40 Pieces of Life Advice for 20-Year Old Me

I turned 40 today. Can hardly believe it. The past 5 years, especially, have flown by.

I traveled from Croatia to Prague on my 35th. In transit, money was stolen from my suitcase. I also remember changing my Facebook profile picture that day—the shirt I wore is packed in my suitcase now, profile picture unchanged. That sort of thing happens at my age.

No way I would’ve predicted I’d be here at 40. Imagine telling my 20-year old self:

“Here’s the thing, Dude: At 40, you’ll be homeless, jobless and newly married. But, hey, you’ll be in Mexico! No, not at the beach. All beaches are closed—there’s a worldwide pandemic. The world got weird after Kobe died. But I’m sure things will get back to normal between now and election time.”

20-year old me:  “Oh yeah, it’s an election year. Who’s President?”

Me:  “Donald Trump”

20-year old me:  “Haha, Dad would think you’re hilarious—his favorite movie is Back to the Future. Remember, Ronald Reagan, the actor? Do you have two television sets?”

Me: “Nah, I don’t have one. In fact, I haven’t watched TV in a long time.”

20-year old me might’ve wrecked himself for not taking school more seriously.

As it is, life is beyond my wildest dreams. Either the worry gene skipped over me in the fam, or I still have prayer reserves leftover from when I was a kid. Lady O & I have no idea what the future holds and wouldn’t have it any other way.

If I have any worries, it’s to make sure I’m learning, loving, exercising, and appreciating every day.

The wife suggested last night I do a Top 40 list for my 40th. So I decided to give 20-year old me life advice.

