Ollie on Work

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 limit
• The "central governor" theory and how your brain protects you by holding you back
• How to build tolerance for uncertainty like elite athletes do
• The exploration vs exploitation dilemma in careers and business decisions
• Why "optimism in the face of uncertainty" is the optimal mathematical strategy
• How to know when to explore new paths vs exploit existing knowledge
• The 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.

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 valuable
• How careers are becoming more like showbiz - constant experimentation with uncertain outcomes
• Why AI might actually force us back to trusting what we can see and touch in person
• The institutions that need to be completely rethought for a post-industrial economy
• Why everyone will need to experiment constantly rather than following set career paths
• How 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.

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 fail
• How to build unforgettable presence that goes beyond just showing up in meetings
• Practical frameworks for speaking up when you're put on the spot
• Why introverts actually have advantages in building visibility (and how to use them)
• The difference between being heard and being the loudest person in the room
• How 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.

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 humans
• The death of knowledge workers
• Creator capitalists - how to use AI and human creativity to build new things of value
• Discovering your superpower - what people come to you for and how to monetise it
• Why 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.

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 strategy
• Engineering serendipity - how to make in-person interactions actually productive instead of accidental
• Performance management revolution - measuring output quality rather than input hours
• Why introverts finally get their chance to lead in distributed teams
• The 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.

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 everything
• Four types of leverage - tools, products, people, and capital, and how to identify which suits you
• High agency as the single most important meta-skill for navigating career shifts in the AI era
• Why there's no "should" in career progression - breaking free from linear thinking
• Recognising genius in others - how curation and connection can become your competitive advantage
• AI'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.

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 you
• Attention as a creative act - how paying attention shapes your career opportunities
• Redefining strengths beyond performance - understanding what truly motivates you
• The specificity of professional passion - why precise activities matter more than broad interests
• Brain 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.

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 most
• The importance of tracking your progress
• Sharing your ideas with the world
• Becoming a recognised expert
• Experimenting with new ideas
• Networking

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.

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 website

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). 

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.

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 LinkedIn

Think 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, 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.