

Ollie on Work
Ollie Henderson
Helping ambitious leaders avoid the Career Expiration Trap.I'm Ollie Henderson. I've spent 15+ years founding businesses and I'm still experimenting today. I've learned what keeps leaders ahead. Entrepreneurial skills that create momentum regardless of what shifts.Real conversations with business and thought leaders like Daniel Pink, Rory Sutherland, and Lynda Gratton about leading multigenerational teams, implementing AI strategy, and building what comes next as the rules of work change.No generic future-of-work trends. Just practical insights for leaders who refuse to expire.You can also read more about these themes in the Ollie on Work newsletter. Hosted on Acast. See acast.com/privacy for more information.
Episodes
Mentioned books

Jul 24, 2025 • 28min
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 labsLINKS:The World is Your Office book Raj's LinkedInInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy 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.

Jul 18, 2025 • 23min
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 prolificLINKS:Eric's websiteScribe MediaThe Almanack of Naval RavikantGeorge Mack's High Agency essayInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie on WorkOllie's LinkedInOllie on Work newsletterMy 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.

Jan 30, 2025 • 42min
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 responseLINKS:Marcus's website Love + Work bookInterested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy 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.

Jan 23, 2025 • 39min
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 ideasNetworkingLINKS:Dorie's websiteDorie's LinkedInThe 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, HEREOllie's LinkedInFuture Work/Life NewsletterMy 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.

Jan 15, 2025 • 34min
Daniel Pink on making bold career decisions using mental time-travel
This week, I'm resharing my conversation with Daniel Pink, in which we explore how to make better decisions using mental time-travel.Dan is the author of five New York Times bestsellers, including his latest, The Power of Regret: How Looking Backward Moves Us Forward, published this month. His other bestsellers include When and A Whole New Mind, To Sell is Human, and Drive, which brought the ideas of intrinsic motivation within business and management to the masses. His books have won multiple awards, have been translated into 42 languages, and have sold millions of copies worldwide. Our chat was packed with insight, and like all the best podcasts I’ve hosted, I learned loads. We discussed why the philosophy of ‘no regrets’ neither reflects reality nor is desirable. As well as breaking down the main types of regret and how we respond to them, Dan explains how harnessing the lessons we learn from these experiences can serve us well in the future and why anticipating regret can be a useful mental model for decision making in the present.We explore why so many people look back on their careers and wish they’d be bolder, whether by going it alone, starting a business or speaking up more. Dan also shares why he became fascinated by the topic in the first place, including what he wished he’d known about maintaining connections with people earlier in his career.Finally, we cover some broader trends related to the future of work, including the pros and cons of remote and the office and whether our work/lives are destined to be defined by independence and autonomy. LINKS:Dan's websiteThe 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, HEREOllie's LinkedInFuture Work/Life NewsletterMy book, Work/Life Flywheel, was shortlisted for the Business Book Awards 2024. You can order your copy HERE (UK) or HERE (US). This is what Daniel Pink says about it:"Creating new opportunities requires fresh thinking. With the Work/Life Flywheel model, Ollie Henderson gives you the system you need to make bold changes in your career and the motivation to share your ideas with the world.”aniel Pink from 2022, when we explored how to make decisions using mental time-travel. Hosted on Acast. See acast.com/privacy for more information.

Jan 9, 2025 • 37min
Grace Lordan on Thinking Big in your Career
This week we're revisiting a standout conversation with Grace Lordan, Associate Professor in Behavioural Science at the LSE and author of Think Big.Grace shares her approach to goal setting, building resilience, and embracing uncertainty as essential ingredients for creating the future you want.Whether you're reflecting on your career path or planning new habits for 2025, this episode offers practical steps to help you think big and take small actions that make a lasting impact.Talking Points:Building Resilience: Learn how to reflect on your energy levels and interactions to reduce emotional drain and preserve your well-being.Three Types of Resolutions: Grace outlines three categories - quick wins, skill-building goals, and habits to quit - and explains how timing impacts success.The Role of Luck: Discover how to increase your chances of serendipitous opportunities by expanding your network and putting yourself out there.Thinking Big: Grace emphasises the importance of focusing on long-term goals and the small steps that make them achievable without overwhelming your life.Links:Grace's LinkedInThink Big: Take Small Steps and Build the Future You Want Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HEREOllie's LinkedInFuture Work/Life NewsletterMy 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.

Dec 17, 2024 • 12min
AI Agents: Our new colleagues
This week I share some thoughts on why 2025 will be the year of the AI Agent.Plus, how it will affect roles in B2B marketing, learning & development, and law.Finally, I share some advice on how you can prepare your company and team.READ:AI Agents: our new colleaguesWork Redesign: Humans + AI AgentsLINKS:Follow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy 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.

Dec 11, 2024 • 35min
David Landman on The Long Exhale and Leadership in an AI World
This week, I’m joined by David Landman, former Goldman Sachs executive turned advisor and educator.After two decades leading performance management, talent mobility, and talent development at Goldman, David embarked on what he calls The Long Exhale - a transformative sabbatical that reshaped his outlook on work and life.David shares his journey into purpose-driven work, reflecting on what it means to create a more sustainable, inclusive, and fulfilling workplace.Whether you’re rethinking your own career or looking for strategies to lead in the AI era, this episode is packed with actionable insights and thought-provoking ideas.TALKING POINTS:David’s transformative career pivot.The intersection of AI and human connection - how technology can amplify humanity in work.Building a culture of gratitude, recognition, and authentic leadership.Reskilling and upskilling for the AI-driven future of work.LINKS:David's LinkedInFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy 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.

Dec 4, 2024 • 24min
Donald Knight on mental fitness & designing a fulfillfing work/life
This week, I'm joined by Donald (DK) Knight, SVP of People & Culture at Warner Bros. Discovery.Donald has had a varied career, working in senior HR and people roles and serving as a venture partner and advisor for Valor VC, PeopleTech Partners, and Lattice.We had great fun discussing various topics related to company culture, wellbeing, and the skills you need to build a fulfilling work/life. You'll enjoy this.TALKING POINTS:The importance of mental fitness in the workplace and why it's a growing challenge.How leaders can cultivate positive cultures in which employees are able to express who they are.The difference between assimilation and authenticity in leadership, and why acclimation matters more.How the next generation is changing norms for the better.Tips on where to focus your time and energy.LINKS:Donald's LinkedInFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy 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.

Nov 20, 2024 • 29min
David Blake on the Skills Gap, AI, and the Future of Learning
This week, I’m joined by David Blake, CEO of Degreed and a pioneer in the world of lifelong learning and skills development. Degreed, founded in 2012, launched with the mission of “jailbreaking the degree”, where all skills are recognised, irrespective of how they are acquired. More than 9 million learners from hundreds of global companies now use Degreed to gain the skills to grow in their careers.If you've been thinking about how to manage talent in the age of AI, or how to future-proof your own skills, this episode is packed with insights.TALKING POINTS:The growing skills gap and why it’s here to stay.How AI can be leveraged to identify and bridge skills gaps within organisations.Moving beyond traditional credentials - why skills are the new currency.Practical advice for leaders on adopting a skills-based approach to workforce development.The importance of lifelong learning and how organisations can create a culture that supports it.LINKS:David's LinkedInDegreed websiteFollow Ollie on LinkedInSubscribe to the Future Work/Life NewsletterMy 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.