mindsets

1.“For me, first of all, dopeness is what I like the most. Dopeness. People who want to make things as dope as possible, and, by default, make money from it.” As everyone who is dope knows, “dopene…

Three rare and powerful skills: 1. Understanding how people justify their beliefs in a way that makes you respect their delusions. A rare and useful skill is understanding that people you find to be deluded likely suffer from the same shortcomings you do. Historian Will Durant wrote in his book The Lessons of History that we should learn enough from history to respect each other’s delusions. He explained: Our knowledge of any past event is always incomplete, probably inaccurate, beclouded by ambivalent evidence and biased historians, and perhaps distorted by our own patriotic or religious partisanship. Most history is guessing, and the rest is prejudice. I think this boils down to three points: Everyone is heavily influenced by what they’ve experienced firsthand, because what you’ve experienced is more persuasive than something you read about. Even our understanding of firsthand experience is sketchy, because we oversimplify what happened and self-justify our involvement. Those who didn’t experience an event firsthand have an even weaker grasp on reality because they can cherry pick the oversimplified, self-justified arguments and data from people with firsthand experience. So everyone has delusions about how the world works. You, me, everyone. We are all prisoners to our past, products of our generation, and influenced by who we’ve met and what we’ve experienced, most of which has been out of our control. Some are worse than others, and some are more aware of their blindspots. But everyone has a firmly held belief that an equally smart and informed person disagrees with. Good questions to ask to combat this reality are: What haven’t I experienced firsthand that leaves me naive to how something works? Which of my current views would I disagree with if I were born in a different country or generation? What do I desperately want to be true, so much that I think it’s true when it’s clearly not? Which of my current views would change if my incentives were different? But an even better skill is realizing that everyone else struggles with those questions and winces at the potential answers. You don’t have to agree with others’ delusions or put up with their collateral damage. Just accepting that everyone wants easy and comforting answers in a complex and painful world is a rare skill. 2. Quitting while you’re ahead, or at least before you’ve had too much. Commenting on how he lived to 97, John D. Rockefeller’s doctor said the oil tycoon “gets up from the table while still a little hungry.” It’s another rare skill, and one that applies beyond eating. The temptation to exploit every drop of opportunity leads many people to push relentlessly for more, more, more. They only discover the limits of what’s possible when they’ve gone too far, when the momentum of decline is often unstoppable. Businesses that don’t want to hold inventory push so hard for efficient supply chains and just-in-time manufacturing, stripped of all shock absorbers and room for error. Then a pandemic hits, and supply chains crumble. Young workers eager for promotion push themselves until they’ve hit burnout, when they physically can’t continue in their positions and quit, which often marks the end of compounding their skills and work relationships. People on social media push relentlessly for more likes and retweets until their audience is sick of them. In each case there’s value in saying, “I could have more and do more, but this is good enough.” But it’s such a rare skill. People don’t like leaving opportunities on the table, and it’s counterintuitive to realize that you’ll likely end up with more than those whose appetite for more is insatiable. 3. Getting to the point. Perhaps the most critical communication skill. Be brief. Use as few words as possible to say what you need, and everyone will appreciate it. Mark Twain said kids provide the most interesting information, “for they tell all they know and then they stop.” Adults lose this skill and falsely associate the number of words with the amount of insight. After writing every sentence it helps to ask “Would the reader still get my point if I deleted that line?” Not “Does that sentence make sense?” Millions of unnecessary sentences make sense. Treating words like they cost you something is the right mindset. A writer once recommended imagining someone pays you $100 for every word you remove from your draft. Another quipped: “Leave out the parts readers tend to skip.” Poor communicators ramble. Good communicators leave out unnecessary details. Great communicators treat words as the scarcest commodity.

David Foster Wallace's remarkable 2005 commencement speech, this is water, is a timeless trove of wisdom for living a meaningful life. Here is a full transcript along with audio.

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Nostalgia for another way of working

Life is a never ending maze of decisions. I’d love to make the right decisions all the time. I’d also like to have George Clooney’s charming good looks. Those two outcomes are equally likely. Instead of obsessing over the right decisions, which is hard, we can simply avoid the worst decisions, whi

