How Can I Be As Unhappy As Possible?

I was happy when I sold my first company and made money. I was happy when I met my first wife.

I loved her and on that first kiss I remember how much she was shaking because she was nervous and so was I.

She wouldn’t kiss me until date 5. “Too fast,” she said. When I made my move on date 3.

But I was unhappy when I lost all the money I made on the first company. I was unhappy when I got separated, ten years after that first kiss.

Tom Shadyac, the director of billions of dollars worth of movies, had a bike accident and injured his brain. His head hurt him so much for a year he could barely move.

When he started to get active again, he gave away most of his money and moved into a trailer park (albeit a nice one…but still).

I called him up to ask him what happened. He was nice enough to tell me.

He said, “The word happy comes from the word ‘happenstance’. Which means ‘something outside of yourself’.”

He said, “I wanted my happiness to come from something inside of myself. Nothing outside was going to make me happy.”

It was around then I made some conscious decisions in my own life. I had been very unhappy. Unhappy to the point of suicide (I think I am second or third result on Google if you search “I want to die”).

Unhappy to the point of waking up every night at three in the morning and wandering the streets and writing on notes that I couldn’t read in the morning.

Unhappy to the point of wondering how was it even possible some people had enough muscles in their mouth to smile.

Mostly because I was always stressed about money. I thought if I had no money then I would disappear. And I was always anxious about people I was dealing with.

Why would they treat me this way? I’d run conversations over and over and over in my head. A horror cinema on repeat.

Some people are not such nice people but you feel you have to deal with them for various reasons. Maybe because of money reasons or maybe out of fear of some sort. Or maybe because you are a good person.

Focusing on life happiness is too hard. That is the key to unhappiness.

I just focus on “am I feeling well-being today?”


(Related: How to Be THE LUCKIEST GUY ON THE PLANET In 4 Easy Steps)


The more competent I am at the things I do, the better I feel about what I am doing here on this planet.

It doesn’t mean I have a purpose. My purpose can change every day.

I just want to get more competent at something. Anything. What my ‘purpose’ will be a month from now, a year from now, whenever, is a total mystery. There is no real purpose.

Competence simply means I am improving at something. Maybe being a better writer. Or businessperson. Or friend. Or idea person. Or parent. Or whatever.

Picture that for yourself right now. Doesn’t it feel a little good? Right in the chest.


I had a girlfriend once who kept saying, “How come you never introduce me to your friends!” And I would try to say, “But I did!”

I don’t have many friends. But that’s OK. The people I am friends with I am very good friends with. I’d do anything for them.

And I do things for them every day. I am constantly trying to think of how to improve my relationships with the people I love (friends, children, even business relationships).

And although I don’t want to be selfish, I also have to make sure I spend more time with people I love, than people who are not so good for me.

One time someone said to me, “I have all these great ideas. But on Friday night I hang out with my friends and they laugh at me.”

I said, “Stay home on Friday night.” I never heard from him again.

This is perhaps the most important thing in my life.


People think money is freedom. This is not true. But it’s a cliche to say that.

Money is pretty good. But only if you use it very little (in my opinion – not necessarily anyone else’s).

Last April I threw out everything in my life except three outfits, a computer, an iPad, and a phone. And two bags to carry them in. I live in Airbnbs that are furnished.

I am living in one right now on Prince street. Stop by and say “hi.”

I am able to do this because I make money thanks to my competence and relationships, built up over 25 years. I work hard.

But in general I always kept my belongings to a minimum, except (looking back) when I was most unhappy.

This is what freedom is: throughout a day we get to make 1000s of choices.

The more choices I can make for myself, the more freedom I have.

The more choices other people make for me, the less freedom I have.

A corporation might make a choice for me. Or a government. Or a parent. Or a boss. Or a colleague. Or someone manipulating you. And so on.

Nobody is 100% free of outside choices. That’s impossible. I don’t look at what % I am at. I just look at direction.

Every day I want to make more choices for me, and follow less the choices of others.

If I’m not choosing myself than someone else is and the results won’t be good for me.

How do I make sure I am constantly able to improve competence, relationships, freedom:

Purpose is BS. Purpose is simply a byproduct of your own well-being.

But to make sure I am always moving forward in well-being I have to make sure I am physically healthy, surround myself with good, decent people, creative every day, grateful every day.

Bad things happen ALL of the time. The world is out of our control.

But I’ve slowly noticed that I bounce back faster. That failures become learning opportunities.

That people are basically damaged but good. That our lives are made up of stories and so creativity is the child of every moment. That a shaken kiss can sometimes melt into love.

Related post: The One Formula For Happiness Nobody Told Me

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