I'm 38. If You're in Your 20's or 30's, Read This.

1. When you turn 35 you'll see the difference between those who took risks and those who didn't.

Image Credit-Midjourney

Getting old sucks.

The one positive is that as we age, we mature. That’s been the case for me. Not much fazes me anymore.

I’ve been part of so much drama – personal bankruptcies, homeless friends, my battles with drugs and alcohol, nearly getting knifed to death, friends in jail, job losses, mental illness, $1.2M theft, online trolling, going from entrepreneur to corporate to entrepreneur, etc.

I’m not that smart but these experiences have given me some powerful lessons to share to anyone in their 20s or 30s (feel free to forward it to them as well).

1. When you turn 35 you'll see the difference between those who took risks and those who didn't.

How old you feel comes down to how you lived.

Not taking risks leads to regrets which ages you faster. You feel like you could have done more but you never do. You always move decisions to the future where you have zero accountability. It’s f*cking sad, man.

If you’re reading this and not taking risks and overthinking $100 purchases, wake the f*ck up. You’re not living if you’re playing it safe and procrastinating on everything.

2. Having kids isn't the end of freedom, it's the beginning. It'll give you meaning that'll fuel your greatness.

People told me at 20 that having kids was bad.

“Your life is over when it happens, Timbo.”

God, these people were so wrong. Having kids is hard. My 2 year old takes up a lot of time. There are a million sacrifices you gotta make, but it’s the best experience of my life. I could die tomorrow now that I’ve met my daughter.

Every minute is pure joy. There’s nothing that comes close.

Her smile pours rocket fuel on every one of my creative pursuits. If you’re able to, have kids. If not, adopt. But don’t rule out this option without thinking it through.

Kids are hard but so are the best things in life. Choose your hard.

3. Chasing obsession is the fastest way to become a high performer.

I’ve felt sad lately.

After interacting with thousands of people online, I’m losing hope in society. It just feels like most people won’t make it ( I know this sounds privileged).

• They’re full of excuses

• Think short term

• Don’t invest in themselves

• Stay on beginner level

• Have a short-term outlook

• Don’t put in the work

• Get sucked into a 9-5 job that leads nowhere

• See hard work as hustle culture, and self-care as their birthright

• Chase lottery opportunities (Medium dot com, Kickstarter, getting famous)

Most of all, their mindset is way off. It’s skewed way too far toward the negative. I can make these honest observations because I suffered from every one of them.

The truth is, if you don’t solve these problems they hold you back and keep you stuck. The world doesn’t care if you stay stuck. It just means you’ll earn peanuts and have to struggle constantly with money and never having enough time.

The only solution I’ve found is to go from being passionate/interested/lukewarm to all-out obsessed with one thing. Hardcore obsession. Pure dedication and discipline.

It saved me. It can save anyone, even my homeless friend Peter.

Here’s how the world works…

Let's say that the person you love the most has just been shot.

He or she is lying in the street, bleeding and screaming. A guy rushes up and says, "Step aside." He looks over your loved one's bullet wound and pulls out a pocket knife -- he's going to operate right there in the street.

You ask, "Are you a doctor?"

The guy says, "No."

You say, "But you know what you're doing, right? You're an old Army medic, or ..."

At this point the guy becomes annoyed. He tells you that he is a nice guy, he is honest, he is always on time. He tells you that he is a great son to his mother and has a rich life full of fulfilling hobbies, and he boasts that he never uses foul language.

Confused, you say, "How does any of that f*cking matter when my son is lying here bleeding! I need somebody who knows how to operate on bullet wounds! Can you do that or not?!?"

Now the man becomes agitated -- why are you being shallow and selfish? Do you not care about any of his other good qualities? Didn't you just hear him say that he always remembers his girlfriend's birthday? In light of all of the good things he does, does it really matter if he knows how to perform surgery?

In that panicked moment, you will take your bloody hands and shake him by the shoulders, screaming, "Yes, I'm saying that none of that other sh*t matters, because in this specific situation, I just need somebody who can stop the bleeding, you crazy f*cking a**hole."

