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.
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.
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:
LINKS:
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
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:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
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:
LINKS:
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
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:
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
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.
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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:
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
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 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:
Work Redesign: Humans + AI Agents
LINKS:
Subscribe to the 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 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:
LINKS:
Subscribe to the 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 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:
LINKS:
Subscribe to the 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 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:
LINKS:
Subscribe to the 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.
Welcome to this special episode of Future Work/Life, in which we take a step back and reflect on the key themes and insights from Season 15 so far.
It’s been a busy few months—between speaking events and connecting with people leaders, I've had the privilege of speaking with incredible guests about the future of work, leadership, learning, and what it means to be human in an AI-powered world.
In this episode, I bring together the standout ideas and discussions from Season 15. We talk about how AI can augment human skills, the changing landscape of workplace connection, the evolving needs of different generations, and the importance of empathy and learning cultures.
More great guests to come before the end of the year...
LINKS:
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 joined by Grief Gang's Amber Jeffrey, a podcaster, speaker, and grief mentor.
Despite tackling a challenging topic, I thoroughly enjoyed our conversation, which was filled with laughter and positivity. We explore how grief is often hidden in the workplace, how creating space for these conversations can help people heal, and why connecting during tough times matters. I finished our conversation feeling more confident about discussing these tough topics—and I hope this episode does the same for you.
TALKING POINTS:
LINKS:
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 joined by Cara Brennan Allamano, cofounder of PeopleTech Partners and experienced people leader at startups and high-growth companies. Cara has been instrumental in scaling people functions at Pinterest, Udemy, and, most recently, Lattice.
In this episode, we explore the biggest challenges and opportunities in the world of work, how AI is reshaping jobs, and Cara's advice for people leaders and executives looking to thrive.
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
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 joined by Pat Wadors, newly appointed CHRO at Intuitive, a leading medical technology company. Pat has previously led HR at UKG, ServiceNow, LinkedIn, and Yahoo and is widely recognised for her transformative leadership in the people space.
In this episode, we explore leadership, storytelling, and the power of human connection. Pat also shares insights from her upcoming book, Unlock Your Leadership Story: How to Build Understanding and Motivate Teams Using Fables and Folktales.
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
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 joined by David Hanrahan, Chief People Officer at Flare.
Flare’s software platform is transforming the delivery of professional services within the legal sector. By simplifying complex processes, Flare empowers lawyers to deliver an elevated experience, ensuring clarity and support during key life events.
In this episode, David and I dig into some of the biggest challenges and opportunities shaping the modern workplace.
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
My book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).
Hosted on Acast. See acast.com/privacy for more information.
This week, I’m joined by Michael Ioffe, co-founder and CEO of Arist.
Arist is used by leading organisations to deliver behavioural training and critical knowledge through the messaging tools employees use every day, like WhatsApp, Slack, and Teams.
Michael’s background is fascinating—from his early entrepreneurial endeavours to building a platform that’s reshaping how people learn on the job. Listen in to discover more...
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
My book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).
Hosted on Acast. See acast.com/privacy for more information.
This week, Melissa Daimler, Chief Learning Officer at Udemy, returns to the podcast.
Melissa brings decades of experience shaping leadership, learning, and organisational culture at some of the world’s leading companies, including Adobe, Twitter, and WeWork (you can listen to what she learned during her brief spell at the latter on her previous pod appearance).
She's also the author of ReCulturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success.
TALKING POINTS:
LINKS:
ReCulturing: Design Your Company Culture to Connect with Strategy and Purpose for Lasting Success
Carolyn Wiley's study on motivation and recognition
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
My book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).
Hosted on Acast. See acast.com/privacy for more information.
This week, I speak with Chloe Combi, an expert on Gen Z and Gen Alpha, who’s spent years researching and advising on how these younger generations are reshaping work, education, and culture.
Chloe is the author of Generation Z: Their Voices, Their Lives and a consultant to some of the world’s leading brands. She helps them connect with and understand the next generation of workers and consumers.
In this episode, Chloe dives into the key factors driving these generations' workplace preferences, from feedback culture to boundary setting, and explores how organisations can adapt to attract and retain the talent of tomorrow.
TALKING POINTS:
Feedback Culture: Gen Z and Gen Alpha expect constant feedback—just like in the rest of their lives.
Boundaries Matter: Younger generations prioritise mental health and set clear boundaries at work.
Career Aspirations: Gen Z and Gen Alpha are choosing entrepreneurship and creativity over traditional careers.
Visibility Drives Motivation: Younger workers need to feel seen to stay engaged and perform at their best.
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
My book, Work/Life Flywheel, was a Business Book Awards 2024 finalist. You can order your copy HERE (UK) or HERE (US).
Hosted on Acast. See acast.com/privacy for more information.
This week, I speak with Nancy Duarte, CEO of Duarte Inc. and the world's leading presentation expert.
Nancy’s career is a masterclass in the art of communication. She has advised TED, worked with Al Gore on the documentary An Inconvenient Truth, and helped some of the world’s biggest companies communicate effectively. She is famous for her deep understanding of storytelling and empathy, and her analysis of speeches by Abraham Lincoln, Martin Luther King Jr., and Steve Jobs is legendary.
Duarte Inc. has helped countless leaders and companies transform how they present ideas, blending empathy, storytelling, and data to craft powerful messages that resonate. In this episode, Nancy shares her insights on communicating authentically, leading with empathy, and adapting to an evolving technological landscape.
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book a free consultation to see how I can help, HERE
My book, Work/Life Flywheel: Harness the work revolution and reimagine your career without fear, was recently 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 speak with Nick Matthews, VP and GM of Europe, Middle East & Africa at Culture Amp.
Nick brings a unique blend of experiences from his early days teaching Liam Neeson’s kids to swim to his career in tech. He started his career at Deloitte Consulting before moving to Yammer, which was later acquired by Microsoft, where he worked for four years before joining Culture Amp in 2016.
Culture Amp is the world’s leading employee experience platform, revolutionizing how 25 million employees across more than 6,500 companies create a better world of work. Culture Amp empowers companies of all sizes and industries to transform employee engagement, drive performance management, and develop high-performing teams.
TALKING POINTS:
LINKS:
Interested in me sharing insights on these topics with your team? Book me to speak with your team.
My book, Work/Life Flywheel: Harness the work revolution and reimagine your career without fear, was recently 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.
In this episode, I interview Isabel Berwick, presenter of the award-winning Financial Times' Working It podcast and co-writer of the Working It newsletter.
Isabel's new book The Future-Proof Career: Strategies for thriving at every stage is published this week. We had a brilliant conversation about careers, management and changes in how we work. The book is a great read, so make sure you order a copy!
"Covering topics as wide-ranging as the four-day working week, bridging the workplace generation gap, making sure your company walks its diversity talk, quiet quitting and the great resignation, achieving workplace equality and even micro-dosing for creativity, The Future-Proof Career spreads the word about understanding modern workplaces so we can all have happier, more productive lives."
TALKING POINTS:
LINKS:
The Future-Proof Career: Strategies for thriving at every stage
Interested in me sharing insights on these topics with your team? Book me to speak with your team.
Work/Life Flywheel: Harness the work revolution and reimagine your career without fear, is out now. You can order your copy HERE (UK) or HERE (US).
Hosted on Acast. See acast.com/privacy for more information.
