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The Best Life Lessons I’ve Learned from Studying the Lives of 10,000+ Ultra-Successful Individuals

by | Nov 13, 2023 | Success

F. Scott Fitzgerald once asked Hemingway to look at his penis.

Fitzgerald’s wife said he had a small one, and it’d never make any woman happy or give them pleasure. Wow. Harsh statement. So the two gentlemen went to the bathroom to pull down Fitzgerald’s pants and find out.

Hemmingway said:

“Your manhood [d*ck) is perfectly fine.”

Hemingway gave Fitzgerald a great solution to his manhood problem. He told him to go to Louvre Museum and look at the statues with male body parts exposed. Then to go home and look at his slong to compare size.

Hemingway was quite smart and told Fitzgerald that when a man looks down on their manhood from above, it naturally looks small because of the angle. Hemingway drops a bomb at the end of this famous encounter:

“It is the size that it becomes.”

So what can we learn from these two ultra-successful writers and their naughty little bathroom competition? Well, it’s that we all struggle with imposter syndrome and insecurity.

It’s normal.

So if fear, insecurity, and imposter syndrome are holding you back then force yourself to take action anyway.

Here are more of the best life lessons I’ve learned from studying the lives of 10,000+ ultra-successful people. Read them then take action on your favorite ones.


The best description of age I’ve ever come across

Getting old gives me the scaries.

A few grey hairs are poking through and I wish I could push them back down into my skull. If my hair starts to fall out I’m gonna lose my sh*t.

But we all get old.

Understanding the various age levels is the cure. Greg Isenberg broke it down perfectly:

When you’re 18, your situation reflects your upbringing.

When you’re 38, your situation reflects your decisions.

When you’re 68, your situation reflects the impact you’ve had on others.

So make better decisions and try hard to have a positive impact on others. I find spreading inspiration is one of the best ways.


What every millionaire doesn’t understand (especially the wannabes)

At 26 I wanted to be a rich b*tch.

Gold chains, Lambo, big house, bikini babes, etc. But Alex Hormozi made me remember that as you get older you want to trade the money to become young again. Read that again.

The secret to life is time and enjoying today. Because today is as young as you’re going to be in the future. All this chasing money nonsense just wastes your time.

Ask twins Charline Munger and Warren Buffett if they want their billions of dollars or to be 21 again with a functioning slong. I dare you. Go to their next Berkshire Hathaway conference and ask them in person.

Time is sexier than money. It’s why I retired from 9–5s at 34.


The path to overcome a major tragedy is counter-intuitive

Everyone will go through some huge life challenge.

Parent dies, friend disappears, layoff happens, business collapses, divorce happens, etc. These are guarantees in life. The solution to move forward is to find a bigger challenge (you choose) to refocus your attention.

Then the big problem looks like a tiny problem when put side by side with the massive challenge you’ve chosen.

I did this with mental illness. I decided to start a new goal and become a writer, start a side business, and turn my life around. Those shiny objects helped me to focus away from the darkness.


The sign of a person who’ll never succeed

Ryan Holiday takes too many holidays. There, I said it.

He said something I’ll never forget, though:

One thing they’ll all tell you is that a person who is afraid to strike out, afraid to miss, afraid to fail is a person who will not succeed.

He’s talking about baseball (boring). But it applies to life. Those who are afraid to take risks, leave their comfort zone, and experiment with new things stay trapped in the past.

Rejection and failure are normal. The more you experience them the faster you figure out what doesn’t work — and that leads to success. Mind blown.


The F-Word guy redefines bravery

Mark Manson is everywhere right now. No idea why.

He has a potty mouth like me, and yeah, I’d have his babies. He says bravery doesn’t mean you have no fear. True bravery is feeling the fear, doubt, and insecurity and taking action anyway.

It’s possible to take that action because you’ve decided a mission/purpose/obsession is more important than the fear you feel.

I feel fear all the time.

Whenever I show up to teach a masterclass I spend way too much time in the toilet doing unnecessary fear poos.

When I hit publish on an essay, sweat runs down my back and I worry cancel culture may come for me. It happened yesterday after I wrote about Jordan Peterson. A few people got mad, but mostly, people got my message.

You can either drown in fear or use it as a form of personal growth.


Getting what you want too fast is a bear trap (ouch!)

Robert Greene wrote a famous listicle book (take that clickbait listicle-hating police).

He said, “It is a curse to have everything go right on your first attempt.” Wow this hit me hard in the nuts.

You see so many young and famous actors/musicians get everything they want and end up deeply depressed. Often it was too easy.

Easy now = Hard later

You want your journey in life to be hard. It’s where all the best wisdom is collected. It’s where mental muscle gets built. That’s why looking for shortcuts and having daddy’s trust fund are boat anchors that hold ya back.


Take more photos when times are tough

One thing I’m upset about is I didn’t take more photos back in the hard days. There’s no photo of me wearing the call center headset.

I have no photos of me in my car next to the Melbourne casino reading finance books. So it’s harder to remember these hard times that led to the good times I have now.

