The Amazing Power of Roots

After divorce, I moved back into the Chelsea Hotel. This was ten years ago.

Robert was behind the desk in 2007. Robert was behind the desk in 1995 when I had originally moved in.

I hadn’t seen him since I moved out in 1998, about three months after I had been married. Which already tells you where I was heading: right back here.

In 2007, I walked in with my one bag. Robert barely looked up.

“You again,” he said. His first words to me in ten years. And then he checked me into a room.

I was home.


The Chelsea Hotel had bad art all over the walls. Sometimes struggling artists would pay the rent in art. You never know!

Sometimes other people paid in... other ways. But I paid with cash each time.

The first time I moved in was in 1995. I had done my first website for money. It still exists: diamondcutters.com.

Shlomo, the owner of the diamond company, paid me with a paper bag filled to the rim with cash. He’s dead now. Died in a plane crash looking for diamonds in Russia.

Shlomo had a secretary with a wine-colored scar, blotting out the landscape of her cheek.

I loved her. I wanted to lick the scar right off of her cheek.

I took the bag of cash and went to The Chelsea Hotel and waited in the lobby for hours for Stanley Bard, the owner to show up.

“What are you? A drug dealer?” he asked me. But he took the money and got me a room.


Back in the hotel again a decade later. I was scared of my life. I figured I would kill myself in six months if things didn't get better.

I was getting to know a woman. Stephanie. We had been to dinner a few times. She was a psychiatrist. I was always afraid she would discover my secret and think (know!) I was crazy.

She came over and we watched a movie. Superbad. She thought the room was disgusting. "How can you live here?" she said.

The hotel had used condoms on the staircases (I had to hide the eyes of my kids once when walking down the stairs).

There was every type of addict living in every other room. Plus a few tourists. I was somewhere in the middle. Never feeling comfortable with anyone.

When the Chelsea Hotel opened in 1884 it was either the largest hotel in the world or one of the largest buildings. I forget which record it broke. It broke a lot of records.

My apartment was missing the door to the bathroom. And all the furniture was really old and probably dirty. I didn’t care. I loved it.

In the mornings I would wake up, feeling both miserable and lonely and lucky at the same time.

I was home, even if I felt too much depression to move in the morning. Why does the sun come through the window? Who asked it?

Stephanie left after the movie. The next day she called me. She had been to her psychiatrist.

She said, “My psychiatrist thinks we shouldn’t date,” she said. “She says because you live in a hotel room that you have no real roots. You have to get rooted.”

“I didn’t know psychiatrists see psychiatrists,” I said. I imagined an infinite ladder of psychiatrists that would filter guidance down to the people who simply know they are ashamed and have nobody to talk to.

“You need to get roots. You need to get a real place.”

This is real, I said. This is where I'm from.

No it isn't, she said.

“What if I live in the building across from yours?”

“Too close. That’s too fast.”

“What if I live downtown,” I said, “Near where I have some friends.”

“Too far,” she said. “I don’t feel like going 45 minutes back and forth every time I see you.”

This makes it seem like she was high maintenance. I don't know. She seemed like an adult and I felt like a little boy.

One time we were on a date and we had a conversation and it made me unhappy and it ended with me crying and her leaving. Or, at least, I didn’t call her back or contact her ever again.

A few weeks later she sent me an email. “What happened? I cancelled all my dating site memberships because of you.”

I just checked her Facebook page. I guess some time in the past ten years she blocked me.


From 2015 to 2017 I lived in Airbnbs. I had no address. I could move in one second’s notice since I never unpacked and lived with just 2-3 outfits and a computer out of one carry on bag.

I guess I had no roots. Nothing seemed to work for me. I just moved from place to place.

During this time I discovered I had friends. After all these books and articles and podcasts, some people wanted to be my friend.

The NY Times wrote about me. A TV company wanted to do a sitcom about me. A reality TV company wanted to do a reality show.

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Everyone said, “I would love to live that sort of life.” People said I was a minimalist but I think I was just lazy. And a voyeur.

I liked looking at everyone’s life. The people who gave me their houses.

This one liked toy planes. This other one had three pianos. This one was an artist who painted nude little boys.

Another one was under indictment for something. Once the police were banging on the door. He was texting me at the same time: “Don’t let them in!”

Another one was in charge of the central bank of a major country. I think Australia or New Zealand. From her place I could see directly into David Bowie's apartment. My favorite of favorites.

Then he died and I left a something at his something.


I was in one floor. Two floor. Three floors. I had pools, views, and sometimes nothing. I lived all over the country in Airbnbs. Every owner wanted to please me because I was THE Airbnb guy.

Everyone had a story. I could only figure out bits and pieces of the story.

About two months ago I moved into a new place. Not an Airbnb. MY place. For the first time in my life I moved into a place by myself and bought furniture.

I felt I had to move. I felt I needed to move to stop moving.

I loved the building.

It’s like an old man’s Chelsea Hotel. Many artists have lived here. Cyndi Lauper. Nora Ephron.

My neighbor is the daughter of one of my favorite authors of all time. He's dead now but he lived in that apartment. I re-read his book twice.

The real estate agent was disgusted with me, “I can show you better apartments.”

Another guy said, “You won’t get your money's worth there.”

I didn’t care.

I wanted to rent this building. My real estate agent said, "the board will never approve you. You never had a credit card. You have no credit score."

I gave 13 months in advance.

"I have never seen them approve someone so fast," the real estate agent said.

I moved in. I didn't even look anywhere else. I KNEW this was the building.

A friend picked out all the furniture. “Keep it very minimalist,” and only blacks and whites and some blues.

I still had only a few outfits so most of the closets are still empty.

But I bought books again.

The books I always loved. It’s like they leapt out of my computer and onto a bookshelf. I love to feel the pages. I want to bathe in a bathtub of books.

And I had friends over. In fact, I had friends. Friends!

I felt good. One morning I woke up and I felt this huge wave of stabilization sweep over me. Like this was home.

Like I was a tree with roots deep into the ground. I felt strong.

Now if I want anyone to enter into my life, they now have to be GOOD enough to enter into my home. My life was gated by my home. By the ghosts and angels that moved in with me and protected me.

I realized the ways I had been always pandering to others. Trying to get people to like me. And I'm the guy who WROTE "Choose Yourself".

Now I could just go home if I got scared outside. I had a home. Even if I was "just" renting.

I re-read my own book. I learn every time I read it. I wrote the book because I needed it. Not because I was an expert. But because I'm always the student.

I still felt like a minimalist.

A minimalist of worries and anxiety. Even of desires. Because desires and moments of happiness are just as addictive as despair.

I was a minimalist of what it would take me to feel well-being. .

I’d like to say my life got better.

That suddenly a gray fog lifted up above me for the first time and everything was clear: who I should be with, what will make me happy, what will make me free and powerful, and what won’t.

I’d like to be able to say this.

So I will.

The Journey towards Personal Freedom Starts with YOU

It's time to make the most important decision of your life: Choose Yourself.

I will show you how...

Every weekday I'll send my latest stories, ideas and exclusive interviews straight to your inbox.

Sign up below for Altucher Confidential, my FREE e-letter.

By submitting your email address, you will receive a free subscription to Altucher Confidential. This daily investment newsletter delivers free independent financial forecasting and commentary along with carefully selected products and services that we think might interest you. We will not share your email address and you can unsubscribe at any time. Privacy Statement.