By DSFP Fellow Stephen Keys
This piece accompanies a conversation I had with Pod O’Sullivan on the Don’t Let The Old Man In podcast.
Sliding doors
A decade ago, I was on what looked like a very clear trajectory.
Group CEO of a rising IT service business. Revenue doubling. Profit improving. Acquisitions underway. Advisors engaged. The early mechanics of a potential IPO beginning to take shape. From the outside, it was the kind of moment that signals arrival. From the inside, it was ego in full flight.
I was in my mid-forties and believed, quite sincerely, that I was climbing toward the peak of my career. And yet, somewhere in that ascent, I had also constructed a version of myself that was efficient, successful, and increasingly incomplete.
That’s when a former boss called me with an opportunity. On paper, it did not make obvious sense. The role was familiar. The financials were comparable. There was no IPO attached. No clear narrative of ‘up and to the right’.
But inside that conversation was something I did not expect: the opportunity to build a genuine CSR programme and, eventually, what would become the IFS Foundation.
That was the moment that ‘broke my saunter’, a phrase I borrowed from a professor at the National University of Singapore. The professor described the ‘when’ of art as something that stops you mid-stride, without explanation, before your rational mind has time to intervene. You are simply caught by it.
That is what happened to me. Not because it was logical. Because something in me recognised the value of building something meaningful at scale. The idea broke my saunter. It spoke to what I value most.
Core values
Around that same period, I had gone through a values exercise, one of those corporate workshops you half-expect to forget by the following week. A deck of cards, fifty-odd values, narrow them down, discuss them, refine them. What surprised me was not the exercise itself, but what stayed with me afterwards. Five values kept resurfacing:
At the time, I might have listed them. These days, I try to live by them. These values have become less like labels and more like a set of lenses. A way of interrogating decisions, behaviours, and direction. When something feels off, I often find it is because I am out of alignment with one or more of them.
For example, I might ask myself, am I prioritising achievement at the expense of community? Am I learning, or simply repeating? Am I being of service, or just being seen? And if I think about my decision to join my former boss, it is because it spoke to my core values.
Applying my values in this way does not always give me perfect answers. But it does tend to prompt better questions. And increasingly, they guide where I choose to spend my time, my energy, and my attention, in work, in relationships, and in how I move through the world.
The persona and the person
Looking back now, I can see that I had spent years building a professional persona that worked extremely well in the world. It was disciplined. Driven. Commercially sharp. Outcome-oriented. Parts of it were, and remain, deeply true. I still value achievement. I still like building things. I still enjoy the discipline of work done properly.
But it was not the whole story.
Along the way, I had outsourced other parts of myself. Relationships were managed at a distance. Friendships became occasional and even transactional. Creativity sat quietly on the sidelines. A sense of community, something I now recognise as fundamental, was present but underdeveloped.
At the time, I thought this was simply what success required. Now, I see it differently. The version of success I was pursuing was narrow. Not wrong, but incomplete. It measured performance, not alignment. It rewarded output, not integration.
What has changed is not my appetite for doing things well. It is the lens through which I now evaluate what “well” actually means.
Community matters
The work that followed, building the IFS Foundation, spending time in Sri Lanka, working alongside communities, shifted something in me quite fundamentally.
We adopted a simple principle at the Foundation: be useful outsiders. Listen before acting. Look for what is strong, not just what is wrong. Build on what already exists rather than imposing solutions from the outside.
That philosophy changed me as much as it shaped the work. The more time I spent in those communities, the more I realised how incomplete my previous understanding of value had been. The people I now consider my heroes are not the business figures I once admired from a distance. They are individuals who show up every day, quietly, consistently, to care for others, to tend shared spaces, to hold communities together.
An elderly couple who clean and maintain a village medical centre, not because they are paid, but because they care. That is leadership. That is community. And somewhere along the way, I realised that this was not just something I admired, it was something I needed to embrace and inhabit.
