And Now It's Like This — On the Grief & Freedom of the Life that Chose You with Alison Matheny

There's a photo of Alison Matheny as a little girl, standing on the bow of a sailboat in a teal bikini, arms spread wide along the edge like she owns the whole ocean. Bare feet. Sun on her face. Taking up space. That's Al then, that's Al today.Alison is 44, single, never married, childless by circumstance. She splits her time between upstate NY and Florida, runs her own business, owns two homes, and is building a life entirely on her own terms.In this episode, we talk about: → Getting more comfortable with yourself as you get older, and being less aware of who you're not → Childless by circumstance — metabolizing grief into power, the ambiguous loss, and why society doesn't have a word for it that fits → The tension between being and doing and learning to go at your own pace without having to prove or perform → Girlfriends as mirrors — the relief of being in rooms where you are already known. ABOUT: Alison is a writer, artist and creative director + founder of the design, content and branding studio, BEST. She splits her time between upstate New York and the Gulf Coast of Florida. A Virgo sun / moon (Cancer rising), she loves to organize information and offers a smart, sharp perspective rooted in artistic integrity and communal equity. In her substack, May I Please Be Excused, she explores living as an undefinable woman. Previous writing exists in her post-collegiate Blogspot, Life of a Harpy (foreshadowing!), and early country essay collection, News from the North. Find her: @amath | @stayBESTFind her: @amath | @stayBESTSHARE THIS PODCAST with a girlfriend you're having these convos with IRL. Subscribe, rate, and review because the more of us who re-write the story of 40, the more powerful we collectively become!CONNECT: Substack: substack.com/@the40portal Website: the40portal.com | catherinezack.com IG: @the40portal CREDITS: Hosted by Catherine Zack | Edited by Ruwantha Gunasinghe © 2026 The 40 Portal. JOIN THE NEXT PORTAL RETREAT: June 17-19, in the Hudson Valley.