The Freedom I'd Been Chasing Felt Like Drowning

Last few months of my competitive career I had a fantasy running on a loop.

No more 4am alarms. No more training schedules dictated down to the minute. No more competition calendars stretching out months in advance telling me exactly where I needed to be & when. No more coach controlling my diet, my sleep, my recovery. Just open, unstructured, glorious time stretching in every direction.

I'd been chasing that fantasy for years. All the brutal mornings, all the sacrifice -- I told myself it was building toward this eventual freedom where I could rest & do whatever I wanted & live like a normal person for the first time since I was fourteen years old.

Then I got it.

Within a few weeks the open time started eating me alive.

Not in any way visible from the outside -- if you'd seen me you would have thought I was living the dream. Sleeping in, traveling, no obligations.

But inside my head it was different. My brain, which had spent fifteen years w/ every hour accounted for, had no structure to push against. And a mind w/ nowhere to go tends to go somewhere dark.

I'd lie awake at 2am replaying races from years ago, conversations I could have handled differently, moments I'd never get back & couldn't change. Things that didn't matter anymore but had somehow expanded to fill all the empty space.

During the day I'd cycle between restlessness and this weird paralysis -- too many options, no urgency behind any of them, so I'd end up doing nothing & feeling worse about it.

The rumination was the part that scared me. In training, my mind had a job -- run splits, analyze competitors, rehearse scenarios, solve the tactical puzzle of the next race. Always working on something specific & the specificity kept it honest.

Without a target it just... looped. Old mistakes, hypothetical disasters, worst-case futures I couldn't control.

I remember calling my dad one night, maybe three months into retirement, and not being able to explain what was wrong. Everything was fine on paper. I had money, I had time, I had freedom.

And I was miserable in a way I hadn't been when I was grinding through the hardest training blocks of my career.

"I think the structure was doing more than I realized," I told him.

Why do high achievers struggle w/ open time?

It took me a while to understand what was happening, but I've since seen the same pattern in so many people that I think it's close to universal.

Goals aren't just about achieving things. They give your mind something to orbit around -- something that organizes all the chaos & noise & random mental energy into a direction. Take away the goal and you don't get peace, you get a spinning top w/ no axis.

This is especially brutal for high achievers bc the transition hits from a direction they don't expect. People who spent years, sometimes decades, building discipline & mental toughness & grit -- and then the chapter ends & all that mental infrastructure has nothing to process. Engine is still running but there's no road underneath it.

I've talked to founders who sold their companies and experienced the exact same thing. Deal closes, wire hits, congratulations roll in, and for a few weeks it feels like vacation. Then the emptiness shows up. The thing that organized their entire existence -- the company, the mission, the daily fires that needed fighting -- is gone. And they start turning all that intensity inward, which is about the worst place it can go.

Executives between roles, athletes leaving their sport, parents whose kids left for college, anyone who built their identity around a structure that no longer exists. Same disorientation. Same 2am loops.

My solution wasn't elegant. I started saying yes to everything.

Investments, advisory roles, speaking engagements, business deals I knew almost nothing about. Not bc I was passionate about any of it -- I want to be honest about that. I said yes bc I needed direction. I needed something to aim at so my brain would stop consuming itself.

The specific goal mattered less than having one. Any target was better than no target bc the target itself was doing the therapeutic work -- gave my mind a job again, & a mind w/ a job is a mind that doesn't have time to run those 2am loops.

Was everything I said yes to the right move? No. Some of those investments didn't work out. Some of those advisory roles weren't a great fit. But the act of pursuing something -- anything -- w/ intention was enough to break the cycle. Gave me ground to stand on while I figured out what I wanted the next chapter to look like.

Over time the yeses got more selective. I started to understand which pursuits energized me vs. which ones were filling space. But I wouldn't have gotten to that clarity without the messy phase first. You can't optimize a direction you haven't picked yet.

If you're in some version of this right now -- between jobs, between chapters, between identities -- and you've got that hollow directionless feeling creeping in at night, I want you to hear something.

That feeling isn't weakness. It's not a sign you're broken or ungrateful or that you made the wrong decision by leaving whatever you left. It's your brain doing what brains do when structure disappears -- looking for something to organize around, & in the absence of a target, organizing around your fears & regrets instead.

The fix isn't to wait until you feel clarity. Clarity comes from movement, not from sitting still & thinking harder.

Pick a direction -- even a provisional one, even one you're not sure about -- and start moving. Give your mind a job. Quality of the job matters less than the fact it exists.

I spent fifteen years w/ every hour accounted for, and when that structure vanished I thought I'd finally be free. What I learned is structure isn't the opposite of freedom -- it's what makes freedom possible. Without it, freedom is another word for drowning w/ no one watching.

Even a temporary structure. Especially a temporary one. Your brain will thank you at 2am.

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--AAO