So here is my terrible truth about the adult world: You are in that very situation every single day. Only you are the confused guy with the pocket knife.

All of society is the bleeding gunshot victim.

If you want to know why society seems to shun you, or why you seem to get no respect, it's because society is full of people who need things.

They need houses built, they need food to eat, they need entertainment, they need fulfilling sexual relationships. You arrived at the scene of that emergency, holding your pocket knife, by virtue of your birth -- the moment you came into the world, you became part of a system designed purely to see to people's needs.

Either you will go about the task of seeing to those needs by learning a unique set of skills, or the world will reject you, no matter how inoffensive and courteous you are. You will be poor, you will be alone, you will be left out in the cold.

Does that seem mean, or crass, or materialistic? What about love and kindness -- don't those things matter? Of course. As long as they result in you doing things for people that they can't get elsewhere. – Jason Pargin

4. Raise your standards so high people think you're a psychopath. Screw being average.

When you reject being average people think you’re a psychopath.

This is a cope. It helps them feel good about where they’re at in life. People need good reasons *not* to chase their dreams and settle for second best. The bad news is the mind is excellent at deluding you.

When you raise your standards life gets easier. A lot of decisions are automated for you. There’s little need to watch sports, overindulge on Netflix, drink alcohol, eat one too many bits of bacon, and sit around and become overweight.

As long as you stick to your higher than normal standards the rewards that come with them are a given … and they’re huge. More money, time, freedom, energy, happiness, and fulfillment.

5. Never follow the conventional path. It's full of boredom and has the most competition.

Get a degree, get into debt, choose a job you pretend is your life’s work, then marry the first person to look at you with a hard-on.

That’s the standard path.

The way I discovered I was on this path was when I realized I was always bored. Monday morning was boring. The drive to work sucked. The office always looked the same. The customers always wanted lower banking fees & more interest paid to them.

I could predict what would happen in a week. The only surprise I’d get was whether I’d eat the Mighty Melbourne burger with beef or the Simon Says chicken burger. If my burger took too long, then that added a bit of variety (which made me rage).

We all sell ourselves a story. The key is to resist selling yourself the story that the conventional path is the right one. It sucks. Stop lying.

6. One of the clearest signs of intelligence is being able to hear an opinion you disagree with and not act emotionally.

Labels have dumbed us right down (me included).

“You’re either this or that.” Life isn’t that simple. The world is more nuanced. In between black and white there is grey and even a rainbow full of other colors.

The people you disagree with can teach you the most. They reveal a part of yourself you’ve hidden or that’s been wrapped up in ego and entitlement.

We can disagree with each other and still hug or be friends.

7. As you get older you'll want to leave your loser friends behind. It's normal.

When you’re young you try to look good.

So you choose friends that fulfill that desire. Later in life you don’t give a f*ck about looking good, so your friends change.

Many of my friends worked in nightclubs. They could get you free drinks or to the front of the line. But at 38 with a 2 year old and an online business, these types of friends are failures. They’re 40 year olds still trying to live like 20 year olds.

What you find cool changes in each phase of life. Still drinking out of a beer bong at 40 years old is one step away from being unemployed.

It’s okay to change friends. Don’t rudely cut them off. Just slowly reduce contact with the ones who you don’t vibe with anymore.

8. The more hard things you do the more successful you become.

My life has been unnecessarily hard.

During childhood we lost both our family homes to bankruptcy. Then growing up in a rough area surrounded by crime made things worse.

I always saw my upbringing as a disadvantage. Now I see it as a huge win. These challenges forced me to develop mental muscle and acquire skills most didn’t have.

It feels amazing to do a hard thing and make it through. What’s worse is to have an easy life and feel nothing at all (the default).

9. No one who climbs the corporate ladder is happy. It's a trap. Choose freedom.

My friend Dickie Bush worked at Blackrock.

He thought he wanted to be a big-time investor or work in the dealing room. Then he met people 10 and 20 years ahead already doing that job. Not one of them was happy.

