The signs you're a generational outlier

Outliers are secret weirdos.

They live a life most people don’t understand. I’ve been lucky to work with many outliers. Some of them became generational high performers. One-in-a-million types that do things most of us can’t even comprehend.

I’ve been fascinated with outliers ever since Malcolm Gladwell wrote the book Outliers. And I’ve applied his learnings to try and spot outliers, because I believe working with and encountering an outlier is a life-changing experience. Some of their awesomeness always seems to rub off on me.

It’s uncomfortable for me to say this, but I have probably become an outlier.

The thing about outliers is they are hard to spot. Here are the signs you’re not broken but are in fact just an outlier.

You’ve experienced untold trauma

In mainstream society, trauma and tragedy get a bad rap.

Most people use it as an excuse. “I can’t do X Tim because bad things happened to me, dontcha know.” So they become a victim, assign a label to their condition, and take meds to make the pain go away. That’s a completely normal reaction. No judgement there. I can see why people do it. But…

I’ve never aligned with this mainstream view.

I’ve always seen trauma and tragedy as an amplifier. Truthfully, as a 20 year old, I hoped I would experience pain, tragedy, and heartbreak. I shouldn’t admit this but I even craved it. And don’t worry, I got a lot of it.

For several decades, I hit rock bottom so many times it felt normal. Each time I imagined myself as Batman in the movie “The Dark Knight” trapped in the bottomless pit of a prison with a bunch of psychos trying to escape.

And like a true loony, I loved it.

When I lost everything multiple times, I smiled. When I had $1.2M stolen from me in 30 minutes back in 2021, I saw it as an advantage. When multiple long-term romantic relationships blew up after I joined a religious cult, it inspired me to be better.

The chance you come from a poor family, rack up millions of followers, hit 1B+ content views, build an email list of almost 400K subscribers, and make millions of dollars online is statistically low. So much of what I’m sharing here makes perfect sense to me because I’ve lived it.

Turns out I’m not alone. Research suggests (study 1 + study 2) that moderate adversity, rather than a charmed and frictionless start, is a common thread among outliers. Enough hardship to forge resilience, but not so much that it breaks them.

Instead of the pain creating more pain, outliers use pain as an advantage.

Their brains are wired a little differently.

A great example of an outlier is my accountant. His family were part of the royal family in Vietnam. When the Vietnam War broke out his family lost everything after they lost the war. They escaped on 8 boats headed for Australia. Only one boat successfully made it to Australia carrying his mother and father. Pirates captured the other 7 boats during their voyage.

Those boats had no living survivors.

When his parents arrived in Australia, they took on massive debt. Then his father walked out and left his mother with nothing plus the huge debt.

They became homeless.

For all of his childhood and teenage life, he was homeless with his mother. They lived in homeless shelters like it was normal.

But it messed with my accountant’s brain.

He wanted to break the curse from a young age. So at school he became top of his class. Then he became top of the state in high school. Then he hit top of the country. He studied so hard he became a genius. Entering the workforce gave him enormous graduate opportunities.

By a young age he built his own business. He now owns multiple businesses doing tens of millions in revenue and a huge property empire.

His family will never be poor again.

When my accountant told me this story, I had tears in my eyes. It broke me. I felt goosebumps all over my body. He’s an incredibly inspiring human. Becoming his client was so obvious to me. That’s the energy of an outlier. It moves people to action and shows regular humans what’s possible.

Trauma can make or break you. For outliers, they experience trauma and use it to ensure they and their family never experience similar trauma again.

You follow the “Three Extremes Rule”

This formula comes from Aura startup founder Zach Pogrob.

1. Extreme focus (1 thing)

An outlier is someone who has achieved a hard goal.

They stand apart from the norm and achieve results that are so extreme it lands outside what is typical. Outliers are the geniuses, superstars, icons, and leaders the world looks up to.

