When the Patriarchy Pushes You Out, Chart a New Course: Cheyenne Richards on Starting Over in Midlife
Cheyenne Richards
Award-winning author, sailor and adventure-seeker
Listen on: Apple Podcasts | Spotify
What do you do when the patriarchy pushes you out of your high-powered job?
If you’re Cheyenne Richards, you pack up your Plan B career, return to your first love—writing—and set sail (literally) into a bold new life.
Cheyenne is a former tech exec (and my former boss) turned historical fiction author and licensed sea captain. After serving as VP of Marketing at a startup she helped take public, she got pushed out by a leadership team of men who were intimidated by her intelligence and creativity (IMHO).
Instead of retreating, she took the opportunity to reinvent everything—her career, her relationship, and her definition of success.
In this episode, we talk about:
✔️Imposter syndrome in male-dominated workplaces
✔️Getting “fired”—and being thankful for it now
✔️Letting go of Plan B and finally choosing Plan A
✔️Reclaiming creativity and writing a novel about a serial killer in her family tree (yes, really!)
✔️Starting a new relationship on her terms
✔️The power of tiny steps and confronting discomfort in building real confidence
Whether you’re navigating your own career pivot, craving more freedom, or wondering if it’s too late to chase your wildest dream—this one’s for you.
About Cheyenne Richards:
Cheyenne is a former tech exec turned award-winning author, sailor, and adventure-seeker. After serving as VP of Marketing at a startup she helped take public, she made a bold midlife pivot—trading boardrooms for blue water. These days, she writes historical sea adventure fiction inspired by her own years cruising the coast of Mexico, and she’s now preparing to sail around the world on a boat being built in France. Her latest story follows a resilient woman navigating storms—both literal and emotional. Something Cheyenne knows a bit about firsthand.
Learn more and connect with Cheyenne:
➡️ cheyennerichards.com
➡️ Get her novel: The Prisoner’s Apprentice*
➡️ Download her free novella: The Navigator
Other Episodes You Might Enjoy 🎧:
Advice for Taking the Career Leap from 2x Pivoter Petra Langer
From Passion to Profession: Starting a Business in Midlife with Catherine Ziegler
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Disclaimer:
Belong Wellness and its members, managers, employees, contractors, and other agents or representatives are not licensed medical care providers and do not provide medical services or advice, including without limitation diagnosing, examining, preventing, treating, or curing any medical conditions. The information shared in this podcast is meant to be educational, not prescriptive. Please consult your medical doctor before making any changes to your diet or lifestyle. Further, the opinions of guests on this show do not necessarily reflect the opinions of Jessica or anyone affiliated with Belong Wellness.
