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The 31 Deepest & Most Insightful Observations I’ve Made About Life

Lessons learned from 31 trips around the sun

This will change and grow every year because I’m a student of life, just as you should be.

I’ve learned some of these lessons from books, life experiences, and patterns I’ve observed in other people. Ovbersation is the key. The world is full of wisdom if you open your eyes to see it.

  1. Pretend like your parents are dead — This is the title of a chapter in the book, The Way of the Superior Man. The section talked about men and their fathers, but it rings true for everyone. Some people are 47 years old and still let their parents’ opinions and actions dictate how they live — become a fly on the wall of a therapist’s office and you’d see. You have to let go of what they did or didn’t do if you want fully to live your life.
  2. People are starving for meaning People who balk at personal development, purpose, and passion are the ones who want it the most. They use apathy and nihilism to cope with their lack of meaning. Deep down, we all want to think our life means something. And if we think it doesn’t, we suffer subtly, silently, and slowly. You want to make a contribution and pretending like you don’t won’t fix that
  3. Politics is the new religion — Politics has stepped in to fill the void in the absence of God. Many people don’t care about the stances of their side at all. They will adopt whatever stances their side takes because they are true believers. Funny, to me, the idea that Jesus walked on water is no less preposterous than the idea that a politician is going to save you and create a utopia. This trend isn’t going to end anytime soon. The tension will grow with each new election. What happens next? I don’t know. But in your case, remember never to outsource all your thinking and sense of purpose to politicians.
  4. We suffer from ‘diseases of abundance’ — In the West, at least, we live in the most abundant society of all time, yet people are unhappy. Why? Sometimes excess causes more problems than it solves. You can have access to too much information, too many sources of entertainment, and too many options. We suffer from the paradox of choice. Also, we invent problems because we need an explanation of why we’re unhappy. So, even when most of us have running water and electricity — something people in parts of the world still don’t have — we will look up and complain. Deep down, people know they have access to a better life. And when you have all the tools available to you, yet still do nothing with them, this causes anxiety. The answers to a better life can’t be found in modernity. They’re found in the proven principles you know but don’t follow.
  5. If you spark anger, your opposition agrees with you — If you have an outrageous opinion that’s clearly false, no one will care. But you’ll hit a nerve if you say something people don’t want to admit, but deep down believe to be true. This anger comes from the cognitive dissonance you feel when a fact contradicts your deep-seated beliefs. Few things piss people off more than the truth. If you tell it like it is, some people will hate you for it because they want to remain blind. Be careful who you tell the truth to and how you say it, now more than ever.
  6. If you know the incentive, you know the outcome — People act based on their incentives. They don’t act based on what you think they should do. Once you see life through the lens of incentives, you can’t unsee it. Incentives drive behavior to a level you’ll never fully understand, myself included. But learning how to observe the world through this lens gives you a better chance at predicting what will happen next. Remove the word ‘should’ from your vocabulary altogether.
  7. Luck plays a large role in life — Replay Bill Gate’s Life 1,000 times and he becomes the founder of Microsoft zero times. Replay his life a couple trillion times and maybe he does it once. Many people reach the top of their field of ‘survivorship’ bias. They get lucky breaks when equally talented peers don’t. Get a large enough pool of people, and a few will be on top out of pure luck. Meritocracy doesn’t exist because there are too many variables. You can’t control these forces, so stop envying the uber-rich and successful. If you do reach the top, understand you didn’t drive all of your success, either. Focus on yourself and work to increase your odds of successstack complementary skills — and create a life that will do well across 1,000 simulations. A successful dentist would likely become successful in most simulations given he or she graduated from dental school.
  8. Disparity doesn’t equal discrimination — Speaking of luck, there are so many variables involved in success that a perfectly equal society is impossible. People get different outcomes in life based on a ton of different factors, many of which you can’t legislate away. You can’t pass a law to remove the effects of factors like luck, upbringing, socioeconomic status at birth, chance experiences in one’s life, intelligence, beauty, one’s network, etc. The best we can aim for is equality of opportunity. Adjusting for those variables, everyone should have a chance at a better life. There are things we can do to accomplish this, but too many people are stuck on the idea of ‘utopia or nothing’ that’s impossible to reach. In a truly equal society, groups wouldn’t be represented equally in every facet of life because of preferences.
  9. Making things makes your life better — People who have ‘pet projects,’ side businesses, and/or creative ventures are usually happier. There’s just something about being able to say ‘I made this’ that gives people the meaning and sense of competence they desperately crave. And these days, working on a hobby you can turn into a side hustle might be necessary because of economic uncertainty,
  10. Reading is (still) undefeated — I know every self-improvement writer talks about the benefits of reading, but you can’t overstate them. You can read one book that gives you insights to change your entire life. Sure, you might not remember everything you read, but you become what you read. You can find the answers to all your deepest questions in books. People who write books spend months, years, or decades of wisdom and put it in a format you can digest in hours. People tell me I’m ‘wise.’ Nope. I just learned from people who already figured things out.