Take photos so you remember your hero’s journey. Use the photos to tell the story later so others can follow in your footsteps.


The bottom and top 1% both follow this rule

The middle 98% of society follow the rules like sheep.

Sales expert Lawrence King taught me that the top and bottom 1% of people don’t follow the rules. The bottom 1% end up in jail or on the streets, and the top 1% make so much money they exit the matrix.

Rules are guidelines. Bend the rules. Reinterpret them.


Life is one big movie and you must notice these key people

Bars, restaurants, parks, schools, buses, trains are full of people. Most of us ignore them.

But Comedic Bizman on X changed my mind. He says these random extras in your life’s movie are actually main characters, there to help you advance the plot of your movie. Wow just wow.

So how do you know the difference between the extras and the main characters? Well, you talk to them. You start random conversations.


A powerful question to shake up your life and achieve higher states of consciousness

Author James Clear has written a lot of success p*rn. I like the guy. He posted a question in his newsletter that I’ll never forget.

Imagine you are at the end of your life and you are granted the ability to repeat one day. Which period of your life do you choose to repeat? Which phase of life would you want to go back to?

Does that tell you anything about how you should be spending your time today?

For me, it’d be the day my daughter was born. I’ve never loved another thing so much in my life. She was pure joy wrapped in a cotton sheet. And she was a daddy’s girl from her first breath.

Once you know what moment this is for you, it tells you a lot about what you should be doing.

That’s why my goal in life right down is to have more daddy-daughter time. It’s the one type of day I’d like to repeat for eternity.


Success is falling in love with the boring parts

Hollywood and social media have done us a huge disservice.

They’ve made success out to be something that’s exciting and fun the whole way. Like every moment is unforgettable.

The reality is far different.

Most parts of success are boring. They’re not even worth talking about or putting in a documentary.

Dr Julie Gurner says “A lot of success is learning to grind when it’s boring. If you expect all building to be exciting, you’ll never make it.”


Redefining pain according to fight club bros

Some people love hate.

Hatebait is popular on platforms like X because holding onto hate is a powerful habit. Keeping hate and spreading it means you aren’t forced to process the real pain underneath.

Fight Club movie creator Chuck Palahniuk said “People fall so in love with their pain, they can’t leave it behind. The same as the stories they tell. We trap ourselves.”

Holding onto pain is a hidden disaster. And it’s addictive.

It’s better to let pain go and use it to help others through theirs. Then you can get out of the hate death loop and discover new parts of life that are more empowering.


The darkness has a lot of light

We all go through dark periods.

Some people get scared in the dark. They try to run from it. Or avoid it. Or think they’re living a nightmare. Yousuf Karsh said this:

Character, like a photograph, develops in darkness.

Status, power, and achievements are a distraction. True success in life is to upgrade your character and become a completely different person every 12 months.

People remember your character and how you made them feel long after they remember your silly little achievements that often do nothing more than make people envious of you. Read that again.


Pleasure junkies are everywhere. And they’ll ruin you.

When a man can’t find a deep sense of meaning, they distract themselves with pleasure — Viktor Frankl

Pleasure is another word for cheap dopamine.

Dopamine is the chemical that is found in the reward center of the brain. The worst way to produce dopamine is to watch naughty movies of people doing it with full skin to skin close-ups.

But life is full of this toxic p*rn. Social media is p*rn. Crypto is p*rn. Junk food is p*rn. Conventional success is often p*rn. Writing online can be p*rn.

The trick isn’t to cut pleasure from your life for good and go live in a cabin in the woods with 5kW of off-grid solar panels. No. It’s to chase healthy dopamine by setting goals and achieving them.

It’s to trade fake dopamine for the dopamine you get from hard work, flow states, and deep work.

Otherwise you become just another mindless pleasure junkie trapped in cyberspace, trying to escape the rat race.


99% of people never change

They just live the same year over and over and then die and label it a “life.”

Change is what makes life worth it. I get in trouble all the time because it’s my job to coach people. Sometimes I offend them because change is hard and it forces them to give up who they are.

If they can’t do it then they prefer to blame me and say “you offended me” or “you’re evil, sir.” Nope. These are just excuses for someone who refuses to change.

Either change … or life will force you to change through random tragedies, many of which will be self-inflicted.


Nearly dying is how you can feel more alive than ever

There’s this concept known as a near-death higher state of consciousness.

It’s one of the most powerful states you’ll ever experience and I’ve lived it multiple times — a near-miss with cancer, and being the victim of a gang knife attack at 16.

It’s best shown through author George Saunders’s near-fatal accident. He was on a commercial flight reading a Vanity Fair magazine. Suddenly he hears a loud bang. The flight he was on hit a flock of geese. WTF?

Black smoke pours out of the engines, and the cabin lights flicker non-stop. Eventually the plane lands safely back at the runway. A bizarre situation happened after he arrived home safely.

For the next 3-4 days the world had never looked more beautiful.

He couldn’t believe he got to come back and try again. The world looked amazing because he finally knew that one day it would end for him.

The secret to life is to live like this all the time.

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