This Is The Most Fun Way To Make Your Life Awesome


We just don’t take humor that seriously.

Yeah, it makes us happier, but its effects are much, much more profound than you might guess.

People who use humor to cope with stress have better immune systems, reduced risk of heart attack and stroke, experience less pain during dental work and live longer. Surgery patients who watched comedies needed 60% less pain medication. Heck, even anticipating humor has been shown to reduce stress.

Humor improves your relationships. Surveys say it’s the second most desirable trait in a partner. When both people in a couple have a good sense of humor they have 67% less conflict. (Want a tip? Reliving moments that made the two of you laugh is a proven way to increase relationship satisfaction.)

Let’s up the stakes, shall we? What about the office? A lot of people think humor isn’t appropriate at work and those people are, as we say, “wrong.” A survey of hundreds of senior executives showed 98% prefer employees who are funny – and 84% thought those people actually did better work.

In fact, if you’re not going for laughs at the office, you may be hurting your career. Humor increases perceptions of power and status. It boosts creativity. It signals intelligence. Making people laugh increases persuasion and made buyers willing to pay higher prices. In fact, studies show work teams often fail simply because they don’t joke around enough. And leaders with a sense of humor were rated as 23% more respected and 25% more pleasant to work with.

Can I stop there? I’ll stop there.

We need to get to the bottom of how to do this humor thing right. We’re gonna pull from a slew of excellent books and studies including Humor, SeriouslyHow to Write Funny, Inside Jokes, and Ha: The Science of Why We Laugh.

Alright, let’s get to it…


What Is Humor?

What alchemy, what ethereal fire, gives mere words the ability to make grown adults involuntarily spit coffee?

Humor is our brain’s way of rewarding us for correcting errors in our thinking. Why does it make us so happy? It takes brainpower to decode the joke and having to think kills bad feelings. When you’re in a bad mood humor cheers you up by literally forcing a change in your perspective.

That twist, the irony, those odd juxtapositions, they hit you so hard your brain does a factory reset. It tickles your limbic system and leads to satirical healing.

Watching more comedy is easy but being funnier yourself, that can seem impossible. If I said, “Be funny right now!” your brain would immediately feel like it’d been filled with liquid cement. “How to be funnier” feels like a mystery on par with dark matter. But it’s not. It’s a skill like any other. Sure, some people have more natural talent, but we can all improve…


How To Be Funnier

The leading theory of humor is that it’s a “benign violation.” If a joke doesn’t violate expectations or rules, it’s probably not funny. If it’s not benign, well, then you have “dark humor” — which isn’t always appropriate, may offend and might get you fired. (But if you like dark humor, I’ve saved a seat for you over here next to me.)

Now there are all kinds of humor. There’s visual comedy. (Like the time I wore an Enron shirt to my accounting final.) There’s wordplay. (I could make an infidelity joke but that would be a sad state of affairs.) But we’re gonna focus on a few of the principles that underlie more complex humor:

1) Surprise

All humor contains surprise. Hearing the beginning of a joke and thinking “I know where this is going” is usually not a great sign. You want the listener’s expectations to be violated with a kind of chiropractic snap. For example:

I don’t like country music, but I don’t mean to denigrate those who do. And for the people who like country music, denigrate means “put down”. — Bob Newhart

So whenever you’re trying to think of a joke, remember: there needs to be a twist.

2) Truth

Yes, the old saying “it’s funny because it’s true” is true. But here’s the part they leave out: that truth must resonate with your audience.

It has to be relatable. They need to have the necessary knowledge to “get it” otherwise you end up in “Well, maybe you had to be there” territory.

Sometimes even a relatable observation that isn’t necessarily funny can provoke a laugh. People think “Oh, yeah, I’ve experienced that—and I didn’t know others had!” This bonds the joke teller and listener over the shared experience. Scott Dikkers, co-founder of The Onion, points out that the more unique and insightful the reference, the more power it will have. If it’s less original, it won’t have the impact: “Isn’t airline food awful?

