Being Funny Opens Doors: Why Humor Belongs in Business

I was fired for telling a joke.

I realize that is a strange way to begin an article about why humor is valuable in business, but it is also the most honest place for me to start.

I was attending one of the biggest media conventions of the year. My team of producers and I had filmed more than twenty interviews, and we absolutely crushed it. We had one of the best booths in the convention center, and people seemed naturally drawn to what we were doing.

For three days, I connected with people in the media space, met new friends, served my boss, and dreamed about what this world could look like for me five or ten years down the road. I felt present, energized, and convinced I was exactly where I needed to be.

Then it was time to pack everything up.

I noticed a woman working near a couch and asked if she needed help moving it.

“No,” she said, “but you can take off the legs.”

In a playful voice, I responded, “Whoa, I didn’t say anything about taking off the legs. I said I could move it.”

I thought we were joking around, being playful, making fun of myself for not being handy or capable of using the tools required to detach the furniture.

She did not think anything I said was funny.

The following Monday, I was called into a conference room. Both of my bosses were sitting there with a lady from human resources. The paperwork was pushed across the table, and I was told I was no longer a good fit.

When I asked for more of an explanation, the joke came up. They also told me they were beginning to see a pattern of “jokes.”

That experience taught me something important about humor, leadership, and business: what gets you in the door will not always be the thing that keeps you in the room.

Humor is powerful. It can create opportunities, form relationships, break tension, and help people connect with you almost instantly. But just like every other gift, it has to be refined, developed, and stewarded well.

Jokes Have Not Always Landed Me in the Promised Land

I have gotten in plenty of trouble for jokes.

I have been fired. I have upset close friends. I have offended people I genuinely cared about. Over the years, there have been plenty of moments when a joke left my mouth and I immediately realized it should have stayed safely inside my head.

So I will say it like this: jokes have not always landed me in the Promised Land.

But nine times out of ten, humor has opened doors I would not have walked through without it. It has given me a seat at tables next to people I had no business sitting beside. It has helped me start conversations, build friendships, and enter rooms where I may have otherwise gone unnoticed.

Oddly enough, humor even once helped me get onto an airplane when I showed up late to the gate carrying seven bags and lithium batteries. That isn't a business strategy I recommend, but humor got me home to my family when I used wit, humor, and charm with the counter girl.

Jokes are the heartbeat of how I connect with people.

When I joke with someone, it usually means I am trying to bring them into my world. I want them to feel included in the moment. Humor has always been the way I create common ground, transfer energy, break tension, and help the people around me feel comfortable.

That matters in business because business is still built on relationships.

People do business with people they enjoy, trust, remember, and feel comfortable around. You can have a great product, an impressive résumé, and the cleanest PowerPoint presentation known to mankind, but if people do not connect with you, something is still missing.

Humor helps create that connection.

Laughter brings walls down. It disarms people. When someone laughs with you, even for a few seconds, you have shared something. There is a commonality in the room that did not exist before, and you can’t buy or engineer that reality.

I have seen this happen while speaking onstage. When people begin leaning over, belly laughing, something changes in the atmosphere. You are no longer simply talking at a room full of strangers. You are sharing a moment with them.

That same principle follows you offstage and into meetings, sales conversations, creative projects, networking events, content, and leadership.

A Joke Is a Story With a Faster Engine

One of the biggest things I have learned as a communicator is that people do not connect with information alone. They connect with stories, truth, reasoning, and moments that feel real.

Jesus understood this better than anyone.

Matthew 13:34 and Mark 4:34 tell us that Jesus did not speak to the crowds without using parables. He chose stories on purpose. They were not filler. Stories were the strategy.

Jesus talked about seeds, nets, coins, sheep, shepherds, weddings, workers, and sons who wasted their inheritance and ended up eating with pigs. He used things people already understood to carry truths that were much deeper.

When He was alone with the disciples, He explained everything in greater detail.

The public received the story. The private circle received the depth.

That is not watering down a message. That is knowing your audience. It is understanding how to reach people instead of simply talking at them and hoping something sticks.

Humor can work the same way.

A joke is a story with a faster engine. The laugh is the moment people realize they have already received the point before they had time to put their guard up.

That is one of the reasons humor is so valuable in communication and business. It gets people engaged. It helps them remember what was said. Not only that, but it gives people a reason to keep listening.

Humor is not shallow when it is carrying something meaningful. It can become a doorway to truth because truth often lands better when people are actually paying attention.

Learn to Laugh at Yourself First

During this journey of being a funnyman who loved God, I also learned that self-deprecating humor is one of the safest forms of comedy.

Self-deprecating humor means taking shots at yourself and speaking honestly about your own flaws in a way that other people can enjoy.

When you learn to laugh at yourself, it removes layers of ego. It also gives the people around you permission to laugh at themselves.

