Are You a Wanderer?

It started when I lost millions of dollars in a day. It ended when my marriage ended.

This year. What an f-ed up year.

I was lost. I was gone. I was destroyed. It was the best year of my life.

First, in February, I lost an enormous amount of money and then got sued. Then my marriage ended. And all in between bad stuff happened.

In a lot of ways, I had to start all over. Just like in 1994. In 2000. In 2004. In 2008. 2010. And 2012. I wasn’t broke. But starting over is not about money.

It’s about finally saying, once again, “Ok, I have to make sure I’m doing my X, Y, and Z.” It’s about following my own advice.

I was ready. I had been through it before. I know the stages I go through every time.

I had to wander again.


Something is off. Something cracked.

The first time I left a job I loved, I was so depressed I couldn’t get out of bed.

So I knew I had to quit. Something was broken inside of me. I quit, I went to start a business, my life changed forever.

I think it’s important to recognize that restlessness. To give permission for it. To even welcome it.

The Search

What the hell do I do now?

The search begins. It’s scary and confusing.

If a relationship ends…will anyone love me again? When I lose a job…will I ever make money again. When I lose all my money…will I go broke and kill myself?

I kept cutting out all the “extra” in my life.

Bad friends, bad people (who are contagious and viral), bad jobs, bad investments. All my belongings and addresses and homes. I cleaned up.

Was ready for the search. Was ready to wander.


Some things won’t work.

Last February, when a company I was on the board of told me they were falling apart I tried everything I could do to save them.

But it didn’t work. Thousands lost jobs. Many lost a lot of money. There was nothing I could do.

I started a novel in early November. But life got in the way. My life turned upside down. I had to stop.

No matter what your routine: a daily practice, a miracle morning, a lot of money, love, family, fun – life happens.

90% of happiness comes from choice, only 10% comes from circumstance.

The wanderer surrenders to the 90%, not the 10%.


People say, “time is money.”

What a pitiful way to look at time.

I took advantage of a friend of mine recently. I’m sorry. She was going to charge me to do some illustrations.

I said, “Ok, tell me what you will charge.”

She sent me a number. I could see what she did. She came up with an hourly rate and figured out how many hours it would take and added it together.

She didn’t have enough confidence in herself.

I agreed and I wired her the money.

Then I told her the truth. I told her she forgot to charge me for the fact that I had chosen her because of her skill. Her creativity. Her brilliance.

I can get “hours” from anyone. I can only get her creativity from her.

She should have charged me a premium for the 13 years of effort she had put into becoming the best in her industry.

She looked down and said, “damn, I didn’t think of that.” I wasn’t going to adjust it either. Next project.

Not that I was such a great teacher here.

I was happy to pay less than I thought she deserved. But I am happy knowing there will be more projects. And I trust who I am. I know things will work out.


When I first lean in to kiss the girl, I’m terrified. 99% of the time I’ve been rejected.

When I start a job, I know it’s going to end in blood. When I start a book, only a 10% chance it will get finished.

Is it the correct decision? It’s so hard to know.

When I started my first company, I gave up all hopes of doing a TV show. Something I had put 100 hours a week into.

When I first got married, I bought the engagement ring and I went to a bar.

I thought to myself, looking at the ring over a drink, I can give this ring to anyone. But I’m about to give it to my soon-to-be wife. Would it be a mistake?

Two daughters and one divorce later, I am so very happy I gave the ring to her. But I think I had a panic attack and died that night.

Every decision is packaged with anxiety. Else your ancestors would have been eaten by lions. Complacency killed the cavemen who had no children.

The key is to make today’s anxiety work for you. And then say goodbye.


Eventually it’s all over. It didn’t work. I got divorced. I lost the job. I lost my money. I make it back.

Every year, no matter what is going on in your life, no matter how “great” you are, bad things will happen. These things don’t make you a wanderer. How you deal with them makes you a wanderer.

Most recently, I gave away everything I owned. When the bank asks for address now I have to give a fake address because I have none.

I’m in California right now. For the next few days, I live here. Then I will live somewhere else.

I’m not starting from scratch. But in my mind every day starts at zero. I’m doing an experiment. I’m surrendering to the moment.


In the latest catastrophe that happened to me, the first thing I did was call five people.

One person gave me a place to live. I didn’t need it. I could’ve gotten my own place.

Don’t worry about it. Here are the keys. Stay as long as you want. You need to be around people.

The second person I called checked in with me every hour on the hour to make sure I was ok. She invited me to be with her friends. To spend time with me. To cheer me up.

The third person I called kept checking in to make sure I was following my daily practice. “Tell me,” and he would count one finger at a time: “Physical. Emotional. Mental. Spiritual.”

The fourth person I called told me he would make sure all my business stuff would keep going as exactly as planned.

And so on.

You don’t seek out mentors. You spend decades building good will with people. Then there is pent up demand of people who want to do good will towards you.

How do you do good will towards people? Start being kind to them. Start coming up with ideas for them. Ten ideas a day.

Start introducing them to others. Start giving constructive advice on their projects.

Offer them a place to live. Offer them a place to rest their hat emotionally, or creatively.

Do it for a year. Do it for 10 years. 20 years. And see what happens.

These become your most valuable mentors. Just like you were for them.


Eventually reinvention kicks in.

You’ve done the search. You’ve had the restlessness. You’ve had the teachers. You’ve had the feedback of what’s wrong or right.

You’ve put in your practice. You’ve rebuilt your energy. You are healthy again. You’ve dealt with the anxiety.

You look out one day and the light is coming through your room and you suddenly have an idea you want to try.

Nobody has ever done it before.

You wrote 10 ideas a day for 20 years to finally come up with something nobody has done before.

I’m excited right now about three or four projects I have. A few months ago I had lost that excitement. Now I’m ready.

The Source

Eventually, you connect with the source again. You are physically healthy, emotionally connecting with people, creative every day, grateful every day for the the magic around you.

You have chosen yourself. You are working on your ideas. They are helping people. They are giving and others are receiving.

You are a still just a drop in the ocean. But it doesn’t matter.

The single drop that is you begins to ripple.

The ripples go out to every shore.

Your search has led you to help the entire world, even in a microcosmic way.

Every day the search begins anew.

But every day I want to be that drop of water. To drift. To float. To bathe in the sun.

Knowing that once again, a storm will come. I will know how to survive it.

A friend told me, “don’t live life like you are going to die tomorrow, live life like you are going to die in a year.”

Ok then. This is the year I’m going to wander.

Share This Post

Other posts you might be interested in: