I used to drive. But then my license was taken away.
One thing I used to hate: whenever I drove the same way over and over again, I would arrive at the destination and have zero memory of how I got there. I couldn’t remember a single thing I saw along the way.
When you take the same path, your mind and body split off. The body takes the path, and the mind travels somewhere and only returns when you get to where you are going.
With writing I try not to have too many routines. I try to mix it up as much as possible. I want my mind and body to be in sync and to experience everything around me.
But it’s not always possible. After all of these years I know when my fingers are at their smartest.
I wake up, I have coffee, I read, I write. By the time I’ve been up for 2 or 3 hours, I am writing. I write for 2 or 3 hours.
Once I’ve written, I stop. I’m done! I did it!
The morning is for my “maker hours”. Only creativity. My afternoon is for my “manager hours” – tasks to keep the wheels of my life turning.
And then I like to play. I make sure I play every day. Sometimes a game like chess or backgammon or poker. Sometimes I take lessons. Like archery lessons or (today) ping pong lessons. And sometimes I take walks with friends. All things to make me laugh and have fun and get other parts of my brain working.
The earlier the better. Nobody is up. I’m creative. I don’t have the worries of the day infecting my thoughts and I am calm.
I think some people write better at night but I always sort of think the whole point of “night” is that people are tired (the brain and body become tired ) and that’s why we sleep. To rejuvenate. So when I am fully rejuvenated, I write.
Every single day between 1000 and 3000 words.
When I first went broke, first lost a home, first was exiled to a small town 70 miles away to try and recover and figure out my life, I had this routine:
I woke up at 5am. I’d go to the kid’s playground and swing by myself on the swingset. Then I’d go shoot baskets at a basketball court right next to the Hudson River. The early train would always pass and the sleepy people would stare out from the train at me.
Then I’d go play scrabble with my friends when the cafe opened at 6am. We’d play for two hours and I would have 2-3 cups of coffee.
By then my kids would be on their way to school. No distractions!
I’d go home and write for 2-3 hours. And that was my writing day. It was so quiet, and I missed New York City so much. And I regretted so many of my decisions. But I wrote. And I wrote every day.
My routine is a little different now. And every month I am sure it will be a little different from the month before.
But I wake up around 5am. I have 2-3 cups of coffee. I read and read and read for two hours. I read high quality literary fiction to be inspired, high quality non-fiction about a topic I am fascinated by in order to learn, I read inspirational or spiritual writing to feel that special something inside, and often I will spend some time studying a game.
Then I might read the literary fiction some more. At some point, I get the urge or the itch to put the books away. I go to my computer and start to write.
But now that I write this, I miss 2004, 6am, the train passing every 25 minutes, my friends Dina and Ari and Tom, ordering bacon and coffee, playing Scrabble with friends before most people are even awake.
I remember this: ETESIAN is a legal seven letter word.
One time I was very scared. Earlier that evening I was playing chess in the Thompson St Chess Club. A girl came in, came up to me, and asked to draw my picture on a napkin.
Then she asked for five dollars and she gave me the picture. She was quirky in this crazy insane way that I try not to fall in love with anymore but I always did back then, 23 years ago.
It started snowing later and I was walking home and by accident I ran into her. “You!” she said.
She said, “Do you want to hang out?” And I felt swept up in everything. New York City was new to me, it was snowing, and quirky and crazy wanted to spend time with me. So I said “yes”.
First she wanted to buy some crack. Then she wanted to buy some heroin. Then we went to her hotel room. The taxi driver said to me, “Don’t have sex with her.”
In her room she started screaming, “My brother is talking to me on the TV. Get out!” And so I left. At first I paced the hallways. Despite heroin crack and a crazy brother in a TV set I actually wasn’t sure I wanted to leave.
But I did. I went home. And the next day I got on a bus and went sixty miles to visit my parents. It was Thanksgiving. My dad said to me, it’s good to see you. And I shook his hand. My parents were proud of me.
