Introduction
What does it take to walk away from the peak of a corporate career and discover that the most meaningful work of your life was waiting somewhere else entirely? In this deeply personal episode of Don’t Let The Old Man In, co-host and producer Stephen Keys steps in front of the microphone to share a story that will resonate with any man navigating midlife reinvention, career transition, or the quiet ache of a life not quite aligned with his values.
Why this conversation matters
Career transition, men’s mental health, purpose after 50 — these are the themes that sit at the heart of what we do at The Wisdom Vault. Stephen’s story is a masterclass in all three. From his days as group CEO of a fast-growing IT services business on the cusp of an IPO, to co-founding a charity that has transformed lives in rural Sri Lanka, to navigating divorce, rebuilding relationships with his sons, and launching a new podcast on philanthropy — this is midlife reinvention lived out loud.
This episode is a rare thing: an honest, unflinching look at what it costs to choose purpose over prestige — and what it gives back.
What we discuss in this episode
- How a single conversation about values led Stephen to walk away from a planned IPO and take what looked like a step backwards — but turned out to be the best decision of his career
- The founding of the IFS Foundation and the community-led approach that helped break the poverty cycle in rural Sri Lanka, including access to clean water, school infrastructure, healthcare, and employment for women
- The personal cost of divorce — the loneliness, the identity crisis, the weekends without his boys — and how volunteering at a soup kitchen on Sydney’s northern beaches became an unexpected lifeline
- How creating “third spaces” with his sons through volunteering, football refereeing and shared adventures helped rebuild connection after the family fell apart
- Bob Buford’s concept of moving from success to significance in the second half of life, and why Stephen chose the single word “community” to navigate his own transition
- The philosophy of “slow is smooth, smooth is fast” — learned from Singapore charity Willing Hearts — and how it applies beyond the kitchen
- Ultra marathon running as a metaphor for midlife resilience, and the mantra “my pain is my privilege” that keeps him going on the hard days
- How writing on Substack and LinkedIn has reconnected him with long-lost friends and helped him process the inner work of midlife
- The launch of The Giving Habit podcast — a new show hosted by Stephen that explores philanthropy as one of the eight pillars of positive aging
For men navigating midlife
Whether you’re a corporate high-achiever starting to wonder what it’s all for, a man on the other side of divorce trying to find your footing, or someone with something to give but no idea where to start — this conversation is for you. Stephen’s story doesn’t offer easy answers. But it does offer something rarer: proof that simplicity lies on the other side of complexity, and that the second half of life can be more meaningful than the first.
If you’ve been searching for real talk about men’s mental health, midlife purpose, career reinvention after 50, or the emotional reality of divorce and fatherhood — this is an episode worth sitting with.
Reflections and Experiments
Pod provides reflections on each conversation, summarises what he has learned from the guest, and suggests one experiment he plans to try as a result of their shared information.
Pod's reflections
Personal follow-on episodes unpacking the themes, insights and lived experience behind each discussion.
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Guest info
Stephen Keys
Stephen Keys is the co-founder and producer of the Don’t Let The Old Man In podcast and a co-founder of The Wisdom Vault. Originally from England, Stephen built a 25-year career in the global IT sector, including a decade at Software AG and the role of group CEO at Sydney-based FTS Group. He joined IFS as Regional President for Asia Pacific, Japan, Middle East and Africa, and currently serves as Chief Talent and Sustainability Officer. He is also the founding chair of the IFS Foundation, an independent charity he helped establish in 2019 to break the poverty cycle in rural Sri Lanka through investment in clean water, sanitation, healthcare, education, and employment. Stephen is an ultra marathon runner, an emerging writer, and the host of The Giving Habit — a forthcoming podcast exploring philanthropy as a pathway to purpose in the second half of life. He lives in Singapore.
