Learning Not to Worry (Because It Was Never Helping)
For a long time, my worry disguised itself as diligence.
It looked responsible. It looked like preparation. It looked like “doing my job.”
And to a point, that was true. I’ve always cared deeply about the things I take on. I prepare. I think ahead. I show up ready.
But somewhere along the way, that preparation crossed a line.
It turned into something else. I started paying the cost of outcomes that hadn’t happened yet. Sometimes outcomes that were unlikely to happen at all.
I would worry “just in case,” telling myself it was protection.
In reality, it was interference.
The Quiet Cost of Worry
Worry costs me a lot of things, but the one I feel most is sleep.
Not just hours of it. Restfulness. The kind where your nervous system actually powers down.
When I worry, my engine never idles. I’m restless. Less patient. Less calm. I’m technically functioning, but not fully at ease.
The more subtle cost is this: I have a really good life, and I do not fully enjoy all of it.
Maybe I am present for 85 percent of it. That is not nothing. But there is another gear available. More appreciation. More ease. More room to actually experience what I have built.
Worry keeps me from that.
What makes it tricky is that worry feels productive. Almost intoxicating. It tricks you into believing it is the thing helping you succeed.
But when I am honest with myself, I have succeeded despite the worry, not because of it.
Evidence Beats Anxiety
I have seen this pattern repeat across my life.
In sales, I have prepared obsessively for high-stakes moments. I worried about timing, outcomes, execution. Then, almost every time, the moment I let go of the “what ifs,” trusted the preparation, and showed up, things went well.
Not perfectly. But well.
Zooming out further, the bigger realization came around money and the future.
Am I saving enough? Investing the right way? Am I going to be okay?
The answer, increasingly and unmistakably, is yes.
There is so much groundwork already laid. So many systems in place. So many right decisions stacked over time.
There is no scenario where this does not work out well.
Letting go of that particular worry did not make me careless.
It made me lighter.
A Warning I Did Not Recognize at the Time
The clearest early warning came much earlier, in baseball.
I spent years worrying about outcomes I could not control. Am I getting drafted? Am I moving up? Is this enough? It wore me out.
I eventually had the opportunity to play professionally and walked away after a year. Not because I could not do it, but because I had exhausted myself long before the story played out.
At the time, I did not have language for what was happening.
Now I do.
That season taught me something I have spent decades relearning: Worry drains energy faster than effort ever will.
Preparation Versus Worry
Here is the distinction I have learned to make:
Preparation moves me forward. Worry keeps me busy.
Preparation is active. Worry is reactive.
Preparation earns confidence. Worry borrows stress from the future.
I am never going to be the person who does not prepare. That is not how I am wired. So the fear that “if I stop worrying, I will stop caring” does not hold up.
The evidence says otherwise.
When I care about something, I put in the work. When I put in the work, I do well.
That is not arrogance.
It is pattern recognition.
What Calm Feels Like
When I do not worry, everything slows down.
The best way I can describe it is through sports. The game comes to me. My head is up. I am scanning. I am present.
When I worry, everything feels fast and reactive. I am scrambling. Playing from behind.
When I am calm, I am actually in control.
What I did not expect is how physical that calm feels. Better sleep. More patience. More space.
I literally feel like I have more hours in the day when I am calm.
Building Trust, Not Denial
The shift did not happen all at once.
First came awareness. This is not helping me.
Then came tools. Move my body. Get outside. Accomplish small, tangible things. Take a walk with my wife. Play cards. Do something grounding.
Now comes the hardest part. Trust.
Trust the preparation. Trust the showing up. Trust the lifetime of evidence.
Not luck. Not fate.
Just the quiet confidence that when I care, I do the work. And when I do the work, things tend to work out.
The Luxury I Am Choosing Now
The luxury I am choosing now is calm.
Peace. Presence. Trust.
Not trying to control things I cannot control. Not paying for problems that do not exist yet.
I have built a path that I am already walking.
I do not need worry to carry me forward anymore.
And that realization, more than any outcome, is what finally feels like enough.
— Stephen
This is part of Intentional Luxury—a newsletter about building wealth, meaning, and legacy through thoughtful decisions. What are you learning to let go of? Hit reply—I’d love to hear what you’re working through.
Nicely said. I especially like “Preparation moves me forward..”.