Fifty-four years ago this month, in a push for publicity, The Sunday Times offered £5,000 to whoever could sail solo nonstop around the world the fastest. It was technically a race, but that was an afterthought, as no one had ever completed the feat. There were no qualification requirements and few rules. Nine men joined the race, one of whom had never sailed. Just one man finished, 312 days and 27,000 miles later. But it was two participants who never completed the race that generated the most news. One ended up dead, the other found himself happier than ever. Both outcomes came from decisions made at sea, but neither had anything to do with sailing. The two men, Donald Crowhurst and Bernard Moitessier, are astounding examples of how the quality of your life is shaped by whom you want to impress. Their stories are extreme, but what they dealt with was just a magnified version of what ordinary people face all the time, and likely something you’re facing right now. Donald Crowhurst was a tinkerer who came up with his own boat modifications. Convinced his innovations could propel him to win the Sunday Times race, he faced just one obstacle: he was broke, and stood no chance of financing the race himself. Crowhurst struck a deal with an English businessman who agreed to cover the cost of the race under two conditions: They would orchestrate a media frenzy, portraying Crowhurst as a sailing savant. And if Crowhurst didn’t finish, he would owe all the money back. Crowhurst left Teignmouth on October 31st, 1968, the last day participants of the race could begin their voyage. His boat, the Electron, had been so heavily modified, so weighed down with half-finished gizmos and gimmicks, that it was barely seaworthy for a short sail near home, let alone a solo trip around the globe. Crowhurst knew it. He broke down in tears in front of his wife the night before he left. Two weeks into the race, as Crowhurst had covered less than half his intended distance, the Electron sprung a leak. “This bloody boat is just falling to pieces due to lack of attention to engineering detail,” Crowhurst wrote in his diary. In the calm waters of the South Atlantic, the small leak posed little threat and could be bailed with a bucket. But continuing on to the treacherous Southern Ocean would bring certain catastrophe. So Crowhurst seemed to have two options: Continue the race and face ruin at sea, or return home and face bankruptcy and humiliation. He in fact chose a third option, which was outright fraud. By mid-November Crowhurst began loitering in the south Atlantic, drifting in circles in calm water. He then began sending fake coordinates back to England, giving the impression that he was still on track, rounding Cape Horn, on his way to circle the globe. He went virtually nowhere for months, which was the plan: By mid-summer, when enough time had passed to have plausibly circled the globe, Crowhurst hoped to quietly sail back to England, “finish” the race, and hope no one noticed that during his round-the-world voyage he never actually left the hemisphere. As Crowhurst sailed back to England he realized he did not want to appear to win the race, because if he did the media and judges would scrutinize his logs and uncover the deception, whereas no one cares about the runner-up. After receiving word on the location of other race participants, Crowhurst timed his return so that he would finish the race in third place, which seemed good enough to maintain dignity yet low enough to avoid suspicion. But then the boat that was in second place sank. And after miscalculating his return time, Crowhurst was suddenly on track to beat the sailor who had been in first place. Crowhurst was now going to cruise into England with what looked like the fastest time. He was going to win the race. The BBC had a crew prepared to meet the man who defied the odds to become the world’s greatest sailor – which, ironically, is the kind of attention a fraudster desperately wanted to avoid. On June 29th, Crowhurst wrote in his diary: I have no need to prolong the game … It has been a good game that must be ended … It is the end of my game. The truth has been revealed. It is finished. IT IS THE MERCY. Soon after he sent his last fake coordinates to his team, and shut his radio off. The Electron was found 11 days later, adrift in the Atlantic. There was no major damage, no sign of an accident – and no sign of Crowhurst. He had presumably thrown himself into the sea. Left behind were his diary and two log books: one real, one fake. Three months before Crowhurst took his life, another sailor in the Sunday Times race made an equally astonishing life decision at sea. Bernard