This, for me, is the beginning of a topic. It’s about fear, and loneliness, and trying to please society around me. It’s about a fresh start. It’s about all the distance that’s occurred between then and now and everything that’s happened.
But it’s only the beginning of a topic.
Three years later I ran into her in the street. She recognized me.
“Where did you go?” she said.
“I don’t know,” was the only answer I had.
My podcast is about my own addiction to people who have achieved peak performance in areas that I either love (like writing, arts, business) or have aspirations about (astronauts, comedians, athletes, etc).
Everybody from Tony Hawk, to Mark Cuban, Sara Blakely, Jim Norton (comedian), Coolio (musician), Garry Kasparov (the greatest chess player in history) and a young man named Ryan Holiday (writing and marketing) and many others.
There are many many many common themes among them.
A) persistence. How to always find a “back door” when every front door is closed.
B) every day. They don’t get inspiration. They get “every day”. Every day is a day they can work on improving.
C) They all have mentors and peers that they learn from. Nobody learns mastery in isolation.
D) Years of effort. Some (Ryan Holiday) skyrocket to success early on. But nobody reaches their peak early on. Usually its a 15-20 year effort where successes happen along the way but improvement and study keeps on improving their natural talents and skills.
E) Creativity. No matter what the field, creatively solving problems is what sets the peak performers apart from their competitors who just take the well-trodden path. And creativity is something you can learn and practice. You learn it by thinking of “what can’t I do?” and then finding dozens of ways to try and do it and then trying some of those ways and continuously tweaking.
F) Networking. I’m a horrible networker and introvert. So for me to go out every day and meet people is very difficult. But I always try to introduce people and every day think of people to touch base with and add value to. Over time, your network is not about who you know but about “who in your network knows each other”. This makes the linkages exponential instead of linear.
G) Umbrella Rather Than Focus. Example: if you want to be a comedian, don’t just do standup. Write jokes for other standups, do improv, do TV, write for TV, write a book, make a movie, act, etc. If you focus on one tiny area within your field, you won’t learn the bigger picture of the interest you are passionate about. With writing: don’t just write serial thrillers. Write non-fiction, literary fiction, songs, comics, etc to really learn the art. With business, Richard Branson is a great example. He was a kid who loved music who started a music magazine. Now he runs an airline which owns 300 other businesses. Focus is a myth. Open the umbrella as wide as possible.
H) Permission Granted. Nobody asked for permission. The basic strategy is “ready. fire. aim”.
I) History. Know the history of whatever field you want to master. Garry Kasparov doesn’t just study the chess playing skills of his competitors, he studies the chess playing of every grandmaster since the 1700s. He’s even written books about all of them.
J) Vision. Eventually, all of these peak performers learned everything they could – then developed their own unique voice and vision. It’s this vision that we look at and say “they were an overnight success” even if it took them 20 years to develop that voice.
Waiter’s pad for ideas. Computer / Gmail for writing.
Why waiter’s pad? It’s cheap to get 100 of them. It’s not a big notebook so you can’t write a diary. just a list of ideas. And it’s always a conversation piece in meetings. “I’ll take fries with that burger” is a joke i hear ONE HUNDRED PERCENT of the time in meetings and then allows me to explain why I have a waiter’s pad.
Gmail: my first draft is always plain text in gmail. Gmail prevents me from doing anything fancy. And also saves in the “cloud” every few seconds just in case I crash.
No music; Always silence. Everything else feels like multi-tasking and I want to just focus on the writing.
Anywhere. No matter where I am I tune out everything else. Sometimes I leave just so I can feel like I am “going to” work. But it just doesn’t matter.
1000-3000. And probably 1000 words will see the light of day in some form or other.
I’ll write. Then I’ll usually take out the first and last paragraph to see what the story looks like without them.
Even though I know I’m always going to try this technique, taking out the first paragraph always throws me more quickly into the story and into my “voice” and the first paragraph was just filler while I got used to the topic.