To outperform in any field you must have extreme focus. It sounds obvious yet most people don’t do it. The average person spends most of their day looking at a smartphone that is nothing more than a casino slot machine.

This takes up most of their time, so they claim they are busy, when in reality they’re just distracted.

Outliers are the opposite. They spend an unreasonable amount of time focused on one thing. Not ten things. One thing.

They don’t have a to-do list or a goal list because what they must do is so blindingly obvious. For me, that means writing like a psychopath and publishing more work on social media than almost anyone else. My focus looks like “write a lot.”

2. Extreme timeline (1 decade)

Most people think short term.

They want money now. They want the Lambo now. They’re focused on the next person they can have s*x with. Outliers are the opposite. They have extreme timelines. They think in decades.

For example, when I started writing on the internet in 2014, I decided to dabble. I was going to try it out. But instead of trying it out for one month or one week, I chose the bizarre timeframe of 10 years. Same with public speaking. When I committed to the craft, I set myself a timeframe of at least 10 years.

Eventually I hit the top 1% in both (not to brag because you don’t care).

Longer timeframes produce better results. They show real commitment. You can’t learn much good or achieve any mastery in a week. But even if you’re normal IQ like me, you can definitely achieve a lot in 10 years.

Extend your time horizon to have more patience and achieve true mastery.

3. Extreme iteration (1% better, every day)

Malcolm Gladwell’s book spread a bullsh*t lie known as the 10,000-hour rule.

And while time in the game is important, most people mistake this rule. It’s why people have 20 years’ experience in their job but still make $50K a year.

If all you have is “years of experience” without extreme iteration, you ended up taking one year of work and learning… and repeating it for 20 years in a row.

That’s dumb.

Outliers do plenty of hours but they also do stupid numbers of iterations on their work, idea, or goal. Why? Because the definition of insanity is doing the same thing over and over and expecting a different result.

Yet that’s how most people live.

They repeat the same boring actions, work hard, and don’t get ahead because they left out extreme iteration.

Extreme iteration is how you experiment, A/B test, learn, and acquire true wisdom.

It’s hard for normal people to iterate and change because their ego gets in the way. The factory-worker education system teaches them to believe they are always right. They can’t comprehend that they might be wrong. And they’re not willing to accept it.

And they don’t change because change is uncomfortable, and right now, we’re living through a comfort crisis. Multiple generations of humans that experience a tiny bit of stress, then quit and think they’re smart and justified (even empowered LOL).

When things get hard normal people quit and call it stress. But when outliers do hard things, they see it as learning and iterate their way to breakthroughs.

There is a downside though.

If you iterate and change too much, it becomes shiny object syndrome. You spend your life chasing false gods, cults, and rainbows looking for a magical solution that doesn’t exist. But if you don’t iterate enough, you learn nothing and think you’re the smartest person in the room.

The formula for iteration is 1% better each day. Small iterations without deviating from the plan or quitting a goal too soon.

You make people uncomfortable and even sweat

Outliers don’t tell you what you want to hear.

They’re not a people-pleaser who will lick your butthole and tell you how great you are. A conversation with an outlier is uncomfortable though. You feel on edge, yet they don’t insult you or say rude stuff. But there is a level of intensity.

They have standards and there’s a subtle pressure and assertiveness.

They’re a little unhinged too. Not so unhinged they sound like a conspiracy theorist, but not so aligned with mainstream culture that they’re a choir boy and part-time boy scout who can’t think for themselves.

It looks and sounds like “John was definitely no BS.”

The no BS is a filter they see the world through. They tell people how it is to save time and get to the point. It creates a slight aura around them and builds trust faster.

It feels authentic and genuine too, which is appealing in a world of fake leaders, politicians, and big corporations doing evil while pretending to do good. They hear feedback and listen, but they call out contradictory behavior and misaligned views.

Being challenged is how we all grow. And outliers can help you do that.

You chase genuine obsession at the risk of looking like a maniac

Most people are lukewarm passionate.