So a good place to start is by noticing the odd, less-than-obvious, but universal absurdities we all experience.

3) An Opinion

Good humor often has a perspective. It doesn’t just convey facts; it has a judgment beneath it. The more astute and original the judgment, the sharper your jokes are.

“How did the frog die? He croaked.”

Not all that funny unless you’re a third grader. There’s no subtext here. No insight. No judgment. It’s just simple wordplay.

Good humor often points out what’s wrong or inconsistent with the world. Something that’s absurd or unfair. Things are not how they should be. When done well, this judgment is implied, leaving room for the listener’s brain to decode it themselves. For example:

“You’ll get unconditional love when you do something to deserve it.” — Merrill Markoe

So a good starting point is asking yourself what is true (but not obvious) that you have a position on. What’s inconsistent or ridiculous or makes no sense that the listener may not have noticed yet?

The possibilities are limitless. Take some time and give this a good think. (People have accused me of overthinking things, but I’m still debating whether that’s true or not.)

4) Incongruous Juxtaposition

This is one of the most common forms that jokes take: contrasting two things that aren’t the same but also, in another way, are:

“My six-year-old just called ranch dressing ‘salad frosting’ and now I’ll never call it anything else.”

This is often done using analogies:

“Big families are like waterbed stores; they used to be everywhere, and now they’re just weird.” — Jim Gaffigan

So think of juxtapositions that seem odd on the surface but also contain an element of truth. (Does it feel disappointing to be #11 on the FBI’s Most Wanted list?) Or combine things that share a similar pattern in one way, but not in another. “CSI: New York” is a serious show. “CSI: Disneyland” sounds hysterical. Or imagine a new show on the Food Network — but Hannibal Lecter is the host.

5) Exaggeration And Specificity

Two simple things that add punch to any joke. Making things more extreme and going overboard increases impact. And concrete language is richer and more relatable than abstractions. For example, comedian Sarah Cooper suggested we change airline seating options from “First Class” and “Economy” to “Economy Discomfort” and “Economy Agony.”

6) Callbacks

This is a powerful type of humor you’ve heard comedians use many times. They tell a joke and then later make another one that calls back to the original, often escalating the humor.

7) The Listener Has To Decode The Joke Themselves

Just something important to keep in mind to avoid many common humor fails. If they are unable to decode what happened and “don’t get it” then it’s not a joke, it’s a Christopher Nolan film.

Like we talked about, their brain correcting the “error” is where the humor comes from. This is why when you have to start explaining, you “kill the joke” and it’s no longer funny. They have to fill in the gap themselves.

“There are two types of people in this world: 1) those who can extrapolate from incomplete data sets.”

Okay, we’ve got some fundamental principles here. But how do we turn them into jokes?


Developing Jokes

Take off that hoodie of maturity for a second. Switch off your Freudian superego. Look around. Think of what’s strange, what doesn’t make sense in life. And think of what kinda makes sense — but doesn’t. What’s wrong or unfair or inconsistent?

If you just state it, it probably not a joke – it’s probably complaining. But then apply some of the principles above. Is there a more unique insight about it? Can you make an incongruous juxtaposition that highlights how crazy it is? An analogy? By exaggeration does it go from whining to laughing?

Ask yourself more questions using the principles above. What is surprising, true, specific, and makes sense in one way but in another way doesn’t? (When Superman uses his X-Ray vision does he ever give people cancer?)

Most of what you come up with is going to be crap. And that’s okay. It’s true for everyone. When I interviewed my friend Andrew Goldberg, who was a writer and producer on “Family Guy”, he said joke writing is a volume thing. As famed comedian Mitch Hedberg once said, “Beware of any comedian who writes for half an hour and then tells you they have thirty minutes of new material.”

And then you want to test your jokes on people. Often they are not going to laugh. You’ll drop a line and it’ll be so quiet you can hear your own synapses. Might be a 9.1 on your Humor Richter Scale but if they’re looking at you like “Why does that stuff keep coming out of the hole in your face?”, the joke isn’t funny. Improve it or drop it. When I do speaking events I’m always using jokes that I know work – but I’m also testing new stuff and gauging the response.

