UPDATED ON APR 27, 2023 : 2512 words, 12 minute read

Life is a long string of making mistakes and learning lessons.

This list is a living document for me to reflect on past experiences.

The more I reflect, the less likely I am to fall for the same mistakes…

or so I hope.

Some of these are quotes I’ve collected from others, unfortunately I don’t have attribution for all of them. Assume most things on this page were written by wiser people than me.

Most Important 🔗︎

  • Be kind - Everyone around you is just trying to get by. Don’t make their life harder because you can’t control your emotions.
  • Operate permissionless - Life is more interesting when you aren’t waiting for others to tell you it’s ok to be you.
  • Pareto Principle 80/20 - Lots of life is spent on the fiddly details that barely have an impact (e.g. timing protein intake when you never workout, the color of button on a website you showed no one). If you put energy into the big factors of whatever you are doing at work/hobbies/life, the little bits will sort themselves out.
  • Extreme Ownership - waste less time assuaging your ego, keep life moving forward.
  • Action over research - This depends on your personality, but if your default is endlessly researching and overthinking and optimizing, try just going with the first option.

🌱 Life Lessons 🔗︎

  • Cliches seem to be cliches because they have to be said a million times, and people still don’t listen until the world punches them in the mouth with it.

  • Waiting for permission is a great path to frustration and nothing happening. This applies across many more areas of life than I realized growing up. Example: not switching careers because you don’t have a degree = waiting for permission to switch.

  • You will never reduce Uncertainty to 0. No matter how much you overthink, no matter how much you research, no matter how many backup plans you put in place. The world will always have a way to flip you upside down. Be flexible.

    • “When I was a brand-new lieutenant, I asked my father, “How would I know if somebody that I worked for or worked for me was going to be a good commander in combat? … How would you tell in peacetime?” He says, “You won’t. You won’t know because people have capabilities or coping mechanisms that in peacetime look fine, that doesn’t play well in war.” Then I asked him, “Okay, when you’re in combat, how do you know?” He said, “Some people keep asking for more information and what they’re trying to do is drive uncertainty to zero so that there’s really not a question on the right course of action because you know everything.” But you can’t do that. It’s not achievable. So they become hesitant. They become tentative, and they become focused on getting more and more information to ratchet the uncertainty out of the situation and they don’t act.”
  • Excuses make you feel better in the short term. Extreme Ownership moves you forward.

  • you can have anything in life, you just can’t have everything

  • Recognize life is a series of obstacles that are opportunities, even if it’s cliche its cliche because it’s true and we don’t accept it usually.

  • The future will take care of itself if you take care of every day . Spend every day drinking and smoking? Probably not gonna lead to anything, but if you attempt things , things will come together.

  • Spend so much time driving places, waiting on deciding what food place to go to in the new place. Lots of life slipping away

  • Lean into your strengths, your competitive advantages. Everyone has different abilities and experiences in life, don’t waste time trying to fight against the tide when you could go with it.

  • plan for failure so you can quickly figure out a better way to do things. Fail quickly, if things aren’t working, cut it and try something else. This is not an excuse to quit trying when things get tough, but if you have experimented and attempted and the signs are pointing to a better path, don’t dilly dally. This applies across much of life. Software - have monitoring in place so that when things break, you know what’s going on.

  • Am I saying yes out of fear or guilt? Life is full of accidental serendipity though, should occasionally say yes even if you would say no just to be there for the occasional accident

  • The things you track are the things that improve in life

  • Build your body and your skills, doesn’t matter if you have money. It’s all a part of you. Would you rather be ripped and poor or fat and rich?

  • The gear, the trappings don’t matter if you haven’t got the core elements down pat. Airsoft gear boys with no skill, running with all the fancy leggings and junk but you only go 1 time a year. Find the core of a new skill if you want to make real progress

  • Brick walls are there for a reason: they let us prove how badly we want something by stopping the people who don’t

  • Celebrate others wins, even if you don’t understand them.

