40 pieces of advice from 40 years of life

1. Do extremely hard things.

This one pisses a lot of people off.

They read it as hustle culture or burnout. Chronic underachievers hate doing hard things. They see stress as a problem. They get frustrated easily. They can’t stick at one goal for 5 years. They chase passive income. They day trade in every area of life.

I’m going to be extremely blunt here. Doing hard things is an IQ test. People who want it to be easy, relaxing or slow never reach their potential. In a world of AI, all the easy things are now done by software, automation, and bots.

“Easy” is dead.

And as soon as you get obsessed with one hard thing, take it beyond the point of comfort, and force it to work… your life will work.

It’s a pattern I can’t ignore. Every person I respect does hard things. They outsource all the easy sh*t to a mountain of monkeys. Hard is the cheat code. Sorry.

2. Have a lot of s*x.

Nothing wrong with bonking your brains out. Gotta balance out all the hard things you do with some fun.

3. Study neuroplasticity.

I credit becoming a millionaire to neuroplasticity.

Your brain either works for you or against you. What you repeat daily becomes the foundation for what your brain believes. Intentions don’t mean anything. Your brain only understands past actions. Your identity is formed by action.

So take the actions of your ideal mentor and your brain will rewire itself around that goal. But train your brain to be lazy and procrastinate, and it will help you to compound that identity all the way to loserville and extreme poverty.

4. Master game theory.

Every game in life is rigged.

Building a business, climbing the corporate ladder, real estate, investing in stocks, having a family, learning new skills, etc.

To win these games most people try to work harder. But you only have so many hours in the day and everyone else is already playing the work harder game. You must understand how a life game works to manipulate it in your favor.

That happens when you understand game theory. Biggest lesson I learned studying game theory: Effort spent inside a rigged game gets absorbed by the game.

It also means once you understand a game you can rig it in your favor. The opposite is also true. If you don’t understand the game you’re playing and the incentives, it’ll be rigged against you and you’ll work harder and harder and not win.

5. Focus on making more money, not saving.

You cannot save your way to wealth.

Once you understand inflation and currency debasement, you realize the math is working against you every day. This is why the cost of living feels like it’s rising higher than your income. But once you understand the math it makes sense.

Your skills and experience must be used to make more money. That’s the mindset that builds wealth. And the internet creates leverage to allow you to reach more people faster so you can make more money faster.

Internet leverage works in your favor if you let it.

But most people hide.

They’ve been taught to be invisible out of fear or weird privacy reasons. So the opportunities can’t find them because no one knows they exist. Most people think the solution is to keep asking for permission and applying for opportunities. It isn’t.

The challenge with that approach is every opportunity is now global. You’re competing against everyone else in the world with the same skills and experience. Some of them are probably more talented than you.

Permission-seeking is a losing game by default.

Income = Skills + Experience + Visibility

6. Make decisions because 99% are reversible.

I learned an uncomfortable truth when I hit 40:

Most people don’t actually make decisions. They don’t say yes or no. They say “maybe” or “someday, mate.” And this f*cks up their life. Because the only way to know if an opportunity works is to have a go.

If you really want to be a psycho, the only way to make an opportunity work is to force it to work and not let any other outcome occur.

You avoid decisions because you see risks and downsides.

What you forget is that most risks are manageable. Say yes, try it, and if it doesn’t work, change course. Most decisions can be reversed. So saying yes is better than saying maybe, which only leads to procrastination.

Mental Model = Yes + Pivots

7. Chase your obsession.

To win in life requires intensity.

If you treat every opportunity like a hobby, hedge all your bets and never truly go all in – nothing much happens. You just get ignored because nobody feels anything.

Intensity creates emotion. It forces people to feel your vision/mission. It’s what helps you stand out with no extra skill or talent.

Intensity comes from obsession. It’s going all in. It’s acting like a psycho. It’s embracing your weirdness. It’s being unreasonable enough to believe you can change the world in some small way.