If you are not willing to make fun of yourself, you should probably receive a yellow light when it comes to making fun of other people.

Proceed with caution.

Poking fun at yourself shows that you are aware of your shortcomings, quirks, and idiosyncrasies. It reveals that you are down-to-earth and easy to be around. It lets people know you are not convinced you are better than everyone else in the room.

That matters in leadership.

Nobody wants to work for, partner with, or follow someone who takes themselves so seriously that every conversation feels like a corporate hostage situation.

Humility strips away ego. It pulls back the curtain on victim mentality and allows us to see where we need to grow. Humor can help us do that without completely destroying ourselves in the process.

If you can laugh at yourself, joke with others, and find humor together through life’s curveballs, your relationships will be stronger. Guaranteed.

Nobody enjoys being around people who force everyone to walk on eggshells.

When everything becomes too serious, controlled, and rigid, people slowly begin pulling away. They may not always have language for why the environment feels off, but their behavior becomes the language.

They stop sharing ideas. They stop speaking honestly. They stop being themselves around you.

That is dangerous in a business. It’s where sudden resignations happen, deals get fumbled, and morale with the team sinks.

Every Leader Needs a Jester

Historically, the jester was not simply an entertainer in the king’s court doing tricks and prop comedy like Carrot Top.

The jester was one of the most important people in the entire system.

He was often the only person who could tell the king the truth without losing his head—literally. The jester could say what everyone else was thinking but was too afraid to say.

He was a pressure-release valve inside a system that could easily become suffocating.

That role still matters today.

A leader can be strong, disciplined, focused, and effective, but if he loses every trace of lightness and laughter, he can become unbearable to be around. Everything becomes about control, productivity, outcomes, and performance.

There is no release. We all need a release, especially in 2026.

Humor protects leaders from becoming tyrants. It reveals absurdity, challenges ego, and delivers truth in a form people may be willing to receive.

A leader who cannot laugh at himself becomes increasingly difficult to correct. When the humor disappears, yes-men often take its place. People begin protecting the leader’s image instead of telling the truth.

That is dangerous in a family, a church, or a business.

As a leader, you set the culture around you. You can be doing everything correctly on paper while slowly becoming someone people no longer enjoy being around.

You can build something successful while losing something essential.

If you are not careful, you will justify it with metrics. You will call it focus, discipline, excellence, or leadership, while underneath all of it you are losing the ability to enjoy the life you are building.

Life should include joy, laughter, presence, and connection.

The Gift Still Has to Be Stewarded

For a long time, I defended my jokes by explaining that they all came from the same place: I wanted to make people laugh.

If I tell a joke and you laugh, I win, you win, and we both get to enjoy the moment.

If I tell a joke and it makes you angry, I lose, you lose, and now we both feel awkward.

In both situations, my intention may have been the same. I wanted to make you laugh.

But intention does not remove responsibility.

Humor is a double-edged sword, and the person telling the joke needs to understand that. I have to use that sword with grace, love, wisdom, and lightheartedness.

Humor should not be used to punch down. It should be used to lift people up.

As frustrated as I have sometimes been by people getting offended, I have also had to learn how to steward the gift God gave me in a way that brings joy instead of pain.

Timing matters, the person matters, the setting matters, and most importantly the heart behind the joke matters.

Being witty often depends on how quickly you can think of and deliver a punchline. Maturity requires learning how to run that punchline through a filter before it leaves your mouth.

That does not mean losing the gift, it means sharpening it.

The quality that gets you into the room can become the same quality that removes you from it if your character does not grow alongside it.

I learned that lesson the hard way the day I was let go.

Joy Is a Currency

We live in a world with more access to tragedy, negativity, fear, and outrage than any generation before us.

Every news story from every corner of the world appears at our fingertips. People carry the weight of events they were never designed to process twenty-four hours a day.

Joy cuts through that heaviness. Joy removes the negative power those headlines hold over you.

I call joy a currency because people value it. They value people who bring life into a room. They value relationships where they can breathe, laugh, and become themselves. They value leaders who can carry responsibility without making everyone else carry their emotional weight.

Humor separates me from the negativity of the world. I do not take everything too seriously unless the moment calls for it.

I am serious about the Father’s business. I am serious about my family. I am serious about my work and getting the job done.

Beyond that, I am bringing the funny—unless I am grumpy and acting like a crab.

Humor has opened doors for me, built relationships, created conversations, and led to opportunities I could never have manufactured on my own.

It has also humbled me, corrected me, and forced me to grow.

That is the tension of the gift.

Jokes have not always landed me in the Promised Land, but when humor is combined with humility, wisdom, preparation, and genuine love for people, it can take you into rooms you never imagined entering.

Use the gift, develop the skill, and let your character grow alongside it.

And never underestimate the business value of bringing joy into the room. Being funny will open doors and get the contracts closed.