30 Directives from 30 Years: A Letter to my 20-Year-Old Self

30 Directives from 30 Years

“It’s not the years in your life that count. It’s the life in your years.”

Abraham Lincoln

I recently turned 30 years old. Yikes.

I remember turning 20 like it was yesterday. It’s hard to believe 10 years has passed in such a flash!

I’ve been told that time seems to move faster the older you get, and what wise words those have turned out to be.

But while seeing that sentiment play out in my own life, it doesn’t quite frighten me as much as if I were to have squandered the last decade with no growth, no evolution, and no progress.

Where I come from, most people think the learning stops after high school. Somehow, I escaped that gravitational pull of limited thinking, and I’ve come to the firm belief that the amount of learning is proportionate to the amount of living you do.

And by living, I mean stepping outside one’s comfort zone and experiencing new things. Unfortunately, it took me about 25 years to fully come to that realization, but better late than never.

Prioritize living

In the last five years, I’ve prioritized living:

But what happened before all that? Well, I went to college for a meaningless political science degree (the fact that “political” and “science” are in the same breath just makes me cringe). I got deeply into student loan debt and worked several jobs I hated just to pay the bills.

I followed the straight and narrow path. Because I thought it was the shortest distance from where I was to where I wanted to be.

But if you’ve ever watched hockey (or any sport for that matter), you know that it’s best to go where the puck will be, not where it is.

Hockey puck logic

Life is very similar. Approaching life in this manner may become a longer process than you intended, but going to where your goal will be can save you a lot of chasing and catching up.

Don’t get me wrong, there is absolutely nothing wrong with the straight and narrow path. It may be safer and more predictable (so you think), but it’s less efficient, and at the end of the day, it’s just not that fun.

So today, in an effort to save years and decades of wrong turns and bad decisions, I have laid out a list of 30 directives for my 20-year-old self, and for you if you find them useful. Here’s what I would do differently at 20:

1. Define your purpose, above all

If there is one thing to devote every waking hour to as a college kid (preferably before college), it should be creating and defining your purpose. Notice I didn’t say “finding” your purpose. Purpose is not something you go out and find. It is found within you. You just have to do the internal work necessary to grow into it. And once you are in alignment with your purpose, life begins to conspire for you to achieve your dreams.

Save yourself from 30 years of wandering

2. Once you have purpose, pursue it like your life depends on it

Because it does. A life without purpose is a road trip without a destination. It’ll be fun for a while, but at a certain point, you’ll begin to panic because you’re lost. That was me at 25. I made a pact with myself that I would never find myself in that situation again. And so every decision I’ve made in the last five years has been geared toward meaningfulness and purpose.

3. Question everything

Gustave Flaubert once said, “be regular and orderly in your life, so that you may be violent and original in your work.” If you’re my age, you were most likely raised by generations that love routine and tradition. And while there is room for those, these cannot be the centerpiece of a fulfilling life. Be regimented in your routines, but within those constraints, experiment. Test different inputs. Break the rules. Crossing lines is the only way for you to know where they are. Throw stuff against the wall and see what sticks. Life is too fleeting to stick to someone else’s limited definition of what it should be.

4. Don’t accept “because that’s how it’s always been done” for an answer

Stemming from the last point, cognitive shortcuts like this one can be useful in surgery and architecture (but even they have their limits). In most areas in life, however, “how it’s always been done” is just a baseline for you to begin your experimentation. After all, if we all followed the same procedures, the world would be a very boring place. Be skeptical of convention, and don’t let it double as a shortcut to the truth.

5. Pursue timeless wisdom, not intellectual fashions

As Thomas Jefferson said, “In matters of style, swim with the current; in matters of principle, stand like a rock.” While procedures should almost never be timeless, the wisdom behind them must be. Study the ancients. They were not blinded by the politics and trends of today. Use the Lindy Effect to your advantage. While everyone else is reading up on the latest crazes, fill your mind with the wisdom of centuries. Because by definition, if it was faulty, it wouldn’t be wisdom and it wouldn’t have lasted for centuries and millennia.

