The Penultimate Rules On Being More Creative

The Penultimate Rules On Being More Creative

“You know that ‘penultimate’ means ‘second’, right?” she said to me.

I forget why. But it was in an horribly embarrassing situation. I remember that. I remember thinking I thought ‘penultimate’ meant ‘number one’.

‘You know it’s not the best. It’s the SECOND best,” she repeated.

I remember the blush. I remember her asking the question again. I remember not knowing what to do.

“Yes!” I said.

The first two rules for being creative:

1. There are absolutely no rules.

2. Whenever someone gives you a list of rules, ALWAYS throw out rule #1.

This is a post about revenge. I can’t tell you why…


One time I secretly videotaped a date happening at the table next to me. The girl knew. She put an ad in the paper. None of the guys knew.

We picked the restaurant. We put cameras in every plant. We sat on both sides of the table of the date. We recorded two dates this way.

On the first date the guy confessed he was gay but he still liked her and was unsure. On the second date the guy got a phone call in the middle of the date. From his wife.

After the first date, the guy called the girl and said, “Life is to be lived. Not videotaped!”

I pitched the show to two different divisions within the same company. They found out about each other and both rejected the idea. One side said, “It feels too mean”.

Ideas can be creative, ideas can be helpful. Ideas can be funny. Ideas can change the world, can entertain others, can change your life.

But they still can be rejected. The important thing is not the idea, or you, or the people who see it. The important thing is tomorrow. What creativity will inspire you tomorrow.

3. Creativity comes from being pre-crative.

I went to the gym today. I haven’t been to the gym in two weeks. I am not a regular gym goer.

“You can’t even do 70 lbs,” She was laughing at me. My trainer.

I can’t even tell you what machine we were on. Some machine where 70 pounds was too heavy for me. “You were doing it two weeks ago. See? This is what happens when you don’t go for two weeks.”

“But my daughter was visiting.”

“This is what happens when you don’t go for two weeks.” No excuses.

Muscles shrink pretty fast. The Creativity Muscle most of all. If you don’t use it every day, it goes away within weeks.

People think, “I’m going to take a shower and have inspiration.”

You’re just going to get up all wet. When I’m in the shower I daydream about money. I count it in my head. ‘How much will I have?’ I never seem to be creative there.

You get creative by exercising the Creativity Muscle. I call this being, “Pre-crative”. I made up that word.


4. One a day.

For awhile I was taking one photograph a day and posting it on Instagram. I’d go up to people who made me feel some sort of curiosity itch and I’d ask them why they were who they were.

Like, if I saw a pretty guy and girl sitting on a bench, I’d want to know how they met. Oh, they are broken up? How come?

Or, if I saw a guy playing piano in the street. How did he get that piano there? OK, let’s take a selfie.

The result: a photograph and a story. And, because I don’t like talking to people, I get out of my comfort zone.

Or I try to write a post every day. Or it’s a day I’m doing a podcast. Or I am working on a book.

One creative thing a day. Or your creative muscle shrinks.

Think about it: write one page a day. In a year you have a book. In five years, five books.

One podcast a day. In a year, you’d be among the best podcasters in the world.

One photograph a day. Within a year or two you’d be a good photographer. When I take a photograph and put it on Instagram I try to tell a story with it. So it also improves my writing.

The real you lives outside of your comfort zone. Creativity is the bridge from our daily zone to the mysterious phantom zone.


5. Ten ideas a day.

I’ve written about this a million times. Pick a topic, any topic. Write ten ideas. Make it so that it’s difficult by idea #6 or idea #7.

Today I wrote: ten ideas for young adult novels.

By the way: they can be bad ideas. Horrible ideas. I had an idea. An unpopular kid is half-vampire. I called my teenage daughter. “Horrible idea,” she said. “I’m so sick of those.”


But that’s not the point. 10 ideas a day is 3,650 ideas in a year. Is 36,500 ideas in a decade.

People say “Ideas are a dime a dozen”. Maybe they are right. But you still need that dozen. Maybe you need that 36,500 to have one good one. I’ve had three or four good ideas in the past 15 years. That’s all you need.


6. Inspiration.

“If you want to stop an argument, just say the word ‘panties’,” she told me. “Everyone stops then. Men become frozen.”

“Panties.” She didn’t say anything. Then: “See. It works every time.”

I fell in love with her. “Panties,” she said again.

