THE WISDOM ORCHARD
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The Day I became the Boss I Swore I'd Never Be
And what a man named Don Karns taught me about the difference between leading and bossing
I still remember the morning it happened. I showed up to work at UPS and everything looked the same — the package cars, the routes, the faces I'd worked alongside for years. But something fundamental had shifted overnight. My browns were traded in for a white shirt and a dark tie. I was the boss now.
UPS was a private company in those days, and they had a strict promote-from-within policy. That meant something. It meant the people handing me the title knew my work, knew my character, and believed I had what it took. I believed it too. Maybe too much.
My assumption going in was simple and, as it turned out, completely wrong. I thought the delivery teams would want to perform at their best for me. We'd been side by side. They knew what I was made of. Surely that counted for something.
What I didn't understand — what nobody told me and I hadn't thought to ask — was that the relationship changes the moment the title does. I didn't wake up as a colleague who got promoted. I woke up as the boss. They saw it before I did.
The relationship changes the moment the title does. I didn't wake up as a colleague who got promoted. I woke up as the boss. They saw it before I did.
When the performance I expected didn't materialize, the frustration set in fast. And frustration, I learned, is a dangerous fuel for a new leader. It doesn't make you better. It makes you reach for the nearest available model of authority — which, in my case, was the boss I'd worked under before. The one I had quietly promised myself I would never become.
I became him anyway. I started managing through pressure and consequence. I punished those who didn't meet expectations. I became, as I came to think of it later, a hard ass. Not because I wanted to be. Because I didn't know what else to do, and the pressure to prove myself was relentless. I had always needed to be the best performer in the room. Now the room was different and I had no idea how to win in it.
This is the part of the story that most leadership books skip over. The wreckage between the mistake and the recovery. The weeks where you know something is wrong but you don't know what to do about it, so you just do more of the thing that isn't working.
ENTER DON KARNS
Don was the division manager. He didn't have a lot of formal education, a fact I mention not as a footnote but as the point. Because Don Karns was one of the finest leaders I have ever encountered in forty years of working with executives, organizations, and some of the most respected thinkers in the field of leadership development. His education came from paying close attention to people, and it showed in everything he did.
Don saw what was happening with me. More importantly, he saw through it — past the bossing behavior to the person underneath. What he recognized, and what I couldn't yet name myself, was that the hard-edged managing wasn't ambition. It was anxiety. My need to outperform everybody, to be recognized, to prove I deserved the title — it had curdled into something that was costing me the very thing I was trying to earn.
His first piece of advice was simple and it reoriented everything: go for respect, not affection.
Those five words were not a reprimand. They were a reframe. I wasn't being asked to stop caring about my drivers. I was being asked to care about them differently. Respect is a longer game than affection. It requires consistency, honesty, and follow-through. It sometimes means disappointing people in the short term for something more sustainable. Affection, I was learning, can be bought and lost overnight. Respect has to be earned — and kept.
Go for respect, not affection. Those five words were not a reprimand. They were a reframe.
Then Don gave me something to do with that philosophy. He called it talk, listen, and act. Fifteen minutes, regularly, with each of my drivers. Not a performance review. Not a check-in designed to catch problems. A genuine conversation: how can we improve your job in a way that benefits everyone?
And then — this was the part that mattered most — I had to commit to act. If I could address something, I would. If it was beyond my authority, I would say so honestly: I can't do that, but here's what I can do. No empty promises. No deflection. Just a straight answer and a follow-through.
It sounds simple. It is not easy. Especially when you've spent weeks burning trust and you're starting from a deficit.
THE FIRST THING THAT CHANGED
When I started showing up differently — consistently, honestly, with genuine curiosity about their work — something shifted. Not in them. In me. I had to change first. I had to earn back what I'd damaged. And that process, uncomfortable and humbling as it was, taught me something I have carried into every leadership engagement in the forty years since.
The leader always goes first.
Not in the sense of working harder or staying later. In the sense that the culture of a team reflects the behavior of its leader before it reflects anything else. If you want trust, you have to be trustworthy before you can expect trust back. If you want people to show up fully, you have to show up fully first. You cannot demand a response you haven't yet earned the right to expect.
Don also did something for me that went beyond the advice. He saw my self-doubt and gave me something to stand on. He helped me understand that being the best leader — not the best performer, not the hardest driver, but the best leader — was where I could put my need to excel and actually have it serve others instead of consuming them. He gave me a version of myself I could grow into rather than a set of behaviors I was supposed to perform.
I made peace, slowly, with the fact that failure didn't mean I was crap. I learned I was human. That turns out to be a prerequisite for leading other humans well.
WHY THIS STORY BELONGS HERE
The Wisdom Orchard exists because of stories like this one. Not because the UPS story is exceptional — it isn't. Some version of it lives in almost every leader I have ever worked with. The new supervisor who becomes the boss they swore they wouldn't be. The senior executive who still hears the voice that says they don't quite deserve the room they're in. The leader caught in disruption who keeps reaching for playbooks that no longer apply.
What is exceptional, I've come to believe, is having a Don Karns. Someone who sees you clearly and tells you the truth with enough care that you can actually hear it. Someone who offers not just philosophy but practice — something concrete to do with the insight so it doesn't just evaporate.
The Wisdom Orchard is my attempt to distill what that accumulation actually produced. Not a catalog of frameworks. Not a set of best practices assembled from books. But the living, tested, sometimes hard-won understanding of what actually helps people lead better — gathered from forty years of being in the room.
It's organized around stories, because stories reach people before frameworks do and stay with them longer after. The UPS story is the first one. There are many more.
As you enter the Wisdom Orchard, think about the leader you became instead of the leader you intended to be. What was the gap — and what would it take to close it?
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