Unlearn Season One Finale: Ask Me Anything with Barry O’Reilly

In this finale episode of Season 1, Barry O’Reilly takes the time to answer questions posed by listeners. He reached out via social media and allowed his followers to ask him anything about himself, the podcast, or things they might want to learn and unlearn. Here are several of the questions posed and Barry’s answers:

Unlearn Podcast Barry O'Reilly Ask Me Anything

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Q: What takes up too much of your time? (Helen, Melbourne AUS)

A: Noisy notifications. Non-specific interruptions that disrupt my flow are frustrating for me. I don’t like interruptions or context switching because it limits my progress. [Listen from 2:35]

Q: How do you measure success for the podcast? (Caroline, New York USA)

A: I’m more interested in outcome-based measures of success. I know it’s going to be a great show when a guest says “I’ve never shared this story before,” or “I never thought of it like that.” Those authentic conversations, and getting feedback from listeners that they feel they’re part of them, are really powerful for me.  [Listen from 3:35]

Q: What has been the single best day of 2019, and why? (Prithi, Bangalore IND)

A: Being sent a photo of Serena Williams reading Unlearn. It was especially poignant because watching her story on TV was a major unlearning moment for me. It forced me to acknowledge that there were things I needed to adapt in myself to achieve the outcomes I wanted. Seeing her reading my book was inspiring and felt like a closed feedback loop. [Listen from 8:45]

Q: What’s the most counterintuitive skill to unlearn? (Simon, San Francisco USA)

A: Definitely the concept of coaching. We seem to think that only people who are underperforming need coaching. However, the highest performing persons have and actively seek out coaches to help them improve. Coaching has certainly been one of the best investments I’ve ever made in myself. [Listen from 12:45]

Q: Getting comfortable with being uncomfortable is nearly impossible for me. What do you do to actively get uncomfortable? (Kirstie, Helsinki FIN)

A: Actually, I feel uncomfortable if I’m not doing something uncomfortable! Trying new things, embracing counterintuitive ideas challenges your thinking and your belief systems, but it also gives you evidence that either supports your original beliefs or the new idea. I encourage you to think about one small step you can take on the edge of your comfort zone. How can you improve by even half a point? Get someone you trust to rate you in that area at the beginning, then at the end of one week. [Listen from 15:05]

Q: It’s often said that the biggest blocker to success is fear. How do you unlearn fear? (Adrian, Johannesburg, SA)

A: By thinking big but starting small. Taking small steps lets you find out what works and what doesn’t. You begin to feel successful. As you continue to take those small steps, you improve and gain momentum. You start to see change happening. This is the antidote to fear: small wins create belief, show evidence and make it safe to fail. [Listen from 22:45]

Q: What’s the best piece of advice you have been given? (Yuko, Tokyo JPN)

A: That you don’t only get one shot at success, there are actually many. Entrepreneurship for me is about life and life is about growth through learning experiences. When things don’t go the way you want, the trick is to pick yourself up, dust yourself off and get ready for your next shot. As my cousin Phillip would say: “if you’re still breathing you haven’t failed. Make sure you learn something for the next spin and go get inspired and do it again.” [Listen from 30:30]

What To Expect in 2020 

Barry says that in the next iteration of the Unlearn Podcast, he will be interviewing guests from a broader range of industries, not just technology. He’s excited to hear about their journey to unlearn. [Listen from 32:40]

Listen and subscribe to the Unlearn Podcast at
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