I'm going to be talking about how to write like a comedian, and hopefully make this a frickin blast for all of you. 

My story starts when I'm about this big, this is my second birthday. I was just talking to my mom, and she was like, yeah, there was one time [00:01:00] we were on an airplane, and you were throwing such a bad temper tantrum and it was before the flight took off and the flight attendants had to come up to my parents and say, we can't have you on the plane. Your son is too disruptive. 

And my mom and my dad put up a fuss. And then eventually they were like, we gotta get this kid off the airplane. So my parents were taking the luggage out of the thing on top and all that. And in order to get everything out, my parents moved me to the window seat.

And I immediately become super peaceful and just calm and happy. And what I learned in that moment is that I'm really stubborn and that I absolutely love airplanes. 

So about ten years later, I'm in fifth grade, sixth grade. And there's this project called the iSearch. And Ms. Peterson allows all of us to write about whatever it is that we want to write about. And I get to write about how [00:02:00] does an airplane fly, focused on the Boeing 787. So you can see I get very into things. I got my Boeing 787 shirt. I got a hat. 

And then, ten years after that, I end up writing this piece called Why Did the Boeing 737 Max Crash? And I get really into it again. And I had people at Boeing reach out to me saying, “How did you know about these leaked internal memos?” I'm like, I got my ways. And ended up getting to meet some people in the aviation industry. And I think this is one of the defining pillars of my life and my career.

Taking things that are innate, that are within us from birth, and trying to investigate what are the things that we innately feel drawn to, and then bringing that out in writing and creativity. 

A few more things about me. When I was in fifth grade, I went to sleepaway camp in Texas, and I won the rodeo on a horse named Rabbit. This is me ripping a [00:03:00] six iron my freshman year of college. And my very first job was managing the world's largest collection of slow motion golf swings. My favorite movie is That's the Way Things Happen and the Polar Express. Then my favorite restaurant, In N Out Burger. I've probably been 500 times.

I always get three patties of meat, two slices of cheese, extra tomato. Brent was talking about Disneyland. I now invite myself to Disneyland with the Beshores every single year. This is us eating a chicken thigh. And we went on that upside down rollercoaster right after. Brent looks at me, he goes, “We're only going one time.”

And then finally I was baptized about ten days ago.

Alright, enough about me. 

I believe that writing online is one of the greatest opportunities in the world right now. And I believe this deeply. Especially for people like you.. And I'm going to talk about that a little bit later on. 

But first I want to talk [00:04:00] about how can we think about writing in a way that you've never thought about writing before.

And what I do for work is I run a company called Write a Passage. And what we do is we do live cohort based courses. Just finished last night with about 400 students from about 75 different countries. I have a blast. I’ve been doing it for about half a decade, and this is just a little bit of a taste of what all that's about.

My writing philosophy is nothing like your 5th grade English teacher’s, and I hope that you get a chance to feel that. What your 5th grade English teacher told you, is writing is solo. And for social people like me, I don't know, maybe you're like me, this was just so lame. It was like, you know, Henry David Thoreau and you would go to some cabin in the woods. He goes to Walden Pond and he sits in this cabin and he writes this book for two years and he talks about escaping from society. Oh you can't see anyone in order to write well?

Okay, okay, fine if you want to do that whole writing is solo [00:05:00] thing. That's not going to work for me. What I believe is not that writing is solo, but that writing is social.

Writing is social. And that the whole writing process can be social from finding ideas to refining them. So that's where we're going to start today.

We're going to start off with finding ideas. Then we're going to go into refining ideas. And then at the end I'll give you some practical writing advice about how you can write in your life.

So who does social writing well? Who does this well? Where in society can we look for answers? And the answer's a little strange. Comedians. Comedians are masters. I lived with a comedian many years ago, and we used to just hang out every night. His name was Sam Davidoff. His dad, Guy Davidoff, was my coach growing up for every [00:06:00] sport.

Sam and I lived in Brooklyn for a little while. He was working on being a comedian and we would just sit down and he just rehearsed jokes all the time and then he would just take note of like how I would laugh. What he was doing is he was looking for the whoa moment, and I'll explain what that means in a second.

This is the Comedy Store. If you go to Los Angeles, it's on Sunset Drive. And this is where many of the big comedians go. And if you're listening to a podcast, like on Rogan or something like that, what the comedians do is they talk about their time at the Comedy Store. You can go to a 8 p.m. show, 10 p.m. show, midnight show, but the comedians are there until four in the morning. 