Before you die, it’s worth chasing at least one obsession beyond its reasonable conclusion to see what happens. You’ll be surprised when you do.

8. Hang around high performers.

I shouldn’t admit this, but I spent most of my life hanging around losers – drug addicts, gamblers, alcoholics, sleaze bags, players, etc.

My life changed when I went to a Tony Robbins seminar and he told me to raise my standards. So I did. I raised the bar. I forced myself to hang around optimists and people building stuff. Then I joined paid masterminds.

It changed everything.

You can’t escape mediocrity if you’re not around a handful of people doing the same.

9. Take risks or you’ll get painful regrets.

Society programs you to avoid taking risks.

It’s how they chop you back down to size, force you to follow orders, brainwash you with politics full of hidden agendas and bribes, and get you to settle for second best.

This model works for some people, but if you’re reading this, it likely doesn’t work for you. It didn’t work for me either.

This tweet I once read changed my mind about risk:

Playing it safe isn’t actually safe. You’re just trading the chance of winning for the guarantee of nothing.

Playing it safe looks smart.

But it’s a hidden avoidance of growth and change, which only makes life worse the longer it persists.

If you avoid risks for long enough, you end up with deep regrets about what you could have done with your life. Ouch. Worse than an ana1 probe.

10. Embrace your weirdness.

11. Never try to fit in.

Fitting in is how we all act by default, whether we admit it or not.

Trying to fit in means not saying the wrong thing, adopting other people’s beliefs and opinions, staying small, wearing an approved uniform, talking like a robot, and finishing emails with “kind regards” or “let’s circle back and focus on synergy.”

Fitting in is people-pleasing in disguise.

I learned the hard way in corporate that you can never please everybody. Someone is always pissed off with your decision or opinion. Sometimes they just hate you because of your gender or race, too, which sucks.

The better approach is to refuse to fit in. It’s to be yourself. The personal branding knobs call it authenticity. I just call it being congruent and not lying to people about who you really are. You choose.

12. Believe anything is possible.

Most people don’t believe this truth.

Not because they’re stupid, but because the news and politics trained them to think small and join a tribe. You’re taught to outsource your resourcefulness to a leader, government, or corporation and in return they’ll look after you. Haha.

This is one of the greatest lies ever told.

No person or organisation is looking out for you. They’re focused on looking out for themselves. Once you see this truth you can’t unsee it.

I learned this truth the hard way when I had a client who was a lobbyist in Washington. It became clear that incentives and money drove decisions, not logic or neediness. Save yourself before you can save others.

13. Quit climbing the corporate ladder young.

I didn’t quit climbing the ladder to nowhere until 34.

Too late if you ask me. But better late than never. What changed my mind is I met with senior leaders who’d got to the top. The ones making $1m+ a year salaries and bonuses.

All of them lived in quiet desperation.

They had some money, although they were taxed to oblivion, but they had no free time. The more I spoke to them the more I realized they just wanted a day of zero meetings, but it didn’t exist.

The younger you realize the corporate ladder is a scam, the happier you end up being (can’t wait to tell my two daughters).

14. Pay to get help for big problems.

Going it alone with trial and error is the dumbest strategy in the world.

And I did it for 5 years. Cost me millions of dollars. Eventually, I paid to get help and ended up moving 3 times faster. Speed is critical. Every day you don’t figure out your life’s problems, you waste your precious time which can never be recovered.

Money is a mythical object. It doesn’t come with you when you’re dead.

And you can always make more money through the internet. Since I’ve learned this lesson I’ve spent more than $500,000 on coaching and consulting.

Investing money in yourself is a cheat code. It compounds faster than buying an Airbnb, investing in the S&P 500, or getting another degree or certification that everybody else has already.

Being a tightarse is an extremely expensive mistake.

15. Fix your mindset to fix your finances.

Your income is directly proportional to your level of personal growth. Most people are unwilling to change, so their finances stay the same.

16. Believe the world is working in your favor.

Every failure or rejection is protecting you from something.

A few years back, a colleague stopped me in the hallway to talk about total B.S. It annoyed me. I went to lunch 15 mins late.

