💪🏻 Episode #46 - Courage & Crazy: What It Really Takes to Start Over in Midlife (Part 2) with Anna Fishman episode artwork

EPISODE · Jan 28, 2026 · 26 MIN

💪🏻 Episode #46 - Courage & Crazy: What It Really Takes to Start Over in Midlife (Part 2) with Anna Fishman

from Peace & Plenty in 20 ❤︎ · host Jeannine Deramo

💭What if the thing holding you back from your dream isn't lack of ability, but lack of permission? 🎙️ In this powerful conversation, I sit down with entrepreneur and risk-taker Anna Fishman  ⁨@oleganatravelboutique⁩   to talk about what it really takes to leave corporate safety and bet on yourself in midlife.We're getting raw and real about the fear that comes with entrepreneurship, the "courage & crazy" combo you need to take the leap, and why sometimes the scariest thing is actually the safest choice for your soul.🔑 WHAT WE COVER:➡️ Why courage isn't the absence of fear - it's taking action despite it➡️ The "safety net" mentality that keeps high-achievers stuck in corporate jobs they've outgrown➡️ Why entrepreneurship at midlife requires a combination of "courage and crazy" (and maybe a little more crazy)➡️ The real costs of playing it safe when your soul is screaming for something different➡️ How to give yourself permission to fail - because the biggest failure is never trying👉 THIS WEEK'S ACTION STEP:Ask yourself: "What would I do if I knew I couldn't fail?" Write it down. Then ask the harder question: What's the real cost of NOT trying? Sometimes the riskiest move is staying exactly where you are.And if you need expert guidance to take that risk...🔗 SIGN UP FOR a FREE Strategy Session with me: https://peaceandplenty.as.me/freestrategysession ✈️ Checkout the trip lineup on the Olegana Travel Boutique website https://oleganatravelboutique.com *Remmber to mention “Peace & Plenty” for $100 off your next travel booking with Anna!🔔 SUBSCRIBE to get new episodes every Wednesday - your midweek reminder that you're allowed to want more AND go after it, even when it scares you! ✨#peaceandplentyin20 #midlifeentrepreneur #courageoverfear #takingrisks #womenover40 #careerchange #startyourbusiness

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💭What if the thing holding you back from your dream isn't lack of ability, but lack of permission? 🎙️ In this powerful conversation, I sit down with entrepreneur and risk-taker Anna Fishman ⁨@oleganatravelboutique⁩ to talk about what it really takes to leave corporate safety and bet on yourself in midlife. We're getting raw and real about the fear that comes with entrepreneurship, the "courage & crazy" combo you need to take the leap, and why sometimes the scariest thing i...

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💪🏻 Episode #46 - Courage & Crazy: What It Really Takes to Start Over in Midlife (Part 2) with Anna Fishman

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This episode was published on January 28, 2026.

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