FEELING: Discernment
In a world that often rewards sharp elbows and relentless ambition, it’s easy to confuse visibility with value. This letter is about discernment, about building something meaningful without sacrificing who you are in the process.
Letter no.25 - February 25th 2026
Dear Leo,
For the first time in 25 weeks, I missed the post.
I was meant to post your letter at the usual 07:00 am window yesterday, but it was a travel day with you and your mum as we headed home from Scotland. I got to tell you, when these trips come up, whether it’s a long weekend in the country, or a visit to Grandma and Grandad, it never quite goes as I plan it in my mind. I see pockets of time where you are content building Lego motorbikes and spaceships. I’ve had an hour in the morning to train in the hotel gym. Mum is reading a book or taking some needed rest. But instead, it is absolute madness.
A topic for my next letter, I think. An honest account of travelling with a toddler…it’s giving me Instagram vs reality.
For now though, I wrote this letter last week during a reflection of something that was weighing on my mind. A snapshot observation of the reality of the world today.
It started in the car with your mum on the way back from Bicester Village. We were talking about people we’ve met over the years, in sport, in business, in media, and something clicked for me.
When you look at people the world calls “successful,” especially in a financial sense, there’s often a common thread.
Not always. There are definitely exceptions.
But often.
To accumulate vast amounts of money, power, status, you have to have a certain edge. A relentlessness. A willingness to prioritise outcome over harmony. To make decisions that aren't always kind.
Your Uncle Adam once said to me, “Nice guys rarely win.” (There would have been much more context to this at the time, but this is going back years and years so I can’t remember the full detail, only the sentiment).
At the time, I didn’t know what to do with that sentence.
And now, I think I do.

It depends on what you’re trying to win.
When I watch old footage of Arnold Schwarzenegger in Pumping Iron, you see a version of ambition that is raw. Calculated. Strategic. He would intimidate, unsettle, destabilise and demoralise competitors. In his mind, it was part of the game. And it worked.
When I look at Michael Jordan, arguably one of the greatest athletes to ever live, his teammates often speak about the sharpness of his edge. The expectations. The pressure. The way he could cut you out if you came with excuses.
And outside of sport, in business, you’ll find similar traits. Ruthless negotiation. Leveraging relationships. Playing the long power game. The ability to detach emotionally when decisions must be made.
History shows us that power and money often gather around people who are comfortable making uncomfortable moves.
But here’s what I want you to understand.
There is a difference between being formidable… and being cruel.
Between being disciplined… and being heartless.
Between being driven… and being consumed.
The world will probe you.
More productivity.
More achievements.
More followers.
More money.
More visibility.
More everything.
And if you’re not careful, you start to believe that the man with the biggest house wins. The loudest voice wins. The sharpest elbows win.
But life isn’t a quarterly earnings report.
It’s a nervous system.
It’s relationships.
It’s the quiet way you treat the waiter when no one is watching.
It’s how you speak to your partner when you’re tired.
It’s how your friends feel around you.
It’s about how you feel about you.
I don’t want you to confuse visibility with value.
I don’t want you to confuse wealth with worth.
And I definitely don’t want you to believe that being less kind is the price you pay for being more successful.
You can be strong without being sharp.
You can be ambitious without being aggressive.
You can build something meaningful without stepping on the hands of others to climb.
Jonny Wilkinson is a great example of this, and the more I think about it, my admiration for him grows. It goes much deeper than his ability to kick a rugby ball or the diligence he brings to his profession.
He is the exception. He is the nice guy who won.
When you reach the later chapters of your life, many, many years from now, you won’t want ghosts of regret standing around your bed. Faces you avoided. Bridges you burned for the sake of speed. Decisions that haunt you your entire life.
You’ll want peace.
The kind that comes from knowing you walked honestly.
“It's nice to be important, but it’s more important to be nice.”
That line has lasted generations for a reason.
Build your foundations on ethics.
Choose loyalty over leverage.
Choose substance over spectacle.
Choose integrity over impulse.
The race is long.
And in the end, it’s only ever with yourself.
If you can look in the mirror and see a man with a clear conscience, a steady moral compass, and a heart that remained open in a world that often rewards closed fists…
Then you’ve won.
Always,
Daddy xxx

