How Learning Will Change Your Life
From Homeless to High Tech Director
In 1994, I was in my early twenties and just came out of a season of homelessness and drug addiction. I had no resume or formal education to lean on. Honestly, I barely made it out of High School.
What I did have was obsessive willingness to learn anything, from anyone, at any pace. That instinct is what got me my first real job. Three decades later, it is still the most valuable thing I own...
The world keeps changing and the job titles keep evolving. The technology stacks keep being torn down and rebuilt over and over again... yet the question that keeps mattering is the same one that opened the door for me when I had nothing else: what can I learn, and how fast.
I wrote a post a few weeks ago about AI fluency, and I know that for a lot of you, the letters “AI” already makes your eyes glaze over because every post is about it these days. I get it. This piece is not really about AI.
It is about the thing underneath AI. The thing underneath every change I have lived through in thirty years of tech and twenty years of pastoring, coaching, and mentoring people towards success. The thing underneath my own rebuild from homelessness living in my truck to wherever I am now.
That thing is deep curiosity.
Curiosity is the most underrated leadership trait I know of, and the most underdiscussed. We celebrate vision. We celebrate decisiveness and execution, but we rarely talk about the leader who sits in a meeting they do not fully understand and asks the next question instead of pretending they do. We rarely talk about the leader who reads outside their lane on a Saturday morning, not for any tactical reason, but because they refuse to atrophy.
“The heart of the discerning acquires knowledge, for the ears of the wise seek it out.”
Wisdom has to be pursued.
For most of us, curiosity peaks in childhood and slowly thins out as life narrows. Bills arrive. Jobs harden into roles. Identity gets tied to expertise. By the time we are leading anything significant, the cost of admitting we do not know something feels too high. So we stop asking. And the moment we stop asking, we stop growing.
In twenty-plus years of coaching, mentoring, pastoring, and managing people, and in three decades of working alongside very smart professionals, I have watched the same pattern over and over. The leaders who keep going never stop being students. They are sponges in their fifties the way most of us were in our twenties. They ask peers half their age what they are seeing. They read books outside their industry. They sit with discomfort when their assumptions get challenged. They resist the trap of mastery, because mastery without ongoing curiosity becomes a trap that outdates them quickly.
That, by the way, is what AI fluency really is at the senior level. It is a curiosity skill applied to a new substrate, not a technical credential.
The leaders I see making the strongest moves with these technology are not just the ones with computer science backgrounds. They are the ones who refused to let themselves to be
The same was true of the leaders who navigated the shift from mainframes to client-server. The same was true of the leaders who took the internet seriously when it was easy to dismiss. The same was true of the leaders who picked up mobile early.
Each wave looked unlearnable to people who had stopped learning, and natural to people who had not.
So I ask myself nearly daily...
Am I still curious?
Am I still teachable?
Am I still willing dig deeply into something I do not yet understand?
I am nearly in my mid fifties. I have walked some hard roads, and I have built a life I never thought I would have. The single thing I refuse to give up is the willingness to be a beginner.
I am not chasing relevance or afraid of being left behind. I refuse to give it up because I have watched what happens to people who do. I have watched brilliant people calcify in their forties and fifties, certain they had arrived.
That feeling of “arriving” is a lie and trap anyways. The journey is never done. And the grace of the journey is curiosity itself.
Stay a sponge. Be deeply curious and soak it up in an endeavor to learn it all... even though you never will.
Much love, Chris