The Most Important Reasons I Waste My Life Writing

waste life writing

“Why are we addicts?” I asked my friend.

“What do you mean?”

“My kids don’t’ even know who the Beatles are. Everything you write, everything I write, will be forgotten within three days of us dying,” I said.

I’m addicted to my past. Afraid of my future.

The past is often too painful. It’s an alphabet made out of rain.

I want to assemble the letters into something sensible. So I can live. Live forever.

Why I write:


I was a spy.

I wrote down “David liked Joanne. He was staring at her”. I wrote down, “Lori likes Jimmy.” I wrote down, “Jennifer likes Robert.”

I think both Robert and Jennifer are dead now.

I was in Fifth grade. I brought in a spiral notebook. The metal at the end of the spiral would stick out and poke me.

And every time I noticed someone in class looking at each other I wrote it down.

What a mystery it is to fall in love!

Everyone wanted to see my notebook. Everyone wanted to know who liked who. “Who likes me?” I still want to know that.

I wouldn’t let anyone look at my notebook. “It’s private!”

Eventually the teacher said, “What is this notebook? Let me see!”

She looked at it. One page. Two pages. Three pages. She said, “Don’t bring this notebook back to class ever again.“

And that is the first time I wrote for a public audience. And the first time someone hated me for something I wrote.

The last time that happened was a few minutes ago (“This guy is stupid and his irrational rants are idiotic” someone wrote in a comment just now on m blog.).

I still write for attention. I hope I get enough confidence in myself to not need other people’s attention to be happy.

But if I’m really honest, I need it. I really need it. And I don’t like it about me.


The first time I had a “book deal” was when my parent’s friend, a publisher, told me he would publish a book about Rubik’s Cube if I wrote it.

I was 13. I started writing the book. I told everyone I was going to be a published author. I wanted them to think I was smart.

Sanford, the publisher’s name, went to jail.

He was also in the steel business. He’d bribe people who delivered steel to him to give him extra steel. I was never sure I understood how it worked.

I remember his wife was pretty and smelled like perfume.

I still want to be seen as smart. If you are an honest and sincere writer then sometimes people think you are smart but often people will think you are stupid.

When I said, “I don’t think kids should go to college” or… “I don’t think people should own a home” many people think I’m stupid.

Important skill tip #1: don’t just say smart facts. Give a story and interweave the facts into the story. Be a writer and not just smart.


I think I can deal with people thinking I’m stupid. I have a tiny bit more confidence. But only a little.


When I was 21, I saw Mark Evenson pretend to be a writer and he and Jen Min started going out.

I don’t remember names of people I met yesterday but I remember Jen Min. Because maybe I was in love with her, whatever that means.

And Mark maybe never wrote a word down but he had read Ulysses and smoked cigarettes and seemed “cool” to me. He was a “writer”. I wanted to be a writer.

So I started writing. I wrote every day. I wrote 3000 words a day. I wrote a novel: “The Book of David”. I wrote another novel, “The Porn Writer, The Romance Writer, The Prostitute, and They’re Lovers”. I wrote another novel: “The Book of Orpheus” (I liked “The Book of” back then for some reason).

I wrote another novel. I wrote about 40 stories.

I had no confidence with women at all. I was still the boy with acne and metal rubber banded braces, and cysts, and glasses, and messy hair and dirty hygiene (I still have the last three).

If only I could publish a book, I thought, I’ll be happy. I’ll be a real human and women would like me. Maybe even love me.

Is this a good reason to write?


There’s a lot of sub-skills to writing.

Telling a good story that people can relate to is one of them. To tell a good story you have to have something “different” and something “the same”. “The same” means people can relate and “different” means you can be unique and rise above the rest.

I’m afraid of the day I stop writing.

Will women stop loving me?

Hold on a second, I’m going to ask ….


Ok, I asked her. I’m on a flight to Miami. It’s our first trip together. She’s watching a movie with Reese Witherspoon.

I leaned over to her and she took out the earbud.

“If I stopped writing would you stop loving me?”