Stripping back
The podcast interview also touches on some deeply personal history, including a divorce. It was painful and disruptive for many people, and I take full responsibility for my part in it. I had been deeply unhappy for some time and had not addressed it honestly or early enough.
What followed was a period I can only describe as disorienting. I left the family home. I moved into an apartment. My sons were no longer with me every day. Weekends became long, quiet stretches of time I did not know how to fill. My identity, particularly as a father, felt fractured.
There is a particular kind of loneliness that comes in those moments, persistent and heavy. I did not have a grand plan for dealing with it.
When you have nothing, you still have something to give
I started volunteering because I needed something to do. It began with a soup kitchen. Then more volunteering. Refereeing football matches with my eldest son. Kids Giving Back with my youngest son.
At first, it was simply a way to occupy time. But something unexpected happened. I found community.
I found people who did not care who I was professionally. I found environments where contribution mattered more than credentials. I found a sense of belonging that had been missing for longer than I realised.
And I learned something that has stayed with me ever since. Even when you feel you have nothing, you still have something to give.
I remember a session at Kids Giving Back where someone spoke about the experience of homelessness, not just the lack of resources, but the invisibility. People avoiding eye contact. Crossing the street, pretending not to see you.
The simple act of saying hello, of acknowledging someone’s presence, can restore a measure of dignity. That costs nothing. But it gives something profound. At a time when I felt stripped of many things, that insight mattered.
Slow is smooth
There is a memory I often return to, and that surfaces in the podcast interview. Volunteering in the kitchen at Willing Hearts in Singapore, trying to keep up with the pace of production, rushing the rice, getting it wrong, and being firmly corrected by the aunties who had been doing this far longer than I had.
The lesson was immediate and unmistakable. Slow is smooth. Smooth is fast. When I rushed, I made mistakes. When I slowed down and found the rhythm, the work flowed. It is a principle that extends well beyond a kitchen.
In moments of pressure, and midlife brings plenty of those, the instinct is often to accelerate. To solve quickly. To force resolution. To outwork the complexity.
But I have learned that much of what matters cannot be rushed without consequence. Sometimes the most effective way forward is to slow down enough to think clearly and move properly.
On the other side of hard
If there is a single thread that runs through the podcast interview, it is this: Simplicity lies on the other side of complexity.
I did not arrive at that understanding intellectually. I arrived at it by living through situations I would perhaps have preferred to avoid.
Divorce. Loneliness. Identity shifts. Difficult conversations. Re-examining what success meant. Letting go of certain narratives and allowing others to emerge.
There is a temptation, particularly in midlife, to circle complexity rather than enter it. To manage it. To distract from it. To hope it resolves itself.
In my experience, that rarely works. At some point, you have to go in. Not recklessly, but with honesty.
Own your mess.
Face what is there. Deal with it while you have the capacity to do so. The life you want is on the other side of the work you are avoiding, for whatever reason.
Because on the other side, not immediately, not easily, but eventually, something does simplify. I now understand myself more clearly. I make decisions with less internal conflict. I align what I do more closely with what actually matters. I have found love with someone whom I care for deeply. I have found a way to provide for myself and my kids, have built a stronger and deeper relationship with Mum, Dad and my brothers, and subsequently found a renewed sense of purpose and meaning in how I choose to spend my time.
It’s by no means perfect, and there is still work to be done.
Pattern recognition
If I reflect on the last decade, I would not describe it as a reinvention in the sense of becoming someone new. It has felt more like a process of uncovering.
Parts of me that were always there, my core values, have moved from the periphery to the centre. The ambition is still there. The drive is still there. But they are now in service of something broader and more meaningful.
And perhaps that is the quiet shift that midlife offers, if we are willing to accept it. Not a rejection of who we have been. But an invitation to become more fully who we are. Maybe that’s how we don’t let the old man in.
If this article resonates with you, then I encourage you to check out the full podcast interview, which is available on YouTube, Spotify or wherever you get your regular podcast fix. You are also more than welcome to drop me a line via LinkedIn.
It’s always good to connect. Community matters.
This article was first published on Stephen’s Substack blog.
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