Not long ago, while half-assing an attempt to Marie Kondo my closet, I found an old shoebox that led me to re-discover a photo of my 13-year-old self. 

I promptly took a photo of that photo and emailed it to my mother. 

Unsurprisingly, my mother said that I looked absolutely adorable. But for me, the photo induced a subtle urge to vomit. Maybe it was because of the curtain hairstyle, or the argyle sweater vest, or the mouth full of orthodontic hardware. (Or the unfortunate combination of all three).

Or maybe it was because the photo was taken at my Bar Mitzvah party, and that was the day I was supposed to become a man…or something. 

It’s astonishing how much we change; and yet, how little we change. And to think that any of us become men (or women) at the age of the 13 is patently ridiculous. 

The female brain doesn’t fully develop until the age of 21. The male brain doesn’t until the age of 25. And personally, I don’t think I started to become a man – or the man I want to be – until the age of 35.

I doubt I’ll ever again look at that photo of my 13-year-old self (at least not purposely). But there are some things I wish I could go back and tell him: 

1. Let your parents know you love them, every day. Even on days when you don’t necessarily like them. Because the truth is, you don’t know how many days you have left with them. The next time you see one of them could also be the last. The same applies to everyone else who’s important to you. 

2. You know that girl you’ve been crushing on? Well, you’re going to feel this way about a lot of girls over the coming years. You may not understand this now, but always remember: She’s just a girl. She has flaws and imperfections and insecurities just like everyone else. She’s not to be worshipped. And she’s not going to solve any of your problems. Oh, by the way, having a crush is a colossal waste of time. Be bold. Put yourself out there. Do something that will lead to either a connection or a rejection. Then, you can move forward. Sitting around and thinking about her is just keeping you stuck. 

3. A whole lot of people are going to tell you to take a certain path in life. You are going to hear a lot about finding a nice, corporate job, getting married, and having kids. But you don’t have to do any of that if you don’t want to. Carve your own path. Do what feels right to you, and don’t feel bad about it. Humans tend to have a weird quirk: They want you to make the same decisions they did, even if those decisions didn’t work out for them or make them happy. 

4. Yes, George Carlin is right. About pretty much everything. 

5. Spend more time doing the things you love. Foremost, because you love them. But also because they will become valuable skills that may lead to great success. 

6. Find a mentor as soon as possible.

7. Don’t try to find happiness. It’s an exercise in futility. Happiness is an abstract concept that nobody can explain, define, or describe. Instead, get rid of anything or anyone making you unhappy. And take action steps toward creating the life that you want for yourself. When you do, you won’t need to find happiness. Eventually, happiness will find you. 

8. Don’t be a Democrat or a Republican. Be an Independent. More importantly, be an independent thinker. If there’s an issue you truly care about, do your own research and draw your own conclusions. 

9. Don’t let anyone treat you badly. Ever. 

10. Don’t try a cigarette. Seriously. Just don’t. Not even once. 

11. If you’re going to spend such an embarrassing amount of time looking in the mirror, repeat the words “I love myself” while you do it. 

12. If someone has a bigger house than you, it doesn’t mean they are happier. In fact, if someone has a bigger house than you, there is a good chance it means they just have more space in which to feel gloomy.   

13. Not long from now, you’re going to be at summer camp and you’re going to stumble across your bunkmate peacefully sitting alone in the woods. When you ask him what he’s doing, he’s going to tell you that he’s meditating. Instead of calling him a weirdo, ask him to teach you his ways. 

14. In about 10 years, you’re going to be introduced to something called Social Media. You’d be wise to limit the time you spend on it. Or just stay away from it altogether. 

15. It’s okay if there are days when you have nothing to do. And it’s okay if there are days when you choose to do nothing. But it’s not okay to complain that you’re bored. You live in an indescribably big world with an infinite number of things to do. When you complain that you’re bored, you’re not actually bored. You’re just an asshole. 

16. When someone tells you they’re honest, don’t believe them. Honest people don’t need to tell you they’re honest. They simply speak the truth and then act in congruence with what they’ve said. 

17. When you read a self-help book that resonates with you, make the effort to apply what you’ve read to your life. Otherwise, it’s just mental masturbation. 

18. Speaking of masturbation, there’s nothing wrong with it (unless you do it compulsively as part of an addiction). And there’s nothing wrong with sex, either. American culture is oddly schizophrenic about sex. It uses sex to sell literally everything and then tells us we’re bad for wanting it. But you’re not bad for wanting sex. You’re not bad for thinking about sex. And you won’t be bad for having sex. Sex is normal and healthy. We’re all sexual beings. Men like sex and women like sex. So, embrace your sexuality. Let your freak flag fly, or whatever. 

19. If you do something nice for someone, do it out of the goodness of your heart. Don’t expect anything in return. If you do expect something in return, make your expectations known. 

20. You don’t always have to be the funniest person in the room. But you should still open your mouth and attempt to be. 

21. If someone pays you a compliment, assume they mean it and just say Thank You. That’s it.

22. Don’t be so quick to judge. Someone you assume to be pleasant could turn out to be an all-star jackass. And someone you assume to be off-putting could turn into one of your best friends. 

23. Even if it’s scary, even if it’s unsettling, even if you have to change course along the way, start your own business as soon as possible. Sitting mindlessly in an office cubicle and building someone else’s dream will prove to be a significant waste of your time and talent. In fact, it will eat away at your soul.  

24. Celebrate your friends’ successes. Jealously will destroy you (and your friendships). Besides, what one man can do, another can do. 

25. Learn all the stereotypical man-stuff, like how to change a tire or start the grill. You’ll save yourself a lot of humiliation down the road.

26. You can say NO.

27. Laugh your ass off. A lot. 

28. You will come across a lot of platitudes about comfort zones. (Great things never came from comfort zones!) Yes, they are annoying. And yes, they are cheesy as hell. But they are also true. If you never do anything that makes you uncomfortable, you’ll never grow. 

29. Make journaling a daily habit. 

30. Read more books. 

31. Take more walks. 

32. Never lose your child-like sense of wonder. Each day can be an adventure if you want it to be. 

33. Don’t eat so much goddamn bread. 

Oh, and one more thing, I guess. If many years from now you find an old shoebox in the back of your closet, don’t be afraid to open it up and look inside.