The Question I Asked After Achieving Everything I Thought I Wanted

I moved out of my childhood home and away from my hometown at 16. I found a way to secure an apartment to live in by myself for my entire junior year. All because I had a dream: I wanted to play basketball for Capital High School and win the state championship.

I lived isolated from family and friends for the sole purpose of pouring every ounce of discipline and focus into the game and my team. Not only did we end up winning state, we also ended up going undefeated the entire season.

On a celebratory, post-season hike with one of my coaches, we reached the mountain top and began to reflect on all we'd accomplished: shiny trophies, shattered state records, unending praise. All that I sacrificed and bled for was finally mine. The view from the top should have represented the victory and achievement that I dreamed of.

Instead it felt... Like nothing.

"Is that all?" I whispered to my coach. Little did I know, I was in for a decade of asking that same question.

The Myth of the Summit

I once thought happiness was a destination. A summit to be reached, a trophy to be won.

Our culture sells us this story every day: "If only you achieve X, then you'll be happy. You'll be fulfilled. You'll finally be worthy." We chase championships, promotions, financial targets and relationship milestones, believing that crossing some invisible finish line will finally fill whatever's aching inside us.

The lie is seductive because it's partly true. There is real pleasure in achievement... For about five minutes.

Then you wake up the next morning and you're still you. You with the same insecurities and questions. The same restlessness because something is still missing. So you set your sights on the next peak. Because surely that one will be different, right? That next step on the ladder will finally be and make you enough?

What Actually Fills the Space

It took years, and many more "summits" that felt just as empty to understand what I was really searching for... Not the feeling of holding a trophy, but the value that came from the training. The relationships forged in those grueling practice sessions and discipline gained by breaking my body over and over. The steadfastness that came with choosing to show up daily. The correction I received that helped a boy turn into a young man.

I thought I just wanted to win. But in reality, the real treasure was buried in the messy middle.

True fulfillment isn't a destination you arrive at. It's a way of traveling. It's about building something meaningful with people who matter, not just achieving something impressive for people to notice. And forget about winning something worth having! The beauty is in becoming someone worth being.

"There's beauty in the struggle, ninja." - J. Cole (I couldn't resist.)

Living in the Ongoing Ascent

You'd think that a decade later, after that mountain moment and all of these poetic words that I'd be an expert on this... And you'd be tragically wrong because I catch myself doing the exact same thing, right now with my business.

I keep deceiving myself by believing that when revenue hits X, when I can quit my day job, when I have financial security, then I'll feel successful. Then things will be different.

I'm trying to navigate a very messy financial situation while building Web Launch Lab from scratch. The temptation to hinge all of my worth on whether it fails or succeeds is strong.

Anyway, I'm writing this as much for me as for you. Because apparently, this is a lesson I need to keep learning...

Hear me out, though: The dreams aren't the problem. The emptiness isn't either.

The problem is thinking that achieving the dream will fill the emptiness. That emptiness is there to forcefully remind us that we're looking in the wrong place. That what we're really searching for can't be won or earned or achieved; it can only be lived.

Let this be your honest and friendly reminder this week: The summit will come... or it won't. But real life is happening in the climb.

I'm curious: What "once I achieve this" thought are you wrestling with right now? How might the messy middle you're in today actually be more valuable than the summit you're climbing toward?

Let's keep learning together in this beautifully inefficient space between where we are and where we think we're going.

Because the mess isn't the problem. The mess is the point.