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    6. Avoid boring people

    This is a saying from James Watson (who discovered the double helix structure of DNA with his partner Crick), and it’s so true. We all want to hang out with the coolest, most interesting people. But let’s take this natural instinct even further. Cultivate a habit of not boring other people! To maximize what you get out of life, you have to be as engaging, if not more engaging. Give more of yourself and you will receive more. It’s something I still battle with, but I’ve learned the value in it.

    7. The more you learn, the less you know

    I look at education (with a lowercase “e”) as an ever-expanding, ever-evolving realm. It is not a finite thing where the more we learn, the less we don’t know. People who think like this tend to have big egos and will eventually be humbled. Everything we learn serves to illuminate everything around it that we don’t know. The sooner you realize that, the sooner you can begin to focus on what means the most to you. Instead of being on a mission to learn everything, be open to learn anything, knowing that there are things you may never know. Don’t be intimidated. The unknown is where the fun is.

    8. Take the stairs, not the elevator

    To gain an edge over your competition, follow what I call Cooks’ Law. Start by picking a hard problem, and then at every decision point, take the harder choice. By doing so, when opportunity comes knocking, you’ll not only be ready for it, you’ll have already been through the adversity in your preparation. You can take the elevator and get to the 9th floor faster, but when it’s time to do anything physical (not to mention aging), you’ll have put yourself behind the 8-ball. Similar to the hockey puck diagram above, the easiest path is not always the best.

    Taking the steps instead of the elevator is high resistance, low immediate-benefit. These are behaviors we tend to avoid. But if you play the long-game—if you see where your goal will be and not where it is—these seemingly inefficient behaviors will put you way ahead of where you would otherwise have ended up.

    9. Following the crowd is a life sentence to ordinariness

    In school, following the crowd kept you safe and accepted… another reason why school is mostly nothing more than a daycare and doesn’t prepare us for real life. In real life, following the crowd keeps you irrelevant and limited. Escape competition through authenticity. A meaningful life is about making an impact that only you can make. Which means taking risks, sticking your neck out, and being different—not being confined to a cubicle working for someone else.

    10. Don’t go to college

    I’ll get a lot of flack for this one, but I don’t care. We’ve been trained only to see one finite pie available to everyone. And the “only” way to get your slice is to play the same game as everyone else. But nobody has told you that there doesn’t have to be just one pie. You can make more pies! And not only does making more pies differentiate you, it can benefit the world, AND you don’t have to go into soul-crushing debt to do it.

    Create something every day and publish it to the internet. Make connections online you wouldn’t be able to in the physical world. Learn to build and sell. These are really the only skills you need to truly succeed. You don’t need some $200,000 piece of parchment that everyone else has from some fancy school that everyone else went to in order to make an impact in the world and become financially free. Ignore this lesson at your own peril. You can read my thoughts on this here.

    11. Most social sciences are bullshit

    Speaking of college, please don’t major in the social sciences. Everything I learned as a political science major could have been learned on my spare time, reading Wikipedia. Science isn’t done by consensus, but by experimentation, falsifiability, verifiability, and rigorous testing. If there is no experiment that could theoretically disprove a claim, then it’s not science. And that’s my beef with the social “sciences.”

    Don’t waste money, and more importantly, don’t waste precious time on subjects that don’t teach you useful, necessary skills to build wealth and attain freedom of time.

    12. Habits define you

    Habits are everything. They behave like setting concrete. The longer you wait, the harder it gets to reshape them. Habits can save you time in the form of automated decision-making, but the wrong habits, if not corrected sooner than later, can set you back for years.

    13. Choices distinguish you

    Imagine what 30 years of habits in either direction can do.

    Choices are the building blocks of habits. In every situation, you have a choice. And the more bad choices you make, the worse your trajectory will be. But look at the diagram again… even one bad choice sets you back. Your ability to learn from them and not make second chance mistakes will be the ultimate differentiator in the long run.