  • you can always find an excuse if you’re looking

  • Something I have noticed is that people like cleaning up my messes even less than they like cleaning up their own messes - Dan Mckinley

  • Life is not a zero sum game

  • You can learn just as much from a bad teacher as a good teacher

  • “Hate isn’t the opposite of love. Indifference is.”

  • You either work out when young, or shuffle between appts & have less active. Either way, you pay the time eventually.

  • The quality of your life is a direct reflection of the quality of the questions you are asking yourself,” wrote Tony Robbins in Awaken the Giant

  • if you go looking for a reason not to do something, you’re sure to find one.

  • Life will act on you even if you haven’t figured out how you want to handle it yet. Even an imperfect decision will be better than no decision paralyzed by fear.

  • Can you actually not do it, or is it just easier to tell yourself you can’t because the alternative is long and full of struggle

  • Automate good decisions first

  • surprise gifts or visits activate more powerful happiness responses, or something like that

  • Oftentimes there can be more impact from removing bad things or circumstances or events from people’s lives than trying to add value on top of their current life.

  • life is not convenient and does not respect our plans. Tragedies will not strike at convenient times for us, it will be messy.

  • “Things that keep talented people from fulfilling their potential: - Trying to please everyone - Imitating the desires of others - Chasing status without questioning why - Playing superhero and trying to do it all alone - Dividing your attention between too many projects”

  • Build and give stuff away for free, life will return you in spades

    The Rule of Reciprocity tells us it’s human to want to return a favor, a gesture.

    We’re programmed to give value after receiving value. And here’s the thing: we tend to give back far more than we originally received.

    This is how small, free samples turn into big sales.

    Give away your content, your expertise, your time — and it will come back to you in spades.

  • “Choose your lifestyle first. Ask yourself what does “freedom” mean to you? House, car, relationships, office, work… What do you want? Then work backwards and write down how much you want to make.” - The lifestyle approach to life

  • To combat over-thinking: “Can you see a way through? No. Can you see your next step? Yes. Just take that.” The boy, the Horse, the Mole (book).

🤼 People Lessons 🔗︎

  • humans, me included, default to additive solutions, rather than simplifying through removal. Relevant XCKD .
  • if people are agreeing with your suggestion, it might be because they just don’t want to think about alternatives or if your idea is any good. Could be setting yourself up for failure by accident.
  • Remember people’s names & birthdays, “the sweetest sound to the human ear is their own name”.

🤑Financial Lessons 🔗︎

  • Money should be spent on experiencing and improving your life. “The point of having money (after securing basic needs) is to add beauty to your life. And the longer you defer beautifying your life, the harder it gets to learn what gives you joy.”
  • FIRE - it’s a great idea for a few people, but for many, you end up chasing a number that is a facade for what you are really chasing. The number is a stand-in for “if I have this amount of money, I don’t have to worry about anything and life is safe”, which is just not true.
  • Time is your most important asset - you are likely a Time Billionaire (1 billion seconds = 31 years). Treat it with the value it has, since it’s the only resource you can’t get more of.

👩‍🏫Teaching Lessons 🔗︎

  • Frame what you’re teaching in terms out outcomes, not topics like is usually done. Can start there to organize your knowledge, but that’s not the best way for someone new to the topic to organize
    • What should they be able to do by the end of a module or course
  • Start by thinking about what you would teach yourself 3 years ago if you could, and put that online. Show your work
  • “headfakes”: best way to teach something is to make them think they are learning something else. e.g. have kids make movies & games, but they’re learning to program while doing it
  • Not sure what you know enough to teach - what would you teach yourself if you met the 3 year ago version of yourself?

⚖ Leadership Lessons 🔗︎

  • Psychological safety Adam Grant, share past mistakes and failures among people. Not enough to say “my door is open for feedback” cuz people don’t know how you’ll react.
  • Good leaders not just open to feedback, make sure to talk about failures and feedback to build humility and show your open to hearing others thoughts
  • Most of the time if you present a solution to a problem, no matter how crappy, people will just go with it and think less on the problem. Plus, even if they do its anchored to what you started at.

