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. 

 

It’s the bit of advice every well-meaning parent gives to every child. Just be yourself. Divorced from external outcomes, this wisdom is pretty unimpeachable. Because, yes, it will be hard to ever be internally tranquil if your social persona is critically divergent from your true self. If we stopped there, all would be fine. But we won’t stop there.

Try as even the best Buddhist might, being completely disconnected from social performance is just not how humans operate. Run Just be yourself through this unavoidable lens and its wisdom begins wilting. What if your true self sucks? Is super weird? Cares about things society ignores? Discards communal values? You could very well end up in a position where you reveal the true self, feel calm inside … and end up a total loser outside. Contrast that against hiding the true self, feeling conflicted inside, and gaining much social credibility from one’s deft playing as a poseur. It’s not obvious which path is preferrable.

Perhaps you think back to that lame kid in high school who pretended to like System of a Down when his real passion was Britney Spears, and you say, “Naw, that second path wouldn’t work because we know poseurs when we see them.” Yea, the bad ones. Just consider all the “successful” people admitting they played a “character” to remember that much posing goes undetected. Or really, just look at yourself. You’ve surely gotten away with claiming to like/believe that which you didn’t like/believe; you’ve seamlessly done things you didn’t want to do.

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An unfortunate aspect of school is being forced to learn things for less than compelling reasons. Since the reasons aren’t hugely inspiring, and since being “forced” to do just about anything stirs rebellious urges, it’s easy to dismiss the thing itself as unimportant. Maybe good to know for a stellar grade, but little else. This is an understandable conclusion. It’s also sometimes terribly incorrect, like in the case of vocabulary. You seem to already understand this. Congratulations! So absorb this book not for better grades, not for a tilting of college admission probabilities, not even so you can seem (and be) intelligent, but because language mastery is foundational to understanding and communicating. Possession of these intertwining skills provides a rightful confidence boost to connect with anyone, anywhere. And human connection, I dare say, is the apotheosis of compelling reasons.

Whenever I feel like crying, I turn on the Zero Dark Thirty trailer:

I want to make something absolutely clear. If you thought there was some working group coming to the rescue, I want you to know that you’re wrong. This is it. There’s nobody else hidden away on some other floor. There is just us. And we are failing. 

You may have spent much of your life unaware that nobody can save you but you. (Feel free to skip ahead to the next section if you were fully aware.) Perhaps you missed the message because Jesus’ promises of salvation drowned out all other voices. More likely, though, “failure” and “saving” were faraway thoughts when everything was going pretty well. And even when you were riding closer to valleys than peaks, minimal responsibility made Just getting through it the more common thought pattern than desperate pleas for a full-blown bailout.

But those innocent times are now gone; it’s probably pretty uncomfortable. One way to know you are in this dreaded place is a longing for tidy external solutions: Maybe this one person will … Maybe the trade will shift to … Maybe if I just get into this program … Go ahead and soothe yourself, sure, but don’t become tranquilized into forgetting that, no, sorry, it’s on you. Oh how you’ll want to forget. Oh how you’ll wish for simpler times. Oh how you’ll bargain that if you could be rescued this time you’ll never, never, never sin again. (more…)

Just as you are cresting some xxxxxxxxx hill on a pleasant evening in May, the magic of shuffle delivers Rufio’s “Above Me.”  You speed up, notice the warm wind rush through your open windows, and begin screaming along. In this moment, you wouldn’t want to be anywhere else.

The stale yellow light ahead rips you back to petty existence. Your foot is now off the accelerator as your right hand reaches for the volume knob. In impressive synchronicity, the counter-clockwise spins on the dial reduce both the music and the decibels of your singing. By the time your car settles at the light, the music is barely audible; your singing is altogether nonexistent. You steal a glance at the driver to your right to confirm that, yes, you have properly saved yourself the embarrassment that would have accompanied a witnessing of your previous state.

A week passes. The weather remains nice enough that windows, not AC, are the appropriate choice. You find yourself at the same place on the same road when, again, “Above Me” starts playing. The only obvious difference between the situations is that you aren’t alone: each seat is occupied by a friend. Together your voices rise. “If I were to walk till time saw no end!!!!” Buoyed by this collective energy, the upcoming yellow light changes nothing. Your car slows, but the volume stays constant. Stopped at the light you look to your right. That other driver wishes he had what we have. No shame. No embarrassment. No behavior adjustment to be a little less yourself and a little more what would seem societally palatable.

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You already know. You may not want to know, but you know. Of course this isn’t true with everything. There are plenty of times when advice is genuinely needed regarding both concrete asks – how to change a tire, what’s the best restaurant in Toronto, etc. – and interpersonal relations in the face of truly confounding behaviors. Still, most of life’s challenges are action, not information problems: you understand vegetables’ health benefits yet the pull of a Dairy Queen Blizzard is too hard to resist.

