It was 2 AM on a Tuesday.
I sat in my office, staring at the screen full of metrics, analytics, and to-do lists. Everything looked great on paper. The business was growing. The numbers were up.
But something felt empty.
In that moment, a question hit me hard: “Is this really what it’s all about?”
Maybe you know that feeling. The late-night doubts that creep in when everyone else is sleeping. The weight of wondering if all this hustle actually means something.
Here’s the truth: If you’re building something meaningful, you’re going to face moments that shake you to your core. Moments where the path ahead seems unclear, and the “why” behind it all feels distant.
I call these existential speedbumps. They’re those moments when success feels hollow, and the endless pursuit of more leaves you questioning everything.
But here’s what I’ve learned: These moments aren’t just normal – they’re necessary.
The Heart of an Existential Crisis
Think of an existential crisis like standing at the summit of a mountain you’ve been climbing for years. Instead of feeling triumphant, you look around and wonder: “Now what?”
It hits different for us entrepreneurs. We’re taught to chase goals, to hustle, to achieve. But no one prepares us for what happens when we get there.
I remember closing a major deal – one I’d been working on for months. Instead of celebration, I felt a strange emptiness. The target I’d been aiming at was gone, and with it, my sense of direction.
This isn’t weakness. It’s human.
And it happens precisely because we’re the kind of people who push boundaries and ask big questions.
Why Entrepreneurs Feel This More Deeply
We’re wired differently, you and I.
We see possibilities where others see problems. We dream bigger, push harder, and often tie our identity to our impact.
But that’s exactly why the existential questions hit us harder.
I learned this lesson when my first company crossed $1M in revenue. Instead of popping champagne, I found myself sitting alone in my backyard, wondering if this was really what I’d worked so hard for.
The truth? Success amplifies our existential questions. It doesn’t answer them.
When you’re sprinting toward a goal, you don’t have time to question the race. But when you pause – even for a moment – the big questions flood in:
Is this making a difference?
Am I building something meaningful?
What happens when I reach all my goals?
Finding Your Way Through the Fog
Here’s what works for me:
- Embrace the questions
Don’t run from the doubt. Sit with it. Let it teach you something about yourself.
- Get physical
Some of my clearest insights come during long runs or heavy lifting sessions. There’s something about moving your body that quiets the mind.
- Find your people
Not the networking kind. The real kind. The ones who get it. The ones who’ve been there.
- Write it down
Get the thoughts out of your head and onto paper. They’re less scary there, and patterns start to emerge.
- Remember death
Sound dark? Maybe. But nothing brings clarity quite like remembering we’re all temporary. It helps separate what matters from what doesn’t.
Turning Crisis into Clarity
The breakthrough came for me on a trail run.
Halfway up a mountain, lungs burning, I realized something: The existential questions weren’t the problem. Running from them was.
These moments of doubt? They’re invitations.
Invitations to go deeper.
To build with more purpose.
To lead with more humanity.
Every time I’ve faced these questions head-on, something powerful has emerged on the other side. A clearer vision. A stronger why. A better way forward.
The Truth About Finding Meaning
Here’s what I know now:
Meaning isn’t something you find once and keep forever. It’s something you create, daily, through small choices and brave actions.
The existential crisis you’re feeling? It might be the best thing that’s happened to your business – and to you.
Because when you emerge (and you will emerge), you’ll build differently. Lead differently. Live differently.
You’ll stop chasing success for its own sake.
And start creating success that matters.
Remember: The questions that keep you up at night are the same ones that can wake you up to a better way of living and leading.
So here’s to the questions.
Here’s to the doubt.
Here’s to building something that matters.