Outliers have transcended to the next level. One outlier I worked with in finance is a good example. On the outside he looked like a normal guy. But he wasn’t. In his spare time he read every piece of financial news he could. In between meetings, he was looking at trading screens and doing financial modelling.

He was already rich so it wasn’t for the money.

He was just obsessed with finance. At a young age, his father made him read the Financial Times every morning.

He started looking for good property investments as a teenager. He had a financial model for exactly what a good property should yield and where it should be located.

While other investors shouted “location, location, location,” he looked at state-level economic data. As an adult, he started buying homes up. He’d look at 300 properties in person before even buying one. His desk was full of town planning papers and population growth numbers for the last 100 years.

His obsession for finance transcended the normal constraints.

When I questioned him about it, he said none of it felt like work.

What he does during work hours and while he’s on holidays or enjoying the weekend looks exactly the same. Finance was a jigsaw puzzle. It kept him endlessly fascinated. There was no end to the game. Only mastery and pure obsession.

I asked him if he had a plan B in case finance didn’t work out. He looked at me like I’d just shat on his desk and slept with his wife. He was disgusted. He saw no existence where he’d be doing anything else.

It had to work. He’d force it to work.

Obsession cannot be beaten. It’s a form of transcendence.

You must prove an enemy wrong

Outliers have a chip on their shoulder.

Not in an angry Karen way. But as a form of quiet rage. The golf course swinging small d*ck that fired me for no reason is one of my enemies.

So are the intellectuals who refused to let me into higher education. As are the gatekeepers who run and operate the pointless corporate ladder that leads nowhere.

An outlier doesn’t let anger take over.

No. Instead, they desire to prove their enemy wrong. To show them through proof of work and results that they were wrong about them.

This is a powerful form of motivation. It’s forced me to get resourceful and do things I otherwise wouldn’t have done. I still remember a recruiter from Oracle 5 years ago who said “Tim, the reason you’ve been unemployed for 6 months is because you’re sh*t.” She alone probably made me at least $5M.

Funny thing is she got made redundant herself right after that and took a “career break” because she probably couldn’t get a new job either.

Having people doubt you is a powerful form of motivation.

You have an eccentric personality

Outliers are weirdos.

Last week I took my kid to the miniature train. We went on the small Thomas The Tank Engine one that was full of children aged between 2 and 5. The train goes like 3 mph. As we got off the tiny train, I recognized the driver.

He’s a well-known guy in the business world. He’s had a lot of success. Been part of many huge mergers and acquisitions. And he was driving a f*cking kids’ train on a Sunday. I pulled him aside. He remembered me from my banking days.

Dude just liked miniature trains. He’d been driving them for 20+ years.

I wish this was a new realization. But it’s not. I’ve seen this repeatedly. Outliers are quirky. They have odd personalities. Their houses are full of things you’ve never seen before. They collect strange stuff. They have hobbies most wouldn’t understand.

When they go to networking events or parties, they struggle to connect. They don’t know how to act normal and ask painful questions like “Soooo….how’s the weather?”

Many of them have non-linear career paths too.

They didn’t get a job at McDonald’s serving fries then eventually become the McDonald’s CEO.

I still remember another outlier I worked with who went from being a journalist in the Middle East, to a banker, to a farmer, to C-level exec, to an entrepreneur. His entire career history looks like one you’d find in the kids’ TV show Bluey (I watch it every day with my kiddo).

Linear careers equal boring.

Outliers are too weird to follow the traditional path to nowhere.

Closing Thought

If you want to spot the outlier in you, look for the strange stuff you do in the shadows, the non-obvious things nobody around you does. What you do doesn’t fit any framework or 10 steps to success model.

You won’t just learn from outliers. You’ll realize you were one all along.

When you embody the traits of an outlier, you have a more exciting life, a non-linear career, and you produce results you wouldn’t have been able to achieve any other way.

Fitting in is massively overrated. Channel the weird witchcraft of outliers.

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— Tim