Lessons for your 18-year-old-self
May 19, 2023
Some time ago, my husband was browsing Twitter when he came across a post he loved. He asked my three boys and I to listen as he read us 38 lessons this young man wrote for his 18-year-old self.
Of course, there were many nuggets of wisdom in there that corroborated what we’d been teaching our kids — but you know kids tend to receive wisdom better when someone else agrees with you!
We read the whole thread and I mentioned how fun it would be to interview that writer. Well, Orlando did something awesome. He got in contact with Tom and asked him if he’d be willing to be a guest on my Connect with Caro.
Tom said yes.
Tomorrow, May 16th, 2023 at 12 noon Tom Harari and I will be talking about Defining Your Own Path and Staying Healthy, Wealthy and Wise. Click here to save your seat.
Tom has also graciously allowed me to share his content with you. I hope you enjoy this article as much as my Five Fingers did. Maybe you have some 18-year-olds that could benefit from this content as well. Be sure to invite them to tomorrow’s interview!
Today, I turn 38.
I’ve raised millions of dollars, married twice, had a kid, and recovered from devastating injury and depression.
Here’s 38 lessons I’d tell my 18 year old self:
First—I don’t know everything but I’ve learned a few things. This is my list to myself. Your mileage may vary.
Here we go…
1. Believe in yourself 100% of the time
You’re a dreamer and a creative mind—that’s a gift. Trust your instincts and believe in yourself even when no one else will. How can you expect anyone to believe in you, if you won’t believe in yourself first?
2. Take much more risk than you think is sane
As you get older your and eventually get married, your risk profile changes. It’ll never be more prudent than now to take massive risks.
3. You won’t truly grow up until your heart gets broken
Losing people is part of life. You’ll fall madly in love, think someone is your soul mate, and then see it all crumble. Own it. Don’t avoid the pain but know it’s temporary and pick yourself up. You’ve just grown as a man.
4. You’ll also break other people’s hearts
Someone will feel the same about you and this time you won’t be into it. This will be devastating to them. Remember they are a human just like you. Don’t ghost, ever. Have the balls to end things in person with grace and empathy.
5. Drop loser friends without remorse
They won’t get you to where you want to go. I’m not talking about childhood friends who may not be as ambitious as you. I’m talking about the ones who only want to party. They will drag you down. Ditch them.
6. Start a habit of investing.
Compounding is the 8th wonder of the world, but that’s not why you should invest early. It’s to develop the muscle of delayed gratification. Money is a tool, learn to use it (not just give it away to buy crap).
7. Lift 4-5x per week with progressive overload
If you start young you’ll have an easier time packing on lean muscle. It will hurt at first. You’ll get callous fingers. Toughen up. Lift heavy and it will transform your whole life.
8. Eat more protein than you did in HS. Like over 150g per day.
You need much more protein than mom (or the lunch lady) was serving you. Greek yogurt, eggs, and whey protein need to be part of your daily routine.
9. You can have anything you want, but you can’t have everything you want
You’ll meet a mentor in @justinkan who will teach you this but I’m teaching it to you now. You can literally bend the universe to your will, but you need to pick one thing. Your ego won’t like that.
10. Whatever you decide to do, don’t half-ass it.
Shiny object syndrome is real. You’re especially susceptible to it. Recognize that and commit to fully immersing yourself in whatever you decide to do. That’s the only way to achieve mastery.
11. Learn how to do financial modeling and start accruing equity
To build generational wealth you must own equity. Learn how equity works. Learn how to build financial models. Then aggressively pursue equity positions while you’re young.
12. Travel more, even if it stretches your budget
Traveling the world will open your eyes and broaden your mind. You’ll learn empathy for other human beings and experience the richness of the world. Don’t let money be the reason you avoid this. It only gets harder as you age.
13. Don’t date for a long time
Shit or get off the pot. If you’re dating for more than two years and still haven’t proposed, just end things. If it’s not a hell yes, it’s a no.
14. It’s OK to have people leave your life
Friends come and go. Relationships end. That’s OK. Avoid Facebook and other social networks that try to manipulate this basic fact of human life.
15. Always bet on yourself
Never think twice about investing in yourself or betting on yourself. When in doubt, go back to lesson one.
16. Don’t ignore red flags
In business partners, friends, and lovers. If someone shows you who they are, believe them. Your gut instinct developed over millenia. Listen to it.
