I’m 39. Here’s What I Wish I Knew at 30

This right here is an iNote that I started several years ago, and it's got in it things that I wish I knew when I was 30, things that I wanted to remember. And I wanted to share with you guys those things in the hopes that they help you navigate some of the pitfalls that I fell into face first. So the first thing I have here is that there's no choice to not feel your feelings. You can deal with them consciously or unconsciously. You can deal with them in the present tense, or you can defer them to deal with them later. The longer you defer feeling your feelings, the higher the interest that accrues. And what I've seen is that for people in their 20s, they can get by by not feeling things. So you have a rough breakup, you just self-improve your way through it. You go to the gym, you get through, you start a new relationship, you're good. Or you're full of stress at work and you blow off steam by drinking on the weekends. So you deal with feelings by piling shit on top of them, basically. In your 30s, the bill begins to come due. You're gonna see it in bodily issues, ongoing relationship problems, things that are stuck in your work and your business that you're smarter than but that keep Being a problem. And so the big theme is that my 30s were about feeling the stuff that I had repressed for a very long time and dealing with the consequences of that repression. Some signs that you may— well, we all are, but signs specifically of where you may be repressing that were important for me: if you find yourself gossiping or complaining to someone that you know, or even someone in the news, that's often unprocessed anger and resentment. And if it is someone in the news, it's usually not towards that person, It's towards someone who represents something about that person in your own life. And it's safer to blow off steam towards that individual who you'll never come into contact with. If you haven't cried, as many men haven't, for months or even years, and this is certainly where I found myself, that's an enormous amount of unprocessed pain and grief. A lot of people don't know why you would wanna feel pain and grief, and I won't take the time to explain it to you, but it's really important, if only because if you don't feel it, you will become numb to beauty. And that is a tragedy, 'cause you can get everything you want, but if you can't feel it, it doesn't really matter. So how do you feel this, or how did I? I think one of the best ways in is to do breathwork. It is like a cheat code for life. There's so many ways to do it. I've got a video that I'll link to, but it's basically, whoosh, whoosh, ah. You do that for 20 or so minutes, and you're gonna find that you are feeling things that you didn't think mattered. You're gonna be reviewing that conversation you had where somebody made a slight that you just thought didn't matter, but it actually stung. And as you begin to do this, you clear out the pipes Not just of your day, but of your month, of your year, of your last decade. It can take a while to do, but the benefit of this is that if your emotional life is like a pipe and the stuff that you haven't felt is like sludge on the side, what you're currently experiencing in any moment is not just the moment, it's all of the sludge that has got like stuff in the water that is coloring that moment. But once you clear that sludge out and you feel it, you can be present now. It makes you more creative, more dynamic, more charismatic. So do your breathwork. Another thing that is huge that I would've thought silly, but dance. Dance is so important. Get comfortable being weird with your body. And I include making noises in that. Today, what I will do in the morning, on the best mornings that I have, is pick a song that I like, go into a private room, and just be weird with my own body. Move in a way that feels good. It's better than traditional weightlifting for feeling good. It's better than traditional stretching for actually loosening up your body. You can still do those things, but the experience of bodily love is best expressed when you hear a song that you enjoy and it hits your body. And like you might see a toddler, it just moves you. At first, it can feel strange to let that happen, to like let your body move to the music because of the times that we've been judged and we've developed this muscular armor. But doing it is one of the most joyful things you can do. opens the possibility of joy throughout the rest of your day and your life. Related to this, it is so important for men, and there's a flip side for women, but you need to be able to get in touch with your feminine side without needing a woman to facilitate it. A problem that I experienced was my 20s were about optimization. These were these, at least culturally masculine things that I was doing with self-improvement and cutting out all of the things that were not related to the goal that I had so that I could drive and penetrate and achieve But I wasn't going to the movie theater. I didn't have a television. I cut out video games and I never ate a sweet. And so when I got in a relationship and she wanted to go spend a night watching a Disney movie or pick up some ice cream, I acted like those things, and I felt like those things were deviations from my plan that I would tolerate for her. But really