Ollie on Work
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.
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- Update frequency
- every 4 days
- Average duration
- 26 minutes
- Episodes
- 240
- Years Active
- 2020 - 2025
Keeping an open mind
This series, I'm sharing insights from my book Work/Life Flywheel.
In this episode, I discuss why it's essential to be open-minded about your capacity to change and grow.
Chapter Summary:
- You're never i…
Forget balance, you need a flywheel
This series, I'm sharing insights from my book Work/Life Flywheel.
In this episode, I discuss why the idea of Work/Life Balance needs rethinking and how the Flywheel model can help you reframe the rel…
Without Fear
This series, I'm sharing insights from my book Work/Life Flywheel.
In today's episode, I discuss why genuine fears, like financial risk, combine with reputational risk to stop people from making posit…
Reimagine your career
This series, I'm sharing insights from my book Work/Life Flywheel.
In today's episode, I explain why we're experiencing the greatest work/life transition in history and how we can start to manage it.
C…
Harness the work revolution
This series, I'm sharing insights from my book Work/Life Flywheel.
In today's episode, I explain why we should embrace the 'flipped workplace' and where the dust is settling when it comes to hybrid an…
Introduction: The big pivot
This series, I'm sharing insights from my book Work/Life Flywheel.
In this episode, I explain why I wrote the book and what the flywheel effect tells us about how to approach work and life.
LINKS:
New series preview: Work/Life Flywheel
This series, I'm sharing insights from my book Work/Life Flywheel.
In this episode, I preview the series and give you a breakdown of what you can expect over the next 25 bite-sized shows.
LINKS:
Why Writing Improves How You Think
In this bonus episode, I share a recent conversation I had with Alison Jones on The Extraordinary Business Book Podcast.
We talked about:
- Why I started writing and the new perspectives it's opened for …
Being a Dad Helps Me Make Better Decisions
In this bonus episode, I share a recent conversation I had with Charlie Rosier on The Babbu Podcast.
We talked about:
- My journey as a dad
- How being a parent changed my perspective on work
- Why I decided I…
Leading in a New Era of Work
In this bonus episode, I share a recent conversation I had with Jean Gomes and Scott Allender on The Evolving Leader Podcast.
We talked about:
- Why work/life balance is a myth
- Why burnout is on the rise …
Designing a Meaningful Life
In this bonus episode, I share a recent conversation I had with Christopher Lochhead on his Follow Your Different podcast.
We talked about how to build a meaningful life, why work and life are interco…
Community: Series 12 Recap
What does community mean to you?
I explored the meaning of community in this podcast series, and the conversations led in many different directions.
In today’s recap episode, I share some of the highli…
The latest hybrid and flex trends with Rob Sadow
This week's guest is Rob Sadow. Rob is the CEO and Co-Founder of Scoop and is recognised as a LinkedIn Top Voice on flexible work.
Scoop is a software company that enables hybrid employees to make bet…
The magic of shared team experiences with Michael McCarroll
This week's guest is Co-Founder and CEO of Teamraderie Michael McCarroll.
Teamraderie offers curated and customised online experiences designed to help build high-performing teams. Their evidence-base…
Leadership through storytelling with Catrin Lewis
This week's guest is culture and transformation consultant Catrin Lewis.
After a decade leading culture and engagement at Employee Engagement Platform business Reward Gateway, Cat recently founded a c…
How to build a remote-first culture with Eryn Peters
Today's guest is Eryn Peters, a startup advisor, community architect, and future of work expert.
Eryn's been working remotely for well over a decade, so she has brings both personal experience and kno…
Tech & Humanity at Work with Marcus Mossberger
In this episode, Ollie and Marcus Mossberger, Future of Work Strategist at Infor, discuss some of the key themes of the moment.
As both of them spend so much time talking to business leaders and organ…
Why work isn't working (and what to do about it) with Jennifer Moss
Today's guest is Jennifer Moss, a workplace speaker and strategist.
Jen's also an award-winning author, journalist, national radio columnist, and the author of The Burnout Epidemic and Unlocking Happ…
Reasons for Optimism with Tom Goodwin
Today's guest is Tom Goodwin, a digital business transformation specialist and the founder of All We Have Is Now, a consultancy created to help companies unleash the power of new technology, focusing…
Finding Meaningful Work with Bruce Feiler
Today's guest is New York Times bestselling author Bruce Feiler.
Bruce's last book Life is in the Transitions greatly impacted Ollie and featured in his book Work/Life Flywheel. His new book is called…