What would have to be true for me to receive one of the Thinkers50 awards when I’m 50?
That’s how my morning started today, on December 26th, 2025.
I’m 38 now.
Bill Gates has this beautiful line:
“Most people overestimate what they can do in one year and underestimate what they can do in ten years.”
Not long ago, I heard Alex Hormozi telling a story:
“In 2016, I had $1,000 in my bank account and was sleeping on my gym’s floor. This August, we made more than $100,000 in a weekend from my book launch, $100M Money Models.”
Most goals are possible.
Just not on the timeline you wish for.
Back to the question.
I’d just finished reading Playing to Win: how strategy really works. One question from the book stood out for me:
What would have to be true for this strategy to succeed?
That was one of the key questions there to help you figure out which strategy to pursue.
You’d ask this question. Come up with a set of criteria. And then you start testing what you can to see whether this is even a winnable game for you. And if it is, what strategy can actually work. For YOU.
I happen to be in direct communication with 2 Thinkers50 recipients. I’m also connected to the founder of the award. I can pressure-test this thinking with some people who’ve already walked the path.
But the power of this question goes way beyond awards.
If you want to get in shape and you’re choosing a strategy - nutrition, training, recovery, quitting bad habits - what would have to be true for that strategy to work?
For YOU.
What skills do you need?
What routines must exist?
What systems need to run even when motivation disappears?
If you want a different career path,
What would have to be true for that path to succeed?
If you want more fulfilling relationships, more meaning, more freedom - what would have to be true for it to enter your life?
And...
You don’t just ask what would have to be true.
You ask whether your current skills, systems, energy, and environment are a match, or could realistically become one.
Sometimes the answer isn’t “try harder.”
Sometimes it’s “choose a better-fitting strategy.”
I've coached clients for 18 years and here's one major thing I learned: people fail a lot mroe when the strategy isn't a match for their life.
One of my strongest skills is learning principles and seeing how they apply across domains. Strategy, behavior, health, work, leadership, life.
So now that I’ve added another strategic lens to my toolkit, and the question becomes:
How do I apply this way of thinking, not to one area like my business, but to my entire life?
Including something as long-horizon and identity-shaping as earning a Thinkers50 award in a decade.
As I set goals for 2026, I’m not trying to get somewhere, or get something this year.
I’m trying to make daily, strategic choices that over a decade add up to someone who fully deserves that recognition.
Over to you dear reader,
What choices, behaviors, and decisions would need to happen consistently for your strategy of success to be true? And do you need some skills to build and say no to some projects and people?