What are they doing till four in the morning? They're always talking about this. So what they're doing is they're throwing out ideas. They're throwing out jokes. They're just hanging out in the green room talking about whatever and they're looking for that whoa moment.

[00:07:00] What is that moment when you get a laugh? You get someone who looks at you and says, hey, that's a good idea. And you're just playing around. It's casual, it's fun, it's play. It's that whoa moment. And what comedians are doing is they're training themselves to scan for whoa moments. That is what the craft is about. 

It was funny, I'll do a quick tangent. One of the things I really like doing, I live in Austin, Texas and I have season tickets to the symphony. And I try to take people who would never go to the symphony. So I took a comedian in town and his name was Reza Jafri.

And so we're sitting, we're waiting, and we're sort of looking around. It was so interesting, you know, he's doing that same Comedy Store thing, just sort of ripping ideas out. And I laughed really hard at this joke that he made. And instantly he goes, Wait, why was that funny? That's so interesting. Okay, so like, break that down for me. What's going on? He pulls out a notebook from his [00:08:00] back pocket. He starts writing out the joke, doing like, X, Y axes. I'm like, Rezo, what are you doing? He goes, the way that my comedy process works, is I'm just in a right brain state of relaxation and play, and then I instantly shift into left brain stage of analysis.

And really focusing on word choice, and all of a sudden I just found that whoa moment and flipped into how do I make this joke better and better? I'm like, okay, I can bring this into my writing. That's pretty interesting. 

What I've learned is that comedians find their ideas in conversations. If you look at Chris Rock, right, when Chris Rock is on a Netflix special, like his most recent one had what, 30 million views or something? It was huge. Or, when he's on stage at the Madison Square Garden, you're watching him, and you're like, Yo, that's good. That rips. And you're like, how does he do that? How does he make it so that every joke lands for like an [00:09:00] hour and a half? Every joke is just going 30, 60, 90 seconds, right? You're getting that constant laughter. What's going on there? What's going on? 

All right, so let's do some x-ray vision investigation. So, I looked at Chris Rock's creative process, and he doesn't start at the Madison Square Garden. When he is at the Garden, he's told those jokes 100, 200, 300 times. He starts in little comedy clubs like this in Trenton, New Jersey, Columbia, Missouri. I don't know, maybe. Who knows? Austin, Texas, right? And he's in these little clubs. And what's great about comedy is you get this instant feedback from people. Comedy is a harsh profession. You cannot will a group into laughing. Your stuff's either funny or it's flat. 

And once again, we're talking about scanning, right? A good comedian, they're scanning. They have the part of their brain. Where they're thinking, okay, I'm at the mic, [00:10:00] what do I really want to focus on here? What's really resonating? And then right after, they then sort of do a debrief. And Chris Rock here, he is writing from conversation. 

So when we remember Thoreau, what do we think of? We think of Thoreau at Walden Pond, the cabin in the woods, sitting there at a desk writing and writing and writing and writing. Oh, you can't talk to anyone. And I'm like, there is no way that I'm gonna write like that in my life. I'm just too social. I like people. I love to blab. I need something where I can write from conversation. So I'm like okay comedians. That's what I can learn. It's okay.

Now let me ask, how does Chris Rock refine his ideas? How does he do it? What he does is he starts off in those small comedy clubs and he'll throw out a set and he'll get to the end of the first set and be like all right purple stuff not that good, but you know what honestly people laugh pretty hard for the two green [00:11:00] things, okay?

So I'm gonna keep those green stories Those are my jokes. And now, I'm gonna go for set two. Throw them at the front. Bunch of new material. Okay, so we'll try this new material. Let's take a look at it after. Alright, the green stuff, we like. The purple stuff, we don't like. Let's let go of the purple stuff.

The green stuff, it's not perfect, but it definitely has potential. And you do that over, and over, and over, and over again, right? And then eventually, we're at Madison Square Garden. Now it's game day, baby. Now it's the Netflix special. And now, you get all green. So when you watch Chris Rock, you're like, how does he do all green?

It's because you're not seeing all this work that went into it. That's the magic, that's the juice, that's what it means to write from conversation, that's what it means to make writing social. 

