You're not funny (but you should be)

You might think the title has a typo. Don't you mean "could be"? Not at all. You should be funny. Humor is associated with both intellectual and emotional intelligence. Finding your funny bone will help you personally and professionally.

Humor seems to be elusive to most people. Why are some people just funny and others aren't? Why can't I be funny? I don't know how to think of jokes.

The truth is that laughter is not as mysterious as you might think. It's just subtle. Being able to land a joke at a party or at the watercooler is a valuable skill. It makes you look smarter, sexier, and more confident.

Most advice about humor is mostly bad

At best, a well-meaning friend might say something like "just be yourself" as if it suddenly means anymore than it did in kindergarten. This advice is meant to calm your nerves about self-judgement but I have yet to meet anyone who found it helpful.

Most people and articles usually just tell you what to avoid. Don't talk about race, politics, etc. Don't get nostalgic. Don't...[insert action] The problem with this approach is that comedy (and any communication really) is a creative act. If you start with what you can't/shouldn't/won't do, you won't get anywhere.

The essence of funny

There's plenty of debate about this but it comes down to a "safe surprise followed by relief". Laughter is almost always the result of mild shock. The rush of fear, uncertainty, and confusion followed by the relief of safety is the ultimate brain hack. That's why people come off bungee cords smiling like maniacs.

It's the same way with humor. You surprise people with an observation, a hidden connection, or a soft insult and for a brief moment, you've stunned them. They're trying to working out what just happened. Then a moment later, they realize you're kidding. The threat isn't real and it's all smiles.

If your listener feels unsafe though, it doesn't matter how funny the joke is. The relief doesn't come. That's why "I'm going to murder you in your sleep" isn't funny. It's why people say "I'm just kidding" when a joke doesn't land.

That's also why those comedians who dance with taboo topics do so fantastically well. Anthony Jeselnik, Bill Burr, Jimmy Carr. These dark humor comedians go to the edge and say obscene things with the knowledge that their audience is along for the ride. The can say anything and everyone knows everything is going to be fine.

That's great in theory but how do I use it?

I'm so glad you asked. Here is my guide of anti-don'ts to get you started. Do these things and you'll be well on your way.

Pay attention

For how often people talk about listening, surprisingly few people do it. If you're reading this thinking, "I'm a pretty good listener. Skip!", you're wrong. You're all wrong. Everyone can and should be a better listener.

People throw off thousands of signals every second. The tone and pace of their voice, their eye movements, their gestures, the way they sit. The topics they don't mention are usually just as those they do. There is more information there than anyone could possibly capture. Those signals are the key to real listening.

They let you get to the reasons behind the conversation. If Jack goes to the bathroom every time politics comes up but seems to perk up at Star Wars references, let him know your theories on the latest Bad Batch episode.

Connections and observations

Idea generation is another major hurdle that seems to encumber aspiring conversational comics. Have you ever seen one of those mind map things?

By Nicoguaro - Own work, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=15442311

Love 'em or hate 'em, they illustrate a useful point. Every topic has dozens of connections to other ideas. If you're really listening (see previous section), the dots connect magically.

Tell jokes

I recognize that's not a revolutionary idea.

Practice makes perfect. Practice, practice, practice.

Thanks Mom. The reality is that most people are so afraid of the risk of embarrassment that they never make an attempt. That fear is real and not unjustified. Really bad jokes can land you in hot water. Start with friends.

Every joke has a degree of risk but with practice, you'll start to feel when a joke will work. It takes time though. Even today, I'm often surprised which jokes work and which ones don't. Occasionally, I'll make a dumb remark and the room will be rolling on the floor. Other times, I'll drop a killer line and get silence.  If you want to get good, just keep it PG and tell as many jokes as possible.

If you do make a bad joke, don't shy away from it. Say "Sorry, I misread the room" and move on. Speaking of reading the room... Frankly, you will make mistakes. Practicing often with people who understand will help you get better.