Eight (more) things I’ve Learned from Judd Apatow

This is part two of 8 things I learned from Judd Apatow. All of the quotes are from Apatow’s book, Sick in the Head. If you want Part 1, it’s here.


Lifestyle creep.

“I didn’t have a lifestyle to maintain.” – Jay Leno, 1984

Leno says that when he graduated college – with hardly any stand-up experience – he would work anywhere. That included retirement communities. “I would drive hundreds and hundreds of miles to work for free for four or five minutes,” Leno says. It didn’t matter, he made 30-40 bucks a week and that was enough. “I didn’t have a lifestyle to maintain.”

If you have the luxury of not needing luxuries, it lets you spend a lot more time creating something. Penn Jillette slept in his car while he worked the streets of Las Vegas. He didnt care. It was enough that he could perform.

Mark Cuban said the same thing. He lived  cheaply, and was willing to retire cheaply. “I was willing to live like a college student,” Cuban says about his mindset at the time. All Cuban wanted was an American Airlines lifetime pass and the time to use it.

Maintaining a lifestyle reduces optionality. Remember how Part 1 started? Jerry Seinfeld said, “Quality. That’s my only real consideration.”  If he needed to make money, he would have needed to take any job. Leno leveraged the same idea.

Diminishing returns.

“And the thing is, Are you willing to compromise quality to keep it going? Of course, the answer to that was no. And that’s why the show ended when it did.” – Jerry Seinfeld, 2014

The hardest part is starting. But it gets immediately easier. Going from one to two is easy, two to three a smaller challenge. And so on.

Seinfeld tells Apatow it was physically hard to make the show. Add in the challenge of making it better and you reach a certain point of resistance.

It’s true beyond television. People losing weight see this all the time. Starting is hard, but the easiest pounds are the first ones. It’s true for fat cats in the same way it’s true for belly fat. This is from When Genius Failed, the book about a hedge fund that failed because of diminishing returns (of good options to invest in):

“By now Long-Term was succumbing to the fatal temptation to put its money someplace. In a clear speculation, it bet on the U.S. stock market to decline, via options.”

The story of hedge fund Long Term Capital Management (LTCM) is one of diminishing returns. There were only so many great investments that could return 18% or 34% – and they found them. They succeeded brilliantly. Investors came with money. Then things got harder.


“Our morning meetings start at nine. We have to pitch out our ideas – and in some ways that is the challenge of a show. It’s to create a factory that doesn’t kill inspiration and imagination. You try to create a process that includes all the aspects of a mechanized process that we recognize as soul killing, while not actually killing souls.” – Jon Stewart, 2014

Apatow had asked Stewart how they were able to create The Daily Show everyday. A good process is key for creative people, a mold that allows wiggle room. It’s why so many creatives have daily rituals.

Mason Currey curated a delightful collection of these in the book, Daily Rituals. Two excerpts from there. First, George Orwell needed a job to supplement his writing income:

“The post at Booklovers’ Corner proved an ideal for for the thirty-one-year-old bachelor. Waking at 7:00, Orwell went to open the shop at 8:45 and stayed there for an hour. Then he had free time until 2:00, when he would return to the shop and work until 6:30. This left him almost four and a half hours of writing time in the morning and early afternoon, which conveniently, were the times that he was most mentally alert. And with his writing day behind him, he could happily yawn through the long afternoons in the shop and look forward to free time in the evening.”

And this from the routine of Ingmar Bergman.

“There (his home in Sweden) he followed essentially the same schedule for decades: up at 8:00, writing from 9:00 until noon, then an austere meal. ‘He constantly eats the same lunch,’ the actress Bibi Andersson remembered…After lunch, Bergman worked again from 1:00 to 3:00, then slept for an hour. In the later afternoon he went for a walk or took the ferry to a neighboring island to pick up the newspaper and the mail. In the evening he read, saw friends, screened movie from his large collection, or watched TV.”

If you want a modern version, listen to Adam McKay on Slate’s working podcast or read The Habitual Hustler.

When you start, your work sucks.

“I remember feeling like, Oh no, I can’t do that. I just watched some magic right there. It was a gut-wrenching feeling.” – Peele, 2014

That’s what happened when Peele showed up at Second City in Chicago. And, this was right after Amy Poehler, Steve Carell, and Stephen Colbert had left. Peele wanted to be in the major leagues, saw a AA fastball, and knew he couldn’t hit it.

At the start you should get comfortable with being bad.

Austin Kleon noted this too. “There’s a big gap when you’re starting out between what you love and what you’re producing.” The only thing to do is get better. Apatow’s interviews began this way. “I want to do that,” Apatow thought, “how do I do that?” He didn’t know, so he started asking. That was the premise of interviewing comedians as a high schooler. He wanted to know how to do their job.

