I’ve been a Bob Dylan fan since I was thirteen.
One of my favorite songs is Positively 4th Street.
On the surface, it’s warm and melodic.
Underneath, it’s one of the harshest songs Dylan ever wrote.
It ends with a line I’ve never forgotten:
“I wish that for just one time you could stand inside my shoes… You’d know what a drag it is to see you.”
In my early 30’s I was a founding partner in what became a global toy phenomenon, Word POG Federation.
They were crazy times. We went from not even having a logo to doing licensing deals with companies around the world in less than two years.
I served as the EVP and Creative Director. As such, my team and I were responsible for all product design and development for the company.
We were a small, but mighty, team of young creatives who worked really hard.
It was there that I realized what a terrible boss I was and what a drag it was for my team to see me.
I micromanaged everything.
I thought that was my job.
I believed that because I had more experience, I usually knew the best way to do things. So I reviewed everything. Changed everything. Second-guessed everyone.
Then one day, I had an uncomfortable realization.
It was exhausting working with me.
And no fun.
If I hated being around someone who questioned every decision I made, why wouldn’t everyone else?
That realization changed the way I lead.
I stopped trying to control every decision and started giving talented people the room to make their own.
Something unexpected happened.
The quality of the work improved.
People became more invested.
Ideas got better.
Not because I had become a better decision-maker.
Because I’d become a better listener.
Here’s what I finally learned:
When you hire great people, your job isn’t to prove you’re the smartest person in the room.
It’s to create an environment where everyone can do their best work.
That doesn’t mean lowering standards.
It means replacing control with trust, coaching instead of correcting, and asking more questions than giving answers.
Ironically, the less I tried to own every decision, the better our decisions became.
It took me years to realize the last line of Positively 4th Street wasn’t teaching me about someone else.
It was teaching me about myself.