    14. Reputation decides you

    When we’re young, we tend to value money, status, and pleasure above everything. But often what happens is that we get addicted to these, at the cost of our reputation. In order to build long-lasting wealth and success, your reputation needs to be your number one priority. It allows people to trust you. It precedes you.

    15. Aim for wealth, not money

    When you aim for money, all you will ever become is a money-chaser. That’s why people play the lottery–it’s a tax on people who aim for money. Wealth, on the other hand, is assets that compound. Wealth is investments that bring a disproportional return to you over the long-term. Wealth is not renting your time out to the highest bidder. And wealth is not limited to money; you can build it in relationships, knowledge, and experience. When you aim for wealth, you suddenly open doors, increase your options, and allow yourself the freedom to do things and meet people that you would never have thought possible.

    16. Aim for meaning over status

    Status is an empty signifier. You are not your status. It is something you can enjoy briefly, but reliance on it tends to only bring you more problems, which money cannot solve.

    Any status you have not earned through doing meaningful work is hollow and can become a facade you hide behind when your accomplishments are in question. Doing meaningful work is the best way to escape this fate, as your status will be a byproduct, and not an end in itself.

    17. You can’t choose your family, but you can choose how to love them

    One of the deepest pains in my life has come from the fact that I’ve never had what you would call “normal” parents. The ones who showed you the right way to live. The ones who took you to football practice. The ones who helped pay for college. The ones who cooked you dinner. And the ones who tucked you in at night.

    Whatever “normal” parents do, I never had growing up. But one of the deepest joys of my life has also come from the fact that I’ve never had what you would call “normal” parents. Read more about my story here.

    Your family may not be perfect. Choose to see your family for what they are, and appreciate them for who they are, no matter what faults they may have.

    18. It’s not about time management, it’s about attention management

    Adam Grant says productivity isn’t about time management. It’s all about attention management. People who say they don’t have time don’t have priorities. If your attention is spread thin, you’ll always feel like you don’t have time. But if you just fix your attention to what is most important, you’ll begin to realize your time management issues where never really about time.

    You could manage your time perfectly, but if your attention is in all the wrong places, does it really matter?

    19. Write. it. down.

    Build a habit of making lists and taking notes. Despite how they trained us in school, the brain is not meant to be bogged down by storage. It is not a memorization tool. When we stress retention over attention, our creativity goes out the window and our humanity goes out the window, as we are programmed to recite rather than excite.

    When you write things down, you get more done. And you never have to reinvent the wheel. Let computers be your storage center. Free up your brain for what it’s truly meant for: creativity.

    20. Build a bias for action.

    Time is the most valuable currency. Sure, Lincoln spent four hours sharpening his ax, but he fully meant to use it to cut down the tree. Don’t spend endless time planning, preparing, and then doing nothing. Consumption is a lecturer, and application is a teacher. When in doubt, just do it, and you’ll figure the rest out along the way.

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      21. Touch it once.

      As an addendum to the previous point, when you have a lot of action items on your list (remember #19: make a list, always), give your attention to each item just once. Don’t let it sit. It will eat you up. If your tasks are not small enough to touch just once, then they are too big and should be broken down anyway.

      Robert Moses, the master-builder of New York City, used to work at a table, not a desk. And he wouldn’t move on with his work until each paper on that table was addressed. Think this will slow you down? Try building New York City with the system you have!

      22. Save your work

      Save your work. Just do it. Every chance you get. Use an external hard drive in addition to the space you have on your computer. If you have written physical documents, scan them into your phone. Utilize cloud storage.

      The point is, you do not want to have one single point of failure. If something happens to your computer, you can be comfortable in knowing you have your work saved elsewhere.
      This practical step will save you unknown amounts of time and will ensure you keep the momentum moving forward.

