courage to try new things
✨ Dirty’s upcoming European tour and her work coaching performers

Whether you love burlesque, are burlesque-curious, or just want to feel more powerful in your body, this conversation is a gift.

🩸 Guest: Dirty Martini
Instagram: @DirtyMartiniNYC

🎙 About Choose the Bear
A podcast for women building joyful, bold, independent lives—single, childfree, and fully themselves. Hosted by activist and author Kat Calvin.

💬 Tell us:
What’s one thing you’d try if you weren’t afraid of being “cringe”?