“Of course not,” she said and, because I like it, she touched my cheek. She looked over at the computer. She read what I was writing. “What are you writing? What’s ‘Hold on a second…’? “

“I had to ask you in order to continue this post.”

“I don’t think you can stop writing,” she said. “Would you stop loving me if I stopped talking?”

“Please god,” I said and she laughed and went back to the movie.


Ryan Holiday wrote an excellent article recently. “PLEASE,” he wrote, “stop writing your ‘books as the new business card.”

He’s right. And, like just about every opinion in the world, he’s wrong.

What’s he’s really saying is: Stop writing lame business self-help books that add no new knowledge to the world.

Don’t just write to get more consulting or speaking gigs. Say something “NEW” so that people can later say, “Your book changed my life.”

If they can’t say that…don’t write it. DON’T.

I get it. Authors get more speaking gigs. But be that person who saves lives. Don’t be boring.

If you write some business self-help book, write about your failures in business and how you overcame them.

Write about the time you lost everything, and the steps (one through ten) that you took to get off of rock bottom. How you often slipped along the way.

How you often disappointed people and felt guilty and ashamed.

How you were embarrassed to tell people the truth about your failures.

And then how you FAILED yet again.

ABS – Always Be Storytelling.

Everyone should write a book. Just don’t write a bad book. Or, if you do, write a second and third book so you can get better.


I got fired when I wrote my first book.

I hate thinking I used to write boring finance books. But I did. I’m sorry.

But this one was fun. It was called “Trade Like a Hedge Fund”.

I revealed every single technique I used in my daytrading. I gave away all my secrets. I still have that terrible habit. I like to share everything.

People thought I was crazy. And my boss at the time thought I was stealing ideas from him.

He wrote to me, “I want nothing to do with you financially”.

I wrote back, “It’s too late, you owe me a lot of money from the profits I generated for you.” So he cut me a check that day and we haven’t spoken since.

I did share every technique.

People always say to me (as recently as yesterday), “why do you share so much?”

Because I don’t care. I like to share.

When I was 12 I bought a bag of candy to school. I gave everyone candy. Someone said to me, “Look! Finally people like James!”

I was humiliated and stopped bringing in candy.

We don’t need to grab every dime in the world. Money is less interesting to me than having fun and helping people.

Why should just a few people on Wall Street or Silicon Valley make money. Why be so critical of me if I share?

One person said to me: “Well, if you are so successful, why not just clothe naked kids instead of selling stuff.”

I make almost zero money selling things compared with what I make in investing. Writing is a very very difficult and painful way to make money unless you are JK Rowling or John Grisham.

And maybe I do clothe naked kids. The highest form of charity is to do charity anonymously.

Charity is my own business. I have a particular technique I use for giving. Maybe one day I’ll write about it.

But for now I like just writing about things that embarrass me and cause me to feel ashamed.


“Are you about to kill yourself?” Max asked me in 2010.


“Because you’re sharing all this embarrassing stuff about yourself. I just got worried, that’s all.”

Max has written three excellent non-fiction books.

And yes, my sharing is a cry for help. Suicide is a horrible wretched thing that destroys families.

But often I felt like killing myself.

Writing is often a way to kill that part of me that wanted to kill all of me.

When I share these stories, and see that people relate to them, it makes me feel part of a community.

I used to feel very lonely all of the time.

And because I was raised that I was “the genius”, it was hard for me to admit the times I was so stupid. Stupid stupid stupid!

Lying in the street at three in the morning, drunk, with a girl I didn’t know, with all my money being lost, with all my businesses failing, with employees and friends depending on me, with two little daughters to raise. Stupid.

Now, because I share, I still feel lonely much of the time. But I don’t feel alone.


I didn’t write “The Power of No” because I was so good at saying ‘No’.

After “Choose Yourself” a publisher called me. “We’ll do any book with you. What do you want to do?”

And I was reading “The Power of Now” right then so I said, “How about the Power of Now but without the ‘w’ at the end. I feel like we don’t need that letter.”