Moitessier was an expert sailor, and five months into the race, he was on track to legitimately win. Moitessier loved sailing but despised the commercialization of his sport. Or, more accurately, he hated the sport side of sailing. He just liked sailing for sailing’s sake. The personality required to spend nine months alone at sea selects people who are fine detaching from society. Moitessier was an extreme version of that, and the idea of sailing for someone else’s pleasure – to perform for the press, the race organizers, the sailing magazines, the fans – was so detestable that midway through his voyage he’d had enough. He wrote in his diary: I really feel sick at the thought of getting back to Europe, back to the snakepit … I am really fed up with false gods, always lying in wait, spider-like, eating our liver, sucking our marrow. I charge the modern world – that’s the Monster, trampling the soul of men … returning to [England] feels like returning to nowhere. But being on his boat, Joshua, was a different story. He loved it, loved being on the water. Moitessier later recalled: There were so many beautiful days on this beautiful boat that it really made time change dimensions … I was just feeling totally alive. And that was just fantastic. As he sailed around Cape Horn – a position Crowhurst could only dream of – Moitessier began contemplating the unthinkable: Abandoning the race and sailing somewhere else. Thinking of his family and friends, he wrote: I do not know how to explain to them my need to be at peace, to continue toward the pacific. They will not understand. I know I’m right, I feel it deeply. I know exactly where I am going, even if I do not know. On March 18th, Moitessier threw a jerrycan onto the deck of a passing commercial ship, whose captain caught it on the fly. Inside was a note addressed to the Sunday Times’ editor. It read: Dear Robert, today is March 18th. I am continuing non-stop toward the Pacific Islands because I am happy at sea, and perhaps to save my soul. Moitessier shouted for the captain to take the message to the French consul. He then changed course, off the race’s path, and set sail for Tahiti. Moitessier wrote in his diary: Now it is a story between Joshua and me, between me and the sky; a story just for us, a great story that does not concern the others any more … To have the time, to have the choice, not knowing what you are heading for and just going there anyway, without a care, without asking any more questions. He anchored in Tahiti in June, where he remained for years. He built a house on the beach, grew his own food, and wrote a book about sailing. “You can’t understand how happy I am,” he wrote. In a twist of irony, Tahiti was so far out of the way and required so much backtracking that, despite dropping out of the race, Moitessier did circle the globe, and set a world record for the longest ever nonstop solo sail – more than 37,000 miles. There is no mention of that fact in his book. He didn’t seem to care. Anyone alone at sea for nine months will start to lose their mind, and there’s evidence both Crowhurst and Moitessier were in poor mental states when their decisions were made. Crowhurst’s last diary entries were incoherent ramblings about submitting your soul to the universe; Moitessier wrote about his long conversations with birds and dolphins. But their outcomes seemed to center on the fact that Crowhurst was addicted to what other people thought of his accomplishments, while Moitessier was disgusted by them. One lived for external benchmarks, the other only cared about internal measures of happiness. They are the most extreme examples you can imagine. But their stories are important because ordinary people so often struggle to find balance between external and internal measures of success. I have no idea how to find the perfect balance between internal and external benchmarks. But I know there’s a strong social pull toward external measures – chasing a path someone else set, whether you enjoy it or not. Social media makes it ten times more powerful. But I also know there’s a strong natural desire for internal measures – being independent, following your quirky habits, and doing what you want, when you want, with whom you want. That’s what people actually want. Last year I had dinner with a financial advisor who has a client that gets angry when hearing about portfolio returns or benchmarks. None of that matters to the client; All he cares about is whether he has enough money to keep traveling with his wife. That’s his sole benchmark. “Everyone else can stress out about outperforming each other,” he says. “I just like Europe.” I think Moitessier would approve.