Elon Musk didn’t sit down and make a space ship from nothing. He read every physics book. He read every book on mechanical engineering and space travel. He hired the best people in the world.

Carl Sagan has a joke. If you want to make an apple pie from scratch first you have to invent the Universe.

People say you are the average of the five people you spend your time with. Fair enough. I spend my time with some good people.

But inspiration also comes from the five people you are most inspired by. And those people can change every day.

I’ll you who it is for me today. Tomorrow it might be different. Today I’m inspired by:

Michael Lewis, Ksenia Anske, Celine, Richard Price, Jessi Klein.


7. Errors.

The history of creativity is a history of errors.

One example: Pfizer created a drug that failed in all of it’s drug trials to solve Angina Pectoris (chest pain when the arteries clog). The drug was a failure. Normally calm scientists jumped off bridges in silent frustration.

Only…it had a strange side effect. Pfizer renamed the drug Viagra and started selling it to create that side effect.

Spencer Silver was trying to create a strong tape for a company called 3M. Instead, he failed. Created a very weak tape that seemed to have no use. Many years later 3M figured, let’s try to sell this and they called them Post-Its.

You can’t have great successes without being littered with failures along the way. Small experiments, small failures, small victories, small celebrations, lead to giant acts of creativity.

tl;dr … Don’t give up.


8. 1 + 1 = 3 (the only rule you need to know).

I went to a party with Randy. He went over to say hi to Wyclef Jean, the main rapper in the group the Fuguees. Wyclef had once been in a play that Randy wrote.

“Think about it,” Randy said to me later about the Fugees latest hit. “You take the song ‘Saturday Night Fever’ by the Bee-gees, put a beat to it and rap to it, and you are guaranteed to have a huge hit.”

Take anything that has resonated through time. Add your own twist to it. And BAM! Creative genius.

Stephen Pressfield describes this process perfectly in his book, ‘The Authentic Swing’. I really admire Pressfield and his books on creativity: The War of Art and Turning Pro.

In ‘The Authentic Swing’ he describes how he took one of the most ancient (and popular) stories ever: The bhavagad Gita, which is the foundation of Hinduism, and he combines that story with …. the story of a golf pro.

The result: The Legend of Bagger Vance, which became a huge bestselling novel and a movie starring Will Smith.

The key was to take something that had already been “focus grouped” by history. He knew that the Bhavagad Gita has resonated with billions of people over thousands of years.

This takes a lot of the risk out of wondering, “Will people like this?” Creativity, like being an entrepreneur, is not about risk taking. It’s about risk mitigation.

Pressfield took something that people had already liked, even loved, even worshipped, added his own spin, and created art.

1 + 1 = 3 means:

Take something focus grouped by history, add your spin, create art.

Leonardo Da Vinci’s best example: The Last Supper.

Take a 1500 year old story, combine it with more modern discoveries of the human body, make a painting.

By the way, greatest modern example of this. 22 year old Elijah Daniel, last January, tweeted he was going to combine 50 Shades of Grey with Donald Trump and put it on Amazon that very night.

He did it four hours later. “Trump Temptation” and it became a hit reaching #1 in ‘humorous erotica’ on Amazon.

I just looked at it. It has 400 reviews, which is more reviews than any of my books except one.

Here’s one of the reviews: “This book changed my life.. 5/5 stars.. The ending is… Amazing. Enjoy.”


9. Do something stupid.

I ruined my career. I kept writing about how I often I lost all of my money. How many times. How much, etc.

I was once trying to raise money for a hedge fund. Some wealthy people were interested. I went to them and they did their research. My friend who introduced us laughed me out of the room.

“Man,” he said, “Nobody is going to give you money. You are constantly writing about losing money.”

Yeah, I reminded him. I lost money investing in your company which went down the tubes.

OK, he said, I get it. But nobody says it.

And he was right. But I did it anyway. And I did it more. And more.

We almost didn’t do a deal with you, said another friend of mine who has since done a very successful deal with me.

You always write about how your deals fall through.

It’s true. Most deals fall through. And most people are too afraid to admit it.

Be fearless, be stupid, be wrong, be exposed.

That’s how you get the deals, raise the money, create art, and get people to laugh.

Just be honest. Don’t be chained by “should”.


10. Immersion.

Hunter S. Thompson loaded up on drugs and drove to Las Vegas with his “attorney” and “Fear & Loathing in Las Vegas” was the result.

