How Do You Know When It’s Time to Move On?

(Rethinking the timing and mindset behind transitioning from sports)

Most people will tell you to “trust your gut” when it’s time to move on.

I think that advice gets people stuck more than it helps.

Because when the gut is full of uncertainty, pressure, and identity loss, what does trusting it even mean?

We glorify decisive exits. We picture big, brave moments where you know it’s time, you walk away, and you never look back. But that’s not how it works for most of us. Especially not for athletes. The truth is, the decision to leave rarely feels clean. It’s messy. Confusing. And full of internal chatter that pulls you in every direction.

That’s why I’ve stopped telling athletes to look for clarity first. Clarity doesn't usually come before the transition. It comes through it.

Why Is Moving On From Sports So Hard?

When you’ve been trained to perform under pressure, respond to structure, and identify as “the athlete,” the idea of stepping away can feel like stepping off a cliff.

In Chatter, Ethan Kross talks about how our internal voice can amplify when our identity is challenged. That voice can help or hijack us, depending on how we respond to it.

"We can’t control whether a worrisome thought pops into our head, but we can control what we do with it."

So when sport starts to feel misaligned, when the thrill fades, or your curiosity turns elsewhere; it’s normal to question your instincts. But staying in that loop too long can make the transition even harder.

What If the Signs Aren’t Dramatic?

They usually aren’t.

Most athletes don’t retire in front of a stadium or at the top of their game. The signs are subtle. You’re not dreading it, but you’re not lit up either. You start daydreaming about life outside the gym or the pitch. You notice yourself staying quiet when teammates talk about next season.

The shift happens quietly before it shows up loudly.

Aleisha McCall, a former competitive figure skater, said this on the 2ndwind Podcast:

“I had to get really honest with myself about what I actually wanted, not what people expected from me, not what I thought I should do after skating, but what I was actually curious about and willing to build.”

What Happens If You Wait Too Long?

Waiting isn't always wise.

The longer you stay in something that’s no longer aligned, the harder it becomes to leave on your own terms. That’s where burnout creeps in. You start resenting the thing you once loved. And when the transition finally happens, it feels like a loss instead of a choice.

We’ve been conditioned to push through discomfort. But pushing through something that no longer fits isn’t the same as resilience. It’s avoidance disguised as commitment.

What Can You Do When the Time Feels Close?

1. Name It Without Needing to Solve It

You don’t need the whole plan. Just acknowledge the shift. “Something feels different” is enough to begin.

2. Externalize the Chatter

In Chatter, Kross talks about the power of distance. Write it out. Say it out loud to someone you trust. Get the loop out of your head and into the world where it can be examined.

3. Shift the Question From “Should I Leave?” to “What Am I Being Pulled Toward?”

You’re not just exiting something. You’re moving toward something else. Make space to explore what that could be, even if you don’t name it yet.

What If The Next Chapter Isn’t a Replacement, But a Reinvention?

You don’t have to become someone else. You just have to become more fully yourself; off the field, off the ice, outside the arena. Transitioning from sports isn’t about walking away from discipline, drive, or purpose. It’s about redirecting those traits into something new.

That’s what Aleisha did. And what many others are doing right now, quietly and courageously.

If you want to see what that looks like in action, listen to Aleisha’s story here:

🎧 Listen to the full episode

Or if you're ready to start exploring your own next step:

👉 Get support from 2ndwind Academy

Let’s stop waiting for perfect clarity. Let’s build it in motion.

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Suggested Book Quotes & Placement

1. Chatter by Ethan Kross

“We can’t control whether a worrisome thought pops into our head, but we can control what we do with it.”

Placement: Under “Why Is Transitioning From Sports So Psychologically Hard?”

2. Stillness is the Key by Ryan Holiday

“If your mind isn't still, you're never really there. Wherever you are.”

Placement: Just before “What Happens If You Wait Too Long?” to highlight the danger of staying in something too long without reflection.

3. The Practice by Seth Godin

“You don’t need more time, you just need to decide.”

Placement: End of “What Can You Do When the Time Feels Close?” section, as a mindset shift toward action.