Somebody else we can learn from, [00:12:00] Pablo Picasso. Picasso was obsessed with bulls, Spanish guy, and what he wanted to do in this series of twelve paintings was find the essence of a bull.

We'll start on the top left. We see that he is making his first drawing. Now, this is where it gets interesting. Look at the second and the third and arguably the fourth bowl. I've had many debates on this. I'm still not sure. It is more complicated than the first one. Right? This first one is a bit of a sketch.

Once he gets to the fourth one, you can see him going from a right brain intuitive sketch into something a little bit more left brain, where he's beginning to dissect the different parts of the bull. And then he goes again, and again, and again, and again, until he ends up on the bottom right, he has the [00:13:00] essence of a bull.

But here's the thing, once again, you can't just start with the bottom right. The proportions wouldn't work, it wouldn't be correct. You have to go through the process. And often, you start off with an idea, and then you begin working on it, and you're like, ah, this is more complicated than I thought. That is standard stuff.

That's par for the course, and it is only through compression, and compression, and compression, and compression, that you end up with the essence of the bull. To distill all the things that don't belong, so that you can end up with the essence of what you're trying to say. Eloquence, clarity, specificity, dynamite.

So where does compression show up in writing? A book called The Networked State just came out. And this book does something really interesting. [00:14:00] Basically the essence of the book, it's a bold claim, to hell with the nation state, we're gonna start the network state. And it's now really becoming a movement. 

And if you go to the very beginning of his book, he has this thing that I now call the babushka doll strategy. And he has a 474 page book, that's the main event. But at the very beginning, he has a 2000 word essay. Before that, he explains the entire concept in 500 words. Before that, in one sentence. And then, hey, you can judge a book by its cover. The network state. 

So you have the same idea. Compressed. Expanded. Compressed. Expanded. That's clear thinking. That compression. The distillation. The clarity. When you're in your work, if you want to be a good communicator, do this.

You don't need to write a 474 page book, but 2000 [00:15:00] word essay, one sentence title. That's good stuff. That's the stuff of clear thinking. I just want to give a shout out to my friend, Eric Jorgensen. He's here. He just wrote the Anthology of Balaji.

So why should you write? Well, if you run a company, I always say that CEOs are professional sloganeers.

I think this is one of the core jobs of a CEO. And I think Jeff Bezos does this very well. “But the number one thing that has made us successful by far is obsessive compulsive focus on the customer as opposed to obsession over the competitor. Obsession over the customer. Focus on the customer, focus on the customer.”

Jeff Bezos is a master at this. I bet if we're sitting here with Jeff Bezos right now, and you said, how many times have you said focus on the customer? He'd probably say, I don't know, a hundred thousand. And then if we looked at him, we said, yo, you said it enough? [00:16:00] He'd be like, no.

Over and over and over again. You know, at the bottom of every Amazon shareholder letter, there is the what he had from the ‘97, his very first shareholder letter. It's always day one. He says that all the time. And day one is about invention and pushing the limits.

This is how much of a sloganeer Bezos is. He worked at Amazon headquarters in Seattle in a building called Day One. They moved the building, they moved Amazon headquarters, and he said, That's my new office. I will always work in the Day One building. I will always work in it. And it's so funny because when I'm hanging out with the very most successful executives I know, they just tell the same stories over and over and over again.

But what they're doing is they're trying to work out the ideas. They're writing like a comedian. And so when I see, okay, these really successful executives are doing something, and these really successful comedians, who are the [00:17:00] best communicators in society right now, are doing the same thing, I'm like, ha, something's going on there.

If you work at a company, why should you write? Well, don't take my word for it. Here is a little clip from an interview I just did with Marc Andreessen. “

This is the kind of thing where I feel like everybody knows this and yet nobody, very few people actually act on it, or maybe people don't know it, which is like, the person who writes down the thing has tremendous power. Huh. Independent of their actual formal role in an organization, or in the world, there are so few people who will just like, write down the thing. Um, and so that I see, we see this at companies all the time, which is, you know, one of the ways you find like the up-and-comers at a tech company. It's just like, okay, who wrote down the plan? And that doesn't mean they came up with everything. And that doesn't mean that they had all the ideas, but like they're actually able to organize their thoughts that actually have the energy and the motivation, the skill to be able to communicate in their written form like that. That actually stands out.”

