ISSUE #022 | THE LEADERSHIP CONTRARIAN
I want to tell you a story about the most confident I have ever been in my entire life.
It didn’t end well. For my ego, anyway.
It was the early 1990s. Kathryn and I had been married just over a year. We were living in Colorado Springs - beautiful weather, blue skies, the kind of afternoon that makes you feel like life had conspired in your favor.
I was on staff at a church, working as a youth pastor. And I was, if I’m being completely honest with you, absolutely killing it.
Or so I thought.
I remember walking from the parking lot across a patch of grass toward our apartment. I had a literal skip in my step. Life was good. Work was good. Marriage was good.
And somewhere in the middle of that walk, a question popped into my head: Where could I grow? What could I be doing better?
I actually thought about it. I genuinely tried to come up with something.
Nothing.
Not a single area. Not one thing I needed to improve. I was 27 years old and I had, apparently, arrived.
Within two steps, I had a second thought - and this one stopped me cold: If I can’t think of a single place where I need to grow, that’s probably a problem.
Kathryn and I have told that story many times over the years. We were among friends when we eventually gave it a name: Syndrome 27.
Syndrome 27 isn’t garden-variety confidence. It’s the full, unshakeable belief that your logic, your answers, and your solutions aren’t just good - they’re the best.
And if you doubt that, the evidence is right there: just look at my life. Everything I touch turns to gold. I didn’t just figure some things out. I figured it out. All of it. At 27.
Which means the rest of the world doesn’t need to teach me anything. They need to ask me to teach them.
Let’s be clear about what that actually is: it’s arrogance. Full stop. It’s pride and cockiness at a level that is, by definition, hubris.
The real trick, the reason it’s so hard to catch, is that it doesn’t feel like that from the inside. Not even a little.
From the inside, it feels like clarity. You walk around with this quiet certainty that you’ve got it figured out. You don’t always say it out loud. You don’t have to.
But when someone brings you a problem, you don’t ask questions. You don’t try to understand what’s really going on. You just tell them how to solve it.
Because you already know. You come across like you have the answer for everything and it doesn’t matter how friendly or nice your tone is.
I was genuinely well-liked. Incredibly nice, and incredibly arrogant, all at the same time. That was just one of my “small” flaws people had to deal with.
And the people most susceptible to Syndrome 27 aren’t the weak, undisciplined leaders. They’re the strong ones. The confident ones. The ones who are, by any reasonable measure, actually good at what they do.
Success doesn’t just reward them - it blinds them.
As you’ve been reading this, I’m guessing someone came to mind. Maybe it’s a young employee who has an answer for everything before you’ve finished asking the question. Maybe it’s one of your kids.
Maybe it’s just someone in your world who is talented, likable, and absolutely certain they have it all figured out.
Go ahead and smile. It’s okay. You might even be giggling a little at yourself right now because there’s a decent chance you suffered from an occasional bout of Syndrome 27 when you were younger too.
Most of us did.
For some of you, it was obvious. You were out front, vocal, and certain. For others it was quieter. You weren’t going to argue or fight.
But if someone got into a serious conversation with you, you could explain - very clearly, very calmly - exactly who was right, who was wrong, and why. Same syndrome. Different personality.
Most of us can laugh at that younger version of ourselves. There’s a safe distance there.
Here’s the part that’s harder to laugh at: Syndrome 27 isn’t restricted to our 20s. To be fair, the name is a bit tongue-in-cheek.
For most people, the years and experiences that accumulate after 27 become their own antidote. Life has a way of teaching us, sometimes gently and sometimes painfully, that we’re not always right.
But Syndrome 27 isn’t just an ailment of youth. If we’re not careful, it can pop up at any point in life - like a resurgence of an illness you thought you’d left behind years ago.
You get older, and suddenly it’s back. You go to the doctor and say, “Why did that happen?” And he just shrugs and says, “Oh, sometimes that can happen.”
Syndrome 27 is the same. Prolonged success has a way of bringing the blindness back. The longer things go well, the easier it is to start believing they’re going well because of you.
Your instincts. Your decisions. Your leadership. And slowly, quietly, the same blindness settles back in. Just with better clothes and a longer track record.
Now, I want to be clear about something. I’m not saying that growing in your skills, your knowledge, and your leadership competencies doesn’t matter. It does.
If you’ve worked hard, studied, grown, and built real expertise, you get to take some credit for that. That’s not Syndrome 27. That’s earned.
But here’s what one billionaire said in a recent interview that stuck with me. He said most people don’t understand that success - real success - is a combination of preparation, skill, and hard work mixed with luck and fortuitous opportunity.
You could have done everything right and it still doesn’t work. You could have made any number of different decisions and still come out ahead.
There’s a humbling truth in that, if you have the eyes to see it and the ears to hear it.
And as we get older and wiser, one of the most important things we learn is how much we need perspective we cannot give ourselves. You cannot read the label from inside the bottle.
We are too close to our own lives, our own companies, our own decisions to always see them clearly. The leaders who thrive over the long haul are the ones who build wise counsel around them.
People who can see what they cannot, who will say what others won’t, and who keep them honest about the gap between where they are and where they think they are.
So how do you know if you have it - now, today, at whatever age you’re reading this?
Here are three honest questions. They’re not complicated. But don’t blow past them.
Not a small preference - a real belief about how you lead, how you communicate, or how your business actually works.
If you can’t remember something you learned that changed your opinion on something significant, that’s worth paying attention to.
Not the people who just encourage you - everyone needs those. I mean the people who care about you enough to push back.
The ones who you know have your best interest at heart and are still willing to say, “I think you’re missing something here.” If you don’t have anyone like that close to you, Syndrome 27 may be silently at work.
There’s a difference between being busy and getting better. A lot of leaders are extraordinarily busy. Fewer are genuinely becoming sharper, more self-aware, and more honest about their own patterns.
Busy is easy. Growth costs something.
The good news - and there is good news - is that recognizing Syndrome 27 is the cure for it.
That’s actually what happened to me on that patch of grass. The moment I realized I couldn’t think of a single area to grow, something inside me said, “That’s a problem.”
I didn’t walk away unchanged. I walked away aware. And awareness, it turns out, is where everything starts.
That doesn’t mean the growing is easy. It isn’t. But you can’t grow in a direction you can’t see.
The recognition comes first. Everything else follows from there.
I think about that 27-year-old version of me walking across the grass, completely certain he had it all together. I want to go back and have a good-natured laugh with him.
Not because he was a bad leader. He wasn’t. But because the certainty that he’d arrived was going to cost him - and it did, more than once, in ways he couldn’t see coming.
The best leaders I know share one thing: they never fully believe they’ve arrived. They stay curious. They stay open. They stay a little unsettled - not anxious, but honest about how much they don’t yet know.
That posture doesn’t weaken you. It’s what keeps you sharp for the long haul.
If this was helpful to you, email me and let me know.
Until next time,
Keep learning.
Keep growing.
And God bless,
Michael