The Older I Get, the Smaller Success Looks

The Older I Get, the Smaller Success Looks

Welcome to the Mellow Madness update, a space for thinking out loud about strategy, leadership, and the lessons life quietly teaches us over time.

Tomorrow is my birthday. Or perhaps it is today. The answer depends on whether you ask biology or bureaucracy. I was born just before the stroke of midnight on the 13th of July, but my mother was never particularly fond of

 the number 13. Like many people of her generation, she considered it unlucky 

and decided to register my birthday as the 14th instead. 

Ever since, I have joked that I celebrate two birthdays. One belongs to nature. The other belongs to paperwork. In truth, I have never minded. If anything, 

it has given me two opportunities each year to pause, reflect, and be grateful 

for another journey around the sun.

Astronomers would simply describe a birthday as another completed orbit of 

the Earth around the Sun. I find something beautiful about that thought. Regardless of where we live, what language we speak, or what occupies our minds from one day to the next, we are all travelling through space together, quietly completing another circuit without ever noticing it. 

Yet while the universe measures time in orbits, we tend to measure it in achievements. We ask ourselves what we have accomplished, what remains unfinished, and whether we are further ahead than we were this time last year. The older I get, however, the less convinced I am that those are the right questions.

For much of my life, success always seemed to exist somewhere ahead of me. 

It was the next opportunity, the next client, the next country, the next project, 

or the next milestone. Whatever I achieved quickly became normal because 

my attention immediately shifted towards what I had not yet accomplished. 

I rarely stopped long enough to appreciate the ground I had already covered because I was too busy studying the horizon.

Looking back now, I realise how unfair that was. By almost any objective measure, I have been blessed far beyond what my younger self could have imagined. As a child, I received international recognition for my writing. I 

have stood on stages performing music before audiences that once existed only in my dreams. 

I have built brands, written books, worked with remarkable organisations, and been welcomed into countries that have profoundly shaped the way I see the world. Yet despite all those experiences, there were moments when I still questioned whether I was truly successful.

The problem was never what I had achieved. The problem was how I chose to measure it.

This is where expertise becomes valuable.

Instead of counting what had been entrusted to me, I measured myself against everything that remained out of reach. I thought about the house I had not

 built instead of the home God had already blessed me with. I noticed the car 

I was not driving rather than appreciating every journey that had brought 

me here.

 I focused on the countries I had not yet visited instead of recognising the privilege of living, working, and building relationships across a continent I deeply love. Without realising it, I had allowed comparison to become my scorecard, and comparison is a game that never ends because there will always be someone with more.

One of the greatest lessons of my adult life has been discovering that gratitude and ambition are not opposites. For a long time, I mistakenly believed that if I became too grateful, I would lose my drive. I worried that contentment might make me comfortable. Instead, I discovered the opposite. Gratitude has not reduced my ambition; it has purified it. It has changed the reason I pursue the things I pursue. 

I no longer feel the need to chase success in order to prove something to myself or anyone else. Instead, I want my work to create value, to honour the gifts God has given me, and to leave people and organisations better than I found them.

Perhaps that is why success has become smaller.

It no longer looks like collecting as many clients as possible. It looks like 

working with people whose values I genuinely admire and whose vision I am excited to help build. It no longer means saying yes to every opportunity that comes my way. 

It means protecting time with my wife and our three daughters, investing in friendships that have stood the test of time, and choosing work that aligns with the life I want to live. Increasingly, I find that success is measured less by accumulation and more by alignment. The older I get, the less success looks 

like having more and the more it looks like becoming more.

As I have reflected on the year behind me, another thought has become increasingly clear. Many of us spend our lives playing not to lose. We become cautious with our dreams, careful with our ambitions, and hesitant to pursue ideas that might expose us to failure. 

There is wisdom in avoiding unnecessary risks, but there is also a hidden 

danger. A life organised entirely around avoiding loss eventually forgets how

 to pursue possibility. It becomes defensive rather than creative, safe rather 

than courageous.

That is not how I want to live the next chapter of my life.

I want to play to win.

By that, I do not mean chasing wealth for its own sake or accumulating achievements to impress other people. I mean having the courage to pursue 

the work I believe I was created to do. I want to write the books that are still inside me. I want to build brands that outlive campaigns and create institutions rather than simply projects.

 I want to serve Africa more intentionally, mentor more generously, and continue growing into the husband, father, friend, and leader my family deserves. Winning, I have come to realise, is not about finishing ahead of someone else. It is about becoming the fullest expression of the person God created you to be.

There is a verse that has become increasingly meaningful as I have grown 

older. In Joel 2:25, God says, “I will restore to you the years that the locust has eaten.” I have come to appreciate that restoration is rarely about recovering the past exactly as it was. More often, it is about discovering that what seemed like delay was actually preparation.

 Looking back, I can see opportunities that arrived at exactly the right time, relationships that could only have been formed through previous disappointments, and lessons that could never have been learnt without 

seasons I once wished away. God’s timing has often made far more sense in hindsight than it did in the moment.

So whether I celebrate on the 13th or the 14th hardly matters anymore. What matters is that I have been given another opportunity to make this next journey around the sun count. My prayer is no longer simply that life would give me more. It is that I would become more. More faithful in the small things. More generous with what I have been entrusted. More intentional with the people I love. More courageous in the work I believe I have been called to do.

Perhaps that is the greatest gift that age has given me. The older I get, the smaller success looks, not because I expect less from life, but because I have finally begun to recognise that the things which matter most were never the biggest things after all. 

They were the relationships we nurture, the lives we influence, the gratitude we cultivate, and the quiet courage to stop living simply so that we do not lose, and instead begin living with the confidence to play to win.

Thank you for reading.

Warm regards,