So he looked into the corporate crystal ball and ran. I did the same. I spoke to General Managers and CEOs about climbing the corporate ladder. Most of them wished they didn’t. But after a while there’s no going back.

You get accustomed to a certain amount of money and status, that it’s impossible to give up.

If you want to be happier then get the hell off the corporate ladder. Stop worrying about promotions, pay rises, and job titles and go build something online that gives you actual freedom. When I did that I figured out my income could be uncapped.

10. If you have 8 hours a day to work a boring job, you have 1 hour in the morning to invest in yourself.

The life you dream of is built before and after work.

You’ll never be less busy, have enough money, or know enough. If you don’t start now you’ll never start. Instead of prioritizing a job, shift that priority to investing in yourself. It’ll make you better at the job and get you closer to building your own thing.

11. Find a dark place. Be at one with it. Enjoy it. Stay there 6-12 months.

Breakups, divorce, and death are a blessing.

When you reach these kind of dark places, stay there. Accept it. Don’t leave right away. Use the darkness as motivation. Let the darkness break your mental patterns and routines so you can become someone new.

12. Maniacs are incredible. They teach you what effort and obsession can do.

I met one this week.

They replied to comments on X for 14 hours a day for a year. They got a large following and made enough money to never work a job. They did it by being a maniac. Commenting for 14 hours a day with no breaks is almost stupidity.

The level of competition, though, is close to zero because it’s hard work. Maniac strategies work if you’ve tried everything else.

13. Avoid being busy. It means you don't know how to focus and it's a sign of low status.

Busyness is a red flag.

Saying you’re busy in productivity terms is like saying in health terms that you casually inject heroin every day.

The key to life is to not be busy so you can make space for living life. If you find yourself saying you’re busy, it’s a death trap. Eliminate calendar events as quickly as possible and treat it as seriously as a friend telling you they want to commit su!cide.

Busyness isn’t cool. It means your life is out of control and you have no focus.

14. Some of the most successful people like Keanu Reeves are bizarrely quiet. Try it.

Most people talk a lot but never listen.

You can learn a lot by having conversations where you don’t talk at all. That’s how you truly learn from someone and hear groundbreaking new ideas most miss.

15. Disappear from public life. Adopt a nickname. Then build something online with zero fear.

Being a public figure creates fear.

No one wants to be a caged animal in a zoo being watched by people with big-ass camera lenses. The easiest way to escape is to do everything online under a nickname.

You’ll then see how this fearless feeling will completely change your life. All of the imposter syndrome and need for permission will vanish. Do it. Thank me later.

( From here on I will be known as Tim Winterbottom… screw that Tim Denning guy)

16. Money isn't evil. It's a resource that'll help you reach personal freedom.

People who think they don’t pursue their goal for money are delusional.

We tell ourselves money doesn’t matter because it’s a way of keeping score. Without the scoreboard it lets you off the hook and takes away all forms of accountability. Now you can blame the market or say “people don’t get me.”

Romantic artists are the worst. So are $0 hobbyists.

Every pursuit in life requires money because it’s a resource. Even if you run a charity you still need money to help the cause it represents.

Be mature enough to understand money matters, and you can change your financial future at any time by owning it – not disconnecting what you do from money.

17. If you don't learn how money works you will always work for money.

Money is a screwed up game.

On the outside it looks like you work hard and follow a predictable path to wealth like becoming a doctor or lawyer. When you dig deeper you realize money has nothing to do with any of this.

Last year I took $1000 and turned it into $120K. Took me less than 5 minutes.

I don’t say that to brag. I tell you because that’s how simple money is when you figure out the game. Trillions of dollars flow through the internet. All you need is one strategy or arbitrage to attract more money.

But strategy isn’t enough because the financial system is messed up. It’s been getting more unfair each year. The gap between rich and poor is increasing. This is because how much an asset is worth isn’t easily visible.

And getting paid bank interest or income from a rental property seems like it’s wealth-building until you understand the dilution of money and the tax system in detail.

Example: rich people pay almost zero tax. Yet tax is the average person’s biggest expense. This occurs because the financial system is unnecessarily complex to stop people from becoming wealthy (by design).

