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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