What did Jordan do? He figured that if he couldn’t make the quality, he’d provide the quantity.

“When I moved to Chicago, I was like, alright, I want to be a sketch comedian and my power is going to be in the fact that I’m going to dedicate myself completely. There’s not going to be a fallback, you know? I’m going to watch people give up and I’ll still be there, learning from it all, and if I stay with it, I’ll be successful.”

The religion of work.

“I’d always wanted to be a person who worked so much that I wasn’t even available to go to dinner.” – Lena Dunham 2014

You can like work. It’s okay. Casey Neistat told Tim Ferriss, “I believe in the religion of work.” Tyler Cowen commented that maybe you don’t need happiness. Maybe you need work, to eat well, and have a stable home life. That can be a full life too.

Louis C.K. on a knife’s edge.

Louis C.K. was so close to being unknown. So, so close. He was a high school dropout. He worked at a fried chicken restaurant. He smoked dope and drank beer.

The comedian we see today, the guy who can do everything was nowhere to be seen when Louis was young. The guy who can release his own special and make so much money he gives most of it away was this close to being the guy who said, “Welcome to KFC.”

So what changed?

When Louis was in high school his mom went to a parent teacher meeting at school and was told that her son dropped out. When asked why, Louis said he just didn’t care about school. “So what will get you to care?” asked Louis’s homeroom teacher. “TV. Movies.” Louis said.

The next day Louis showed up and his teacher handed him a business card for the local TV station. “It won’t pay well,” the teacher said, “but they take kids your age.” “I had direction in my life,” Louis tells Apatow.

Louis fixed equipment. He learned to edit. How to shoot and write and do all the behind the scenes stuff. All the stuff that he does now is possible because he cut his teeth on it as a high school student. And it almost never happened.

What if Louis hadn’t shown up for that meeting, or if the teacher hadn’t? What if the teacher had a bad day and thought, this kid doesn’t care? If the TV station had enough interns? If Louis never showed up at the station? If someone there had a bad day and said ‘get the hell out’?

That’s how closely Louis came to not being Louis C.K.

Look for ‘organic’ as a signal in the noise.

“When you see a movie that Sean Penn directs, you realize he’s not fucking around. It’s like listening to a Nirvana record or something. This is not a job. They have something to say. And in comedy, the people that we like the most, when they score, they have something to say that’s important to them. And to me, that’s what I’m always looking for.” – Judd Apatow, 2010

That’s from Marc Maron’s interview with Apatow. It’s fantastic. I’m looking forward to more Maron interviews and this one is why. Maron and Apatow cover a lot of good ground. It’s emotional. It’s funny. It’s humanizing.

The lesson in this quote is to create something real. Not linkbait. Not slideshows. Something that speaks a truth.

One of the macro themes in the book is that the comedians don’t succeed until they find their true voice. That’s what Casey Neistat told Tim Ferriss about making YouTube videos. It’s what Arthur Samberg told Barry Ritholtz about investing. Brett Steenbarger said, “you don’t find generic super-successful traders.” It’s what Peter Thiel wrote about in Zero to One.

If you do something creative, it needs to be done by you and for you. Anything else won’t work.

Roseanne Barr and Jim Carrey.

This is personal. I remember flipping past Roseanne on TV in the early 1990’s and thought, how can anyone watch that. She’s a jerk, a diva, loud and obnoxious. (Carrey I thought was okay, though not that funny)

I was so wrong.

Roseanne Barr may have been those things, but not without reason. Of all the people in the book, it’s her interview with Apatow that left me with “the feelz.”

Jim Carrey too. Apatow recalls this story:

“Jim Carrey always used to say that when he saw homeless people he would have this image of the guy patting the ground going, “Here, this spots for you.” That gave me chills.

Carrey dropped out of high school because he had to help his dad clean buildings. To earn money for their family. It wasn’t enough, and they became homeless.

People are complex. They aren’t jerks or divas or loud and obnoxious without reasons. They may not have good reasons – though Roseanne had some good ones – but they are reasons. If I want to connect with a person, I need to understand that. People are always serving some interest or habit and there’s a sequence that led to that.

There’s humanity in everyone and the people who seem like they need it the most get it the least. Roseanne had a terrible childhood. A difficult adulthood. An uphill professional situation. None of it was good, and neither was Roseanne.

Roseanne got crapped on by a lot of people. She’s not blameless, but she almost certainly got more than she deserved. This chapter reminded me to be empathetic. To be kind. To love others.

Someone who I never thought about was someone who reminded me to think about others.

Thanks Roseanne.

Thank you for reading, I’m @mikedariano on Twitter.

If you liked the post, you can donate here:

Update: An earlier version of this post has “starting” misspelled as “staring.” Thank you Rhett for the heads up.

15 thoughts on “Eight (more) things I’ve Learned from Judd Apatow”

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.