You’ve decided to leave your children $0. Or not. Either way, you certainly want them properly developed such that they need not be left anything. So how does one “let kids be kids” while also cultivating a confident, independent resourcefulness in them?

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Pillar One: Take pride in being quite competent in many, many domains. Sounds obvious… until you recall how the world dispenses prestige. It’s a dinner party with well-educated professionals casually bragging about their lives. By accepting Pillar One, you are accepting that these guests will likely have you beat. They will flaunt social currency that you don’t have, and what you do have won’t be as valuable. “That’s cool you fixed the garbage disposal. I had my maid do it when mine broke. By the way, I just made president! Look at my new Porsche.” Without true belief in Pillar One, it will be all too easy to surrender your values and compete with this fuck on his terms.

(more…)

You thought last year was a one-time thing, didn’t you? Wrong! Happy Father’s Day 2025!

For whatever reason, my mind associates you with this holiday. Part of the association, sure, is you losing your father. I think about that loss, and I hope you are doing as well as you can with it. But also there’s that still-vivid image of you being a father in your backyard with xxxxxxxxx in his karate outfit. There is xxxxxxxxx: man, father, husband, strong and vulnerable, and trying to do what is right.

Of course basically everyone is trying to do what is right… but some think more deeply, try a little harder, and are more open to discussing their uncertainties about what, exactly, defines “right.” Package these distinct behaviors together, and future efforts will likely improve. Never to perfect, obviously. Never guaranteed to be linear either. Just an overall arc that justifiably induces pride.

You would not have been proud if xxxxxxxxx was in the sixsome (!!!) golfing in front of me at xxxxxxxxx a few Sundays ago. The course is slammed. And even if it wasn’t, the fact that I’m waiting to hit should be a blaring signal to (a) break up the group or (b) let me to play through. The sixsome chooses to (c) ignore everyone but themselves.

(more…)

They’ll keep repeating it: Just be yourself. If the repetition commences before you enter the snake pit that is teenage social hierarchies, the advice will seem banal. How could I be anything but myself? Why would I even try to be anything else? Once in the snake pit, the encouragement will feel not banal but dumb and impossible. Don’t these people understand that to stand out is to open oneself to ostracization?

Enter Be confident. Another oft-repeated phrase without deep thinking attached. Here’s some deep thinking. Your mom has one form of confidence; your dad has another; and both are important forms.

(more…)

Soon enough, the world will become loud and overwhelming. All these well-intentioned people telling you what to do and how to do it which partially sends the message that you don’t know what you are doing. And sure, there’s much to learn in youth. But also, adults can learn from you; your age provides vision behind doors adults don’t even know exist. Furthermore, you are the future, so however much adults might disapprove of Generation Alpha’s actions, those actions will indeed grow to dominate.

Therefore, I want to learn from you. But maybe you don’t want to teach. Maybe you see me as competition. Maybe for that aforementioned domination to optimally occur, it’s best to keep your insights tightly locked within your mind. Ok, ok, ok. The negotiation has already begun. Fine.

Does it gain me anything to compliment your father? What if I say he’s outstanding at living his values? It’s true. He pays attention. He finds ways to translate his political views into everyday actions such that even non-adherents find value. Like riding bikes instead of taking an Uber. Like planting trees as a gift. Like generously cooking instead of caving to capitalism’s pressures of convenience.

What if I tell you your mum is so sweet, so pleasant to be around, so quick to laugh, but also so able to express deep intelligence without coming across as better than? Does that gain me anything? It does? Really? Nicceeeeeee.

(more…)

You are able to straddle two contrasting worlds in a way that reminds me of Dexter Holland in 1994. You know Dexter, the lead singer of The Offspring whose shine has faded over the years as his band gained popularity but who in 1994 was an iconic blend of two worlds not often blended: punk style and intelligence. You see punk style—be it a skater, snowboarder, or musician—with its nonchalant coolness and assume the person can’t also be smart, because, well, the person often isn’t smart. You see intelligence, and while the person may also be stellar at traditional sports and perhaps piano, you think that for God to keep things reasonably fair, that nerd can’t also possess what the skaters behind the school possess.

But God isn’t fair. And so Dexter Holland can somehow pull off dreadlocks, front a raw punk band that released the best-selling independent record ever… and be the valedictorian of his high school, earn the nickname “Dexter” because of his mathematical prowess, and go on to earn a PhD in molecular biology. While your bio is not as well-known to me, a single snowboard run alongside you is enough to prove your skate-style, and a single conversation is enough to prove you may already have a PhD (but are too cool to mention it).

So here are two things I’m quite confident you (or Dexter for that matter) will enjoy.

I’ve been granted the God-like power to issue commandments. And similar to normal deities, these commandments are nothing more than strong suggestions carrying a special weight of importance. If my commandment is too obvious — Thou shall not kill — I’ve squandered an incredible opportunity. Even if I declare something less obvious — Thou shall sleep eight hours per night — I’m not helping much since lack of information isn’t the reason you’re sleep deprived. So it is, really, with most matters: the challenge comes not in the form of missing information, but rather the difficulty of actually following through on what you already know you should do. Plus, I’m God-like (at least in this respect), so I ought to find something peculiarly wise.

