A Letter I Would Send To My Teenage Self

When you called Steve G. and said, “Do you think I’m so ugly that no girl will ever like me?” and he said, “Maybe in college or later someone will like you”, remember to not listen to him.

In fact, probably better not to ask that question but I know that is a big ask.

Your acne went away. Your braces went away. And you met more people with curly or wild hair.

Steve G. is a good guy and was trying to be a good friend.

BUT DON’T outsource your self-esteem to other people.

Treat your mom better. She had polio and I still don’t know all the ways that changed her psychologically.

Treat your dad better. Because he’s dead now and you’re going to miss him. STOP STEALING from his wallet every morning.

When you were debating skipping 12th grade but you didn’t because you wanted to be “normal”, LISTEN TO ME RIGHT NOW: skip 12th grade.

You went to college and then graduate school to learn “computers”.

When you were a teenager you didn’t think you’d like computers but you became obsessed. You started programming 20 out of 24 hours a day.

“OBSESSIONS” IS THE BEST COLLEGE. You can’t be the greatest without obsession.

College was great because you finally met girls who liked you. But that was going to happen anyway.

So SKIP college and just learn computers (embrace obsession). And then charge a lot of money to do computer-y things.

Then start a company and sell it. Then start another one and sell that.

Move to New York City as soon as possible.

All the opportunity is there. All of the money is there. All of your future friends are there. Every subculture is there.

Immerse yourself.

You start doing standup comedy when you are 48 years old.

Why don’t you start right now? You love it. Don’t be afraid. Just get on stage in front of 12 people and do it. Nobody is going to die.

Communication skills are the most important skills for any successful person. Learning how to motivate, learning how to make people laugh. Learning how to take a vision in your brain and transplant it into other people’s brains.

Comedy will help with all of that.

BUT make money with computers.

Do 100 pushups a day instead of zero.

Stop breakdancing and start getting obsessed with chess earlier.

People think “chess” equals “intelligence”. Once you become a chess master everyone thinks you’re a genius so you make a lot of money that way.

Also, the great thing about becoming a chess master is that the learning skills you developed to learn a hard thing can then be applied to learning other things.

Trust me, you will need those learning skills to survive.

You love reading but you didn’t start writing obsessively until you were 23 years old.

Start earlier. See above: communication skills are important.

I would say, “read more” but you already do that.

Reading is a great way to connect the dots between history, your life now, and the future.

This gives you the ability to have a vision of how to make things better.

This will help you lead people, create businesses, sell businesses, sell products, sell yourself.

So keep it up!

Never buy a home. DO NOT BUY A HOME.


A) Never invest more than 2% of your net worth in any one investment.

B) Always invest with co-investors smarter than you.

C) Always invest in a CEO who has done it before.

D) Never break these rules.

Don’t be greedy.

Whenever you make a lot of money, don’t spend it on material possessions. Spend it on experiences.

Give a lot to charity. Try to do it anonymously.

But rent a nice apartment. Convenience is everything.

Don’t stay in a relationship where you are unhappy.

You’re the type of person who hates confrontation.

If you turn into me, then you will have spent an extra decade of your life in relationships where you were unhappy.

What’s the best way to end a relationship?

I know you hate difficult or confrontational conversations.


A) Don’t move in with someone too fast.

B) Don’t stay with someone out of fear.

C) Just say, “I don’t know what’s wrong with me. I’m feeling confused and I have to be focused on my business stuff right now. I’m sorry.”

Oh! That just reminded me.


Every decision is either one or the other.

Like when you stayed with that one person because you were afraid what she would say to other people you worked with.

Yeah…dump that person.


A) Start it as a service business (for example, a consulting business).

B) But turn it into a software business (what you consult on, automate with software).

A profitable software business can be sold for 20 to 100 times what your profits are.

A profitable service business will be sold for three times what your profits are.

This is an important business rule you didn’t learn until your 30s.

Example: You had a business that made websites for big companies (don’t worry what a “website” is yet).

That’s a service business.

But make software so that companies can make their own websites. Automate what you were doing for them.

Then package yourself as a software business.

I know you’re never going to follow the rules of society so I don’t need to remind you of that.

Good job!

Listen to the lyrics of early 70s (or late 60s) rock songs. All of the wisdom of the world is there.

For instance, study word for word “All Along the Watchtower” and “Everybody’s Talkin’”

Remember this: all of school is useless. School teaches facts but you’re going to forget all the facts.