what was happening is I was only able to feel some of the sweetness and softness and relaxation of my life when I was with her. So when we broke up, I wasn't just dealing with the loss of the relationship, I was dealing with the loss of softness, sweetness, and relaxation in my own life. And it made me very stuck on this particular relationship. I imagine there's an analogous thing that can happen with men or women, but if there's anything in your life that you can't access that is available to you, like dancing or sweetness or structure, whatever it is, unless you're in a relationship, then you have a codependent toxic cocktail waiting to explode that is gonna attach you to people that are not right for you and make you tolerate things. that are not in your best interest. So practice these phrases, whether it's in a relationship, business, anything. I love you. No. Or no, and I love you. Literally say those phrases out loud. If you're like me, those felt antithetical. To tell someone in the same breath that I loved them, but they couldn't join or they weren't going to be part of my business felt like a total contradiction existing in the same sentence. So for me, what that meant is that if I ever had to separate or draw a boundary with someone, I had to first cut off my love for them. And not wanting to do that, I stayed in relationships and schemes of relationships that didn't feel good for an incredibly long time. But the first time that I was finally had to fire someone after many, many violations, and I just got into that call, didn't wanna do the corporate thing and started with, I love you, this is so hard, it actually flowed much better. Much easier. Do not let your no and your I love you stand in opposition to one another. In fact, they're not just copacetic, they're necessary for a healthy relationship. Another phrase, it just doesn't feel right for me. If you need, like I did for so many years as the philosophy major and the writer, to justify your gut feeling with logic, you are operating at, I'm just gonna throw out a number, a 10th of the speed of your innate intelligence. Your gut knows things before your brain can piece together how and why. Now, I'm someone who loves analysis. I look at charisma, things that are gut feelings, and I break them down, but it takes me longer to do it. We feel who— when we like or we're repulsed by anyone immediately. So trust that gut feeling. Don't fall into the trap, whether it's with a salesperson or anyone, of needing to justify that gut. But neither fall into the trap of thinking that your gut is about objective reality. Your gut tells you about subjective reality. It tells you this doesn't sit right for me. It doesn't mean that this is an evil person, and you don't need that. In fact, when I thought that I needed to have an objective verdict on people if I was gonna do business or not do business with them, not only did it slow me down, but it made the whole process so much heavier, 'cause I felt like I needed to gather all the data lest I condemn someone who actually oughtn't be condemned. But when it was just— This isn't right for me. And I didn't need to justify it. Things moved so much more smoothly, and I avoided problems that I would've had earlier. And I certainly stepped into problems that my gut told me I could've avoided. Connected to that is that success creates the problem of people being drawn to you in a way that anonymity does not. For young, low-status men like myself coming up, you don't realize the gift that you have. There's a tremendous gift in being low status, and it's that people show you who they are. If you're a waiter, you're gonna overhear the most vile and sometimes beautiful things at tables that you wait because you can feel like a fly on the wall to most people. They're not worried if you hear them. But as you become higher status, people show facets, sides of themselves. I was not ready for that transition. I was so used to being rejected flatly, outright, cleanly, and being shown who people were without them trying to fake it. That once I started to have a million subscribers and I was offering a salary to people to join my business, I didn't realize that there was an incentive for them to deceive me in order to get close. My self-image could not accommodate that. But you need to know, if in life you become more successful through your 20s and through your 30s, which often happens, at least relative to 19, this is gonna happen. You need to develop a bullshit meter. That's your gut. We talked about it earlier because people will— Deceive. Related to this, people who want to work with and for you in any sort of capacity will feel really excited, and they might say that they share the same mission as you. But you will measure mission and commitment, whether it's in workplace or in a relationship, not by someone's passionate speaking about it, but by their track record. And this one sounds so obvious. I've heard it a million times, but it did not occur to me that if someone had the same mission as me, they would have shown it through their behavior earlier. Meaning if they love charisma, they're gonna have written on it. This is the first job post or the first submission that they make to my company should not have been the first evidence of it. And I had a lot of situations where I thought that people