In this episode of In Confidence, Lisa sits down with Lindsay Shookus—former SNL producer, co-founder of Women Work F#cking Hard, and speaker—to talk about reinvention, resilience, and redefining success.Lindsay shares what it looks like to embrace uncertainty, build a “portfolio life,” and trust in your own talents, even through wobbly moments.

Key Takeaways:

• Why “normalizing wobbliness” is crucial when navigating career transitions or reinvention
• How to build a portfolio career based on energy, joy, and trust in your talents
• Strategies for making meaningful connections (even if you're introverted)
• Why showing up, especially when you don’t feel like it, can change your life

00:00 Intro

00:50 Meet Lindsay Shookus

03:48 What It Really Takes to Leave a 20-Year Career

11:03 Founding WWFH and Creating a Space for Women to Support Each Other

17:55 Authentic Connection, Showing Up, and Advice for Introverts

21:20 Letting the Universe Guide What's Next

22:52 The Portfolio Life: Reinvention, Speaking, and Creative Problem Solving

33:50 Normalizing Wobbliness and Discomfort

37:06 Final Thoughts and What She's Most Excited About

41:07 Outro

42:01 Disclaimer

Seen on Lisa in this episode: the ⁠Unbossed & Unbought Sweatshirt⁠, inspired by Shirley Chisholm's 1972 Presidential campaign slogan. Chisholm challenged societal norms to give marginalized groups a voice, becoming the first Black Congresswoman and the first Black woman to run for a major-party presidential nomination. Get yours today on ⁠GravitasNewYork.com⁠.

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