Schooling Struggle

138: Uncorked Resilience - Ian O'Reilly


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Ian O'Reilly joins Pete and Brian for a fun conversation on a variety of topics. This episode centers on the idea of mastery, not just mastering a skill, but mastering how you live alongside other people. Ian's path from a New Hampshire restaurant to Napa Valley’s wine world is filled with moments of intense focus, curiosity, and discipline. Episode 138 is a thoughtful exploration of passion, people, and the quiet power of showing up for one another.


🍷 Mastery takes time. Ian breaks down the grueling sommelier certification process and what 10,000 hours of commitment really looks like.

🧠 Chase what you love, but not alone. Success is about surrounding yourself with people who lift you up and share your energy.

🤝 Service creates connection. Making people feel noticed and enjoyed is a quiet but transformative leadership skill.

🌍 Distance has a cost. Living far from home can open professional doors, but it can also result in disconnection from our closest people.

🌱 Giving back completes the journey. True growth isn’t just achieving expertise, it’s mentoring others and helping someone else cross the finish line.


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