I was very lonely when I first moved to New York. It’s this totally strange thing because you’re constantly surrounded by people but you feel like you can’t talk to them. Everyone is busy busy busy.

It makes you even more lonely. I would see a pretty face, or an interesting look, or even someone I just wanted to be friends with, and they would be three feet from me, two feet from me, sometimes even touching me (subway, jostling at a corner, in line for a coffee) but there was no way to really reach out and…touch.

Making me even feel more loneliness. The loneliness would punch me in the chest and often I would gasp for the air to live.

One time I went into a bar. I watched a band play and sat really close and watched the singer. She came over and sat down next to me when they were finished.

I wanted to say something cool. Something that would make me fit in. She asked me what I did for a living.

I said I was unemployed. Which was a lie. I worked at HBO. But I thought that saying I was unemployed would make me cooler. I didn’t know how to shake off the masks attaching themselves to me and just be myself.

Literally shake.

When you shake it’s like you put your body in danger. So your brain turns off for a second. It’s actually easier to be yourself then.

But I didn’t do that. And…and this is particular to New York…the second I said I was unemployed the woman turned away and walked off.

Chimpanzees meet their romantic prospects by helping each other groom. If I take the flies off of your back then maybe you will mate with me.

But I didn’t know how to do that then. I’m a little better now. I can pick flies off of people.

A few years later I was very lonely again. I had just lost $15 million and I was about to go bankrupt and lose my house.

I had lost all my friends and most of my family wouldn’t speak to me. I had lost all my jobs and chances at a career. I had no opportunities. Nothing was going for me and nobody to talk to about it.

I would sit all night when my mind was going completely insane with fear and anxiety.

When the sun began to peek out, nothing more than a slight bruise splattered across the morning sky, I’d start walking around the city. I’d completely circle downtown New York, looking for relief, looking for hope, looking for a friend. But finding nothing.

A few years after that I was lonely again. The worst loneliness. I was broke again. Lying in a hammock. It was raining. I was going to get a divorce. I once again had been fired. I once again had little to no friends. I once again had no prospects or anything to hope for.

When you have nobody to talk to and no imaginary castle in your mind to hope for, then loneliness erupts like a volcano. It starts in your chest, spreads to your brain, and every other part of your body until you can’t walk or move.

Do you know what I mean by that?

I moved back to the city, where I would stare out my window, unable to move or respond to anything.

I was too ashamed of my condition to tell anyone I knew. Which probably meant that all the people I knew were not real friends.

Eventually I wanted to do something: I foolishly wanted to be a standup comic.

I would go to open mic nights but I was too afraid to go up. I was usually the only one in the audience who wasn’t performing. I wanted to be friends with the performers but I was too afraid to open my mouth.

This is after all those businesses started. After making websites with millions of users. After interviewing thousands of people for HBO. After making and losing millions several times over. I still couldn’t talk to the people right in front of me that I so desperately wanted to be friends with.

Such a difficult bridge to cross for someone who is shy. I was shy in front of three people but not in front of three million people.

Afterwards I would go out and eat waffles for dinner along with about ten glasses of any sort of alcohol. I’d write down jokes and call a guy I knew who was a sitcom writer in California and ask him if he thought which ones were funny and which weren’t. He’d say, “That one has potential.” Or “I don’t get it.”

Then I’d drink enough to go to sleep and when I’d wake up the room would be spinning, even on the days when my kids were going to visit.

One time the sitcom guy from California visited and we played ping pong and talked for an afternoon. I had a friend and it was fun.

Then I made another friend that I would take long walks with late into the night. And I started working on different ideas. All of those ideas failed but at the time I didn’t know that. At least they gave me a chance to move my brain a little.

Loneliness is a bottomless pit. It’s solitary confinement in the brain. Here’s what I will do the next time I am seized with the sickness of loneliness.

• Call a friend I haven’t spoken to in years.
• Ask a random person to go to coffee with me. This is hard and takes practice but this skill will save your life. So practice it. Today ask someone for coffee. It works.
• Invite a bunch of people out to a dinner and introduce them to each other. Call it a “networking dinner,” but for you it’s really an anti-loneliness dinner.

• Don’t ever forget the people you are grateful for. @jaltucher (Click to Tweet!)

  Write to them and tell them why. I promise you they will write back. They will be grateful to know they had an impact on someone.

• Don’t be afraid to talk to the people who share your interests. Be vulnerable. I wish I had done that. Just go up and say, “That’s really good” to them. You can practice this by walking in the street and complimenting people on their clothes.
• I’d go to some sort of twelve step meeting. Everyone there wants a friend.
• Use an online dating site in a way that it was not intended to be used: write to interesting people and say, “Hey, I don’t want to date or anything but I’m putting together a dinner of three or four people who have interesting profiles and would like to invite you.”

When I first moved to New York I started hanging around the SW corner of Washington Sq Park, where all the chessplayers were. Most of them were the worst addict scumbags.

They would play chess all day, gambling, trying to hustle you, and then sleep in their respective homeless shelters until the next day, when the hustling would begin again.

Everyone would call each other names. They would laugh at you. They would try to cheat if given the chance. They would hit you and argue if they started losing too much and they could NEVER afford to lose too much.

I moved in with one of them for awhile. We’d play chess all night. Then go back to the park during the day for another round of cheating, hustling, insulting, and mutual humiliation.

But they were my first friends in NY. And twenty years later still are.

James Altucher has built and sold several companies, and failed at dozens more. He’s written twelve books, and The Power of No is the book to RULE THEM ALL. (Although he is also fond of Choose Yourself.) He’s an investor in twenty different companies. He writes every day. He doesn’t have enough friends. Still interested in knowing him? Follow him on Facebook and Twitter.

 Image courtesy of Michael Korchia.