The best way to explain white male privilege to a privileged white male.

Especially if he’s ever ridden a bike.

I get it now.

I didn’t always get it, but I do now.

Not that I didn’t WANT to get it. I did. I just didn’t.

But I do now.

Get it?


I’ve never felt privileged.

I’ve worked my ass off my whole life.

Where I live, when I was growing up, you were eligible to work for pay at age 16. So my 16th birthday was my first day on the job bagging groceries at the store my father worked at.

Photo by Clem Onojeghuo on Unsplash

I’m 44 now. I’ve had a job, sometimes two or three at a time, ever since. During high school, during two stints in college. School during the day, work at night.

Bagging groceries, cleaning restaurant tables, manning the cash register at an office supply store, prepping crabcakes and shrimp cocktail at a popular seafood restaurant. These are just a few.

I spent one summer interviewing former patients of the state’s primary mental hospital. To see how they’re doing. I was the only male on staff, so I got to interview the male patients with histories of sexual assault. Some of them were in prison. They said terrible things. I took those terrible things home with me. My relationships suffered. All for $9/hour.

I’ve worked my ass off my whole life.

When I hear that some fraction of what I have is due to privilege, and not due to hard work, my defenses go up. And I discredit the notion. And the person using the phrase. And I get pissed.


I was on a business trip with my boss. Brilliant engineer. Even better leader. Empowering, vulnerable, made me feel like a partner rather than an employee. The whole package.

Also, black.

We’d arrived at our destination and were at a convenience store to pick up a few things. We’d each paid by credit card. Walking out, he has this slight smirk on his face.

“What’s up?” I ask.

“I always have to show ID when I use my credit card,” he says. “Not this time. Guess I need to bring you with me more often.”

I don’t really believe him. Coincidence, I think.


Photo by Ehud Neuhaus on Unsplash

Same business trip. Same boss. Bar across the parking lot from the hotel. We’d planned to meet there to review some last-minute changes to the presentation we were making the next day.

I walk in. He’s waiting at a table, no drink. I sit down across from him. Bartender comes over. Takes our order. Leaves.

Again, the slight smirk.

“Now what?” I ask.

He glances at his watch. “I’ve been here 10 minutes.”

I believe him a little more. Still, coincidence.


Same business trip. Same boss. Meeting with our vendor. They don’t know us, don’t know who’s in charge.

He walks into the conference room slightly ahead of me. They shake my hand first. They’re talking to me.

“I don’t know, what do you think, boss?” I ask, glancing at him.

Slight smirk.

I believe him.

I can’t concentrate for the rest of the meeting. Thinking about it all. He handles everything.


Same business trip. Same boss. Same bar.

He opens up.

It’s like riding a bike. You ever start out riding a bike with the wind behind you? How much do you notice that tailwind? You don’t. But what happens when you turn around to go home? Then you notice. You had no idea you even had a tailwind until it became a headwind. You never notice the tailwind.

Brilliant engineer. Even better leader.

Doing it all with a headwind.


Check out my new publication — Management Matters — real leadership & management advice for the future C-suite.