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The Curiosity Chronicle has quickly become one of the most popular newsletters for growth-minded individuals in the world. Each week, subscribers receive a deep dive that covers topics ranging from growth and decision-making to business, finance, startups, and technology. In addition, subscribers receive The Friday Five, a weekly newsletter with five ideas curated to spark curiosity headed into the weekend.

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Thomas McCrae was a young 19th Century doctor still unsure of his skills. One day he diagnosed a patient with a common, insignificant stomach ailment. McCrae’s medical school professor watched the diagnosis and interrupted with every student’s nightmare: In fact, the patient had a rare and serious disease. McCrae had never heard of it. The diagnosis required immediate surgery. After opening the patient up, the professor realized that McCrae’s initial diagnosis was correct. The patient was fine. McCrae later wrote that he actually felt fortunate for having never heard of the rare disease. It allowed his mind settle on the most likely diagnosis, rather than be burdened by searching for rare diseases, like his more-educated professor. He wrote: “The moral of this is not that ignorance is an advantage. But some of us are too much attracted by the thought of rare things and forget the law of averages in diagnosis.” A truth that applies to almost every field is that it’s possible to try too hard, and when doing so you can get worse results than those who knew less, cared less, and put in less effort than you did. It’s not intuitive, so it can drive you crazy. And it’s hard to pinpoint when it occurs – maybe McCrae’s professor was being appropriately cautious? But there are mistakes that only an expert can make. Errors – often catastrophic – that novices aren’t smart enough to make because they lack the information and experience needed to try to exploit an opportunity that doesn’t exist. Two big ones: Being an expert from an era that no longer exists Investor Dean Williams once said, “Expertise is great, but it has a bad side effect. It tends to create an inability to accept new ideas.” Henry Ford banned his factory workers from documenting new ideas that didn’t work, because he feared it would create a list of things people refused to try again even when new technologies improved their chances of success. What was impossible in one era might later not only be doable, but the key to success. Ford wrote in his biography: I am not particularly anxious for the men to remember what someone else has tried to do in the past, for then we might quickly accumulate far too many things that could not be done … Hardly a week passes without some improvement being made somewhere in machine or process, and sometimes this is made in defiance of what is called “the best shop practice.” Marc Andreessen explained how this has worked in tech: “All of the ideas that people had in the 1990s were basically all correct. They were just early.” The infrastructure necessary to make most tech businesses work didn’t exist in the 1990s. But it does exist today. So almost every business plan that was mocked for being a ridiculous idea that failed is now, 20 years later, a viable industry. Pets.com was ridiculed – how could that ever work? – but Chewy is now worth more than $10 billion. Experiencing what didn’t work in 1995 may have left you incapable of realizing what could work in 2015. The experts of one era were disadvantaged over the new crop of thinkers who weren’t burdened with old wisdom. The same thing happens in investing. Michael Batnick has made the point that having experienced a big event doesn’t necessarily make you better prepared for the next big event. Interest rates have mostly fallen for 40 years, so few bond investors – even grizzled veterans – have lived through a sustained rise in interest rates. But, he writes: So what? Will the current rate hike look like the last one, or the one before that? Will different asset classes behave similarly, the same, or the exact opposite? On the one hand, people that have been investing through the events of 1987, 2000 and 2008 have experienced a lot of different markets. On the other hand, isn’t it possible that this experience can lead to overconfidence? Failing to admit you’re wrong? Anchoring to previous outcomes? Of course. It happens all the time. The feeling of power you get from hard-fought experience is stronger than the urge to change your mind, even when it’s necessary. Career incentives can push complexity in a field where simplicity leads to the best outcomes. Jason Zweig of the Wall Street Journal says there are three ways to earn money as a writer: Lie to people who want to be lied to, and you’ll get rich. Tell the truth to those who want the truth, and you’ll make a living. Tell the truth to those who want to be lied to, and you’ll go broke. Some variation of this applies to many fields, especially service industries where someone pays for an expert’s opinion. There can be a difference between knowing what’s right and making a living delivering what you know to be right. This may be most common in investing, law, and medicine, when “do nothing” is the best answer, but “do something” is the career incentive. Sometimes it’s amoral, but it can be an innocent form of “cover your ass.” Mostly, though, I think an advisor just feels useless if they tell a client, “we don’t need to do anything here.” In the quest to be helpful they add complexity even when none is needed, or when it might backfire. Years ago Jon Stewart interviewed Jim Cramer. When pressed on CNBC content that ranged from contradictory to inane, Cramer said, “Look, we’ve got 17 hours of live TV a day to do.” Stewart responded, “Maybe you can cut down on that.” He’s right. But if you’re in the TV business, you can’t. Most of this I think is truly innocent. Experts believe their complexity adds value because reality is too painful to bear, especially in a competitive career with stress and long hours. A doctor once told me the biggest thing they don’t teach in medical school is the difference between medicine and being a doctor – medicine is a biological science, while being a doctor is often a social skill of managing expectations, understanding the insurance system, communicating effectively, and so on. The gap between the two, which applies to many fields beyond medicine, can lead to mistakes only experts can make, or only an expert can advise. “Half of the 15,000 mutual funds in the US are run by portfolio managers who do not invest a single dollar of their own money in their products,” the FT writes. Doctors have their own version, as one article highlights: Almost all medical professionals have seen what we call “futile care” being performed on people. That’s when doctors bring the cutting edge of technology to bear on a grievously ill person near the end of life. The patient will get cut open, perforated with tubes, hooked up to machines, and assaulted with drugs. All of this occurs in the Intensive Care Unit at a cost of tens of thousands of dollars a day. What it buys is misery we would not inflict on a terrorist. I cannot count the number of times fellow physicians have told me, in words that vary only slightly, “Promise me if you find me like this that you’ll kill me.” They mean it. Some medical personnel wear medallions stamped “NO CODE” to tell physicians not to perform CPR on them. I have even seen it as a tattoo. The trouble is that even doctors who hate to administer futile care must find a way to address the wishes of patients and families. Imagine, once again, the emergency room with those grieving, possibly hysterical, family members. They do not know the doctor. Establishing trust and confidence under such circumstances is a very delicate thing. People are prepared to think the doctor is acting out of base motives, trying to save time, or money, or effort, especially if the doctor is advising against further treatment. It’s a huge problem that affects many fields, and I don’t know a good solution. But it’s good to acknowledge: There is one set of skills that comes from being an expert, and another that comes from being a novice, unburdened by the weight of experience or incentives. The former is obvious, the latter too easy to ignore.