Ollie on Work

Ollie Henderson
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Conversations about work, AI, and careers - what's changing and what to do about it. Previous guests include Azeem Azhar, Daniel Pink, Lynda Gratton, Rory Sutherland, and Tyler Cowen. You can also read more about these themes in the Ollie on Work newsletter. Hosted on Acast. See acast.com/privacy for more information.

  1. Alex Hutchinson - Breaking Through Mental Barriers & Exploration vs Exploitation

    20/08/2025

    Alex Hutchinson - Breaking Through Mental Barriers & Exploration vs Exploitation

    Most people think they've hit their limits when they're actually nowhere close. Alex Hutchinson returns to the show for his second appearance. As a journalist and author, he's spent years studying the science of human performance. His first book Endure was a New York Times bestseller. His latest book, The Explorer's Gene, tackles a fundamental question: when do you push into unknown territory, and when do you stick with what works? Today we explore the exploration versus exploitation dilemma - the choice athletes face every race between sticking with proven strategies or risking everything to test new approaches. The same decision defines careers, businesses, and life. Alex's research reveals we have a "central governor" in our brains that pulls the plug early, protecting us from discomfort but also preventing breakthroughs. TALKING POINTS: Why the wall you think you've hit probably isn't your actual limitThe "central governor" theory and how your brain protects you by holding you backHow to build tolerance for uncertainty like elite athletes doThe exploration vs exploitation dilemma in careers and business decisionsWhy "optimism in the face of uncertainty" is the optimal mathematical strategyHow to know when to explore new paths vs exploit existing knowledgeThe danger of stopping exploration too early in life and career LINKS: The Explorer's Gene book Endure book Alex's writing at Outside Magazine Alex's LinkedIn Interested in me sharing insights on these topics with your team? Book a free consultation - HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    45 min
  2. Dror Poleg - Why Careers Are Becoming Like Showbiz

    13/08/2025

    Dror Poleg - Why Careers Are Becoming Like Showbiz

    Most people are still planning careers like it's 1995. But time itself has compressed. ChatGPT reached 100 million users in eight weeks. The Ford Model T took 70 years to hit the same milestone. Today I'm joined by Dror Poleg for his second appearance on the show. He's an economic historian and one of the sharpest minds thinking about how this time compression changes everything. His newsletter reaches 35,000+ readers across tech, finance, and government. Dror's insight? The predictable career path is shrinking fast. What used to be a 40-year "paint by numbers" journey is becoming more like showbiz - constant experimentation with uncertain outcomes. TALKING POINTS: Why the "productivity paradox" means more of our work will seem useless until it's suddenly valuableHow careers are becoming more like showbiz - constant experimentation with uncertain outcomesWhy AI might actually force us back to trusting what we can see and touch in personThe institutions that need to be completely rethought for a post-industrial economyWhy everyone will need to experiment constantly rather than following set career pathsHow energy constraints might save humans from being replaced by AI LINKS: Dror's newsletter: Old/New Dror's LinkedIn Interested in me sharing insights on these topics with your team? Book a free consultation - HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    34 min
  3. Lorraine Lee - Why Hard Work Isn't Enough, Building Visibility & Getting Noticed

    06/08/2025

    Lorraine Lee - Why Hard Work Isn't Enough, Building Visibility & Getting Noticed

    Most people assume hard work speaks for itself. Lorraine Lee knows that's a dangerous mistake. As the author of Unforgettable Presence and former LinkedIn editor, Lorraine has seen firsthand how talented people get overlooked while less qualified colleagues get promoted - simply because they knew how to make themselves visible. Today I'm joined by Lorraine to explore why visibility matters more than ever in our distracted workplace, and how to build what she calls "unforgettable presence" without feeling fake or inauthentic. Her insight? Your manager isn't noticing your great work - not because they don't care, but because they're too busy dealing with their own challenges to spot your contributions. TALKING POINTS: Why the "lottery ticket" approach to career advancement is doomed to failHow to build unforgettable presence that goes beyond just showing up in meetingsPractical frameworks for speaking up when you're put on the spotWhy introverts actually have advantages in building visibility (and how to use them)The difference between being heard and being the loudest person in the roomHow to advocate for yourself without feeling like you're bragging LINKS: Lorraine's LinkedIn Unforgettable Presence Interested in me sharing insights on these topics with your team? Book a free consultation - HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    31 min
  4. Christopher Lochhead - Finding Your Superpower & The Death of Knowledge Workers

    30/07/2025

    Christopher Lochhead - Finding Your Superpower & The Death of Knowledge Workers

    Most people think AI will just make their jobs more efficient. Christopher Lochhead thinks it's about to make their jobs extinct. Christopher returns to the show for the third time. The co-creator of Category Pirates and author of Play Bigger believes we're witnessing the end of the knowledge worker era - the 70-year period where getting paid meant applying existing knowledge to solve problems. AI can now do that better, faster, and cheaper than any human. But he believes this creates the greatest opportunity in human history. The future belongs to what he calls "creator capitalists" - people who use AI and human creativity to build entirely new things of value. TALKING POINTS: Native analogue vs native digital humansThe death of knowledge workersCreator capitalists - how to use AI and human creativity to build new things of valueDiscovering your superpower - what people come to you for and how to monetise itWhy creativity got beaten out of you Building your moat in an AI world LINKS: Christopher's LinkedIn Category Pirates Play Bigger The Existing Marketing Trap High Agency Interested in me sharing insights on these topics with your team? Book a free consultation - HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My Book Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    51 min
  5. Raj Choudhury – Work From Anywhere & Engineering Serendipity