Jack Kerouac hitchhiked across the US and wrote “On the Road” in three weeks.

Truman Capote spent months covering a murder trial and “In Cold Blood” was the result.

Brian Koppelman and David Levien threw themselves into the underground subculture of poker in NYC in the 90s and out came their first movie “Rounders”. Now they are working on the hit TV show “Billions”.

My friend, AJ Jacobs read The Encyclopedia Britannica from A-Z and then wrote the bestselling “The Know-It-All”.

It’s not possible every day to throw yourself into a story. And it’s not always healthy. If you’re in a happy marriage, don’t do something stupid for the sake of a story.

But what is life without experience. And when you create something out of your experiences, you can help expand the lives of others as they read it through your art.


11. What’s your truth?

The Matrix was a masterpiece about virtual reality, and the question: what if the world we live in is not the real world.

It asks the immortal question: red pill or blue pill? Will you discover the real world you live in, or stay in the fake one.

But… was it really about virtual reality?

The Warchowski Brothers, who made the movie, are now…the Warchowski sisters – they both became women.

Did they take the red pill and find their real reality?

Everyone looks down their nose at genre fiction. Kurt Vonnegut was a pulp science fiction novelist when he started.

The book, “Slaughterhouse Five” could be considered a pulpy book about aliens and time travel.

But dig a little deep and it’s a book about the horrific bombing of Dresden in World War II and Kurt Vonnegut’s real-life experiences during the bombing.

Always tell the truth, wrap it in art.


12. Write what you don’t know.

People always say, “Write what you know” and even above I say, “What is your truth”.

But the reality is: sometimes the truth is that we don’t know things.

I wrote “the Power of No” not because I was so great at saying “No”. In fact, I was awful at it. I couldn’t say ” No” to anyone and I still have trouble with it. This inability was ruining my life.

But when I am able to say “No” it allows me to find time to say “yes” to the things important to me: like family, friends, writing.

You don’t take dating lessons from Brad Pitt. You take it from someone who was awful at it and got better. Documenting the process of learning how to say “No” is how I wrote “The Power of No”.

Ditto for “Choose Yourself”. I was always looking for validation from others. From my parents, from friends, from girlfriends, from teachers and bosses and publishers.

It was a 20 year process to learn I could be happier by first finding happiness from within and not needing validation from without. It’s that process I painfully describe through failure after failure.

It’s a cliche to say, ‘go out of your comfort zone’. Unfortunately, that’s where all the creativity is waiting for you.


13. Process is art. 

Read Raymond Carver’s original short story for “What We Talk About When We Talk About Love”, his most famous short story.

Only…that’s not the version that appears in his books. Gordon Lish’s edit is what appears.

I love seeing the two versions and the edits that resulted in the final draft. The two versions, seen together, is just as much art as the final story.

The process of creating art is art itself. Always keep track of your process.


14. Get irritated.

When something irritates me, I tease it out into a story. What were you doing when you were most irritated?

Don’t say why it irritates you. Let the story say it. And don’t take revenge on anyone.

It’s all your fault. When you blame someone else, you are really underlining your own faults in dealing with people.

There are many weak people out there. They are trying constantly to drag you down into the swamp.

We all have our tragedies. We can all pull them out of our hearts and examine them and tell story after story about them. Your tragedies are your creative best friends.

True creativity is the way to rise above the people who dislike you. The way to fly in the sky. The pleasure is immense.

And the more you are creative, the more people will hate you. Because you have explored a world outside of everyone’s comfort zone. That’s why it’s ‘creative’. And when you try to take people out of their comfort zones, they will hate you.

The more people who hate you, the more creative you are. OR…the more people who hate you, the more hateful you are. Fall on the right side of this.

The best revenge is not ‘living well’. That’s just something small people say.

Living well is a choice. The best revenge is being creative. To see the world from above. To paint it. To strangle it to kiss it to tease it to love it to wish for it to want it to miss it to run from it to be scared of it.

It’s hypocritical to write about creativity. Because nobody knows. And everyone is different.

Happiness comes from outside. Being creative comes from inside. Comes from exploring the world that is outside by looking at how it changes you inside.

By exploring the question, over and over again, ‘who am I?’

What’s great is that the answer changes every second and, yet, deep down it never changes at all.


Related reading: 50 Things I Pretend To Know Now That I Am Nearing 50

Share This Post

Other posts you might be interested in: