Make Things That Matter

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

Listen on

Episode notes

Click here to directly email Andrew your questions, comments, and feedback! He reads everything that is sent in:

Show notes

  • 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