  11. You have to contend with both sides of contentment — On the one hand, you live in the material world and you’re wired to compare yourself to others. This means you care about achieving goals and earning worldly rewards. On the other hand, you can chase desires and end up deeply unhappy. The answer? Work on finding balance without ever achieving it, which will make you grow over the long-term. If you can master the art of reaching long-term goals without continuing to move the goalposts, you can reach a point of peace.
  12. It’s nearly impossible to predict how to make yourself happy — I just said you’ll never achieve full balance. Why? You can’t predict the future. Read the book Stumbling on Happiness for a deeper explanation. You try to achieve goals for ‘future you’ but you don’t know what ‘future you’ wants. ‘Future you’ will have different tastes, values, and goals. To make yourself happier in the present, focus on the progress you’re making in real-time. Stop looking for easier answers altogether. I stopped ‘trying to be happy’ because it’s not some eternal state of bliss you can capture.
  13. Small moments matter more than big ones — I once read an article about a woman who divorced her husband because he placed his cup on the counter instead of the dishwasher every day. Doing this day-in and day-out over years signaled to his wife that he doesn’t care about what she wants. This is how resentment builds — slowly, subtly, and moment by moment — but you also build bonds and positive emotions this way. Think — giving your wife one compliment per day for ten years. You’ll remember the overall themes of your life, but they’ll you’ll never assemble them in a short time-frame. Remember the famous Warren Buffet quote “The chains of habit are too light to be felt until they’re too heavy to be broken.”
  14. Nobody is rational — We use emotional and psychological shortcuts to make decisions, not logic. Persuasion matters, facts don’t. Once you understand this, you’ll be able to persuade others, predict their behavior, and understand why they behave the way they do instead of getting frustrated about it. In your case, if you can focus on being less wrong, instead of always believing you know the objective truth, you’ll get closer to the objective truth because you’re trying to see your biases upfront. You can learn to work with your emotions instead of fighting them or pretending like they don’t exist.
  15. Everyone believes everyone else believes the same thing — I’ll add another one of my favorite quotes here, from Morgan Housel: “Your personal experiences make up maybe 0.00000001% of what’s happened in the world but maybe 80% of how you think the world works.” You think you know how the world works. People who disagree with you are wrong. And you can’t fathom how they can’t see the obvious truth that you’re right. We can’t have a healthy discourse because people can’t accept that others see the world differently than they do. This speaks to the religious aspect of politics I talked about earlier. To varying degrees, you take opinions that contradict yours as blaspheme instead of a disagreement. You can try to combat this, notice I always say try because it’s hard, to look at conflicting viewpoints and attempt to disconfirm your own beliefs.
  16. Responsibility matters — People who don’t take responsibility for their lives have difficult lives. People who do take responsibility for their lives may have difficult lives as well, but they’re more resilient and have a better chance of moving up. Doesn’t matter what race, color, age, tax bracket, religion, […], you are — you’ll be better of taking responsibility for everything that happens to you, even if you think you shouldn’t, even if it’s unfair.
  17. You (probably) need to make more money — Money buys you freedom and time. People say they don’t care about money, but spend the majority of their lives working for it. The average person in society doesn’t have enough money for retirement. They don’t have emergency savings. They’re in debt a few paychecks away from ruin. We don’t have enough honest conversations about money. Why? Because it would cause an upheaval of our top-down society. You’re taught to have a negative relationship with money by people who profit from your poverty. It is your ethical duty to earn more money doing something you enjoy. Not for materials, but for your peace of mind.
  18. We’re afraid of dying, but act like we’re going to live forever — Seneca says: “You act like mortals in all that you fear, and like immortals in all that you desire.” We give away time like it’s not precious. You struggle to focus on your mortality because — who wants to think about dying? We put things off until ‘tomorrow’ because we think we’ll see tomorrow. Our fear of death pushes us further away from our dreams. If you build a healthy relationship with your mortality and use it to motivate you, you’ll guard your time and spend it doing what matters most. Instead of using time management, use priority management. Understand you don’t have to give equal weight to different obligations, not at all. You should favor some much more than others.
  19. Everyone is just as self-conscious as you are — We assume positive qualities about people without really knowing them. They’re the confident ones who have it together. Everyone thinks the same think about everyone else. Knowing this can ease your anxiety and increase your confidence. You’ll also learn to take people less seriously when you look into their minds. From Marcus Aurelius: “You want praise from people who kick themselves every fifteen minutes, the approval of people who despise themselves. (Is it a sign of self-respect to regret nearly everything you do?)”
  20. We’re all monkeys — When you view human beings as animals, everything makes much more sense. We’re the same as our hunter-gatherer ancestors, but we live in a modern environment. We avoid fear and skew toward negativity (avoid sabertooth tigers). We want to fit in with the tribe and behave in a tribalist way (rejection from the tribe means death). Most of the problems we have in life stem from a mismatch between our caveman brains and the environment. You can improve your life by understanding and correcting these mismatches, e.g., understanding and embracing that social rejection doesn’t equal real harm.