17. Learn to master your mind
So much of how you ‘feel’ is your mind playing tricks on you. Start meditating. Learn breath work. Become OK sitting still with just your thoughts until you develop the muscle to control your mind. Or your mind will control you.
18. Steak is eaten medium rare
Salt, pepper, reverse sear and char for 2 min. each side to get a nice crust.
19. Start publishing your writing
The best time to start writing was 20 years ago. The second best time is now. Share your gift with the world. Even if it impacts one person on the other side of the planet, that makes it worth it.
20. Getting drunk is stupid
Seriously, what’s the point? You’re killing your body. Learn to have a single quality drink and enjoy a light buzz or don’t drink at all. You’ll learn this anyway as you get older but take it from me—it’s pointless.
21. If any substance has control over your, you’ve lost
You’re smart enough to avoid drugs, but even things like alcohol and caffeine are substances which you can become dependent on. Fuck that. Nobody and No substance should have control over you. Only you control you.
22. Hold yourself to a ridiculously high standard
In health, nutrition, fitness, education, business—no one will tell you what to do. You’re on your own. Be your own leader and hold yourself to a high standard. Lead yourself.
23. You’ll regret the things you didn’t do, not the things you did
You’re going to make a lot of mistakes. 99.9% of them you’ll recover from. And you’ll have a lesson to learn from. But the true, deep regrets, come from actions you didn’t take.
24. Call your grandparents more
They won’t be around forever. You know this. Even if they are in seemingly good health, one day you’ll get the call from someone in your family that grandma and grandpa passed. Call them and visit them as much as you can.
25. Your parents did the best they could
It’s easy when you’re young to blame your parents. Drop that immediately and give your parents some slack. They did the best they could and they’re not perfect—nobody is.
26. Nothing feels better than helping others for nothing in return
Most people are selfish and do nothing for others. Break that chain and be the one who gives, not the one who takes. And expect nothing in return—the highest form of help.
27. Get aligned on the big things
Square away the big things with partners (both business and love). You’ll always have small disagreements but if you’re locked in on the big questions, everything else is easy.
28. Don’t try to beat the market
Learn how stocks work, how options are traded, and how companies are valued, but when it comes to your personal portfolio choose 3-5 ETFs and dollar cost average. Set it and forget. You’re not Warren Buffett.
29. Showing off your money is a fool’s game
Wealth is what you don’t see. Focus on building wealth, not trying to look cool in front of people you don’t care about.
30. Barbell strategy for everything
When you get a little older you’ll read several books by @nntaleb. You’ll learn the barbell strategy. Safe investments on one side, speculative moonshots on the other. No mediocre in-between stuff. That’s for suckers.
31. Take things lightly
As a young man you’re full of energy and adrenaline. You’ll want to fight and battle every perceived slight. Calm down. Learn to take things easy and be chill. Focus on your long-term mission and let nothing knock you off.
32. Never tolerate disrespect
You can still take things easy while setting boundaries. If someone disrespects you, end that relationship. Be ruthless in pruning the energy that’s around you. Nobody is entitled to be in your circle. It’s a privilege.
33. Remember people’s names
Someone’s name is the most important word to them. Don’t be rude and repeatedly start every sentence with the other person’s name, but pull it out when you see someone and watch them light up.
34. Be a connector
Always think about who in your circle you can connect with others and make introductions. Over time you will develop so much goodwill it’s ridiculous. You want your bank of reciprocity to be overflowing. Plus it feels good—see Lesson 26.
35. Avoid bad-mouthing about other people
If you want to vent get a therapist. Talking negatively about someone when they’re not in the room just signals you would do the same about others. Not a good look.
36. Be long-term patient and short-term impatient
You need both a sense of urgency to go after your dreams with the willingness to wait a long time for them to come to fruition.
37. Watch sports moderately or not at all
Spending all your free time watching other grown men play a sport means you’re not developing yourself. Enjoy entertainment but don’t let it consume you.
38. Nobody cares
The Spotlight Effect is real. You think you’re the center of a reality TV show and everyone is watching your every move. They aren’t. Try things out. Be willing to look stupid. Everyone is in their heads worrying about themselves. Have fun and live your life.
The number one rule is don’t disappoint your 18 year old self (credit: Taleb). I’ve done a good job of that.
If any of this hit a nerve feel free to retweet it to share with others.