During that time a madman drove his car up the footpath outside the office and killed a bunch of people, including a baby.

Had I been on time for lunch I would have been standing on the footpath with my headphones on right where the car would have hit me.

That annoying colleague saved my life. The inconvenience worked in my favor.

17. Study human psychology instead of math.

Human thinking runs the world. Understand your mind and how others think, and you’ll have a cheat code for getting what you want. Feels like Jedi mind control.

18. Ignore opinions from unsuccessful people.

They can find problems with every solution.

19. Nobody is thinking about you.

They’re too busy thinking about themselves. They have too many problems of their own to give two sh*ts about what you posted on InstaBAM.

20. Use money to create good.

Money is a resource for good. Yes, it can be used for evil or to buy luxury junk. But money can be used to do good too. Money isn’t evil in itself. How you use it determines its goodness… and you get to choose.

21. Do work that doesn’t feel like work.

You don’t really wanna sit on a beach and do nothing. Deep down you just want to stop doing boring work, and use your creativity and imagination. Solve for that and you’ll fall in love with working hard. Boring work is the only cancer.

22. Dare to build a personal brand.

Sharing your ideas and experiences attracts people to your world. People carry opportunities – not phones, platforms, or computers.

23. Start a weekly newsletter.

Publish your deepest thinking here. Let it wow a small crowd. Nail the headlines if you want readers.

24. Write online daily.

Use writing as a form of deep thinking. It benefits you even if nobody reads it. Choose only one platform. Master the psychology and culture of that platform. Read a lot of content on that platform. Then write your own posts.

25. It's never the right time to do anything.

It’s either today or it’s a p0rn fantasy. Stop kidding yourself.

26. Build a digital business.

You probably won’t get wealthy and have freedom by earning a salary. A salary lets someone else profit from your work and your unrealised potential.

27. Get good at dealing with uncertainty.

28. Make decisions instead of saying maybe.

A decision is yes or no. Every other outcome is procrastination.

29. Get wealthy then help others.

You can’t help anyone if you’re broke and obsessing over money 24/7.

30. Never become a victim.

Victims are insufferable. Appealing to people’s charitable nature has an extremely low chance of success and is manipulation. Turn a tragedy into a hero’s journey that lets you climb out of rock bottom and inspire people.

31. Never outsource blame.

You own every outcome. Always placing blame on yourself gives you more control, even if somebody else did f*ck up.

32. Never trust a politician.

They’re professional liars. Nice words with no actions. They will try to buy your vote with free central bank money they created from nowhere.

33. Never believe governments fix problems.

They create more problems than they fix.

34. Never believe someone is coming to save you.

The incentives to save you or be your free mentor are extremely low.

35. Plan in decades, execute in days.

The vision should be big. The execution should be extreme.

36. Don’t worry about publishing a book.

Authors are mostly broke. Have you noticed?

The authors who do well have massive pre-built audiences. And monetizing your skills and experience with a $20 book where you don’t get the reader’s contact details has the worst ROI in history.

37. Create proof-of-work.

“Trust me, bro” doesn’t f*cking work anymore. Produce these instead…

Experiments. Results. Testimonials. Case studies.

38. Don’t drink alcohol.

I reached 7 years sober the other day. Never felt better. No losing a day to a hangover. Acting like myself. In control. A good role model for my two daughters. Seeing reality as it is, not through beer goggles.

Alcohol is a perfect lie.

Straight life is the best life.

39. Ego is the enemy.

Realize you don’t know 1/100th of f*ck all. That’s how you win. Think you’re King D*ck and people will run away. Humble people learn. Big egos think they’re too good to learn, so they miss new opportunities and their skills fade.

40. Be cringe.

Cringe = Bravery

Cringe = Doing what already works

---

If you found this helpful:

1. Follow me @timdenning for more posts on money, freedom, and digital businesses.

2. Then, I'd appreciate it if you could scroll back to the top and repost this X article to help others.

— Tim