  21. Writing well is a superpower — Everyone needs to write. If you can write well — structure a sentence, omit needless words, and get your point across — you’ll appear competent and authoritative. The opposite is also true. Have you received a poorly written email before? Exactly. If you can write well, you can think well. If you think well, you can plan your life well. Why do you think some of the top entrepreneurs know how to write amazing essays? They know how to structure their thoughts. Regardless of whether or not you want to build a writing career, you should learn skills like basic business writing, copywriting, essay writing, etc.
  22. Act as if’ — Pretending like you’re more confident and competent than you are can help you make those traits become real. Try smiling and feeling sad or standing up straight with your chest out and feeling like a loser. You can’t do it. You can use superficial techniques to make real changes. When you’re trying to accomplish a long-term goal, you have to fake it a bit, because you’re trying to create something that doesn’t yet exist.
  23. Nobody is coming to save you — Think about it. When, in the history of life, has the magical Utopian policy come to save the masses? It never has and it never will. Nothing moves more slowly than the government and the institutions of society. I repeat… no one is coming to save you. You have to do it on your own. I don’t come to this conclusion lightly. I’ve thought about it. If I thought a collective answer would work, I’d promote it. But I don’t
  24. Talent matters — I can’t decide to play basketball like Lebron James. Nor can I build rocket ships like Elon Musk (well maybe if I had enough time on my hands.) I’ve only succeeded at things I thought I’d be good at before trying them. I play games I think I can win. When your parents said, “You can do anything you want in life, even become president,” they were wrong. You can do well at a wide enough range of things to be successful. Find those things, do them, and as Gary Vaynerchuk said, “Don’t give a f*** about what you suck at.”
  25. Everyone suffers from special snowflake syndrome — You think good things are supposed to happen to you because you are you. We believe that if something goes wrong, we should blame the world instead of ourselves. We all think our situation is so unique when in reality, human beings have continued to go through the same patterns and problems over thousands of years. This is why you must understand history and human nature. Once you realize that you aren’t special, you can do the work needed to build a better life because you embrace the idea that a better life requires work.
  26. Group-think is toxic — Nietzsche said, “Madness is rare in individuals, but in groups, states, and societies, it’s the norm.” Mark Twain said, “Whenever you find yourself on the side of the majority, it is time to pause and reflect.” Most successful people are contrarians because it’s hard to have above-average results by doing what everyone else does because everyone else is doing it. You shouldn’t reject all conventional wisdom. Just have a careful eye and avoid the hysteria of the masses.
  27. Not being stupid > being smart — We live in a “do something,” culture. We always look at success as addition when often subtraction works better. In short, stop doing dumb stuff! Don’t smoke, lie, complain, waste money, eat like crap, make bad/risky choices, argue too much, gossip, watch sad news, break promises, […] and you’ll be better off. You can improve your life much faster by stopping all of the actions and habits that harm it.
  28. You are blessed — We have an easy time comparing up, but a harm time comparing down. No matter who you are, you have privileges. You have some advantages that others don’t — advantages you didn’t earn. You can play the inequality game all day long. Or you can use the blessings you do have to build a better life. Speaking of life, I bet there are many people who died early that wish they were alive to have your problems. I practice gratitude daily by writing down 3 things I’m grateful for. This keeps me grounded and alleviates anxiety when I’m pushing too hard to achieve more.
  29. We can do the things we love (right now) — I didn’t have to wait for the perfect opportunity to start writing — I worked it into a busy life. I didn’t have to become a full-time writer before I enjoyed putting my work into the world. You can do the things you love, right now. Once you realize that, you’ll start doing them more often. If you want to be an artist, buy a canvas and start painting — it doesn’t matter if you sell any of it. If you wish you didn’t need to work so you could spend more time doing things you enjoy….carve out more time doing the things you really enjoy while having your job (this means less Netflix). Your dream life where you get to do what you want doesn’t have to be far away. You can live a version of it right now.
  30. You can transform your life (given enough time) — I never give easy tips and tricks. I wrote an article called The 5 Year rule, which is one of my most popular articles ever. I’m guessing that timeframe resonates with people because it’s not enough to not sound like a ‘get rich quick’ scheme and short enough that it seems doable. If you can sacrifice a few years of your life, you can have the rest of your life back to live the way you please.
  31. Love yourself — Yes, it’s corny and cheesy and cliche, but you have to constantly be around you. Read the book Love Yourself Like Your Life Depends on it because it does. Your relationship with yourself dictates your relationships with…everyone else. Most of the observations tie into the idea of getting right with yourself first before you can expect tangible improvements. It’s hard to love yourself sometimes because you know everything about yourself — including the things you don’t want anyone else to know. You know your sins, your flaws, and your shortcomings. But you can also acknowledge your beauty, your resilience, and the parts of yourself you want to amplify. You are both the good and bad and fully accepting that makes a life of suffering a little bit easier.

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