

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

Nov 15, 2023 • 5min
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 and remote work.Chapter summary from Work/Life Flywheel:Work has been flipped - we’re now more likely to work at home than in an office.Younger generations care more that their values align with employers than how much money they earn.More people are becoming freelancers, solopreneurs and entrepreneurs than ever before.Technology and the internet are reducing the barriers to finding paid work.We’re now reimagining job design based on dimensions like location and time.It will soon become normal to work for multiple businesses at a time.LINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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).Here’s what Lynda Gratton, author of Redesigning Work, Professor of Management Practice at London Business School has said about it:“We all know that the old three-stage life course of full-time education, full-time work and full-time retirement is not fit for purpose. But we also know that to make the changes to a more flexible and adaptive multi-stage life, we need to be bold and courageous. In this inspiring book, Henderson shows the foundations for this courage and shares the stories of those who have created momentum and energy in their working life.” Hosted on Acast. See acast.com/privacy for more information.

Nov 14, 2023 • 4min
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:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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).Here’s what Annie Auerbach, author of FLEX, Reinventing Work for a Smarter and Happier Life, has said about it:“Ollie is an important and empathetic voice in the conversation around the future of work. His book will help us all navigate a better way to work and live.” Hosted on Acast. See acast.com/privacy for more information.

Nov 13, 2023 • 2min
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:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Damian Hughes, host of The High Performance podcast and author of High Performance and Liquid Thinker has said about it:“Ollie’s excellent book will show you the practical techniques of reimagining your life and career and reveals how much better things could be for you, if you can adopt his hard-earned wisdom.” Hosted on Acast. See acast.com/privacy for more information.

Oct 18, 2023 • 44min
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 meHow I've stuck with newsletter writing and podcasting (and their benefits)The insights I've had about work/life balance and why there's a better wayHow following my curiosity has given me the motivation to pivot my career.The connection between building a high-performance work and personal life.LINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Damian Hughes, host of The High Performance podcast and author of High Performance and Liquid Thinker has said about it:“Ollie’s excellent book will show you the practical techniques of reimagining your life and career and reveals how much better things could be for you, if you can adopt his hard-earned wisdom.” Hosted on Acast. See acast.com/privacy for more information.

Oct 11, 2023 • 42min
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 dadHow being a parent changed my perspective on workWhy I decided I needed to prioritise designing my work/life after leaving my first companyMy perspective on work/life balance and why we need a more positive and productive frameHow micro-journaling has unlocked new insights into my career AND improved my memoryLINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Annie Auerbach, author of FLEX, Reinventing Work for a Smarter and Happier Life has said about it:“Ollie is an important and empathetic voice in the conversation around the future of work. His book will help us all navigate a better way to work and live. “ Hosted on Acast. See acast.com/privacy for more information.

Oct 4, 2023 • 49min
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 mythWhy burnout is on the rise and how we can tackle itThe emergence of the multi-stage life and the multi-generational workforceWhy so many people feel unfulfilled in their work, but are unsure what to do nextThe importance of leaders being open to discussing the relationship between people's work and personal lives.LINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Lynda Gratton, author of Redesigning Work, Professor of Management Practice at London Business School has said about it:“We all know that the old three-stage life course of full-time education, full-time work and full-time retirement is not fit for purpose. But we also know that to make the changes to a more flexible and adaptive multi-stage life, we need to be bold and courageous. In this inspiring book, Henderson shows the foundations for this courage and shares the stories of those who have created momentum and energy in their working life.” Hosted on Acast. See acast.com/privacy for more information.

Sep 27, 2023 • 1h 7min
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 interconnected, and plenty of practical ideas and tips on growing your career.Check out the episode details here.LINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Christopher Lochhead, 11x #1 Bestselling author of Category Pirates, Play Bigger & Niche Down has said about it:"Ollie Henderson gives you the tools to create a legendary career by embracing being different, harnessing your creativity and building a system to share your ideas. Forget chasing work/life balance and build a Work/Life Flywheel instead.” Hosted on Acast. See acast.com/privacy for more information.

Sep 20, 2023 • 37min
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 highlights, including:Bruce Daisley and Michael McCarroll on the magic of shared experiences.Catrin Lewis and Eryn Peters on designing culture fit for a new era of work.Bruce Feiler on understanding your life through the ABCs of meaning – Agency, Belonging, Cause.David Spinks and Gina Bianchini on the power of community to connect those with some similar interests and careers.Jennifer Moss and Tom Goodwin on the impact digital transformation and changing work modes are having on businesses.Dan Bladen and Rob Sadow on how flexibility and hybrid work patterns are changing our relationship with our local and work communities.Jeff Schwartz and Marcus Mossberger on the role of technology in creating new workforce ecosystems and the difference between timely and timeless priorities.LINKS:Book Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Ogilvy Vice-Chairman Rory Sutherland has said about it:“Work and leisure have become a false dichotomy. As Ollie Henderson shows using the superb Flywheel metaphor, done right, each can make you better at the other.” Hosted on Acast. See acast.com/privacy for more information.

Sep 13, 2023 • 41min
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 better decisions on where and how they spend their time. They also create the Flex Index, the global repository of company office requirements. Flex Index covers more than 6,500 companies across 45,000 offices, and their most recent report was released yesterday - you can download a copy of Flex Report: Fortune 500 here.Ollie and Rob discuss:The latest hybrid work data and trendsThe challenge of upskilling managers to support new work modesHow different organisations approach the personalisation of work schedulesScoop's journey from a product focused on commuting to addressing hybrid workHow Rob thinks about the evolving role and meaning of communityLINKS:Scoop's websiteFlex Index websiteRob's LinkedInBook Ollie to speak with your teamOllie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Hung Lee, Curator of Recruiting Brainfood, has said about it:"There isn't a person out there that hasn't thought about radically reinventing work and life. What's been missing is an accessible guidebook to transform desire-to-action, and action-to-outcome. Ollie Henderson's Work/Life Flywheel sketches out a framework for thinking about transformation, bringing the lessons to life with his own personal journey, along with expert insight from industry figures who have themselves gone on idiosyncratic paths to successful unconventional futures. Fantastic read, and essential for anyone thinking about career change" Hosted on Acast. See acast.com/privacy for more information.

Sep 6, 2023 • 45min
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-based approach to collaborative learning is delivered by a network of trusted creators and work experts (which they call 'hosts') from a wide range of fields, including sport, music and even chess (here's a link to a session on improving your perspective with Chess Grand Master Garry Kasparov).Ollie and Michael discussed:How the increasing focus on performance cultures impacts learning and development budgets.The most popular types of sessions booked by Teamraderie clients and how hosts facilitate them.Why new work modes add increasing complexity to management and the effect that has on skill development.How learning together improves the retention of knowledge, and the value of the 'epiphany effect'.The role of shared learning experiences in building a positive team culture.LINKS:Teamraderie websiteMichael's LinkedInGallup's 12 Engagement QuestionsBook Ollie to speak with your team.Ollie's LinkedInFuture Work/Life NewsletterWork/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). Here’s what Dr. Christian Busch, bestselling author of The Serendipity Mindset: The Art & Science of Creating Good Luck and Professor at New York University, has said about it:“The world is changing fast, and life can be short – so we might as well start making it meaningful today. This book provides a superbly pragmatic and useful take on how we can reimagine our career and life. A book worth reading and an approach worth taking.” Hosted on Acast. See acast.com/privacy for more information.