Let Go or Be Dragged: The Skill Every Athlete Needs When Transitioning

There's an old Zen proverb that has really stuck with me ever since I read it:

Let go or be dragged.

Four words. No fluff. And yet it describes one of the hardest things a human being — and especially a competitive athlete — will ever have to do.

I've been sitting with this phrase a lot lately. Not because it's some motivational quote I stumbled across on Instagram, but because I lived it. And I'm still learning to live it now, in a completely different arena.

The 14-Month Project That Taught Me Everything

In 2025, I partnered with a close business colleague on what was the biggest project I had ever taken on. We're talking millions of dollars in budgeting, large-scale fundraising conversations, pitching to people when I wasn't quite ready, and stretching myself into areas of business where I didn't have the expertise.

For 14 months, I poured time, money, energy, and identity into this thing. I told myself the story athletes tell themselves constantly: push through, find a way, you didn't quit on the field, don't quit now.

And then, eventually, my business partner and I looked at each other and had the honest conversation. The project wasn't going to happen. Not in the way we had envisioned. The smart move — the right move — was to let it go.

But those words — let go — are easier said than done when you've invested 14 months of your life, a significant amount of capital, and tied your ambition to an outcome.

If you've ever competed at a high level, you know exactly what I mean.

Why Letting Go Is So Hard for Athletes Transitioning

Athletes are not wired to quit. The entire culture of sport is built around persistence, resilience, and refusing to accept defeat. It's what makes great competitors. It's also what makes the transition out of sport — and into business and investing — deeply complicated.

Research shows that about 70% of elite athletes suffer from post-professional career depression. The reason isn't simply that the sport is gone. It's that the identity is gone. An athlete's choice to abandon an elite sports career is directly linked to the loss of their athletic identity — that internal self-concept that has existed for their entire life.

The transition out of sport is often filled with negative emotions, feelings of loss, identity crisis, and distress. And yet, there's an irony buried in there: the same relentless, never-say-die mindset that made you successful in sport is the very thing that can destroy you in the next chapter — if you don't learn when to release.

Being dragged isn't weakness. It's actually a natural consequence of strength misapplied.

The Real Enemy: Ego and Obligation

When my project in 2025 came to an end, I had to be honest about what was keeping me in it longer than I should have stayed. It wasn't just belief in the vision.

Two other forces were at play:

Ego. I had told people about this project. I had built a narrative around it. Letting go meant letting people see that something I had publicly committed to didn't work out. For a former professional athlete — someone conditioned to perform in public — that's a particular kind of painful. It feels like failure, and that is not something athletes are conditioned to accept.

Obligation. When you've invested resources, relationships, and reputation into something, you can start to feel obligated to see it through. Not because the opportunity still makes sense, but because walking away feels like it dishonors the sacrifice already made. This is what economists call the sunk cost fallacy, and athletes — especially ones who've ground through injury, adversity, and losing seasons — are extraordinarily susceptible to it.

The Zen masters had it right. You don't get dragged because you're weak. You get dragged because you're gripping something that has already passed its moment.

Now I'm Applying It to Investing — And It's Humbling

After the project ended, I turned my attention more deliberately toward investing. Due diligence on companies. Looking at opportunities. Sitting across from founders and asking the hard questions.

And here's what I quickly realized: letting go is the central skill of investing, too.

The process is seductive. You get deep into a deal. You spend hours on calls, review financials, talk to industry contacts, get excited about the upside. And then you find something that gives you pause. Maybe the numbers don't hold up. Maybe the founder can't answer a critical question. Maybe the market timing is off.

This is the moment FOMO (Fear of Missing Out) shows up. You think:

What if this is the one I passed on that became something? What if I'm too cautious? What if the competitor I respect takes this deal?

FOMO is just a dressed-up version of being dragged. It's not logic. It's the grip.

I'm learning — slowly, and sometimes painfully — that the best investors aren't the ones who chase every opportunity. They're the ones who can walk away from a good deal because it isn't the right deal. Conviction requires clarity, and clarity requires the willingness to release.

The Athlete Application: Your Career Is a Deal You're Always Evaluating

Here's where I want to speak directly to athletes — especially those who are in the middle of the transition, trying to figure out what comes next.

You are already doing due diligence. Every opportunity you explore, every conversation you have, every venture you consider — you are evaluating a deal. And you bring with you the greatest competitive asset imaginable: the ability to outwork, outlast, and out-commit almost anyone in the room.

But that very asset will become a liability if you don't learn the discipline of letting go.

Studies show that athletes who have willingly retired and accepted the transition may experience less difficulty as they begin to explore new activities and identities outside of sports prior to retirement. The key word there is accepted. Acceptance isn't giving up. Acceptance is choosing clarity over comfort.

Here's what letting go looks like in practice after sport:

Letting go of the old identity. You are more than your sport. You always were. But you have to release the version of yourself defined by the jersey number and the scoreboard. That chapter was real and it mattered — and it's also over. The athlete who tries to relive it in every business meeting, every pitch, every networking event, is the one being dragged.

Letting go of opportunities that don't fit. Not every partnership deserves a yes. Not every project deserves 14 months. Part of becoming a sophisticated businessperson is developing the discernment to know when something isn't right for you — even when you want it to be.

Letting go of the need to perform certainty. Athletes are conditioned to project confidence. In sport, hesitation can be exploited. But in business and investing, the honest admission of "I don't know enough yet" is not weakness — it's wisdom. Some of the smartest people I've encountered in the investment world are the ones most comfortable saying no, and most comfortable with not knowing.

The Skill Nobody Teaches

Pre-retirement planning, development of a rounded identity, and voluntary retirement are critical factors associated with smooth transitions out of sport. In other words, the athletes who fare best are the ones who begin releasing before they have to. They build new identities alongside the athletic one, so when the moment of transition arrives, they're not white-knuckling a grip on something that's already gone.

That is the skill nobody teaches: the proactive, intentional release.

Most of us learn it the hard way. I did. I held a 14-month project longer than I should have because I hadn't yet built enough fluency with letting go. Now I'm in the investment world applying it every week — asking myself not just "Is this a good opportunity?" but "Am I holding this because it makes sense, or because I can't bring myself to walk away?"

The difference between those two questions is everything.

Final Thoughts

Sport will teach you to fight. Business will teach you to think. But the transition between them — and the life that follows — will teach you something neither one prepared you for: when to open your hands.

Let go or be dragged. It's not a surrender. It's a strategy.

The athletes who build great second chapters aren't the ones who gripped tightest. They're the ones who learned — sometimes through failure, sometimes through 14 months of hard work that didn't pan out — that releasing something at the right time is an act of strength, not weakness.

Your next opportunity is already out there. But you might be too busy holding something that's passed to see it.

What have you been holding onto longer than you should? I'd love to hear your story — connect with me on LinkedIn or reach out directly. And if you're navigating your own transition out of sport or into investing, subscribe to the blog. This is the conversation I'm committed to having.