were mission-aligned because they were enthusiastic in their words. And what I found over time is one, they weren't. So it meant that their work didn't really develop and get much better. And then when we split, they went into totally different industries, which made me realize, Oh, there was never mission alignment. They were excited about this job. They may have wanted to work for it, and I certainly was a low-stress boss, but that was never actually there. Here's one for those of you who are quite heady, like I definitely used to be, and it's that philosophizing, figuring out, debating, talking about morality is a stepping stone. It is the head attempting to do what it fears the heart cannot. I was really, Wanting to know what the good life was, to know what a good man was. And that's why I became a philosophy major after my gen ed philosophy class. I thought that at some point in the curriculum that would be revealed to me. Oh, this is good. It was disappointing to find out that they never really agreed on what that meant. And so I tried to find things that were bulletproof. I was like, okay, well, giving to charity is good, and the Christians say 10%, so if I give 15%, I'm probably in the clear. And I need to stop eating meat because that's probably gonna be a problem in the future. And these were beautiful impulses. But if I really slowed down, which I did years later, they were not impulses from love. They were impulses from fear. It was the fear of being bad. And so often when we grow up, we are raised with fear and shame around being a bad boy or a bad girl. It's a normal thing that a lot of parents have done, though not— it creates quick compliance, but it actually slows our long-term development. And we begin to think that we need this superego chastising us, telling us to donate more, give more, et cetera, because we don't trust that we have that goodness inside of our heart, that it will not rise instinctually, so it needs to be commanded from the top down. The last several years have been me letting go of the structures of goodness. I took, I don't know if it was a year or 2 off of charitable giving because it was so built into the structure of what I had to do. Just so that I could feel my own impulse. It took a while for me to really connect and feel it come online and deal with the stress, but I started giving again this year, and it came from a place of connection and joy instead of obligation. And my bet over the course of my life is that reconnecting with the heart, which is not giving to someone because they're afraid of a bad person, but because they feel an empathetic connection with that person in need, With a boundary, which I had to describe earlier, because the head, I was like, well, if I gave 15, why not 16? 16 is close to 15. Why not 17? If I'm gonna give 17, why not just give it? Why not give it all? 'Cause everybody, if you can't have a felt non-logical boundary, this becomes very scary. So that boundary plus that heart openness is a 2-part combo, I think, for living a much more effortless, generous, open-hearted life that I believe in the long term will have a greater impact. Greater positive physical impact on the lives of other people than all the effective altruism head giving in the world, where we sit down and we spreadsheet what good is. In my experience, there are second and third order effects of that that are not, the head can't account for, that the heart does feel, and that the gut can draw the boundary around. Aw, here's one. Spend time with grandma. My grandma was my last surviving grandparent into my 30s. And this could be your grandmother, your grandfather, Her blessings are always available, but her personal insight into her life is not. Get the life stories of your relatives, mom, dad, grandma. There are family patterns and understanding them helps. So specifically ask about their upbringing, first Christmas, what they remember, what Little League was like, what they remember of you. I have had the privilege of getting to do this with my mother and my father. And the things that I've learned about them and myself and the soup that I grew up in that I'd sort of just forgotten about was so valuable for seeing the patterns and then deciding, do I wanna continue that when I become a father in my relationship? And I wish that I could see those patterns with my grandma. I'll tell you one quick thing that I learned is my grandfather actually started a business around public speaking and charisma, and I had no idea. And to see that lineage and to see that thread in a lot of the men on my dad's side connected me to him in a way that I couldn't even feel in life because he was somewhat gruff and he had failed in that endeavor. But it makes me feel more connected and like I am continuing a family legacy, which has in part been the thing that at 39, I'm childless, but has inspired me to actually go, fuck, I can begin to see as I unravel these family patterns, the ways that I do want to have children and the ways in which I wanna stop some of the old family patterns and start new ones. Another one, persuasion past a certain point is a liability. This was tough for me. I make a lot of videos about persuasion and you want to have some degree of persuasion, but if you get so good at talking people into things that they enthusiastically assent in the moment, but