1. Keep a journal. Your mind will adjust memories to make them consistent with your current circumstances. You’ll want to look back and see what you thought was a big deal, what you believed and predicted. You can’t imagine the value of consistently writing (which is thinking).
2. The self-educated don’t need credentials or validation. They’re results-focused. When I was your age, I had to buy all the shit you get free now. Use it.
3. Don’t bother telling people what you plan to do—just do it. Lil Wayne had it right: “Real G’s move in silence like lasagna.”
4. As fast as possible, work for someone who is in a lot of ways just like you. One person who thinks you resemble a younger version of themselves can make your whole career.
5. You don’t need a leadership title to be a leader. If you see potential in someone who doesn’t see it, offer to help them. That’s all it takes to be a leader.
6. They say don’t gamble with friends because it’s an easy way to lose friends. But some of my best memories are from gambling with friends. I say it’s worth the gamble.
7. Figure out how to maximize your energy. Pay attention to how you feel when you eat clean, exercise everyday & sleep well. Enough of those days added up makes all the difference in the world.
8. Pay attention to how your body reacts to people & ideas. If muscles twitch or you feel energized, your body is telling you to take action. Conversely, if you hear or read something that drains your energy even slightly, reconsider. Your body is smart—don’t underestimate its connection to the mind.
9. Your family will always encourage you to play it safe rather than take risks. The reason is they share your pain of losing much more than they share in the fruits of your success. Always seek wise counsel, then draw your own conclusions.
10. Life is single-player. People are mostly self-interested. Yes, even those who most love you. The biggest red-pill for a man is seeing how fast his first love moves on. You’re not an exception. Just remember all that you experience, and how you experience it, is a creation inside your own mind. Improve your experience by taking care of your mind.
11. Find your tribe—your inner-circle. Start building & investing in those relationships. That person you met a few months ago, one day you’ll say you’ve known them for 15 years. Relationships compound the same way money does. If you wouldn’t delay investing to miss out on compound interest, don’t delay surrounding yourself with the right people.
12. Once you find the right people, be just as excited for their success as your own. Since you’ve surrounded yourself with studs, there’ll be lots of wins. Wonderful. You’ve multiplied your opportunities for joy & happiness. It’s one of life’s little-known cheat codes (you’re not even required to share in the losses).
13. Words are powerful. None more powerful than “I love you.” Tell your tribe you love them. Men have a harder time saying, “I love you,” than women do. That’s because when a man says “I love you,” what he means is “I would die for you.” Go first. It doesn’t matter if they say it back. And don’t forget to love yourself. A younger version of you worked hard so you could be where you are today.
14. Ask your tribe what they like about you. Their answers will surprise you. Then do more of that.
15. Those who would mistake kindness for weakness won’t be smart enough to know when it’s a test. Cut ’em loose.
16. Crave criticism. Consider it feedback or data to be considered. Weigh it according to how much you respect the person criticizing you or your work. Good litmus test: “Would I hire this person?” If not, ignore it.
17. True self-confidence is rare because it’s hard to attain and there are no shortcuts 1) If and when you encounter unexpected hardship, you must endure it without alcohol or drugs 2) You’ll develop an enthusiasm about yourself when you can force yourself to do things others aren’t willing to do.
18. Our world is filled with people who are 1) unaware 2) have no desire for the truth 3) can’t even bear to tell themselves the truth. In fact, truth offends them, so they will go to great lengths to protect themselves from it. It’s as if a mental block exists in their head to protect themselves from uncomfortable thoughts & feelings. So unaccustomed to dealing with honesty, they’ll accuse you of lying too. In 2120, it will be the same. Human nature doesn’t change.
19. My generation, thanks to social media, is the first to see how arrogance and meanness ages people. Spoiler: Men grow to be friendless and women disgruntled.
20. Even though we’re all self-promoters now, resist exaggerating your own importance. Everything you cherish will eventually be destroyed. All things go to zero.
21. Life is better when you can be “fascinated” instead of “frustrated.” When you’re stuck in traffic because one person is looking at their phone in the left lane, only to go around and see everyone is late for work because of one guy checking Instagram on the freeway—that’s fascinating.
22. If a “friend” tells you they’re too busy, it means you’re not a priority. If they don’t suggest another day & time, you’re really not a priority. Cut ’em loose. You want people in your life who value you (and your time).
23. Don’t waste time debating politics with someone who doesn’t know both sides of the argument. However, don’t be ruthless in declining a debate—allow for exceptions if they don’t have access to Google.
24. Spend time in other cultures as soon as possible. Not a small enclave within your own country i.e. Chinatown or Little Havana (although that’s not a bad idea), But actually leave the US and stay a while. You need to know just how many of your beliefs and thought patterns are conditioning.
25. Everyone wants their life to improve, but not everyone wants to improve their life. Therefore, don’t help people who won’t help themselves. There are too many people in this world who genuinely need help to waste your time with those unwilling to better their circumstances.
26. If you give someone advice and they don’t take it, then ask for advice again, point them in the direction of 4.57 billion other possible helpers (Internet users, 2020). This way, you’re allowing them to figure things out in their own time, at their own pace. How generous!
27. ‘Know-it-alls’ never seem to know their certitude repels people. It’s fascinating.
28. Interpersonal skills are at an all-time low thanks to 10 years of human screen-addictions. If you  have enough self-awareness to know this could be you (poor eye-contact, extreme literalism, etc.), be a great listener instead of the opposite.
29. Listen more than you talk, and don’t talk to talkers. You may think they’ll want you to share in the pleasures they get from talking by allowing you to talk. But don’t kid yourself. And don’t think next time will be different. Say, “Hello” instead of “How are you?”
30. You’ll live a more peaceful life expecting incompetence and being pleasantly surprised than the reverse. Unless someone works with you or for you, expect incompetence.
31. Happiness is your responsibility. If you’re not happy now, you won’t be happy when you get what you want. Since happiness & gratitude are intertwined, good news is you can always find a reason to thank someone. The more sincere the ‘thank you,’ the more happiness-inducing. Text messaging makes this easy: “Hey man, just want to tell you how much I appreciate our friendship.”
32. God may have made Hollywood celebrities a thing just to demonstrate that fame & fortune don’t make for a happy life.
33. Learn to negotiate. Make it a study. All those classes in school and not one of them taught you to negotiate—something you’ll be doing the rest of your life. Take six months out of your 20s and dedicate it to studying negotiation. I once worked on a team of 50 salespeople, where the ability to negotiate could dramatically impact one’s income (and career trajectory). Guess how many studied negotiation? It’s a rare skillset.
34. Two things to study continuously: communication & human nature. The former because at present there is no more important skillset—it used to be hunting (for men) and gathering (for women). Read, write, read more, give presentations, read more. Study the latter because it will make you a calmer and more strategic observer of people.
35. Take time to meditate. Stare out the window. Not to see what’s going on outside, but what’s going on inside. Gaze at the stars. Remind yourself of the vast space of time before & after you. A little insignificance will balance your ego
36. Get to acceptance as fast as possible. By acceptance, I mean welcome everything that happens in your life. The best time to prepare for a crisis is before it comes. An overreaction is an indication you either didn’t prepare or lack imagination [to think this couldn’t happen].
37. On sex. Will Durant said it best, “Understand that sex is a river of fire that must be banked and cooled by a hundred restraints if it is not to consume in chaos both the individual and the group.” If you can learn to delay sexual gratification when young and it’s most difficult, you’ll develop an edge lesser men can’t understand.
38. On money. A man on the way to his first million sprints through soft sand while helping others build their sandcastles along the way. His second million is a stroll on the boardwalk while others build sandcastles for him. He still helps others build their castles, but his advice is more valuable than his labor.
39. On women. Much of what you’ve been taught about women isn’t true. Seek femininity, sweetness and a willingness to be vulnerable. Avoid the arrogant & disrespectful.
40. Invest well. You can’t believe what you can see & do once you get money out of the way.

Pass this list down when you turn 40, and add to it. Much of what you think is obvious is not obvious to most people. The world has never seen anyone just like you, and there’ll never be another.

Penetrate the world with your unique sum of talents, books you’ve read, people you’ve met and places you’ve been. Give us what you got [for a pork chop]!

Just remember, the easiest thing in the world is to be like everyone else. Don’t think for a second you can’t create the life you want—you can—but only to some extent. And to that extent, ride that motherfucker hard to the edge.