Crippled CEO Blog #009: Be Funny — hurry up!

I’m fucking hilarious.

It took being told how extra funny I am (and quick, and witty) roughly 6,000 times over several years before I started actually believing that my sense of humor isn’t just like everyone else’s. I always thought most people were funny.

Being funny is good. It’s useful. It makes people like you. It makes giving hard news a bit more bearable. It’s great for public speaking. It’s a secret weapon in sales. And it’s probably responsible for almost every time I’ve seen a lady naked who wasn’t on a stage paying for college. But most importantly, being funny is fun. Making people laugh feels good. And it’s my goal pretty much all the time. I mean, this blog is literally called “Crippled CEO.” I find that funny every time I type it.

I didn’t start this funny, though. Like anything else, you might have a natural propensity towards something, but getting really good at it takes practice. And that’s what I did. I started seeking out chances to throw in a funny line or anecdote. All the time. And now it just happens naturally. In FACT, I have a tough time turning it off, and struggle to hold back jokes in inappropriate situations, like certain meetings or funerals (I definitely made a couple while speaking at my dad’s) or during sexy time with my lady. I consider this a worthwhile sacrifice.

So, how do you go about being funnier? First, just… start. Start learning and telling silly jokes. Start saying the funny thing you keep to yourself. Stop holding back because you think it’ll be bad or dumb — that’s funny, too! My jokes bomb CONSTANTLY. I usually follow a flopped one-liner with, “They can’t all be winners,” because they can’t. You’ll inevitably screw up on the way to comedic gold. Also, start watching funny things — comedic movies, standup specials on Netflix, etc. It’s both instructional and inspirational. Steal and re-tell the jokes you hear. You don’t even have to take credit; tell people about this funny thing you watched.

Possibly most importantly, you have to be fairly happy in order to be funny. It’s hard to be hilarious while angry, bitter, or resentful. And vice versa: it’s hard to stay in a bad mood while being funny. By practicing humor, you’ll improve your baseline level of happiness — truly. Also, you’ll learn not to take yourself so seriously. And that’s always a good thing. For you, your family, and the lady who got your name wrong at Starbucks.