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#2 Barry O'Reilly: Unlearning and creating culture change

#2 Barry O'Reilly: Unlearning and creating culture change

Barry O'Reilly

Barry O'Reilly is a business advisor, entrepreneur, and author who helps people invent their future instead of fearing it. We start by dropping right into a powerful moment in Barry's career as an entrepreneur, and go on to cover everything from deliberate practice, to culture change within an organization, to how thinking we're right gets in the way of our own growth.

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Links & resources mentioned

  • Barry moving to America and the "American Dream" [0:06:11]

  • Experimentation as a lifestyle -- the kitchen table talk [0:13:14]

  • Navigating uncertainty [0:15:09]

  • Modeling behaviors [0:22:25]

  • Barry's hack to get new perspectives on problems you don't know how to solve [0:24:12]

  • Stumbling blocks in unlearning [0:26:36]

  • Bill Gates, Warren Buffett, and "time to think" [0:31:07]

  • Barry's personal reflection practices [0:33:11]

  • "We're trained for more" [0:35:19]

  • How do I know I need to unlearn? [0:45:27]

  • Hotseat: Barry puts Andrew through unlearning exercise on the spot [0:48:11]

  • Andrew's embarrassing insight [0:54:50]

  • The #1 obstacle to being a learner [1:00:04]

  • "Steve always got it right" [1:02:24]

  • How to make being wrong, feel good [1:04:09]

  • Debunking the 10,000 hour rule [1:07:49]

  • The levels of deliberate practice [1:08:24]

  • Applying deliberate practice to day-to-day life [1:15:12]

  • Building systems & countermeasures around yourself to be successful [1:18:42]

  • The origin of the Enliven podcast [1:22:44]

  • How to start a cultural transformation [1:26:37]

  • Barry's #1 hack for meetings [1:33:01]

People, companies, books, etc mentioned


  • "If something important comes up, I'll put it on my calendar. But I'm going to make time for thinking."

  • making two or three bets and exploring them well is better than making one hundred bets and half-assing them"

  • "I've been right a million times...and it's bought me jack shit."

  • "Innovation is new insight that leads to better action"

  • "we're building these systems that are so example that we don't even know how they work"

  • "in all our meetings we just talk about output, the things we got done...if we're going to be agile we have to talk about outcomes"

  • "organizational transformation is just the collective impact of individual transformation"

Lessons and key takeaways

  • how eager am I to get information that is contrary to my view?

  • the essentials to unlearning: curiosity, ownership

  • reflection is a habit of top performers

  • signs you need to unlearn

    • challenge facing and not living up to expectation

    • place you're struggling or avoiding a challenge

    • tried everything can think of and not getting results you want

  • What's the real outcome you're aiming for?

  • when frustrated with the obstacles, zoom back out to the outcomes in order to discover new things to try

  • we often know what to do...but we can't execute shared things on our own

  • Andy Grove and Steve Jobs "getting it right"

  • create and cultivate a personal board of directors to re-energize and gain new perspectives

  • always have agency for how we show up in a system—so it starts with us—and each of us has a

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Make Things That Matter
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