How Unlearning Leads to Progress

November 10, 2023



How Unlearning Leads to Progress

How Unlearning Leads to Progress

Barry O’Reilly is the author of the best-seller “Unlearn: Let Go of Past Success to Achieve Extraordinary Results”. He also co-authored best-seller “Lean Enterprise” — part of the Eric Ries series. Barry is also Co-Founder and Chief Incubation Officer at venture studio, Nobody Studios, and faculty at Singularity University. Barry brings insights from his career at the intersection of business model innovation, product development, organizational design, and culture transformation. He describes how we can learn, but not make progress, and how some discomfort enables breakthroughs. He explains what questions can help you identify where you get in your own way, and what small iterative changes can do for you.


[02:22] Barry was interested in business, but a new university tech course takes him by surprise.

[04:49] Barry moves to San Francisco to work for which almost merges with Elon Musk’s first venture, Zip2.

[05:39] The power of technology in business becomes clear to Barry.

[06:28] When Barry finishes his degree his pre-signed job with an economic downturn.

[08:24] Barry moves to Edinburgh and starts building games for Sony, Sega, and Disney.

[09:20] Barry and team find out they have no idea how to scale when the business takes off.

[10:12] A 6-month sabbatical after 3 years working is Barry’s preferred working rhythm.

[11:44] Australia offers Barry an interesting opportunity in e-learning and ‘game’ businesses.

[13:02] On to London, Barry joins pioneers in the agile movement and shares the genesis story.

[14:34] Working at ThoughtWorks is a mad experience and a huge accelerator for Barry.

[15:11] The company was contrarian. It had no-rules, but a strong culture, setting the bar for how people showed up.

[16:12] Barry was inspired by Ricardo Semler, the young CEO of a Brazilian manufacturing company.

[18:17] Why have people report to you if they know what they’re doing?

[19:29] ThoughtWorks was 30% female engineers—publishing this data openly which supported diversity.

[21:16] Barry co-authors Lean Enterprise his first book.

[24:03] Barry’s ‘unlearning’ Aha! And Eureka moments in a Sichuan restaurant in San Francisco.

[25:40] Diagnosing limiting beliefs, ‘Unlearn’ as a system of experimentation.

[27:00] Asking the questions to find out where you’re stuck, what you’re afraid of doing.

[28:04] Barry offers piercing diagnostic questions--what 3-4 ideas do these questions raise for you?

[28:42] Barry’s personal example of using the Unlearn method.

[29:18] Figuring out what the outcome is you actually want.

[30:42] After defining the goal, experimentation starts with small uncomfortable shifts in behavior.

[33:48] Leaning into discomfort is one way to find breakthroughs.

[35:01] A senior bank executive used unlearning to stop making any decisions!

[38:10] Barry trains with BJ Fogg an innovators of behavior design, author of Tiny Habits.

[39:24] Defining your vision and future is key to finding focus and moving forward.

[43:22] IMMEDIATE ACTION TIP: You don’t just have one shot, you actually have many. If something didn’t go how you would like, that wasn’t IT. It was just a moment. Take the lessons from it—look for some hard lessons rather than to other folks as to why it didn’t work. Then dust yourself down and prepare for the next opportunity because it WILL arrive.


“Every single person that walked through that door was bright, talented, and capable. Culture has a huge impact on the way people feel comfortable and how it can also cause an adverse reaction.”

“I strive not to have anyone to report to me. I want them to own their work. I want people to be engaged and focused on their work. I'll be there to provide feedback, guidance, mentorship, whatever it is. That's my responsibility.”

“If you don't make diversity visible people will not know it's a place that they can be. They need to see people like them in leadership roles.”

“A lot of Unlearn is a system of experimentation. You are diagnosing limiting behaviors or beliefs and reframing them as outcomes that you want, and then experimenting to drive those outcomes.”

“The trick is doing uncomfortable things but making them smaller.”

“You never learn stuff, if you don't create the space for it to happen.”

“What can hinder us from creating an exciting future for ourselves, each one of us is the habits of the past.”