What if retirement is the wrong goal? What if the future of work isn’t about stopping work, but redesigning it?
In this episode of The Future of Less Work, host Nirit Cohen sits down with Lyndsey Simpson, founder and CEO of 55/Redefined and author of The Age Rebellion, to explore how longer lives are forcing us to rethink careers, retirement, flexibility, and purpose.
As people routinely live into their 90s and beyond, the traditional model of education, career, and retirement is breaking down. Simpson argues that many people no longer want a cliff-edge retirement. Instead, they want more control over how they work, when they work, and what they work on as they move through different stages of life.
The conversation explores why flexibility means much more than remote work, why experienced workers are becoming one of the most overlooked talent pools in the economy, and how organizations are discovering the business value of experience. Simpson shares surprising examples of how older workers outperform common stereotypes around adaptability, attendance, customer service, and even AI adoption.
Together, they discuss the rise of second careers, entrepreneurship after 50, age bias in hiring, the changing role of lifelong learning, and why the most important question may no longer be “When do you want to retire?” but rather “What do you want to be when you grow up?”
Whether you’re navigating a career transition, leading a workforce spanning multiple generations, or wondering how AI and longevity will reshape work, this conversation offers a fresh perspective on what comes next.
Guest Information:
Lyndsey Simpson is the Founder & CEO, 55/Redefined and a Sunday Times bestselling author, The Age Rebellion; Supercharge the Second Half of Your Life
Lyndsey Simpson is a leading voice on the future of work, health and longevity. As Founder and CEO of 55/Redefined, she is enabling organizations to rethink how people live, work and stay well in an era of longer lives.
Her work sits at the intersection of workforce transformation, preventive health and human performance, supporting organizations to build truly age-inclusive environments where people of every generation can thrive and perform at their best.
Lyndsey is also the author of The Age Rebellion, an international bestseller challenging how individually we think about longevity, purpose and reinvention. An award-winning entrepreneur and influential media commentator, she brings an energizing, evidence-backed perspective to one of today’s defining challenges: how we create longer, healthier, more fulfilling lives for everyone.
Buy The Age Rebellion here: The Age Rebellion – Amazon US
Chapters:
00:00 Why Retirement No Longer Fits A 100-Year Life
01:20 What Does A Career After 50 Look Like?
03:35 What Is A Squiggly Career?
05:05 Why More People Start Businesses After 50
06:46 What Does Flexible Work Really Mean Today?
10:12 Are Older Workers Better At AI Than Younger Workers?
11:08 Why Companies Are Hiring More Experienced Workers
15:31 Why AI Needs Human Experience
17:18 What Is Return On Experience (ROE)?
20:06 Why Companies Measure Employee Performance Wrong
22:30 How Do You Stay Relevant After 30 Years In Your Career?
23:43 How Do You Reinvent Your Career After 50?
25:00 How To Change Careers Later In Life
28:52 Why Transferable Skills Matter More Than Technical Skills
31:06 How To Build A Life You Never Want To Retire From
32:07 What Do You Want To Be When You Grow Up?
