Put Yourself In The Room
Why some of the most valuable opportunities in life begin with a conversation you almost never have.
A few hours ago I upgraded my flight from Nadi to Sydney. (I am currently up in the air)
It wasn’t a particularly logical decision.
The upgrade cost me around $250 more than my original ticket. The flight isn’t that long. Economy would’ve been completely fine. I have just finished a family holiday in Fiji and was heading back to Sydney before jumping on another flight to New York the following day.
Part of me thought it was unnecessary.
Fortunately, the other part of me won.
As I boarded the aircraft, I noticed a bag rolling onto the plane in front of me with a United Airlines 1 Million Miler tag attached to it.
For those who aren’t aviation nerds, that’s a lot of flying.
The kind of flying where airports become familiar, flight numbers become second nature and entire chapters of your life are measured in boarding passes.
As I was putting my bag into the overhead locker, an older gentleman quickly (& rudely) shut the compartment and informed me that it was reserved for business class passengers.
I smiled and replied, “I am sitting here.” Pointing at the seat in front of him.
His face immediately went bright red.
I don’t think he meant anything by it, but I had a quiet laugh to myself as I sat down.
A few moments later, the gentleman next to me, the owner of the million-mile tag, was searching through his bag for something. I helped him find it and, as naturally happens with me, curiosity took over.
I pointed at the tag and asked,
“So what’s it like having one million miles with United?”
That single question turned into a conversation for most of the time we have been in the air so far.
We spoke about travel.
We spoke about New York.
We realised he was flying the exact same route I’m taking this weekend, just one day earlier.
We compared favourite neighbourhoods, restaurants and places we’d discovered over the years.
At one point I mentioned Via Carota, one of my favourite restaurants in New York.
Without missing a beat he replied,
“I grow the tomatoes for Via Carota.”
I laughed.
Of all the responses I expected, that wasn’t one of them.
We have exchanged numbers and have agreed to catch up for a drink and some food when I arrive in New York.
Now maybe nothing comes of it.
Maybe it’s simply a great conversation and a funny story.
Or maybe it turns into a friendship that lasts years.
The point isn’t what happens next.
The point is that the conversation happened at all.
Because the more I think about it, the more I realised this wasn’t really a story about a business class upgrade.
It was a story about proximity.
Looking back, almost every meaningful chapter of my life started because I put myself somewhere I wasn’t required to be.
The first client.
The mentor.
The friendship.
The relationship.
The run club.
The trip.
The opportunity.
None of them arrived while I was sitting at home waiting for certainty.
They arrived because I was willing to enter the room before I knew exactly what would come from it.
The thing I’ve learned as I’ve gotten older is that most opportunities don’t announce themselves when they arrive.
They don’t walk up and introduce themselves as your next client, your future business partner or someone who will have a meaningful impact on your life.
Most opportunities arrive disguised as ordinary moments.
A dinner invitation.
A random introduction.
A seat assignment.
A conversation with a stranger.
The challenge is that you never know which moment will matter.
You only find out afterwards.
That’s why I’ve become increasingly willing to invest in proximity.
Not just financially, but with my time and energy.
The flights to New York.
The dinners.
The events.
The meetings.
The introductions.
The uncomfortable moments where it would be easier to stay home, stick to what’s familiar and convince yourself you’ll do it next time.
People often ask me if all the travel is worth it.
Whether building a business across multiple cities makes sense.
Whether the investment justifies the outcome.
The truth is that some of the highest-return decisions I’ve ever made would look terrible on a spreadsheet.
Because the return isn’t always measurable.
Sometimes the return is perspective.
Sometimes it’s inspiration.
Sometimes it’s a friendship.
Sometimes it’s an opportunity that changes the trajectory of your career.
And sometimes it’s simply a reminder that life has a funny way of rewarding curiosity.
I’ve found that the most interesting people tend to know other interesting people.
The most interesting rooms tend to create more interesting rooms.
And the more consistently you put yourself into environments where opportunity can exist, the luckier you seem to become.
Not because you’re lucky.
Because you’re present.
Because you’re available.
Because you’re there when the conversation happens.
The $250 upgrade wasn’t valuable because it got me a bigger seat.
It was valuable because it put me in the room.
And in my experience, that’s where almost everything good starts.
As with all of my substacks, I write them (often from the sky), but as the words come to mind. They are free flowing thoughts from where I am at a given moment in time.
If this inspires you, makes you think of a question or simply has you curious…
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