The Ultimate Guide To Being A Happy And Successful Introvert


John Waters, the movie director, told me the other day where I could go if I wanted to kill myself.

I suspect he was even more of an introvert than me. I’ll tell you where he suggested in a second.

A few months ago I was at a dinner where everyone was “networking”.

I was totally frozen. I was speaking inside my head but I couldn’t open my mouth.

People were talking and laughing and getting to know each other.

On the inside, I wanted desperately to talk, to think of things to say, to bond with the people. But suddenly, I felt tired and dumb and like I had nothing to say.

And then I was afraid everyone thought I was stupid and boring. Then I thought they didn’t like me. So that made me want to talk even less.

I didn’t speak for the rest of the dinner. I went home but I couldn’t sleep. I kept whispering “sh*t” out loud even though I was trying not to. I just wanted to go to sleep and disappear.

My mind wouldn’t let me. For hours: “sh*t”.

Being an introvert has nothing to do with being shy. Or being outgoing or not outgoing. Or being socially awkward.

All it means is that some people recharge when they are by themselves (introverts).

Other people recharge when they are interacting with many other people (extroverts) and most people are in the middle.

Maybe introverts think they are shy because if they are around people long enough (like at a party) they need to recharge by being by themselves.

Extroverts can be shy also, but it’s easier for them to cope with it by talking to MORE people instead of less.

I lose energy very quickly when in a group of people. Getting invited to a party is horrible for me.

I say “no” to almost every social situation. Because I know they will take energy away from me doing the things I love.

If I’m giving a talk it’s no problem. Because I’m by myself on the stage. It’s one too many instead of me just one in a mess of people. I recharge on the stage.

How I Deal With Being an Introvert


Quiet” by Susan Cain is a good book. She’s a successful businesswoman and author and I love her and think she does great work.

She studied the whole introvert thing. And to meet her she is a very kind and warm person and you don’t get any sense that she is shy or awkward or anything. She just recharges by herself.

2. Create a life where you can have more alone time.

I write and read every morning. And, as awkward as this sounds, when I want to meet with a friend I often say, “let’s record it” so then it becomes a podcast and it’s still part of my work.

I go to sleep early. I don’t really go out to parties because I don’t get my energy from being around lots of people.

How do you create that life?

3. Remember the 1% rule.

You can’t do it overnight.

Just make small incremental moves towards the life you want to live.

Every day we make about 10,000 choices, small and big.

You either make a choice or someone makes it for you. I decide to write…or a boss tells me what to write.

Every day I want to make more choices for myself, instead of letting other people make choices for me.

I’m not a minimalist, I’m a CHOICE-IST. Every day I try to make more choices for myself than I did the day before.

How long does it take?

4. Wait 15 Years…give or take 10.

It took me a long time to realize I wasn’t shy. I thought the reason I had trouble talking to people in groups was because I was shy or insecure.

That’s the ten years part. I was so deluded about my strengths that it took me ten years. Maybe it will take you fewer.

Then it takes about five years to bit by bit transform your life into one where you are getting as much energy as possible BECAUSE of your introversion.

Once you know how to recharge, you can be enormously creative and successful.

Just don’t fall into the path walked by everyone else. You have to find your own path to maximize your energy.

If I were an extrovert I’d be dying by now because of lack of energy.

But because I’m an introvert and I am alone a good chunk of the day, I have MAXIMUM energy when I deal with people, or give a talk, or make a video, or do a podcast, or spend a short amount of time with friends.

Does it require money?

5. No money required.

It requires asking yourself throughout the day: is this activity giving me energy or draining me?

And then over time, you realize when your energy peaks.

Energy is everything in life. At night we have little of it, so we need to sleep.

When an introvert is around a lot of people, it drains quickly.

When you are around people who put you down, it drains instantly.

When you aren’t creative, it drains.

When you aren’t happy with your current moment, it drains because anxiety and regret are leeches on our energy.

When you are with someone you don’t love, it drains.

When you are at a job you don’t like, it disappears.

Note that none of the above has anything to do with money.

Energy is more important than money. Energy is what makes you live a long and productive and happy life.

If I wanted a billion dollars I wouldn’t sit around writing and reading and podcasting a good chunk of the day.

I wouldn’t hire people to help me run the various businesses I’m involved in because it’s hard for me to meet with employees and do “business things”.

I’d run a hedge fund, or directly run my businesses, or buy a company and become a CEO. I’ve done these things before and failed miserably.

Not because I don’t have the knowledge. But because it doesn’t make me happy. And those activities drain me.

6. Humility is more important than self-esteem.

Be humble enough to realize what you are not good at.

Sometimes I’ve had too much self-esteem. I’d think, “I’m a genius!”

And I’d proceed to lose a marriage or money or a relationship or totally screw up an opportunity.

Self-esteem is great if you earn it. But if you have no gas in the car, faking your gas gauge won’t make the car run longer.

Humility is great to recognize what you are truly good at and passionate about and what you should delegate to others to conserve your energy.

So be aware of the ten or so things you need to put in place to maximize your energy. Not 100 things. Ten things.

I’m not good at managing employees. I’m not good at having a boss. I’m not good at going to networking conferences. I’m not good with groups.