then have regrets later, you have created more problems than you've solved. I got really good at the inspiring halftime speech of like, we're gonna do this and this business is gonna be great. We're gonna go in this direction. You can imagine if you did it, we came together and it was like, yeah, rah! But I never created that moment of friction for the other person, like in Fight Club, to stand on the porch for the proverbial 3 days and show their commitment to me. Instead, my persuasion did all the work of Faking a moment of commitment, or at least getting a real moment of commitment that wound up not surviving impact with challenge. Don't wanna over-persuade. You need friction to allow people into your dating life, into your company, into your friend circle. It doesn't have to be manufactured, but that friction can simply be you asking them what they're about without tipping your hand and going, here's what we're doing, it's gonna be amazing, you should be part of it. You don't wanna oversell. You need to let people show up Show you their track record, tell you what they're about. Otherwise, they can just get really excited 'cause you seem like you've got a mission and they feel like they could use one. There's more than one transformational phase, at least in my life. The first one was from sort of just hanging out to taking control of my life. And I thought that was it. I thought life was gonna be an iteration of further optimization. And fortunately, that's not the case. What I see is that for many men, it goes complacency, optimization, connection with feelings, and then spirituality. And at each of those phases, there's a culling that happens, and it's unfortunate, but you might lose connection with old hobbies, with old friends, with old ways of being. And there's a real temptation at that to disavow the way that you used to do things and try to make everyone come with you because the old way is wrong. And I've learned that that is the immature way to handle it. Everyone's on their own timeline. Everyone has their own path. And if you disavow the way that you were before, you are missing important pieces of the truth. I am so grateful for that introverted kid who hung out and played video games all day. Gosh, I mean, he's in me still, his hunger for knowledge and his headiness, like, and his heart that he would just play the games that he loved and hang out with his animals, with his cat sitting on his lap downstairs. That connects me to my joy. And then the next phase of that optimizer, like, man, that guy built a platform upon which I now stand, financial, social status, amazing. But what I did was at each stage I said, oh, I'm not that introverted kid anymore, I'm the extrovert. And then when I got into the emotional healing, I said, I'm not that doer anymore, I'm the feeler. Slow down with that. You will have to, you'll have to integrate everything eventually. So if you don't demonize it, it makes it a bit easier. The final one, I mentioned spirituality. It's real and it matters, and if you do not attend to your spiritual life, you will find a recurring set of issues that you are never able to touch in any other way. I do not say this as someone who tilted towards spirituality. When I was 17, I had the first several chapters of my book on atheism already written, and And then I read End of Faith by Sam Harris, and then Christopher Hitchens came out with God Is Not Great. And I was like, oh, this is done and dusted. I'm not needed for this. I'll go do something else because this argument has been settled. And without going too deep into it, what I didn't realize is that religion and the way it is practiced in our childhoods by the people around us is not the same as spirituality, nor is it the same as what religion, the way that we come together and practice spirituality collective, could be. I know that I never would have accepted this, but if I could blow my 30-year-old self's mind, what I would tell him is that you are a soul. God is. And I'm not here to persuade you about any of that because I don't want your logical assent. That would do nothing for you nor for me. I'm not interested. All that I can do is encourage you to do your breathwork, dance, and when the time is right, Charlie, not everybody in the audience, Psychedelics can help with opening that experience. And knowing that I'm saying this on a platform, not to my 30-year-old self, let me say, do it safely if you decide to do it, with a facilitator. All of that kind of stuff is incredibly, incredibly important because like any powerful tool, there's a dark side of it if you're not grounded. But those things, breathwork, dance, psychedelics, have been wildly powerful for connecting me to Myself. Not just the self that is felt within this body, but the big self. And what a relief, because if you can't feel your spiritual self, you can experience that disconnection that is such an unfindable ache in your life. So I'm not here to profess any religion that needs to be followed or any particular path But open up to something greater than your ego, than the thoughts in your head, than the day-to-day experience that you have. There is a greater thing, and it is real, and it matters. So that's what I would tell my old self. I hope that that has been helpful to you guys. I look forward to seeing the next video. Peace.