I had a boss in Chicago once. Total asshole. The kind of guy who made Gordon Ramsay look like a motivational speaker.
I was young, working as a headhunter, full of fire, chaos, and the kind of ambition that doesn’t think it needs a plan. He didn’t buy into that. Not for a second. Every night before I left the office, he made me clear my desk completely—one clean sheet of paper left behind, with exactly what I was going to do the next day. Every call. Every target. Every objective. If it wasn’t there, I wasn’t leaving.
At the time, I despised him for it. I thought he was killing my vibe, cramping my spontaneity. I wanted to fly free—he was handing me a map and a leash.
But looking back? I thank that man more than almost anyone else in my life.
He taught me the value of structure—not just for productivity, but for sanity. Ever since then, I’ve gone to bed knowing exactly where I’m going the next day. No spinning wheels. No waking up aimless. Just a clear path and forward motion. That one routine—setting tomorrow’s direction before today ends—became the backbone of everything I’ve built since.
And the irony? That structure gave me the freedom I was chasing all along.
The Takeaway
You don’t need more freedom. You need direction. Real freedom isn’t waking up and winging it—it’s waking up already in motion. Build the structure. Set the course. Even if you hate it at first, it may just become the thing that sets you free.
Keep Moving Forward!
The Not-So-Guru