Love is not a feeling of happiness. Love is a willingness to sacrifice
Michael Novak
Have you ever looked back and tried to pinpoint the exact moments where everything changed? Those seemingly small decisions that—only in hindsight—reveal themselves as turning points that shaped everything that followed?
Perhaps you didn’t realise how profound it was at the time, and its far-reaching, long-lasting consequences only came into focus years later. Or perhaps you agonised over the decision before finally making a choice.
Maybe hindsight has left you regretting the path you took—or, hopefully, time has helped you see how that decision led you here, even if you wouldn't make the same choice again.
For some reason, recently, I have found myself reflecting deeply on the major decision nodes in my life so far.
Decisions like spending a year in Australia before university. Whether to go into medicine or finance. Leaving JP Morgan for a hedge fund. Leaving finance altogether. Uprooting from London to New York. Choosing to make certain investments. Pursuing an MBA at NYU. Joining Ample Hills.
All major junctions—some considered at length, others made on a relative whim.
However, for me, none of these decisions had as profound an impact on my life as the one I made to go to boarding school at Rugby School, aged 16.
Or perhaps more accurately—the opportunity that was created for me to go away to school.
I was a straight-A student at my local comprehensive school when my dad suggested I apply for a scholarship at Rugby School—which at the time was the top coeducational school in the United Kingdom.
We knew about the school through another family from my primary school—my first crush had three older brothers who went there.
My dad saw an advertisement for scholarship applications in the education section of The Sunday Times and suggested I apply.
His point was that it would be a great experience to see the school, learn what life might be like there—and if nothing else, the entrance exams would be a useful dry run for my upcoming state tests.
I don’t remember much about the visit itself—just the grand library where I sat the exams and the iconic playing fields where, in 1567, the game of rugby was born.
I remember feeling like I did okay on the tests, but I wasn’t nervous. Why would I move schools? I was doing well, I was happy. My rugby career was progressing nicely, my grades were strong, and I had a core group of friends I enjoyed being with.
I received an offer of an academic scholarship and an all-round bursary award from a fund set up by a Welsh alumni who wanted to support strong academic students with sporting prowess. With these awards, 50% of my tuition would be covered.
I had no idea what kind of financial burden my parents were taking on. Nor could I have imagined the many hidden costs—uniforms, equipment, trips—that would follow.
I was placed in “School House”—the school’s marquee house (a fact my non-School House friends may begrudgingly acknowledge!). Thanks to a recent renovation, our year group there was unusually small, creating space for a new, diverse mix of students.
Why did this matter? I’ve come to learn that boarding school can be a brutal place. Being a newbie—especially one from a different background than most students—can leave you very exposed.
But our cohort was different. A smaller group, forming anew. A mix of boys from all over the world.
That diversity became a blessing. We bonded, and the lads welcomed me into the school and helped me understand and assimilate into life at Rugby.
More than friendship, they gave me perspective.
The fact that they hailed from Thailand, Malaysia, Saudi Arabia, Hong Kong, and Zambia opened my eyes to a world I had never encountered. We also had a Scouser and a Geordie to keep me grounded in my British roots.
The diversity of that group not only grounded me in friendship—it expanded my worldview at an age when I was just starting to shape my identity.
As a result of the perspectives and experiences Rugby School provided me, I turned down places at multiple medical schools and ultimately went on to study economics.
I went into finance instead of becoming a doctor on the guidance and advice of my tutor. Which led me, amongst other things, to meet my now-wife and—through a long and winding road—to be writing this, here in New York.
During my time at Rugby School, I toured New Zealand and Fiji for six weeks with the first XV rugby team. This played a significant role in the decision I made to play rugby and live in Australia for nine months before university.
While at Rugby School, I was coached by one of the head coaches of the England under-18 national team. His influence and mentorship, along with the exposure from playing in the world's largest youth 7-a-side tournament, helped me get noticed—and eventually represent Wales at under-18 level.
The friendships I forged during those two impactful years have resulted in me travelling to Jeddah, George Town, Hong Kong, Bangkok, Lusaka, and Leeds ;)
We’ve attended each other’s weddings, introduced our kids, vacationed together, caught up at World Cup matches, over dinners, and opportunistic beers when we happen to be in the same city.
Of course, life moves fast now. Work, family, and distance mean we don’t connect nearly as often as we used to. But the wonders of technology—especially WhatsApp—keep us in almost daily touch.
As I’ve written before, I’ve had numerous setbacks, losses, and questionable decisions. All of them have taught me about life, about myself, and about the journey we’re all on.
Unpacking these moments—through writing this blog—has led me to examine how my life arrived at this point. It’s given me fresh lenses through which to revisit the decisions I’ve made and how deeply I considered (or didn’t consider) their long-term impact.
More than anything, reflecting on the decision to go to Rugby School has made me appreciate not only the incredible friendships I have with the School House lads—27 years on—but also the immense sacrifice my parents made to send me there.
Their foresight, courage, and willingness to let go—to let me go—changed my life.
Many of my friends from back home never really left our town. They went on to live stable, grounded lives—blue-collar jobs, families, a deep sense of community.
In contrast, I left home at 16 and discovered a whole world of possibilities.
It’s not about which path is better, or which life leads to more happiness. I just know how grateful I am for the path I was able to walk—and the doors it opened.
I’ve always said boarding school isn’t for everyone. And the right age, environment, and temperament all matter deeply.
But now that I’m a parent, I feel that truth even more deeply: my parents loved me fiercely—and that love gave them the strength to push me toward something greater, even when it meant letting me go.
