Originally Published February 28th, 2019

Hey Gang,

Raise your hand with me if you’ve ever told a joke that nobody laughed at?

“Want to hear a joke about paper? Nevermind it’s tearable.”

Somewhere off in the distance you can hear crickets chirping as you awkwardly fumble to recover.

“Uhh, ummm…”

Your friends look at you in silence.

Your face turns red.

You feel a slight diarrhea pang.

The world as you know it begins to crumble.

Then someone cracks their own joke making fun of you and the conversation rolls on. 

Now pause and think back on a time when you told an awesome joke.

“I’m so good at sleeping. I can do it with my eyes closed.”

You timed it perfectly. 

You catch your friends off guard.

One person laughs so hard they begin choking on a bite of their burrito. (Julie?)

Another friend shoots milkshake out of her nose. (Kelley?)

You get a rush.

It’s fun making people laugh. 

It’s even more fun making people humiliate themselves.

Humor & Risk

Lately I’ve been thinking about how telling jokes is a perfect analogy for taking risks.

Whenever you tell a joke—you’re taking a risk. 

I’ve told lots of jokes, I’ve taken lots of risks.

Some jokes that I’ve told have made a whole room of people bust into laughing fits.

Other jokes—not so much.

This is a secret. Don’t tell anyone. But I once made my wife’s grandma cry over a joke.

Not from laughter.

Needless to say—it wasn’t my proudest moment.

If you’re going to try to be funny—you have to be willing to accept the fact that people might not react the way you want them to. You might tell a joke that bombs—or worse, makes someone’s grandma cry.

Taking risks in life is the same.

Some of the risks that you take will be glorious. They will add meaning & purpose to your life.

Other risks—not so much.

What Humor Has Taught Me About Taking Risks

I have a very dry sense of humor. It usually takes people a while to realize I’m actually joking. I’m almost never serious—but I’m good at faking it.

When I’m with a group of people—my default mode is to try to be funny, it helps relieve my anxiety and quiet the demons.

At one point I had to decide—

“I’m either going to try to be funny and accept the fact that I will probably look stupid or I’m not going to try at all.“

I decided to try and look stupid.

How does this relate to taking risks in life?

I learned quickly that if I’m going to tell jokes—I’m going to bomb and I have to immediately move on.

I can’t dwell on the fact that my joke wasn’t funny.

I’m not going to win every time.

I can’t overanalyze it.

I have to drop any negative emotions and move on. 

No face turning red.

No diarrhea pangs.

The same goes for when you take a risk in life and you fail. 

If I create something that flops, no big deal.

If I try to do something new and I fall on my face—ok, move on.

You have to be willing to try. 

Take risks like you’re telling jokes. 

Because at some point—your timing will be perfect, you’ll be in the right place at the right time with the right audience, you’ll have the best hand of Cards Against Humanity, and you may even have luck on your side. 

If you want to be an artist, a creative, an entrepreneur—you must learn to take risks. But more importantly—you must learn to take risks, move on after you bomb, and don’t let your failures discourage you.

Keep telling jokes.

Keep taking risks.

It’s hard—but it’s worth it.

That’s what she said.

-Tim