      23. Process over payoff

      “[The] goal will be simply a by-product of all the hard work and good thinking you do along the way – your preparation. The preparation is where success is truly found.” –John Wooden

      Don’t be the kid in the back seat asking “are we there yet?” With that mindset, you subject yourself to misery and mediocrity because you are not interested in the process of achieving your goal. But, if you take ownership of the process, enjoy every step of the way, no matter how mundane, as the great Bill Walsh said, the score will always take care of itself.

      24. When in doubt, look to Occam’s Razor

      It’s called a razor for a reason: it shaves away unnecessary assumptions. Occam’s Razor tells us that the simplest explanation is most likely the right one. Instead of wasting precious energy and brainpower wondering what the cause of something could be, look to the simplest plausible reason. You won’t be right 100% of the time, but you will save yourself a lot of time and suspense.

      25. Stop and do nothing.

      “All of humanity’s problems stem from man’s inability to sit quietly in a room alone” -Blaise Pascal

      This might actually be the best lesson I’ve learned, and happens to be the most recent. We spend so much of our life running. Running from pain. Running from responsibility. Running from accountability. Running from the voices in our head. In order to avoid anxiety, worry, and the incessant self-talk, take an hour in the morning to sit and literally do nothing. As Naval Ravikant says, it’s like clearing the inbox of your mind every morning. After a couple weeks of this, I already feel remarkably calmer and freer.

      26. The sooner you stop living someone else’s life…

      …the sooner you can begin building the life you want. Every second you spend wishing you had someone else’s life is a second spent wasting yours. In an era of sharing our lives so openly on the Internet, it’s easy to fall into a vortex of comparing yourself to others. The Internet is a wonderful place, but it can be destructive if you let it shape you instead of shaping it yourself. Don’t compare yourself to others. Listen to Chris Sacca: “Be your unapologetically weird self.”

      27. Plant seeds of compound interest

      30 years from now, what will your investments look like?

      Hearkening back to #15, compound interest is the result of earning interest upon interest. This concept doesn’t just apply to money. It applies to social relationships, your reputation, the learning process, and the creative process.

      Cultivate symbiotic friendships, instead of hierarchical relationships. Implement systems that allow you to build trust over time. Build a reliable note-taking system where you can build upon your current knowledge instead of holding it in your head. Create compelling online content, produce new things consistently, provide value in your efforts, and compound interest will inevitably accrue over time.

      28. Your competitive advantage is staying power.

      “My whole system of life is keeping at it. The task of life is not to see clearly in the distance but to do the task at hand” — Charlie Munger

      Most success comes from repetition, not new things. If you think there’s too much competition, never fear: longevity is hard to come by. Going back to #1, if you can zero in on your purpose, double down on it, triple down on it, and stay with it for years to come, you A) get better and better, and B) You lose the competition.

      Don’t focus too broadly on other people. Don’t focus to far into the future or past. Your mission is here and now. Take care of business every day and…you guessed it: the score will take care of itself.

      29. Do it now.

      Your fear of a particular outcome is inversely proportionate to your confidence in your resilience. We tend to procrastinate and put off things out of fear because we don’t want to face our mind’s concoction of worst case scenarios. The vast majority of the time, taking action is the antidote to doubt. Standing face to face with your fears, heading into the fog of uncertainty, can put your mind at ease and build your confidence.

      Because if you don’t take action to get what you want, someone else will. Do it now.

      30. If you are reading this, you are among the luckiest humans in the history of the planet.

      Think about it. In all of human history, in all of the history of planet Earth, we are living at this very moment in time, on the cusp of a technological explosion. It’s a time when we can connect with someone in Australia instantaneously from our apartment in suburban Philadelphia. It’s a time when we can produce value on the internet for the entire world, not just finite products in a local store. It’s a time when we can extend our lifespan and healthspan. It’s a time when we are exploring new frontiers for humans in space. It’s a time when the whole of human knowledge is just a Google search away. What are the chances that you sit here at this moment with a universe of possibilities at your fingertips?

      The future is blindingly bright.

      Waste no more time.

      Wander aimlessly no more.

      The future is yours for the taking.

      It’s here and now.

      Don’t wait for your future. Create it.

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