    24/07/2025

    Raj Choudhury – Work From Anywhere & Engineering Serendipity

    Most leaders are still fighting yesterday's battles about remote work. But the conversation has already moved on. A few leaders have figured out that this isn't a policy question - it's a talent question. Today I'm joined by Professor Prithwiraj Choudhury, who recently moved from Harvard Business School to the London School of Economics. Raj has spent years studying what he calls "work from anywhere"—and his research shows this isn't about working from home. It's about fundamentally rethinking how you build and scale teams. His book, The World is Your Office, reveals why the leaders who master this shift will have access to global talent pools while others remain stuck hiring from a single city. TALKING POINTS: Work from anywhere vs work from home - why the distinction matters for talent strategyEngineering serendipity - how to make in-person interactions actually productive instead of accidentalPerformance management revolution - measuring output quality rather than input hoursWhy introverts finally get their chance to lead in distributed teamsThe isolation myth - practical solutions beyond just "bringing people back to the office"Digital nomad villages and the future of coworking spaces as learning labs LINKS: The World is Your Office book Raj's LinkedIn Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    28 min
  6. Eric Jorgensen – Career Leverage & Why AI Will Make The Best Better

    18/07/2025

    Eric Jorgensen – Career Leverage & Why AI Will Make The Best Better

    Welcome back to Ollie on Work after a six-month hiatus. I've been speaking to hundreds of people - founders, leaders, workers who've been laid off - trying to understand what's really happening as work fundamentally changes. Those conversations convinced me it was time to refocus. The podcast and newsletter have a new name, and I'm doubling down on what I think I'm uniquely placed to tackle: helping people avoid the career expiration trap and build momentum as the rules keep changing. Today, I'm joined by Eric Jorgensen, CEO of Scribe Media, the world's number one professional publishing company. He's the host of the Smart Friends podcast, author of The Almanac of Naval Ravikant (which has sold over a million copies), and a master at recognising genius in others. His upcoming book will share secrets from Elon Musk's entrepreneurial journey. TALKING POINTS: Career leverage - the craft of increasing your input-to-output ratio and why it changes everythingFour types of leverage - tools, products, people, and capital, and how to identify which suits youHigh agency as the single most important meta-skill for navigating career shifts in the AI eraWhy there's no "should" in career progression - breaking free from linear thinkingRecognising genius in others - how curation and connection can become your competitive advantageAI's impact on creative industries - why it will make the best better and more prolific LINKS: Eric's website Scribe Media The Almanack of Naval Ravikant George Mack's High Agency essay Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie on Work Ollie's LinkedIn Ollie on Work newsletter My book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    23 min
  7. Marcus Buckingham on the Hidden Signals of Career Success

    30/01/2025 · BONUS

    Marcus Buckingham on the Hidden Signals of Career Success

    This is the final episode in a mini-series focused on setting you up for a successful and fulfilling 2025. Today, I'm sharing my conversation with Marcus Buckingham, bestselling author and renowned research director, about understanding the hidden patterns that drive career success. Marcus spent two decades at Gallup Organization co-creating the StrengthsFinder tool, built his own coaching and education firm, and now leads research at the ADP Research Institute. He's the author of 10 books, including his latest, Love + Work, which explores how we can find meaning and fulfilment in our professional lives. TALKING POINTS: Identifying "Red Threads" - the unique patterns of work that naturally energise youAttention as a creative act - how paying attention shapes your career opportunitiesRedefining strengths beyond performance - understanding what truly motivates youThe specificity of professional passion - why precise activities matter more than broad interestsBrain chemistry and career fulfilment - how doing what you love changes your neurological response LINKS: Marcus's website Love + Work book Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    42 min
  8. Dorie Clark on Playing the Long Game in Your Career

    23/01/2025 · BONUS

    Dorie Clark on Playing the Long Game in Your Career

    This week, I'm resharing my 2022 conversation with strategy consultant, executive coach, and keynote speaker Dorie Clark. Dorie has twice been named one of the Top 50 Business Thinkers in the World by Thinkers50, and the #1 Communication Coach in the World by the Marshall Goldsmith Leading Global Coaches Awards, as well as one of the Top 10 Communication Professionals in the World by Global Gurus. She's also the author of several books, including the WSJ bestseller "The Long Game" (Harvard Business Review Press, 2021), as well as "Entrepreneurial You," which was named "one of the most important business books of the year" by Inc. magazine and one of the Top 5 Books of the Year by Forbes. I really enjoyed our conversation in which we discussed: Prioritising your time to focus on the things that matter mostThe importance of tracking your progressSharing your ideas with the worldBecoming a recognised expertExperimenting with new ideasNetworking LINKS: Dorie's website Dorie's LinkedIn The Power of Regret: How Looking Backward Moves Us Forward, Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE Ollie's LinkedIn Future Work/Life Newsletter My book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US).  Hosted on Acast. See acast.com/privacy for more information.

    39 min
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5
out of 5
19 Ratings

About

Conversations about work, AI, and careers - what's changing and what to do about it. Previous guests include Azeem Azhar, Daniel Pink, Lynda Gratton, Rory Sutherland, and Tyler Cowen. You can also read more about these themes in the Ollie on Work newsletter. Hosted on Acast. See acast.com/privacy for more information.

Information

  • Creator
    Ollie Henderson
  • Years Active
    2020 - 2025
  • Episodes
    240
  • Rating
    Explicit
  • Copyright
    © Ollie Henderson
  • Show Website
    Ollie on Work