A good business meeting tip:

But I am good at communicating. I am good at being creative. I am good at meeting people over a game like ping pong or chess.

These are my best business meetings. I’m good at figuring out how to help people without expecting anything in return.

In little steps I build my network.

A good networking tip:

One thing about introversion that works well for me is that I don’t need to be in the middle.

If I know A, and I know B, and I think A can help B and vice-versa, I’ll introduce them and say, “no need to keep me in the loop”.

Surprisingly to me, this turned out to be a powerful networking technique. A and B NEVER FORGET who introduced them.

The next thing I know, I’m considered “the source” for many successful combinations so I am always sought out for advice, which feeds my various business interests.

Can an introvert date an extrovert?

7. I hate to say it, but introverts should mostly date other introverts.

This doesn’t mean outgoing people should date outgoing people and shy people should date shy people.

I’m outgoing. And I’m not very shy. I can go up to anyone and talk to them. Even if I’m afraid, I’ll still do it.

The other day I was on a train.

When I was getting off the train, the only other person getting off was the famous director John Waters.

I said, “John Waters! I loved your last book, ‘Make Trouble‘.”

I had no problem talking to him. He told me something about the train route.

He said, “The ‘suicide community’ knows about this train route because there’s one point where the train is not allowed to stop. They all know where that point is. So they jump in front of the train there.”

I thought that was a strange phrase, “suicide community”. I didn’t know there was such a community.

On second thought, maybe he was bothered that I spoke to him and he was giving me a tip of what I should do.

I asked him if he could go on my podcast. I’d promote his new book. He said, “No” and walked away. No problem. I get rejected a lot.

I dated a girl who liked to go out at night. She is an extreme extrovert. It was the worst experience ever even though we both liked each other.

She simply liked to go out EVERY night and talk to EVERY person at the party.

And I always wanted to go home and recharge. I hated going out.

Our different styles would/could/and maybe even should lead to arguments.

Much better to meet a person who recharges when you do.

This is just my opinion. Not everyone agrees. This is what works for me. The opposite might work for others.

8. How does an introvert get things done?

Here’s how I do it.

  • I write down ten ideas a day to keep being creative.
  • I read a lot so I keep learning.
  • “Execution ideas” are a subset of ideas. So when I have an idea I want to test I think of the next execution ideas to get the idea done.
  • I talk with friends who can help me if I think the idea is starting to gain traction.
  • I focus my execution efforts on the things I’m skilled at and hire or outsource the other things.
  • I work with people who are good at what they do so I can be good at what I do.
  • I have no problem reaching out to people who can help BUT FIRST I research thoroughly about WHY they can benefit from listening to me.
  • I meet people one on one in a game-playing situation, or at a bookstore. NEVER in their offices.
  • I introduce A and B and say, “leave me out of the middle”.

Repeat. Every day. All day.

10. Can introverts and extroverts work together?

I am not good at conferences. But I work well with people who can go to conferences, make connections, and can teach me later what they learned.

I work well with extroverts if we meet one on one and brainstorm together.

I have one daughter who is probably an extrovert and one who is probably an introvert.

I love them both equally. They are both equally kind.

Introverts or extroverts can’t help who they are. But you CAN regulate your humility so you can figure out what you are.

The daughter who is an extrovert often wants to go out more with her friends. I have to be ok with this and then enjoy the time with her.

The daughter who is an introvert spends more time with me. But then she goes to her room and reads more. I have to be ok with this also.

I think you can work just about any relationship situation except romance between introverts and extroverts.

But, again, this is just me because I believe I’m extreme on the spectrum but most people are somewhere in the middle.

10. What about “getting out of your comfort zone”?

I don’t need to get out of my comfort zone and go to lots of parties and talk to a lot of people. I tried it.

It never worked. 30 years of trying and I failed.

Again, 90% of the game is being aware of what you are good at and what you are not so good at. Usually, I’m hopelessly unaware. Finally, I got more aware in this one area.

I’m not 6′7″ so I probably won’t be a professional basketball player at this point.

Trying to be a professional basketball player for a 5′9″ 49-year-old is not called “getting out your comfort zone”. It’s called “stupid”.

It’s not “you can do anything you want to!” It’s self-delusion instead of self-esteem.

But most other things I can do if I put in the time and I have the desire.

I simply don’t have the desire to learn how to recharge by being in a party or very social situation that I don’t enjoy.

I say, “No” now instead of saying, “Ok, I’ll say ‘yes’ because this will be practice for being around people”.

I used to say “yes”. Because I wanted to be an extrovert. So many hours wasted. I only have one life. And I only have about 15,000 days left, tops. I don’t want to waste them in parties.


Quiet” by Susan Cain
Choose Yourself” by me
Tiny Beautiful Things” by Chery Strayed
Tools of the Titans” by Tim Ferriss
Graceful” by Seth Godin

There’s probably a lot of other good books out there but these are the first few I think of.

I was in a camp as a kid. I couldn’t speak at all.

Some kids would pick on me. Other kids thought I was mentally ill so they would defend me.

Eventually, the counselors had to ask my parents if I was dysfunctional in some way.

My parents pulled me out of the camp but they didn’t know what to do with me. So I just stayed at home and read all day. It was the best summer of my life.

I was alone but not lonely.

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