A friend of mine left his corporate job yesterday after 23 years of being trapped in the Matrix. I hate it because I’m envious of that moment.

The day I left a corporate job to be on my own for the first time. Suddenly you go from managing a cubicle from the hours of 9 to 5 to having to manage ALL OF TIME AND SPACE. The holograph screens that altered the universe around you peel away to show you what the real world looks like. The extra colors and intensity that had been hidden from you behind tinted-black glass windows and fluorescent lights.

I wish I had done it differently. I wish I had known what I know now.

I was working at HBO. I had a cubicle on the 6th Floor of 1100 Sixth Avenue. My boss was down the hall. His boss was in the room next to his. His boss was in the room next to that. And the real boss (the top guy’s secretary) was in front of all of their offices. I had a view of the McDonalds at Sixth Avenue which is now the big Bank of America building.

Work in the corporate world is like a hazy drug dream to me now. You could get in at 10am. Everyone took breaks downstairs to smoke. I didn’t smoke so I took licorice with me. Then at noon, LUNCH! And then after lunch, chess in Bryant Park. Then my boss left to catch his train at 4:15. So I would leave at 4:16. Before I had my own business on the side I’d take the subway to Astoria and go to Steinway Billiards. Everyone there was Greek. We’d all sit and play backgammon and chess and drink thick Greek coffee until about two in the morning. Sometimes my friends from HBO would come with me and it would be like a party every night. And I loved all the girls in the place but not a single one ever talked to me or looked at me no matter how many two dollar bills I tipped with.

There were goals and deadlines at work. Except for the summer. There was never anything to do in the summer. And all other times the deadlines were mild. Like if you missed one then it just meant a meeting was rescheduled.

Nobody would get fired. The saying was, “if you want to get fired you have to stand on Albie’s desk and pee on him.” That was the boss’s boss’s boss.

As part of my job I got to go to San Francisco for the first time, Los Angeles, and sunny Orlando (to make the website for the series “From the Earth to the Moon” which was shot right in Disneyworld.)

And then I quit.

I had to. I was running a business on the side. We had clients, some of whom were even competitors to HBO. We had employees. I had payroll to meet. And I felt myself stagnating at my job.

I couldn’t get out of bed in the morning. I stopped enjoying the meager things I was doing. And I thought I could handle the psychology of being on my own. What could be different, I thought. I wanted to spread my wings even though I had no idea how to fly.

I cried twice the first day on my own.

First time, at lunch with one of my partners, Randy. It suddenly hit me that I didn’t have a multi billion media empire as my backstop. I was on my own. I felt alone. Which is another way of saying, if I fucked up I had nobody to blame. Like we all did in corporate America. So over pizza I cried. “Are you ok?” Randy said. Poking at my weakness. “Yeah,” I said.

Then later at dinner with all my ex-employees and friends at HBO. I ordered pasta AND fries. Everyone started to laugh at what I had ordered and I wasn’t sure why. That made me cry again but nobody noticed. I felt like a four year old in a room filled with laughing adults. I had no idea what I was or what I was supposed to be.

I had been anchored close to shore with Time Warner as the dock. Now I was in deep waters. Too deep to anchor. I had to fish now. I had to find food. I had to get water. I had to feed a lot of people. I had to kill or be killed. I learned a lot in the next few months:

A) It was always my fault when things went wrong. If you blame others, you go out of business. Take responsibility for your problems and fix them or move on.

B) I had to communicate to people. If you hide from customers, they will fire you. If you hide from employees they lose respect for you. If you hide from investors, they sue you.

C) I had to help employees feel good about their jobs. I had to help customers feel their jobs were about to get a lot easier because now I was in their lives. I had to learn to reward people. I wanted everyone around me to feel good about it. To spread the word that I was someone to work with, to be around.

D) Every idea was fair game. We were a web design company but we considered being a tea company, a rap label, a magazine, a TV show, a cable channel, and a social network for dead people. A porn site. A software company. An ad agency. And a dozen other things. We just wanted to make money. We were in the business of business.

E) People steal. I was robbed by customers, by employees, by friends, by partners, and twice by random criminals including one guy who just walked into our office and started unscrewing lightbulbs until he was chased out.

F) I had to educate. You demonstrate credibility when you teach your employees and when you teach your customers. Where do you get your knowledge? You have to get to the destination before everyone else. You have to read everything. You have to have spies. An important side effect of educating people is that you build presence, you build charisma, you exude confidence that is earned.

G) I had to learn when the day ended. The candles are always lit in the modern age. The day never has to end. But if it doesn’t, you lose track of the map and find yourself adrift with no horizon in any direction.

H) I had to forgive myself. When you run things, 50% of your decisions will still be bad. Good opportunities sometimes spring from bad decisions. But you have to forgive yourself first as the first process in learning from your mistakes.

I) I had to make tough decisions. I couldn’t complain to my boss. I had to fire people. Fire customers. Make decisions that might be right or wrong about people. Making decisions is directly correlated to building your idea muscle until you are an idea machine.

J) I had to network. I never had to do that before. I would hire people specifically to help me network because I was so bad at it but I got better. Your value goes up exponentially depending on the number of people in your network. Keith Ferrazzi hits the nail on the head in his book “Never Eat Alone”. You need to not only consciously arrange to meet people but also put yourself in many situations where you are going to randomly collide with people. My most random collisions often made me the most money.

K) I had to sell the company. When web design was being taught in junior high school classes I knew that 3 page websites being built for $75,000 was going to be a thing of the past. Knowing when to sell is just as important as knowing when to start a business. Selling a business gives you the greatest gift of all – freedom to start another business.

Most importantly, I had to build a discipline of every day, every hour, seeking out opportunities. Either opportunities for the business, or even for myself. My own improvement became vital to the improvement of the business, to my customers, and to employees. I cried the first day, and many many days after that. And looking back, I can’t really tell you if it was worth it or not. Who really knows? So many things have worked out and so many things have failed. Maybe I’m mediocre as an entrepreneur, best case.

But I do feel like I’ve escaped the Matrix of corporate slavery that first day. Eventually I realized that there was yet another matrix outside of that matrix. Like Russian nesting dolls, each matrix is a creation of the matrix outside of it. On and on, forever. Each day another escape but only if I’m brave enough.