Dear James at 106: I Hope You Can Read This

Although you probably won’t care. Why would you care what I have to say?

Hi James, you’re 106 years old. Congrats! Boy, I never thought you would get there. You were too stressed. It’s not like you’re an athlete or anything.

I’m writing you this letter but you don’t even give a shit. You’re 106 years old! I wish you could write me a letter back and tell me how you did it.

Can you? But what advice would you even want to give me. I know you: you TOTALLY don’t care.

I don’t even know if I want to be 106 years old. Like, if I die tomorrow that’s fine with me. Maybe that’s a selfish way to think. I don’t know.

I’m going to be arrogant enough to give you advice on what you should be doing at age 106. Because that’s the kind of punk you were.



You can’t cradle a grudge and love a grudge in the same way as when you were much younger.

Historical is hysterical. A grudge is a hysterical historical. Why would you care?


I hope I have a garden when I’m 106. So I can put things in dirt. And make sure I cover up those things correctly. And then water the dirt. And then clean up.

And then look at what I did. Love dirt.


If you’re 106, maybe it means you’ve stored up a lot of life force.

It must be great to share that with kids. So then they get older with that life force.

Or maybe it’s vice versa. Either way: spend time with kids.


A lot of old people seem angry all the time. I’m going to smile at people in creepy ways.

They won’t even be able to look at me, the light from smile will be too bright.

Either that or they will think I’m a pervert. Either one. I’m ok with it. I’m 106. I’m ok with anything.


The other day Claudia threw out all of our 15 inch plates. She was listening to one of my podcasts. “People who have 15 inch plates eat 30% more calories on average”.

The cause of almost every major illness is how you eat. So I guess eating on 8 inch plates will give you a chance to live to 107. Or three inch plates. I’ll switch to three inch plates.


I wish I had more friends. How many people can I call right this second and make some jokes with.

Do you think I can have a friend at 106 that I can call and talk to and laugh with. I hope so.

I want to be able to call a friend and just be silent on the phone while we do our thing.


Amy Schumer put out a video yesterday that’s a fake rap video with girls “twerking” and a fake rap song about the object of fascination being a “poop machine”. I laughed because “poop machine” was funny.

I hope I still laugh at things with the word “poop” in it.


My daughter and I got to an event almost two hours early. There was nobody even in the parking lot.

It turns out I had a tennis ball in the trunk. We played catch for an hour and made up all sorts of games around it. She was laughing.

Do you know how hard it is for a father to make his 16 year old girl laugh?

Answer: it’s impossible.

But playing catch did it.

And laughter leads to a longer life. Which means playing leads to a longer life.

I want to play.


Why should I? I’m 106 years old. Beat that!

I can walk around the street naked and the worst they will do is just take me home and tell my great-great grandkids that maybe I need “help”.

But, if they know me, my grandkids will wink and just say, “thanks. We’ll take over from here.”

Take over!


Am I really going to be sentimental about anything at that age. I’m about to die. All sentiments die with me. All my past dies with me.

I don’t need any extra clothes. Or plates. or furniture. Or sheets. Or extra towels. Whenever I need a towel I’ll just hit the 3D printing machine in the bathroom, get the towel, and then put it back in to be reused when I’m done.

Will I need photos? Why waste time looking at the past when I’ll have people I love in my present. If I’m 106 I hope there’s even more people around me that I love than now.


This sounds trite. Everyone says “learn something new every day”. But you would think at 106 I would get tired of learning new things.

Today so far I’ve learned that the exact things that bring creative partnerships together also often end them.

Opposites attract (Jobs and Wozniak, Lennon and McCartney) but often the “opposite” becomes too much to handle and people split apart.

That’s ok. You then meet new opposites. You learn to love many opposites. Elon Musk doesn’t build spaceships. He finds his opposites that do. Then he moves on to the next thing.

At age 106, why should I care? Because it’s fun! Maybe then I’ll put on a Beatles song. Like “Yesterday”.


Claudia might be dead before me. She insists on it actually.

Will I be sad? I’m going to be about to see her. Or not. Either way. Because there’s nothing I can do about it.


Right now I’m involved in maybe too many things. I think about each thing. When I’m 106 I’m not going to think about ANYTHING. Most thinking is really boring and useless.

If I stop writing this for a second, I can hear something I didn’t hear one minute ago because I was so focused on writing: birds singing.

If I just don’t think I bet I can hear more singing. Naked people singing.

Why not?


When I’m 106 years old I think my only advice will be this: don’t predict anything.

My 13 year old daughter told me two days ago she was going to be sick yesterday. “All my friends are sick and I’m not getting any sleep so I know I’ll be sick.”

I told her that second to write it down that she will be sick tomorrow. What happened?

She didn’t get sick. I have yet to meet anyone who can predict the future.

Today I got an email from an economist friend of mine. He told me his predictions were right: we’re experiencing deflation in the economy and we’ll all be ruined.

So I pulled up his email from exactly one year ago today. He was predicting “spiraling inflation” that would “ruin the economy.”

I sent him his email from last year. Waiting for a response still. He won’t respond to me because I know deep down he doesn’t like me. Because people in their 40s don’t like people a lot of the time.


Bad things happen. And we get scared and sad about them. And then they turn out to be good things.

One time, a guy who had funded me to run a hedge fund pulled all the money away from me. He was very angry.

He said, “I don’t care if you make or lose money for me. I care that you didn’t return my calls.”

We didn’t talk for five years after that. I felt very bad. I would avoid walking on his corner in NYC because maybe I would run into him. I was ashamed.

Now, eight years later, we talk almost every day and we do a lot of business together.

The only way things stay bad is if you clutch to your heart the “badness” of the experience. An experience is only “bad” if you label it that way.

It’s all your choice.

If you let go of that bad feeling, then you invite in good things to replace it.

That sounds simplistic. But, hey, you can’t live to 106 if life is complicated.

Where does money lie into all of this. Well, if you’re 106 you don’t need to worry about money. You’re going to probably die quickly.

But what about when you’re younger? Don’t you need to worry about money?

Yes. But only if you don’t do the things I describe above.

You don’t have to believe me on this. I only know this is true for me.

I can only do one thing in my brain at a time: either worry about money, or do something else. The “something else” is more likely to make me money than worrying about money.

So play, laugh, learn, love, be simplistic, listen to a bird, don’t own anything, don’t give a shit, no grudges, don’t predict anything, don’t assume something is bad, call a friend, and be excited about what is on your plate today (your three inch plate).

Dear James at 106, I hope you are doing all of these things.

Because these are the things I intend to do today.

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