How to Practice Humor + Last-Minute Run-Through Today!

Humor isn’t learned alone. It’s practiced out loud.

Editor’s Note (aka: A Cry for Help): I have an event tomorrow and could use one final run-through of my keynote. Are you free today at 3pm ET? Join me for a test-run, give your honest feedback, and in return you’ll learn the skill of humor and see the keynote before the lawyers do… Register Here.

I’m currently in Paris where, tomorrow, I’ll be delivering a keynote to 200+ lawyers from all over the world on the skill of humor (it turns out that lawyers are humans too and also partake in humor from time-to-time).

Fun side note: this is my first booked client who found me via ChatGPT. I do wonder what the prompt was that the organizer put in to find me? “Nerdy speakers who look like Danel Medvedev?”

We decided to turn the engagement into a family trip to see Pretzel’s (my wife) family in Cologne, and I had a bit of downtime in between. So I did what any normal person would do: to go to Berlin to do some stand-up, workshop a bit of material, and prep for the keynote.

Boy am I glad I did.

Over the course of my prep for the event, I wrote a joke that I thought was amazing. I just knew that it would crush with an international audience, lawyers or otherwise. It was one of those times where I couldn’t wait to say it on stage (like the first time I told my revolving door story).

But I’ve learned (the hard way) that it’s important to always test material, so I decided to try it out at one of the stand-up shows…

And it bombed. No laughs, just silence.

I thought it might have just been my delivery, so I tried it again on the next show. Still nothing. And the next show, nada.

Is the joke salvageable? Maybe. But it’s definitely not ready for 200 lawyers who bill by the quarter-hour.

I’m a bit bummed that the joke didn’t work, but I’m grateful I got the bomb out of my system in a safe space.

Humor is not a solo sport

You can learn to play piano in your basement. You can practice yoga alone in your living room (though your cat will judge you). But humor requires other people.

It’s a social skill. You don’t know if a joke works until it enters the wild and either:

A) Sparks laughter
B) Sparks confusion
C) Sparks a Slack message asking, “Was that... intentional?”

That’s why stand-up comics have open mics and improvisers gather in tiny black box theaters to say things like, “Yes, and the banana is my lawyer.”

Because what’s funny in your head isn’t always funny out loud. And you don’t find that out until you try.

Safe spaces make silly possible

The first time I did improv, I was terrified. Not of being unfunny (I’d made peace with that in high school), but of looking foolish.

But everyone looked foolish. That was the point.

The best environments for practicing humor are ones where failure is expected, celebrated, and possibly turned into an inside joke to reference time and time again.

Because humor isn’t about being perfect. It’s about experimenting. Tinkering. Testing. Sometimes you find gold. Sometimes you find a joke was technically just a sentence.

But you only get there by trying. In front of people. Repeatedly.

Humor needs a feedback loop

Most people never intentionally practice humor. They just hope that they’ll say something funny, and someone will laugh. But that’s like pushing to production without ever going through QA (for the non-programmers, that’s a big no-no).

If you want to get funnier, you need to put your humor out there. You need feedback. Not necessarily a standing ovation, but a raised eyebrow, a smirk, or the coveted Zoom “forcefully blew air out of their nose in an amused way.”

It’s hard to practice funny in isolation

If you want to effectively use humor—in meetings, in keynotes, on dates where you accidentally reference Star Trek—surround yourself with people who let you test, tweak, and fail with style.

Find your version of an open mic:

• A group chat where you can send dumb ideas before adding them into an email.

• A work team that lets you dry run a story before sharing it in front of clients.

• A friend who will tell you when your "cheesy dad jokes" are no gouda.

Humor is a skill, but it’s one you build together.

(an)drew

PS. We’re launching a program to help you not just learn humor, but practice it safely, consistently, and with feedback. Stay tuned.

PPS. Want to help me workshop my keynote? I’m doing a final run-through today at 3pm ET. Feedback welcome, nerdy references likely. Register here.