Then I might write the whole piece again. or I might write paragraphs over. Then I take out extra words. Then extra syllables. And I don’t like punctuation except for the period.
Today I didn’t like what I wrote. I wrote a piece about a tiny business I started once that didn’t work out. I had never written this exact story before.
For me, it was a footnote that linked together my divorce, losing a home, losing my family, and the bigger backdrop of the financial crisis in 2008.
It was ok. It wasn’t the best thing I had ever written.
But I celebrated. I wrote! Every time a story, article, post, book, whatever (even a list of ideas) comes out of me, it’s a reason to celebrate.
I did it again. I wrote today!
And then I’m done. I don’t need to write again. I need to take care of my life so I can keep experiencing things. How you experience the world translates into how you write about that experience.
Today I took ping pong lessons for the first time. I reached out to one of the best players in the country. He had started off his career as a 13 year old drug dealer in Brooklyn. He was sent away by his family to keep out of trouble and he became one of the best ping pong players in the world.
Today he gave me a lesson and I learned and I experienced.
One day I watched the rooftop concert of the Beatles. It was the last time they ever performed together.
They were in the process of all suing each other. They would never be friends again the way they were in years prior.
Men and women on the street heard them playing from the rooftop and climbed ladders and buildings and stretched out of windows to try and get a peek of the Beatles playing.
At the end John Lennon said, “Thanks for the audition”.
I loved the concert. I listened to it over and over. One of the best bands in music taking their art all the way to the end.
I wrote about how I felt. I wrote my own interpretation of what I saw and what I listened to and how it made me feel.
That’s the way I research my writing.
That said, if I have someone on my podcast, the way I try to stand out is by going above and beyond on research:
– I read every book by the guest
– I read other interviews they’ve done or listen to other podcasts so I can figure out how to be unique
– I watch shows or specials they might have done or appeared on.
– I read work they might have worked on that might be a little more obscure.
And on and on. I do as much research as possible for each guest. I know this is where I can have an edge over other podcasters.
Yes. I have many people who I view as my mentors in writing. All virtual in the sense that I don’t talk to them and perhaps many are now dead. I usually read some mix of them every day before I write. Probably about 50 different writers are my go-to writers.
Writing is difficult and depressing. I never know before I begin what I should write about. If someone asks me to write something specific then that becomes the one thing I can’t write about ever.
I feel like all my stories are now cliches with the rise of “failure porn” in every article I read on the Internet. So I am constantly trying to figure out how to go down a path, and then surprise myself with a sudden turn or leap into the jungle.
I used to say “I need to put a knife in my veins and bleed”. But that’s a cliche. Everything is a cliche. So every day it becomes a challenge to free myself from the cliches and produce something unique to me that I feel says something new. Else…worthless.
I wanted to be a writer when I was 11. David P. liked Joanna A and I wrote it in my notebook. And Lori G. liked Jimmy B and I wrote it in my notebook.
And if Robert talked to Jennifer, I wrote it in my notebook.
All of my classmates wanted to see what I was writing. I had to take my notebook with me to the bathroom else people would try to take it from my desk. Eventually everyone complained and the teacher BANNED me from writing in my notebook during school hours.
Later, in college, my friends who called themselves “writers” were dating all the girls who called themselves “writers”. I happened to be in love with those very same girls.
So in two different cases I saw the power of the pen. I also didn’t want to work at a real job. Writing seemed a way out of that. I was naive and stupid. I thought I would write and publish and people would love me. But I wrote and wrote and wrote and nobody liked anything I wrote. Then I was thrown out of graduate school. I’d work all day and night but wake up super early just to write.
And I kept doing it and not succeeding. For about four years I wrote every day, 3000 words a day, and nothing at all happened. I wrote four novels. I wrote about 50 short stories. I read every day. I read literary criticism every afternoon. Nothing. Nothing. Nothing.