They said, “Deal!”

So now I had a book deal. “The Power of No”.

I am always bad at saying “No” to people. Ask me to a wedding and rather than saying “No” I will just never speak to you again, even if you are my best friend ever (sorry Peter!).

Saying “No” is something I had to learn all my life. That’s what I wrote about in the book. Every way I learned to say “No”. Stories.

You don’t read a book about “How to meet women” by Brad Pitt. Brad Pitt can’t tell me stories of the lifelong struggle to meet someone to date. I can’t relate to him.

The best books are people who have been through the struggle. The only way to really learn is to have hardship, overcome it in various ways as you encounter more and more difficulties, and the come back a changed person to tell the tale.

In other words: Star Wars.

And every other great story ever told. This is called The Arc of the Hero.

Every good writing: a novel, a movie, a non-fiction book, a self-help book, even a tweet, can use the Arc of the Hero to make the writing better.

So sometimes i write in order to become the hero. To look at my hardships, to study how I overcame them, to learn how to better overcome them,


People sometimes ask me, “how do I market my book?”

The only real answer is: “Write another book”.

Keep on writing. Keep on reading. Keep on building a network. Keep on learning to deal with anxiety. Keep on dealing with writer’s block.

Writing is a marathon. Skill is a marathon. Luck is a marathon.

And that’s painful. It hurts to know how many years we all have in front of us to be true experts and successes at what we do.

Paul Reiser (star of the classic TV series, “Mad About You”, and more recently, “Stranger Things”), told me, “It’s almost as if people beginning to get better are like babies in the womb. The fetus doesn’t realize it can drown in all of the fluids. But the womb protects it. Same with comedians and artists. Else we’d all quit in the beginning.”

We’d all fall apart at the beginning if we realized how truly bad we were. But something protects us.

Perhaps love of what we are doing (which is why one should only do something for love).

The best way to market a book is to simply get GREAT. Getting great makes everything else easy.


I watched the movie “8 Mile” and read the book “Influence” by Robert Cialdini on the same day.

While I was watching “8 Mile” I realized, “Eminem, if he knows it or not, is using Cialdini’s EXACT same techniques and cognitive biases to win his rap battle.”

I loved 8 Mile. I loved Cialdini’s book (he came on my podcast).

So I wrote the article: “How to Get an MBA from Eminem”.

It’s one of my most popular posts ever.

I love the rooftop concert of The Beatles. I wrote about it. It’s one of my favorite posts ever.

When I realized, what it took for me to bounce back from suicidal depression to potential success I wrote “How to be the Luckiest Person Alive in 4 Easy Steps”. It’s by far my most popular post ever.

I only write about what I love. I only write stories from my life that had an impact on me.

It reminds me of doing standup comedy. I’ve been doing standup comedy 3-6 times a week now for the past year.

Every month I’m 100% better than the month before (I hope).

One of the most recent things I’ve realized is: if I’m having fun, the audience will have fun. They want to join in the fun I am having.

The audience (the readership) is an X-Ray machine. They know when you are having a party. They know when you are nervous. They know when you are afraid of them. They know when you love them.

They will then treat you the way you deserve.

Writing is hard. Typing is boring. The past is dark.

But if you don’t start with love, you’ll never end with beauty.

I’m being honest.

I write to get people to like me. I write because after 25 years, I’m pretty good at it and I use this skill to help me communicate my desires and feelings and needs. I write because I’m insecure. Because I’m afraid.

And because I love it. I love being stopped in the street and someone saying, “You’re writing changed my life. Thank you.” I hope I always love it. We’ll see.

Money can be a side effect of writing (or any art). But you can’t do art just for money.

Once you accept money, you just capped your career and growth.

Nothing wrong with that. Just be aware of it.

The past two years I’ve written fiction, non-fiction, memoir, a children’s book, TV scripts, a comic book, and I’ve helped many other people with their writing.

I hope I never stop. But I never predict the future.

I love it.

Thank you for reading.

I love you.

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