The escape route is to obsessively learn how it works.

Then you go from working for money to money working for you. Sounds like clickbait but it’s true. This is why I spent a decade working in banking. I wanted to see from the inside. And it was worse than I thought.

18. Read every popular finance book and invest money early on.

If you don’t want to work in a bank then read the most popular finance books. You’ll start to see there are patterns. Make sure to read plenty about the new blockchain-based financial system, too, so you’re not buying treasury bonds like it’s 1970.

19. Keeping your dopamine addiction under control will help you more than any other health hack.

Motivation is a struggle for most.

How you invest your dopamine will either uplift you or leave you feeling bored and unmotivated. If you’re addicted to dopamine then cut back on TikTok, Netflix, video games, and anything with an easy payoff.

20. The strongest animals only eat plants. Eat more plants to have more energy.

Without energy you can’t achieve much.

Eat in a way that maximizes energy.

Shorter lessons

• 21. Turn off news and politics to naturally increase your IQ.

• 22. Writing online is the easiest way to attract more opportunities so you can stop asking for permission.

• 23. Read "The Bitcoin Standard." Then buy Bitcoin before major governments like the U.S. do.

• 24. Live in the city while you're young to network. Then as you get older move to the outer suburbs to save money and reduce debt.

• 25. Get an electric self-driving car instead of a gasoline one.

• 26. Exercise every day, preferably in nature. It'll keep you younger for longer.

• 27. Give up alcohol. It's a scam that'll steal your energy & help you sleep with strangers & get STDs.

• 28. Video games are fine when you're younger. But when you're older they become a time suck.

• 29. Spend more time with your parents than feels normal. Soon they'll be gone.

• 30. Go visit a retirement home so you know what dying feels like. Then use it as motivation.

31. Flow states are more important than productivity.

To-do lists won't motivate you. Feeling like 8 hours happened in 1 hour will feel better.

Less hours worked, more flow states.

32. Take your parent's plan for your life & light it on fire. The best path is one you create.

The world moves too fast to do what your parents did and be successful.

In a world of AI, all the rules are now broken. Your parents mean well but don’t follow their path in life. Carve your own. Feels better, too, because you become self-made.

33. Be wary of religion. Most are mindless cults.

No judgment here.

I got trapped in a religious cult using god as a way to do evil and extract money from people to fund extravagant minister lifestyles. It’s too easy for the lines between religion and manipulation to be broken. Best to be extremely careful or opt out.

34. Most workplaces are adult daycare centers. Break into the real world through solopreneurship as fast as you can.

A job is a great place to start, terrible place to finish.

At work if your family member dies everyone is sorry. You get time off. In the real world no one cares that your dad died, and you’re still expected to show up each day.

Corporations pretend to care about people to protect their corporate image and lure more victims. But layoff culture shows they don’t care at all. One minute “thoughts and prayers.” Next minute “you’ve been let go.” Don’t get sucker punched in the head.

Transcend to the real world as soon as possible, and away from workplace daycare.

35. Building a startup unicorn by raising VC money is one of the stupidest fantasies in existence.

In the old world you raised money from investors, used it to hire people and pay for expensive ads, then maybe did okay. The barrier to entry was high and most failed playing this game. It gave entrepreneurship a bad name.

In the new world you don’t need to raise money or buy ads. Instead you can just use free social media to build an email list and launch a business.

The best businesses are now bootstrapped & profitable, not built on WeWork-style fake revenue projections and stock price manipulation.

36. Understand human psychology and you can make as much money as you want.

Business is just a psychology masterclass.

Life is too. If you understand psychology you can persuade supermodels to date you, readers to buy your books, or strangers to give you money.

Most people who fail just don’t understand human nature. Key: humans act out of self-interest. Appeal to it.

---

I send this email weekly. If you would also like to receive it, join the 135,000+ other smart people who absolutely love it today.

👉 If you enjoy reading this post, feel free to share it with friends! Or feel free to click the ❤️ button on this post so more people can discover it on Substack 🙏