How To Start Over At 40


At 40 I lost my wife, my home, and my job. And many of my friends.

And I was ashamed. I didn’t want to tell people my wife had left. I didn’t want to tell people my home was for sale. And the website I had been writing for for seven years, had bought a company I had started, had won over my loyalty for what I thought was forever, was now blocking me from their system.

And I was going broke. Again.

I feel like when I write this it’s like I’m writing the same newspaper twice. In one form or other I’ve written this many times. I’m almost embarrassed to write it yet again.


People tell me, “This is a typical James blog post: I lost everything, I thought about killing myself, and then I did A, B, and C to make it back….and then I lost everything again.” And then I conclude with, “I am still alive”.

(Life is never too busy to “play”). Every day.

When I turned 40, a friend of mine threw me a party. My wife wasn’t there. My daughters weren’t there. My friends weren’t there.

Just the one friend who “threw” the party. He invited all his friends and his girlfriend. They all celebrated the BIG 40 for me.

I didn’t know any of them at all. I barely spoke all night. I paid the bill.

A year later I had nothing left. And even that friend who threw the party conveniently forgot I had lent him money when he was broke and he disappeared.

Like people do.

I was so sad all the time. I thought to myself, “How could this be happening at 40?”

When I was 30 I had a great company, great family, great wife, tons of friends, and I was creative all the time.

My company was soaring and when I was 30 we sold it for a lot. I thought I had it all figured out.

I thought my “job” of growing as a human was all over. That now I can just stop improving my life and just enjoy it.

I had no clue. The second I began to think that way began the long, horrible decade of realizing that improvement never stops.

STOPPING IMPROVEMENT is death. There is no goal. There is no final destination. There is only direction.

Live life by themes and a set of values. A code.

19 years after I turned 30, this is my code:

  • Honesty
  • Creativity
  • Responsibility (Certainty), mixed with
  • Mystery (exploration)
  • Emotional connection. Be good to people and love the people close to me.
  • Significance. Always try to do things that can help people.
  • Energy. Whether it’s health, or integrity, or spirituality, do the things that will give me energy to do all of the above.

Money is not on this list. Career is not on this list. Fame is not on this list.

When I was 41 there was a moment when I was day trading and I lost a ton of money.

I called my new wife into the room. “I can’t take it,” I said. I don’t like my life.

We took a walk. I lived right on the banks of the Hudson River. We found a path and a trail and walked along it. Eventually we came to this beach through the woods.

I emptied my pockets. Keys, phones, money, debit cards.

I went into the water. I went underwater and just stayed there. Floating with all my clothes on. I didn’t want to go. The sun was setting. I felt the water become colder.

Eventually, she called me to come back on shore.

I did.

The next day I started blogging about my personal issues. About everything I had done wrong in the prior twenty years. Particularly what I did wrong in my 30s.

Did I write about everything? No. Not yet. But I wrote about many things.

Losing money. Losing friends. Losing my feeling that I wanted to live. Being depressed for years.

Even at age 40, having no sense of where my life was. Not even realizing that I needed to find out.

I felt I needed money first. I was so scared about money and what people thought about me that I didn’t even want to consider what my “real” code was. The values that I wanted to live by.

I’ve been writing every day about my stories since then. And those stories have given me so many opportunities that it changed my life into what it is today and I am so grateful.

It turns out that having that code comes first. And then all life is a side effect of that.

A code to live by, values to stand by, creativity to fuel my heart’s desires…this is what goes into a good life.

And then the output is stronger relationships, stronger possibilities, more certainty, more creativity, and eventually success.

Every year is hard. Life is hard. No year is easy. No business is easy. No relationship is easy.

This past year is one of my hardest ever in relationships and in business.

But I’m more creative than ever. And I live by my code described above. So now things get solved faster than when I was 40. Faster than when I was 30. Faster than when I was 20.

A child laughs on average…300 times a day.

An adult on average…5 times a day.

I’m up to about 50 times a day. Maybe more.

Every day we have about 10,000 choices to make. Small and big. My goal each day is that more and more of my choices are made because I WANT them. Not because someone else wants me to make those choices.

That is how I laugh more. That’s how I enjoy more. That’s how 40 was just a starting point for me. That’s why even today is a starting point for me. I am so looking forward to the rest of my day.

I’m going to do a podcast with one of my heroes and I’m scared to death of it.

Then I’m going to read to prepare for more podcasts. Then tonight I’m going to try standup comedy and I am terrified. I’ve been going over my jokes all morning.

The other day a friend of mine, a great artist and photographer, passed away in his sleep. I’ve known him for 22 years and we worked together for three of those in some of the most creative years of my life.

He was younger than me, but had AIDS and maybe his death was related to that.

I remember when we worked together on a project. He took a beautiful photo of a transvestite prostitute working in the meat packing district.

He captured her sadness, her despair at her life situation, the lights barely highlighting her surgical beauty, her shadow looming large behind her.

He is dead. I am still alive.