I thought maybe the problem was that I didn’t have the right connections. I lived in Pittsburgh at the time. I had gone to graduate school at Carnegie Mellon and decided to stay there because it was cheap to live and I could write.
But it was far from the connections. I took a job at HBO in the IT department, doing random programming, thinking it would put me one step closer to where art, entertainment, creativity, and writing was happening.
I pitched and original idea to them. I said to the CEO: just like you have original shows on TV, do original shows for your website. He said, what should we do?
I pitched an idea: “III:am” (3am).
I would go out and interview people, drug dealers, prostitutes, whoever I could find at three in the morning on a weeknight in NYC. For three years I turned over every rock in the city and did over 1000 interviews.
Then I’d transcribe the interviews, had designers design around them, and I’d write up an into.
Finally I was getting paid to write. It was something.
Many things happened after that. NYC requires money to survive and ultimately what I was doing was not being noticed by other writers but by other businesses who wanted websites. I started a business and this led me down a completely different path: combining my computer skills, my content skills, and business.
Only after I crashed, burned, and started to come back did I finally put it all together and start making a living writing.
I wrote books, wrote for many newspapers and magazines, wrote newsletters that people subscribed to…and then wrote more books. For eight years all I did was write about finance and investing.
And then I woke up. I got back to my roots. I got back to my favorite writers. I got back to the subtle pleasures I saw in simply telling a story. I was blessed with good editors who forced me back into story telling instead of the boring typical finance article. “Go crazy or you are fired,” the editor in chief of The Financial Times told me.
I went crazy. And then I amped it up further. And then I stopped writing about finance. And finally I was writing with my voice, about things that I cared about , that were important to me, that were entertaining, and hopefully helpful to others.
And finally I made money from writing with my voice, a full 20 years almost to the day after I started writing.
Choose Yourself combined my stories, with my theories on how to live a good and successful life, with my theories on the direction of our culture. I loved writing it. It was a pleasure from beginning to end.
Altogether now I’ve written 18 books of all types. Each one has been its own blessing but Choose Yourself stands above them.
The best books on writing are the best written books.
The collection of short stories, Jesus’ Son by Denis Johnson is a book I buy for anyone interested in writing.
Slaughterhouse Five by Kurt Vonnegut is a beautiful example of how to stretch the form.
Ham on Rye by Charles Bukowski, along with any collection of Raymond Carver stories, are the best examples of “Dirty realism” – how to take a true story, squeeze even more truth out of it, and yet call it fiction.
Hunter S. Thompson’s Fear and Loathing in Las Vegas is a great example of how writer and subject can merger and the literary quality still stay high above a typical piece of journalism.
James Frey’s Million Little Pieces, despite all controversy, is a great case study in how the style of the writing can mimic the mind of the main character, and change and grow as the main character grows throughout the story.
James Baldwin’s Go Tell it On the Mountain is like music made out of printed words.
And on and on. There’s no one book about writing. What makes writing such a special art is that there are hundreds of beautiful books that are such a pleasure to read that they make you want to cry.
If only I can write one sentence like any of the authors above and a hundred others that I admire, I would be very happy.
I write something I would like. But not because I don’t care what the audience thinks. I do care what the audience thinks. But I know if I like something, if I feel something hits all the right beats, then I know the audience that I look up to the most, my very most favorite readers, will also like it.
Sometimes I’m wrong. That’s ok. People don’t remember the times when you are wrong and don’t perform at your best. People remember your best.
Most books should be magazine articles. In fact, most books ARE magazine articles and then a publishing company says: add 250 pages and make it a book.
Those books are awful.
Pack a book’s worth of material into a single article, or post, or chapter. Pack an article’s worth of material into a single paragraph. And so on.
What is a book? Imagine all of that value in interconnecting 15-25 chapters that are rewritten so they all fit together like puzzle pieces and now there’s a book.
A book is not one idea. A book is everything you have inside of you that moment or year, vomited out onto the page with a thread sewing it together to connect it all up.