I love that line. And all of you can follow this. The person who writes down the [00:18:00] thing has tremendous power. And so just being the person inside of your organization, inside of your business, inside of your company, whatever it is, if you're the person who writes down the thing, you have that power, that influence.

Now, if you want to listen to the episode go to www.dparrell.com/mark. It's a fun one. He's got a mind about him. 

So we've talked about writing and refining ideas. But at some point, you actually need to get words on the page, right? So we've spoken about writing like a comedian. Where do these ideas come from? And this is the single best piece of writing advice I've ever seen, and it is so simple. It goes like this. 

This sentence has five words. Here are five more words. Five word sentences are fine. But several together become monotonous. 

Listen to what is happening. The [00:19:00] writing is getting boring. The sound of it drones. It's like a stuck record. The ear demands some variety. 

Now listen. I vary the sentence length, and I create music. The writing sings. It has a pleasant rhythm. A lilt. A harmony. I use short sentences, and I use sentences of medium length. And sometimes, when I am certain the reader is rested, I will engage him with a sentence of considerable length, a sentence that burns with energy and builds with the impetus of a crescendo, the roll of the drums, the crash of the cymbals, sounds that say, listen to this! It is important. 

So write with a combination of short, medium, and long sentences. Don't just write words. Write music! Write with a combination of short, medium, and long sentences. 

Now, my mother taught me to [00:20:00] beg for forgiveness instead of ask for permission, so I went into Brent's annual letter. And, uh, broke it down.

And here's what it says. I've always had the attitude enthusiastically shared by the team that the more inherently risky the activity, the more it pays to be conservative. Volatility can be a wonderful thing if you're able to withstand it. All businesses are loosley functioning disasters, and some of them happen to make money.

Typically, the smaller the business, the more loosely it functions. All businesses lack something, and small businesses typically lack many things, which is why almost all small businesses stay small. 

Well, Brent crushed it. And I want to break it down. So this is a technique that I developed called reading the right edge.

And you can see that Brent is driving to this sentence “and some of them happen to make money.” All of this is happening intuitively for him because he spent so much time reading. But what is going on is he's got these long sentences and he's driving [00:21:00] into the main climax of this paragraph. All businesses are loosely functioning disasters, which is the lead into Boom. And some of them happen to make money. 

And then right after, you can see that he builds from it. So, he's got his short sentences. The short sentences, remember, that is the sounds that say, listen to this, it is important. Then he's got the long sentences, and most of them are in the middle. So vary your sentence length.

Just do this, and your writing will get better. I know it's so simple, how can that possibly be true? It actually works. And this is what it looks like in Buffett's annual letter. With Bezos, with Morgan Housel, every great writer does this, and it's so simple. Short, long, medium. 

So, for a recap, we've talked about finding ideas, refining ideas, and writing with life. And that writing is social. 

And so your next step, there's homework, your next step is to write from conversation. And now is a perfect time to practice because we're all here together. We can all work on this. And in conversations in The Atrium, at lunch today, dinner tonight.

And it reminds me of a story from J. R. R. Tolkien. And he was really good friends with C. S. Lewis. Tolkien and Lewis, they would chat, and they were part of this group called the Inklings. And they'd talk about their writing, and Tolkien was a bit of a weird guy. Like, normal people don't really come up with strange, elvish languages on their own. That's just not something that I think anyone in this room is doing. 

And he was really insecure about his ideas, and he was scared to put them out there. And C. S. Lewis was there, and he was like, I believe in you, man. [00:23:00] I think you can do this. And then he starts ribbing him. He goes, Come on, give me your book. Give me the manuscript. Tries day after day after day. And he does it.

And C. S. Lewis comes back and he says, I can quite honestly say that it is ages since I've had an evening of such delight, after reading Tolkien's manuscript. And Tolkien, I mean you can just imagine it, like his heart just warming up, the sense of confidence that he has, going from fear to love. Hopelessness to hope, pain to possibility. 

And, in The Lord of the Rings Tolkien says, but for the encouragement of C. S. Lewis, I do not think I should have ever completed or offered for publication The Lord of the Rings. This book doesn't get written without C. S. Lewis. 

And what I want you to think about, my send-off message is, are you Tolkien or Lewis?

Are you the person with an idea to [00:24:00] share that you're holding back from the world, or are you the person that can encourage somebody else here at Main Street and give them a look in the eye and say, Hey, I just had a whoa moment. Got to share that.

This transcript was generated with Descript AI