Humor & Humility

In today’s tense and divided world, a well-placed smile or self-deprecating joke can be more powerful than a podium-pounding speech. Two men I’ve always admired, Senator Alan Simpson of Wyoming and President Ronald Reagan, were not just statesmen; they were master storytellers. Their greatest tools? Humor and humility.

 

I’ve tried to carry that lesson into my own life. Just recently, while organizing a family trip, I made a small but serious mistake by booking only one hotel room when my wife had clearly wanted two. When she found out, I smiled and said, “Well, I guess we’ll have to pack sleeping bags.” It didn’t solve the problem (we did get the second room), but it changed the temperature. That moment could have sparked frustration. Instead, it sparked a laugh.

 

The joke wasn’t brilliant, but it was enough to remind us that we’re on the same team.

 

Al Simpson: Cowboy Charm, Capitol Smarts.

Senator Simpson brought the dry wit of the West into the marble halls of Congress. During tense budget debates, while others lost their tempers, Al would crack a line like:

“I’m not worried about the deficit. It’s big enough to take care of itself.”

Remember the “Simpson/Bowles deal,” that bipartisan agreement, might have resulted in a balanced budget today.

 

Behind the one-liners was wisdom and a deep sense of self-awareness. He understood what Mark Twain meant when he said, “Humor is mankind’s greatest blessing.” It opens doors. It calms storms. It lets people see your heart without you having to pound your chest.

 

Reagan: The Smile That Saved the Day.

President Reagan had the same gift. After being shot in 1981, he turned to his surgeons and said: “Please tell me you're all Republicans.” Or when his age became a campaign issue in 1984, he replied: “I will not exploit, for political purposes, my opponent’s youth and inexperience.” Even his opponent laughed.

 

Reagan wasn’t just being funny; he was demonstrating grace under pressure and winning the room not by force, but by ease.

 

And that’s the thing: It’s not the dragons that bug me…it’s the flies.

 

The dragons, or life’s big challenges, get our full attention. We rally. We prepare. But it’s the little annoyances, the buzzing irritations of daily life, that wear us down. That’s where humor matters most. A quick quip, a raised eyebrow, a shared laugh…they will swat the flies before they ruin your day.

 

Patricia Limerick: The Academic Fool (on Purpose).

Perhaps no one embodied humor with humility more brilliantly than Patricia Nelson Limerick, the Western historian and long-time faculty member at the University of Colorado.

 

At both Harvard and CU, she famously volunteered to serve as the “Fool in April,” a real role with deep historical roots in European court life, meant to bring levity, perspective, and self-deprecation to otherwise rigid academic institutions. She would don a jester’s hat (literally), write satirical verse, and gently poke fun at the seriousness of scholars, administrators, and even herself. In one address, she joked: “A Fool has license to say what others won’t, but must also be the first to laugh at her own expense.”

 

And at her 70th birthday celebration, Patricia didn’t just talk about humor, she lived it. As a MacArthur “genius,” after a dignified lecture, she asked to be pied in the face, and she insisted on no advance notice. I volunteered to be pied with her.

 

When it happened, mid-celebration, the audience was momentarily mortified and stunned, unsure whether it was a prank gone wrong or a breach of etiquette. But then the laughter erupted. Whipped cream flew, and joy followed. It was pure Patricia: turning formality into fun, reminding us that humor isn’t beneath brilliance—it’s often what makes it shine.

 

Her role reminded everyone that intellect without perspective is brittle, and that sometimes the best way to convey truth is through laughter. She deflated egos with grace and reminded even the most brilliant minds not to take themselves too seriously.

 

Chop Wood. Carry Water. Smile.

Humor and humility also show up in quieter, older wisdom. A Zen parable tells of a young monk who seeks enlightenment. He’s told simply: “Chop wood. Carry water.”

 

Years later, after finding peace and spiritual insight, he returns to the master.“I am enlightened,” he says, believing that now his life would change for the better.

“Good work, son. Now get back to chopping wood and carrying water.”

What’s the point? Even after transformation, the tasks don’t change, but your spirit should.

 

Life doesn’t get less complicated or easier. Business deals still involve tension. Family trips still involve politics and logistics. But if you carry yourself with lightness and humility, you can smile your way through life’s gnarliest moments.

 

Why Humor Wins in Business.

In my career, I’ve found that humor, especially when aimed at myself, is one of the best tools I have:

 

· It defuses opposition without confrontation

· It builds trust in tense negotiations

· It makes people feel seen, not steamrolled

 

Even the physical act of smiling lowers stress hormones, improves communication, and reminds everyone: we’re all human.

 

Lead with a Smile, Not a Sword.

Whether you're debating in the Senate, leading a company, booking the wrong hotel room, or dressing as a Fool in April, humor isn't a gimmick. It's a form of leadership. When paired with humility, it reminds people that you’re not above them, you’re beside them.

 

So, chop wood. Carry water. Book the second room.

And don’t forget to smile while you're at it.