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The 25 Deepest & Most Insightful Observations I’ve Made About Life

A few will surprise you


This post originally appeared as a response to this question on Quora — “In observing life deeply, what are your conclusions?”

Some of the conclusions are simple and cliche — as with most useful pieces of advice. Some of them were counter intuitive. Some of them were things I wish weren’t true, but are.

See the list for yourself. If you have observations to add, leave them in the comments below.


  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 — no matter how bad — if you want to live your life.
  2. People are starving for meaning I’ve come to the conclusion that people who balk at personal development, purpose, and passion are the ones who want it the most. It’s their coping mechanism. 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. Luck plays a large role in life — Replay Bill Gate’s Life 1,000 times and he becomes the founder of Microsoft once. Many people at the top of their field are there because of ‘survivorship’ bias. Get a large enough pool of people, and a few will be on top out of pure luck. The best you can do is increase your odds of success — stack complimentary skills — and create a life that will do well across 1,000 simulations. A successful dentist would likely become a successful dentist in 999/1,000 simulations given he or she graduated from dental school.
  4. 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.
  5. It’s nearly impossible to predict how to make yourself happy — Read the book Stumbling on Happiness for a deeper explanation. There’s problem with doing something for ‘future you.’ You don’t know what ‘future you’ wants. The future version of yourself will have different tastes, values, and goals. To make yourself happier in the present, focus on the progress you’re making in real time.
  6. 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 it’s also how positive emotions and bonds build. Think — giving your wife one compliment per day for ten years. You’ll remember the overall themes of your life, but they’ll never be assembled in a short time-frame — they’re all accumulations.
  7. 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.
  8. 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.
  9. Time-tested > New — Books that have been around for 1,000 years almost always trump the knowledge found in new releases. This is known as ‘the Lindy effect.’ It’s good to know the time-tested wisdom about human nature because we haven’t changed all that much — at our core — over time.
  10. Listeners rule the world — You don’t need to be a great conversationalist to get people to like you. If you listen, show interest in them, and reflect back what they’ve said to you, they’ll think your a genius at conversation even if you barely talk. Why? Because…
  11. Everyone thinks they’re the most important person in the world — If you treat people like they’re important — regardless of their perceived status — you’ll live a better life. This is textbook How to Win Friends and Influence People. Which reminds me …
  12. Arguing is for fools — Arguments stir up negative emotions, rarely get your point across to the other person, and make people like you less.
  13. We’re afraid of dying, but act like we’re going to live forever — This idea comes from the Stoic philosopher Seneca. We give away time like it’s not precious. We put things off until ‘tomorrow’ because we think tomorrow is always going to come. We’re so scared that it won’t so we live like it always will, thus pushing our dreams further away. The ones who truly live think the opposite — “I could die tomorrow. I better get on with it.”
  14. 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 their shit together. The truth is, everyone thinks the same think about everyone else. Knowing this can ease your anxiety and increase your confidence.
  15. Appearance matters — People judge you by your outward appearance. This should be treated like s scientific law. Now that doesn’t mean that it’s okay, but if you know this to be true, why not present yourself in the best way? Plus, you’ll feel more confident if you’re well-groomed, well-dressed, and appear professional. This idea matters much much more than you think.
  16. We’re all monkeys — When you look at life from an evolutionary perspective, everything makes much more sense. We’re exactly the same as our hunter-gatherer ancestors. Negativity is wired into us (avoid sabertooth tigers). So is wanting to fit in and tribalism (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. Knowing this is one of the keys to making your life better.
  17. 80/20 –80 percent of your results come from 20 percent of your effort. Narrow your efforts down to the ones that produce the most results, remove the ones that don’t, double down, repeat.
  18. 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.
  19. 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.
  20. 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.
  21. Talent matters (a lot) — 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 either wrong or lying. You can, however, 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.”
  22. Group-think is toxic — When Nietzsche said, “Madness is rare in individuals, but in groups, states, and societies, it’s the norm,” he hit the nail on the head. Listen to the advice of Mark Twain when he 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 disproportionate results by doing what everyone else does because…everyone else is doing it.
  23. Not being stupid > being smart — We live in a “do something,” culture. We’re always talking about positive actions when a high quality of life comes mostly from what we don’t do. In layman’s terms, 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.
  24. We can do the things we love (right now) — I love writing. I’m writing 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, without your circumstances changing. 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. If you don’t have time for your ‘ideal day’ have an ‘ideal hour.’ Make the dream fit.
  25. 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 deep dark 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 the most to the world. You are both the good and bad — the yin and yang — and fully accepting that makes a life of suffering a little bit easier.

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