Some weekends are planned meticulously. Others just happen to you.
This one fell firmly into the second category — and somehow turned into one of the most memorable weekends I’ve had in a long time.
On Friday, I was off the south coast pretending to be an experienced sailor alongside TAB franchisee Stuart McCulloch and a brilliant bunch of his members. By Saturday, I was in a suit sitting in the royal box at Wembley, proudly watching my wife, Davnet, present the play-off trophy in front of a packed stadium of Hull and Middlesbrough fans.
It was surreal. Slightly ridiculous. And full of moments I’d quite like to bottle up and keep.
Friday started exactly as every good Friday should: waking up in a very decent pub with rooms, opening the curtains to wall-to-wall blue sky and a light breeze. If you were designing a sailing day from scratch, this was it.
After demolishing bacon rolls in the harbour, we headed out towards The Needles off the Isle of Wight. People took turns at the helm, had a go at crewing, and generally behaved like seasoned sailors while Stuart quietly made sure none of us ended up drifting towards France.
Somewhere between the tacking, rope-pulling and pretending we understood nautical terminology, something interesting happened: strangers became proper company. That’s the thing about experiences like this. You skip the small talk very quickly.
Then, just as we were heading in for lunch, a WWII Spitfire appeared out of nowhere and gave us a fly-past at close quarters. Now, I don’t think Stuart arranged that part of the day… but honestly, I wouldn’t completely rule it out.
We eventually ended up back in Lymington Harbour with a well-earned pint, slightly sunburnt faces and very genuine smiles. At that point I remember thinking: “Well, this weekend isn’t going to get much better than this.”
Turns out, I was wrong.
Saturday had other ideas.
Thanks to Dav’s role as “presenter of the trophy”, we swapped deck shoes for lanyards and headed to Wembley.
The build-up alone was brilliant. Pitch-side access. Walking out into that enormous bowl of noise. Watching our boys and friends take photos at every available opportunity like excited tourists — which, to be fair, we absolutely were.
Then came the slightly surreal bit. Our seats for the match were in the royal box.
Watching football from there feels like entering a parallel universe. I found myself sitting next to the Hull City owner, who somehow managed to remain impressively calm while his club edged closer to the Premier League and a financial prize reportedly worth around £250 million. I’d have needed oxygen.
The atmosphere inside Wembley was electric. After all the controversy surrounding the previous week, you could feel the emotion pouring out of every tackle, every chance, every decision. And when the final whistle went, the contrast was extraordinary.
To one side: absolute joy.
To the other: complete devastation.
Football has a brutal way of compressing success and failure into the same square footage. Meanwhile, my phone had started exploding with messages from friends and colleagues in Australia, America, Sri Lanka and various other parts of the world:
“What on earth are you doing on TV in the royal box?!”
The truthful answer?
Hanging onto Dav’s coat-tails and trying not to look like someone who’d accidentally wandered into the wrong area.
A few things, actually.
First, I’m incredibly lucky. Most people don’t get one day like either of those. I somehow got both in the same weekend — and I’m very aware of that.
Second, I nearly missed half of it. When Stuart first invited me sailing, my instinctive reaction was the usual one: “Thanks, but I’m too busy.” And there’s the trap.
There will always be another email.
Another meeting.
Another “urgent” issue demanding attention.
Business owners are particularly good at convincing themselves that life can wait until next week. But sometimes the best opportunities arrive disguised as inconvenient timing. Saying yes required a tiny leap of faith. It was completely worth it.
Third, the conversations that matter rarely happen in formal settings. On that boat, people opened up properly. We talked about business, life, pressure, family, ambition, worries — all the things that often sit just below the surface during normal meetings and coffee catch-ups.
A change of environment changes people. It’s why some of the best thinking in business happens away from boardrooms altogether.
And finally, Wembley was a very vivid reminder of how thin the line is between success and failure.
To my left, Hull fans were living their best lives.
To my right, Boro supporters looked utterly broken.
Yet both sets of owners showed real humility and respect throughout. Because deep down, they know the truth every business owner eventually learns:
Sometimes the margin between triumph and disappointment is tiny.
One bounce of a ball.
One decision.
One moment.
And the entire story changes.
A quote often attributed to Churchill kept running through my mind throughout the day:
“Success is not final, failure is not fatal: it is the courage to continue that counts.”
That feels about right to me.
So, two days.
One yacht.
One stadium.
One very proud husband.
And a quiet promise to myself to say “yes” a little more often.
— Ed Reid