So no, advice from others won’t really help contend with these emotional desires.[1] Part of the reason is that the outsider is unattached and experiencing zero cravings. This doesn’t make the outsider any smarter, just better able to access wisdom. Hence the phenomenon of I can’t even follow my own advice! Obviously. Standing between advice and execution is emotion. If you can ignore the emotion and altogether avoid action, the pipeline to “answers” is clean. This reality tends to leave the advice-receiver (AR) in a doubly uncomfortable position.

First comes the shame. This thing that seems so easy to everyone else is hard for the AR. What is wrong with me!??!?!?! How did I not see this when this person who pondered it for 10 seconds can?!?!??! FML. Plus, there’s the unfortunate fact that advice often feels like judgement.

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If you think your life’s purpose needs to hit you like a lightning bolt, you’ll overlook the little day-to-day things that fascinate you.

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When you’re on to something great, it won’t feel like a revolution. It’ll feel like uncommon sense.

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Success come from persistently improving and inventing not from persistently doing what’s not working.

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We all have lots of ideas, creations, and projects. When you present one to the world, and it’s not a hit, don’t keep pushing as-is. Instead, get back to improving and inventing.

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No plan survives first contact with the customer.

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By not having money to waste, you never waste money.

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People often ask me if I have any suggestions for what kind of business they should get into. I tell them the only thing I know how to recommend: Start by sharing whatever you’ve got.

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“Huh? I don’t have any of that legalese stuff. I’ve never hired a lawyer.”

“That’s crazy! What if some kid buys a cd from you and then kills himself? What if you get sued over that?”

“Then no stupid footnote legalese would protect me anyway, so I’ll worry about it if it happens.”

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I just generated a wholly original interview question.^[1] You know how it’s so hard for non-narcissists to talk about themselves? You know how in interviews one is supposed to subtly brag and hit specific beats in specific ways that show both competence and self-awareness and how this delicate dance probably reveals more about one’s ability to successfully play games than deliver useful labor? I have a solution.

You can’t fake friends. In one’s mind, sure, but never in reality since reality offers the most objective of tests: how much time do you spend engaged with said “friends”? And if you aren’t actually spending time, you won’t actually know these “friends,” and thus you’ll be unable to really talk about what makes them tick. Yea, but people present a fraudulent depiction of themselves all the time, so surely they can pretend to have friends they don’t have. Not so much, I think. People are well-versed at lying about themselves – I’m a great team player; my weakness is that I work just a little too hard – but they don’t have nearly the same reps lying on behalf of other people. So when pushed to describe a fake friend in more than superficial terms, words won’t come so easily. This reality marks the first foundation of this new interview question.

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Look at some of your friends’ friends and you can’t help but wonder why the friendship exists. Then look closer. Past the bad decisions, shared histories one feels guilty about severing, and sheer loneliness, you’ll see that some people simply need different things from friendship – we are all unique. But we are also similar. Like, days pass and pass and pass and boy it sure would be nice if I had a friend to help transform this bound-to-be-forgettable Saturday into something memorable. No amount of uniqueness makes this type of friend undesirable. Of course, you are just such a friend: you’ve made my life better than anyone else I’ve met in xxxxxxxxx.

I first really considered this during one of those xxxxxxxxx holiday extravaganzas. What most struck me was your generosity. Here you were providing food, a house, a boat, jet skis, gasoline, etc. and asking for nothing in return. Importantly, there appeared no arrogance or give-me-social-credibility-for-all-that-I’ve-given attitude that is common in such situations. Even as we were all fortunate to have you as a friend, you gave off the impression that you were simply happy that people would trek out for a hang. When both parties feel “lucky” sharing time, you have a cornerstone trait of a great relationship.

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For so long they cheered you with the purity of a pre-teen at a Taylor Swift concert. They celebrated even your tiniest accomplishments. They wanted you to be successful. They sometimes even believed you were capable of things you yourself doubted. And then, at some point, it all stopped. The purity was replaced by jealousy, and the words of encouragement were shifted to lesser folks. We love seeing people do well … just as long as they don’t surpass our own status. And once they do, He really needs a measly compliment with a title like THAT?! Probably had to know somebody to get the job anyway. LOL to those who think he got there with “merit.” And don’t get me started on wealth inequality. Tell me what he actually does to earn 20x more than that earnest janitor. I’m not seeing it!

But of course the same human needs for acceptance and appreciation don’t disappear once one owns an ungodly # of VTI shares. So here I am cheering and celebrating you. Here I am thanking you for the past two months of working together, which were my favorite at xxxxxxxxx. You said something this summer about me “thinking too much of you,” and I’m convinced you were/are obviously incorrect. Aside from my parents, I truly don’t think there’s a single elder I’ve learned more from than you. Here’s a little list of learnings that may well read like a fanboy writing T Swift:

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