Transformation, Challenges and Going Alone
This morning, I was up at 4:30 AM. I made myself a peanut butter and honey sandwich, had a cup of coffee, a glass of water, and packed my gear for a 16-mile training run along Chicago’s lakefront. By just after 5:00 AM, I was out the door and on my way.
When I got to the path, something hit me: there was no one else out. Not a soul. I could see a mile or two in both directions—completely empty. The sun hadn’t come up yet, but the conditions were perfect. I knew that in just a couple of hours, the path would be packed. But at that moment, it was just me and the sound of my feet hitting pavement.
By mile one, the sun was beginning to peek over the horizon. It was 55 degrees with a soft five-mile-an-hour breeze from the east. The sky was clear. I passed Navy Pier, Monroe Harbor, the Shedd Aquarium, Soldier Field… and maybe saw a few other early risers—some runners and a couple cyclists. But no groups. No herds.
And that’s when it hit me: today is Monday, May 12th, 2025. Not a Saturday. Not a Sunday. Not a day for the herds. No running clubs. No pack of cyclists. Just me. Alone. And I realized—that’s exactly where transformation starts.
The Illusion of the Herd
When we’re building something meaningful—our health, wealth, relationships, or careers—it’s tempting to look for a crowd to follow. We want affirmation. We crave direction. There’s comfort in the pack.
But here’s the thing: the herd isn't always going where you need to go. In fact, sometimes it’s headed in the opposite direction.
I see this in my practice all the time—people taking bold steps that no one in their family or social circle has taken before. Hiring a financial planner. Building a team. Paying for legal or financial advice. Making a plan. Following through. None of it is familiar. All of it is scary. And because they didn’t grow up seeing it, they don’t know if it’s right.
But just because it’s unfamiliar doesn’t mean it’s wrong. It just means you’re stepping out of the pack.
Who Are You Becoming?
To become the person you want to be, you’ll have to step away from the familiar. You’ll have to do things no one else around you is doing. And you’ll have to upgrade the voices around you—from friends who commiserate to mentors who challenge you, from casual conversations to deliberate counsel.
Transformation happens in those moments when you realize the herd can’t take you where you’re trying to go. When you choose to take a new route, you’ll find yourself out early, on the path alone, without validation or applause. But it’s in those moments that you begin to grow into your future self.
The Fear Is Real—and So Is the Opportunity
I’m not going to pretend it’s always empowering. I had anxiety at 4:30 this morning. I didn’t want to go. I second-guessed myself. I considered the treadmill. The bike. Anything but that run.
But my plan didn’t call for that. And more importantly—I didn’t call for that.
Sometimes, the only thing separating you from progress is a story your anxiety is telling you. That story can convince you to stay inside, to not take the leap, to stay in the herd. But if you’ve ever broken with tradition or what those who came before have done such as - pursuing an education, moving across the country to take a career opportunity, exercise to cultivate good health, or building better habits—then you already know how this works. From time to time you can and need to run your own race.
Your 5:00 AM Moment
So let me ask you this:
Who are you becoming?
What transformations are you in the middle of?
What’s keeping you from your 5:00 AM moment?
Sometimes the excuse is valid. Sometimes it’s just familiar. But if you’re going to reach for something greater—if you’re going to transcend what’s expected of you— and become what you expect of yourself you’ll need to step out the door in a different manner than you did yesterday.
You’ll need to run toward your values, practice the discipline desire, and trust your potential. And most importantly—you’ll from time to time need to be willing to go alone.
Because the version of you that’s waiting on the other side? They don’t live in the herd. They’re out there. On the path. Alone. At 5:00 AM. Running toward the life they were meant to live.