7 Lessons I Learned in My 20's…


When I was in my 20s often people didn’t respect me or give a shit about anything I said or did.

And now that I’m 50, often people treat me with even less respect if I say something that doesn’t fit their world view.

But it doesn’t matter whether someone hates me or likes me – I treat them with dignity.

Dignity shows who you are. Respect only shows who they are.


You have control over who you are. Always. Reminding yourself to treat EVERYONE with dignity is a powerful way to build self-awareness.

One act of dignity is like throwing a pebble into the middle of the ocean. The waves will burst out and eventually hit all shores.

Dignity compounds. The more you do it, the more you will see later the powerful effect it will have on every area of your life: romance, wealth, friendship, freedom.




Always be creating value. I tell my daughters to ask themselves at the end of each day, “Who did you help today?”

If they help someone, then I respect them.

If they do something just for the attention – then I don’t care. Attention is fleeting. Helping people is what builds legacy.

If the people you trust and honor respect you, then your life will be good.

A friend of mine was describing an experience he had with an Instagrammer who has 25 million followers. Instagram is all this guy is known for.

“I invited him to a charity event,” my friend said, “and all he wanted to do when he landed was get coke and hook up with transvestites and get into fights.”

This Instagram genius had a lot of attention but as my friend told me, “he is by far the WORST person I have ever met.”

Attention adds up to nothing. Respect from the right people adds up to everything.



There’s a lot of books and advice out there that says, “Invest in yourself”.

This is mostly bullshit.

What does “Invest in yourself” mean? It could mean self-improvement or building a skill that can make you money. Maybe you start a business. I don’t know.

This is ok advice but it only works if, like in all investing, you diversify.

Scott Adams, creator of the cartoon “Dilbert”, explained it best to me.

“Build a talent stack,” he told me.

“For instance,” he said, “I’m pretty good at drawing but not the greatest. I’m pretty funny but not the funniest. And I’m pretty good at business but not the best.”

But combining those talents allowed him to create Dilbert, which is the most syndicated cartoon in the world right now.



Invest in developing multiple talents.

People often ask me, “What do you do for a living?”

I have no answer. I have no label to describe myself. I write, I podcast, I run a business, I do angel investing (from tech companies to food companies to oil companies to…), I’m an adviser to several companies, I speak, and, just for the heck of it, I own part of a comedy club in NYC.

So what do I say? I usually say “I’m a writer” and depending on the audience they either have respect for me or lose respect for me.

Dignity > Respect.



I hate to give cliché advice. “Read” is cliché advice.

But I’m so grateful I started reading a book every day or so starting around the age of 21.

When I was in my 20s I thought I knew a lot about life. And maybe I did. Maybe I was a super genius about life in my 20s.

But probably not. I messed up relationships, jobs, careers, money, marriage, family and a lot more. And I can say I was a victim. But when I’m the common thing in every bad situation then the problem is probably me.

By the way, in my 40s I thought I knew a lot about life (I’m 50 now and basically know about the same as in my 40s). And I still mess up everything.

Messing up everything is annoying.


(best library I’ve ever been in)

But if not for reading, I would mess up even more.

When you live your life you are living ONLY ONE life.

Every book you read allows you to absorb an entirely new life. When you read 1000 books it’s like you have 1000 more lives inside of you.

And when you read good non-fiction books, it’s as if you’ve absorbed an entire lifetime’s worth of work in a few hours by downloading all of the experiences of the person who did do the lifetime’s worth of work.

Reading is like a super power. And when you can relate books to each other (combining what you learn from “Old Man and the Sea” with the latest book on “Bitcoin”, for example) then it’s as if you’ve read an exponential number of books.

Any success I’ve had in life I owe to reading a few books a week.

Plus, every book you read makes you a better writer. And learning to communicate is one of the most important skills you can have.



A year ago I wanted to get better at ping pong.

I had been playing since I was five years old and I thought I was good. But I wanted to get better.

It turned out I was horribly wrong. I did EVERYTHING SINGLE THING wrong in ping pong. For the prior 45 years.


Over the past 30 or 40 years I’ve learned many thing: chess, computers, poker, business, investing, comedy, writing, etc etc.

Some people play ping pong every day and never learn everything (like I did for decades). But learning how to learn has taught me how to get better when the time is right. When I’m really passionate about something.

Do this:

PLUS: Find a mentor, or a set of mentors, or virtual mentors (videos, books, etc) . This is how I learned I was doing everything wrong in ping pong.

EQUALS: Find people to compete with or study with who are at your level. You will rise up as a peer group. You will challenge each other and then help each other as you start to achieve success.

The best people I do business with now are the people I would stumble and stagger and fail with in 2002.

MINUS: If you can’t explain simply what you are learning, then you haven’t learned. Find people to teach and you will realize you are learning.

I became the best I ever was in chess when I was in my 20s and I started giving lessons as well as getting lessons.



I wish I had known this in my 20s. It was so easy to just think about myself and how situations benefited me.

But connection is the key to building your network. And your network is your legacy and your key to freedom.

Connection with loved ones.

Connection with friends.

Connection with co-workers.

Connection with community.

Connection with your spiritual or religious community.

Connection with people interested in the same things you are.

Connection with the world.

At my first major job (when I was 26) I focused on connection. I would learn about the interests of my co-workers and talk to them about those interests.

I would help my co-workers with projects at work without expecting any credit. Give credit and you will receive everything else.

I did this every day. It worked. This opened my eyes to the power of connection and I started connecting more and more with everyone around me.

It didn’t always help. But I’m a good parent, a good friend, a good colleague and business partner (I’ve been partners for the same people for up to 20 years), and hopefully a good loved one.

And every time I connect with someone, I feel less anxious about life. Which is hard for me. My brain loves anxiety. My brain always assumes the worst case scenario and throws it at me. Which leads me to the final lesson:



This is a BS phrase that people throw around like it’s easy.

It’s not.

From the time we are born we are taught awareness about everything else but ourselves.

Our parents teach us to be aware of their needs. Then schools teach us to be aware of society’s expectations. Then jobs teach us to be aware of the boss’s needs.

How many people have thrown away their careers because of their parents’s expectations. How many people have married the wrong person because of their friends and family’s expectations. How many people have thrown their loyalty towards a business that could care less?

How can you practice self-awareness?

Start small.

Every time I’m angry I try to say to myself, “I’m angry”. This puts the anger at arm’s length and helps me view it as an observer than an immersed participant.

I was upset at my girlfriend and I said to myself, “I’m angry”. Then I realized that from her point of view she had every right to act as she did.

I was upset at my daughter and I said to myself, “I’m angry.” But then I realized the sorrow and loneliness she was coming from in a recent decision and I changed my behavior completely.

After that you can say to yourself (when it happens), “I’m anxious.”

Or “I’m afraid”.

Or…”My gut is saying something” and you learn to listen to what the subconscious is saying.

And then finally, when you get good at labeling everything around you and understanding the forces that are constantly trying to control you, you can finally say,

“I’m in love”.

This is the greatest lesson I wish I knew in my 20s and that I’m learning now.

I love you. And I will treat you with dignity. And I will learn to win your respect

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