Want a quicker way to develop funny bits? Work from stuff you already have. Start with stories you tell that usually get a giggle. (If you have a kid or a dog, you do have funny stories.) Become a collector of funny moments, anecdotes and lines. Or recount fun tales told to you by friends. Run them through the principles above to see if you can strengthen them. Then keep testing.

And now we need to get to the scary part…


Warning: Humor Can Offend

Every week I get a dozen emails saying, “I love your humor!” — and one saying, “Normally I enjoy your emails but this time I was deeply offended by…

Best part? They’re usually both referencing the same joke. I have come to regard this as inevitable. (There is no malpractice insurance for bloggers. I checked.)

Humor may be a “benign violation” but people’s definition of “benign” can vary – a lot. Yes, some things should not be joked about, but the problem is everyone has a different list. If you ignore this fact the same way you do your New Year’s Resolutions you’re going to get into more trouble in three seconds than most people get into in three years.

There is always a bit of risk-reward in joking. There is rarely a totally safe “index fund” for humor. Something is usually being criticized and something is usually the butt of the joke. There are truths other people don’t agree with – or don’t want to be true. (Yes, self-deprecating humor can be an exception but tell too many jokes like that and people will think you’re clinically depressed.)

If you always strive for twee and bloodless, you’re probably not going to be very funny. But if your jokes routinely display levels of cruelty seen in a YouTube comments section, you’re going to be competing in the back-pedaling Olympics. And you might get fired.

So always know your audience. Always consider the context.

Alright, we’ve covered a lot. Let’s round everything up and we’ll also find out how you can get the benefits of humor in the workplace, even if you’re not that funny…


Sum Up

This is how to be funnier:

  • What Is Humor?: It’s the reward your brain gives you for correcting errors in your thinking. And its warm embrace is a travel agency for the soul.
  • How To Be Funny: Play with the principles listed above: surprise, truth, opinion, incongruous juxtaposition, exaggeration, specificity, and callbacks. It’s worth the time. (Being funny is this blogger’s best defense against the looming threat of ChatGPT.)
  • Developing Jokes: Yes, some people have two-digit SAT scores and just don’t get the joke but in the end, humor is very democratic. Sometimes people will not laugh out loud — or even very quietly. You have to come up with a lot of groaners to find the gems. You can cheat by working from the best stories you have or that others have told you.
  • Warning: Humor Can Offend: Welcome to 2023 where everything is outside someones’s comfort zone. Know your audience and consider the context. (I will be over here trying to keep my entendres single.)

We all fear our attempts at humor will fail. And I respond: fear not!

A study from Harvard and Wharton that looked at humor in professional settings found that as long as the humor wasn’t inappropriate, just making the joke boosted perceptions of confidence, status and competence. In other words, there is value in merely conveying that you have a sense of humor. Even if people don’t laugh, you get points just for trying. So as long as it’s not inappropriate, go for it.

Please do. More humor will make the world a better place. I swear on my mother’s grave…

And my mother’s still alive so that should tell you how serious I am. (Was that violation non-benign? Sorry, mom.) And if you need a laugh, follow my Twitter account. I post awesome jokes there daily.

A lot of life isn’t all that funny the first time around. It can be painful. But humor teaches us the right way to handle that pain: laugh at it. You’re not supposed to laugh at your boss because it conveys you don’t take them seriously. But that’s the best reason to laugh at the hard times in life, to tell it: I do not take you seriously.

Humor is the most powerful disappointment sponge we have. A power rises from behind the words and disinfects the difficulties of existence. With time all tragedies fade and negative emotions soften but humor helps speed the fermentation process, turning old pain into funny memories. The lowlights becomes highlights.

Humor is a spell. It’s tricky to understand how it works but the results are powerful. A few words that, when spoken correctly, magically transform your life. Cast that spell as often as you can…

And wear an Enron shirt to your accounting final.

(See? Callbacks work.)


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