📈 Personal Growth Lessons 🔗︎

  • Focus on things that compound and do them first
  • The things you track are the things that improve in life
  • Invest in non traditional assets. Trying things, spend time helping other people, meeting mentors, networking, random ideas, investing in yourself.
  • “In my experience, if you complete just ONE meaningful, concrete piece of work every day, no matter how small, you are in the top 10% of most productive people If that piece of work is in any way evergreen and reusable, easily top 1%”
  • Early career is all about growth and meeting people, you can earn money and actually draw value when you’re older. Like creating potential energy
  • You won’t get very far listening to the same advice on medium 1 million others are also reading, the big successes are from people forging their own path despite adversity or the common sense saying not to like Airbnb

Career Lessons 🔗︎

  • Businesses are not hyper-efficient money-making machines. They will celebrate cost savings in one area by throwing a lavish happy hour.
  • “lift as you climb - each time you make a move, bring others along with you”.
  • “Imagine life as a game in which you are juggling some five balls in the air. You name them—work, family, health, friends, and spirit—and you’re keeping all of these in the air. You will soon understand that work is a rubber ball. If you drop it, it will bounce back. But the other four balls—family, health, friends, and spirit—are made of glass. If you drop one of these, they will be irrevocably scuffed, marked, nicked, damaged, or even shattered. They will never be the same. You must understand that and strive for balance in your life.”-Brian Dyson
  • When you work too hard and too much, it’s like a powerlifter going for too much weight. It’s a big risk for something bad to happen.
  • Consider: will you have more impact at a small company doing a lot of good, or at a large company reducing the bad by a tiny fraction? Scale of company has a huge effect on what your personal impact is.

🚧 Startup/Creativity/Product/Indiehacker Lessons 🔗︎

  • For creativity to thrive it needs constraints, even if artificial
  • Are you asking questions because you want answers or because you want to feel like you’re making progress without doing anything hard?
  • If it was obvious and easy, everyone would already be doing it
  • Have good monitoring for events that matter because users won’t talk to you, happybara learnings
  • You can launch a startup with shitty logo & website and still be really successful, promise. Just have to start.
  • Companies (People) don’t buy features, they buy solutions to really painful problems
    • Postman is a huge company, despite being the GUI equivalent of curl scripts. The command line is scary to tackle, so even developers run away from it.
  • Your biggest competitor is a spreadsheet | by Hjalmar Gislason | GRID — the new face of spreadsheets
  • Doesn’t matter how many features you have if people don’t love the core of your product, todo lists are great examples, they all have many features but if you don’t nail the todo experience it don’t matter
  • “Is it a good problem?” don’t worry about if it’s a good business always
  • Struggling with perfectionism with creating things, flip the script. Aim for 20% of things to be wrong, otherwise you’re spending too much time on it
  • keep it simple, remove administrative bottlenecks where you find them, go slow and manual first, automate later.
  • Before you can build a business that helps people, you must become a person who helps people.
  • As a founder, you may never know the impact you have on the lives of individual users. There is so much more to life than curing cancer. Anything that makes someone smile & feel better about their current situation is worth building.
  • No marketing leads to no sales. Some marketing leads to some sales. And lots of marketing leads to lots of sales.
  • You’re not offering a product, you’re offering the 2 sentence description of that product. If they bite, then build it Offer-Led Growth
  • “Build a startup around something that doesn’t feel like work to you. Find a customer you’d love to serve, find a problem you’d love to solve, and you’ll go far.”
  • features are very easy to add, but almost impossible to remove.
  • “First-time founders focus on product. Second-time founders focus on distribution.” - Justin Kan
  • “Your customer cares literally zero about your company, your story, your brand, or even your product. What they do care, is what it can do for them. Don’t fight this, embrace it.”

See Also