THOU SHALL NOT DEMEAN THYSELF

FOR HAVING ATTENDED xxxxxxxxx

(more…)

People who claim, “I don’t care what others think” are either liars or psychopaths. For better or worse, status matters. People who claim, “I know exactly what I want for me” are either liars or live in an isolated cave. For all non-cave dwellers, the unending influence of people, adverts, media, art, etc. means it’s quite impossible to totally disentangle your unadulterated desires from socially-conditioned desires.

But that doesn’t mean we can’t partially disentangle the two. And even partial understanding meaningfully enhances self-awareness. Consider possessing zero self-awareness. Instead of having some idea about what you really want, you are solely guided by what society says you should want. All the times when your mysterious true desires fail to overlap with socially-conditioned ones, you may well “achieve” … and still be empty.  Because if you attain things the deep-down-unique-you didn’t truly covet, there’s a profound disconnect which shows remarkable concentricity with emptiness.

So we might as well try to get that partial understanding, right? Right. But how? Well, if you grew up in that cave, you would only have unadulterated desires. Of course this wasn’t your upbringing (thankfully), but we can extract a framework from the hypothetical: imagine what you would do if you couldn’t tell anyone what you did? It works both in your imagination and in practice. Like, go to a concert by yourself, snap zero pictures, and tell nobody you attended. Little dips into this practice can yield rapid insights. Oh shit, I don’t really like this band. Rather, I like being able to tell people I saw a band that’s considered “cool” which, by association, enhances my “coolness.” And, again, this may not be a bad thing! Status confers many benefits! But status doesn’t mean happiness, and so upgraded enlightenment can help better prioritize actions going forward. You may still rank, say, female attractiveness just as highly, but you’ll be doing so from a position of greater self-awareness where you can more confidently declare that I want this for me.

How many people here witnessed xxxxxxxxx in a state where she was clearly struggling?

And how many here were then angry, sad, scared, confused, annoyed, frustrated?

I certainly was all of those things at some point during the past four years when she was my roommate. Over time I came to view her situation as akin to cancer: she wasn’t actively choosing in any meaningful sense to struggle. She had a disease and it was with her on both good days and bad.

While this realization didn’t erase the negative feelings, it did imbue the positive ones with more meaning because while it’s certainly nice when a man with a closet of shirts gives you the shirt off his back, it means something else entirely when he has no other shirt.

And xxxxxxxxx indeed provided me with much to be grateful for.

(more…)

Reminders of not having money are everywhere because prices are everywhere. Positive-thinking and paeans of You Are Enough fail miserably in preventing these reminders from extracting a psychological toll – even Tony Robbins’ mind would be helpless in surrendering to the objective, concrete reality of money. So, yea, this leads to stress that can only be escaped by multiplying one’s bank account to the point where a purchase of whatever represents an irrelevant dent in the account balance.

But there is another stressor associated with financial deprivation that will not vanish simply because you now make six figures. Quadrupling a salary is hard, positive-thinking is ineffective, but value-hunting can begin today and deliver today. Finding deals, collecting coupons, negotiating constantly, stretching the limits of return policies: spend less by spending smarter, by never getting ripped off, by always finding a deal. And so the must-find-value stressor develops. For a certain type of person, this stress may well become an energizing and adored personality trait. Let me tell you about the INSANE deal I just got!!! This positive affect is probably adaptive, but it still remains a stress response. And the deeper it’s ingrained, the harder to shed when it’s no longer adaptive. Like when you do, in fact, quadruple your salary and saving $1.25 on 2lbs of chicken breasts doesn’t matter. Yet it will matter if must-find-value is left unadjusted. You want to still find value because it’s fun? Do it. You want to still find value because you have to or because you feel dumb if you don’t or you really, really should? Well, then you’ve unfortunately managed to escape the conditions that created stress without dropping the stress. 

You are great. You are thoughtful, kind, cool, and fun. I will miss you. I feel I also possess some other insights about you given the time we’ve shared together. If you want to hear them, continue below. If not, that’s fine too.

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What you have is not a moral failing. You might not believe this. In fact, I think, given your remarkable level of shame, you resist accepting what now seems so obvious to me. Take your parents’ recent visit as an illustrative example of why blame strikes me as so misplaced. If there ever was a time when you’d want to be in top form, xxxxxxxxx visiting would be the time, right? You hate to worry your parents, and if you could just hold it together for a few days, perhaps they would return home with a little less concern. You are a thoughtful person! Instead, you were helpless to stop that which you surely didn’t want to have happen. But of course: it’s a disease, not a matter of personal will, and so just as a cancer patient can’t be expected to stop negative cell growth and division, you can’t be expected to be in “top form” simply because you hope to please your parents – diseases of this sort aren’t a matter of positive intentions.

I get that I, your parents, and society have often failed to properly convey the idea that “it’s not your fault.” Especially when I was clueless as to what was happening, I know I sent both explicit and implicit messages that contradict what I’m saying now. That must not have been comfortable or helpful. I wish I had the wisdom then that I have now. What I wish more, though, is that you can see what I’m suggesting here as actual wisdom that actually applies to your situation.

Perhaps you want to fight and say it’s your fault that you got this disease – like a smoker being blameworthy for getting lung cancer. I’d protest while declaring such a disagreement largely irrelevant: what matters is how to get better. That’s where you still have agency. And that’s where I hope for an acceptance to seek serious, comprehensive help for a disease that will not bend to only your effort and goodness.

Whatever you do, you remain the same great person mentioned in the first sentence. That is constant and unchanging. Unfortunately, if you keep going as you are, I fear those who love you will only get to experience you for minimal years before this disease kills you.