Don’t believe me? Ask any adult when Charlemagne (the most important Emperor in all of European history) was born. Nobody will get it right within 300 years.

Here’s what you need to learn:

A) Communication skills (speaking, writing, motivating).

B) Learning skills (which you’ll get when you become a chess master but learn it earlier).

C) Business skills (sales, negotiating, leadership, motivation, execution, problem solving, copywriting, over delivering).

D) Networking skills (don’t just meet people, introduce the people you meet to each other. Focus on creating value for your connections more than just making more connections).

The only things you ever learn in life are the things you are enthusiastic about.

The people who are enthusiastic will beat the people who don’t care.

You get enthusiastic by reading a lot and trying lots of things. Not going to school. Never ONCE will you get enthusiastic about something you discover in a classroom.

You’re the average of the five people you surround yourself with.

This is always true.

So if you are around bad people, get rid of them.

How can you be around good people? Fake it till you make it.

Here’s an idea: start a radio show or a magazine and call up all of your heroes and interview them.

This is how you learn, network, have better friends, create more opportunities, live a larger life.

If you ever feel like you have to kiss someone’s ass to get what you want then you are making fear decisions.


People often say “the key to success is knowing when to say ‘NO’. “

This is true in your 30s and later.

But in your teens and 20s say “YES” to most things.

This will give you a lot of good stories at the very least.

Always go where it’s least crowded.

I mean this metaphorically.

Literally, though: go where it’s most crowded.

Be the person everyone wants to be friends with.

Not because you are nice. But because you are interesting and inspiring and are creative and, finally, because you are giving.

Give away all of your ideas.


Which means: don’t be a sore loser. Learn from the losses. Lose frequently so you learn more.

I was too afraid of losing when I was your age.

Now I lose every day. I’m a loser.

Very important: never spell loser as “looser”.


– Be insanely curious about them.

– Be vulnerable. But don’t offer facts unless they ask.

– Connect people who can help each other (but ask permission on each side first)

– Give ideas freely

– Know that everyone is going through their own insecurities and pains.

– Don’t judge people. don’t gossip.

– Talk about ideas instead of other people. HEROES TALK ABOUT IDEAS, VILLAINS TALK ABOUT OTHER PEOPLE.

– Always be honest. No exceptions.

Keep in touch with your best friend, Robert. You have no idea where he is when you’re older and you miss him.

Maybe he’s dead. I don’t even know.

People say, “under promise and over deliver”.

This is bullshit. ALWAYS “over promise and over deliver.”

Never be arrogant. You become pretty arrogant in your 20s. And a lot of people don’t like the way you look so they’ll hate you for arrogance.

Always have beginner’s mind.

Assume everyone around you is secretly an alien that was sent down to Earth to teach you a lesson or send you on a mission.

Listen closely.

Don’t take a “No” from someone who can’t say “Yes”.

Corollary: steal great quotes from smart people (thanks Steve Cohen and Gillian Segal for the above).

Don’t feel bad when you can’t sexually function with girls you are not that into. You’re not a machine.

Oh, and don’t feel bad when you can’t sexually function with girls you are falling in love with.

Sometimes you’ll just feel awkward and it takes time for you/me to get comfortable with someone. If someone loves you, they’ll simply love you and you’ll get comfortable with each other.

That’s nothing to feel bad about despite our porn culture.


Don’t pay attention to this letter.

If you make all your mistakes, have all of your fears, get kicked out of bed by that girl in 1995 at 3 in the morning because you were impotent, lose money in all of those businesses, be at the World Trade Center on “that day” (figure it out for yourself), get into all of those unhealthy relationships, write those first five or six shitty books, have those awful first bosses, get disappointed by those 20 or 40 or 60 friends, throw that coconut in the street at midnight because a psychic told you to, don’t say “bye” to dad, waste all that time on chess, Go, poker, scrabble, writing bad novels, etc., start that “Twitter dating site”, start that mobile software company that loses $100 million, make that horrible decision about that one woman (you’ll know what I mean – several times), be filled with so much regret you’ll want to repeatedly kill yourself, get thrown out of school, get rejected over 1,000 times by women, publishers, investors, TV channels, customers, more women, and in situations that don’t exist yet…

Then you’re going to have an amazing life.

See you soon and I love you.

– James at 50

P.S. (Get it? That was a TV show when you were a kid: “James at 15”)

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