Finding Humor in the Everyday
Just ask, "How could this be more fun?"
Programming Note: These emails are switching to Wednesdays! The goal is to be a bright spot in the middle of your week and give you some tips you can implement right away.
I love the Q&A section of my programs. It allows me to address people’s concerns about using humor head-on and gives me a chance to improvise a bit and pull insights from the recesses of my mind (or make them up).
At a recent event, a somewhat frazzled and exasperated man asked, “How am I supposed to do this when I’m already pressed for time?”
The this he was referring to was using humor to be a more effective project manager. And I get it.
There’s this misconception that if you want to use humor in your work, it has to be big.
Like, “rent a gorilla suit and storm the Monday all-hands” kind of big. Or, “spend three hours workshopping a joke that lands exactly 12% of the time but crushes when it does” kind of big.
Or “become a divorce lawyer, come up with a clever idea for an ad, get it printed out, and stick it to your elevator doors” kind of big…
But the truth is, most of the best humor—the kind that makes work suck less, builds connection, and relieves stress—doesn’t come from grand moments. It comes from the small ones.
The post-it note that says “Step 1: Drink water. Step 2: World domination.”
The email subject line: “Quarterly Report: Now With 37% More Graphs!”
The Zoom background that makes your coworkers ask, “Wait… is that the bridge from the USS Enterprise?”
Humor doesn’t have to be a big production, it can just be a small change in perspective.
Why You Should Think Small
When we think humor has to be perfect, planned, or polished, we make it way harder than it needs to be.
It becomes something “other people do.” Something for comedians. Or extroverts. Or that one guy in your office who is always cracking jokes but never seems to work.
But humor isn’t just for the spotlight. It’s how we choose to see the world.
How we handle stress. How we turn awkward silences into laughable moments. How we respond when we read an email, decide to reply later, forget about it for two weeks, and then remember you owe someone a response… (sorry about that Tom, I hope you enjoyed the gif I sent).
The key to bringing more humor into your life isn't necessarily taking a stand-up class. (Though if you want to learn timing, confidence, and how to bomb gracefully, it’ll definitely help.)
The real key is much simpler, and it’s what I suggested to the frazzled PM.
It’s asking one small question: “How could this be more fun?”
That question is the gateway to playful thinking. It’s not about being the funniest—it’s about being the most intentional about levity.
Waiting for a meeting to start? What’s a playful way to kick it off?
Stuck in a long email chain? Can you add a clever PS?
Planning a team offsite? What’s a team-building activity that isn’t “trust falls or mandatory fun”?
The more you practice this mentality—even in small ways—the stronger it becomes.
So the next time you feel stuck, bored, or that the world is way too serious (because let’s be honest, it often is)... ask yourself:
How could this be more fun?
Which brings me to one of my favorite examples of that mindset in action…
🎉 Announcing the 2025 Humor Awards! 🎉
It’s that time of year where we roll out the red carpet (and occasionally the whoopee cushion) to recognize the brilliant individuals and organizations using humor to make work—and life—a little more fun.
This isn’t about who can do the best stand-up set or write the perfect punchline.
It’s about celebrating those everyday moments of levity that make a difference. The people who ask, “How can this be more fun?”—and then do something about it.
Do you know someone whose meetings actually keep you awake?
A coworker with an elite-level pun game in Slack?
A team with Zoom backgrounds so good they deserve their own gallery?
Nominate them for a Humor Award!
Categories include“Comedic Communications Award,” “Greatest Use of a Meme,” “Humorist of the Year,” and more.
We’d love to add your favorite funny humans (or whole teams!) to the list. Because one of the best ways to encourage more humor at work is to recognize the people who already do it well.
👉 Click here to nominate someone for a 2025 Humor Award
To more laughter, less stress, and one epic Zoom background at a time.
(an)drew
PS: We’re now in full swing of 30 Days of Humor honoring International Humor Month. See what’s on the upcoming schedule at humormonth.com.