27 Things I Learned Turning 27

Writing this in a cafe in Tel Aviv, Israel, I can’t help but think about my friend Beane while typing this. That guy is obsessed with this number. Well, it feels like just the other day I was the 17-year-old, skinny, acne-prone, cocky, full-of-himself boy who thought he was going to take on the world. Come to think of it…all of that still holds true.

Reflecting on my short time here in this massive playground we call “life,” here’s 27 things I have realized and am trying to understand/implement in my day to day:

(Note: Like most things in life, few of these ideas are original. Inspirations and mentors include, but are not limited to: Tim Ferriss, Naval Ravikant, Jim Rohn, Napoleon Hill, Stephen Covey, Gary Vee, Alex Hormozi, Bill Perkins, Zig Ziglar, and others)

  1. No one owes you anything. And no one cares about what you are feeling or how “hard you’ve had it.” People only care about what you can do for them. How you’ve made them feel.
  2. Privilege breeds more privilege. I’ve lived an easy life according to most definitions. And because I’ve been “born ahead” of other people, the race to certain life milestones has been more accessible, which gives me the ability to get to the next one quicker, and so on. If you are the best football player on your team at a young age, you will play more minutes than your peers, giving you more touches on the ball, more game time experiences, and more opportunities to grow. This only widens the gap. Making it harder and harder for those with less to catch up. It’s incredibly important for me to recognize that I was born with pocket Aces, show gratitude for the life I’ve been handed, and try to pay it forward / even the scales for others I cross paths with.
  3. Life is like Netflix. Avoid the endless scrolling, pick a goddamn movie, and see it through.
  4. Focus on ROE – not return on equity, but return on experience. Memories are all we get to keep at the end of the day. So invest in things that will give you the most memory dividends. For one-time purchases, you can have a memory dividend that pays out every time you relive or retell your stories. With this in mind, it pays more to have experiences earlier in life. Instead of constantly worrying about your Work Resume, think about your Life Resume. What would you put on it?
  5. Add a little bit of spice. Brush your teeth / eat with your non-dominant hand, angle your hats differently, lift up one sock, grow out your hair. Have fun.
  6. Personalize everything. Create your own brand. Create a unique system of writing, thinking, and talking that is specific to you and works for you. Pick a favorite number, favorite color, favorite sports team, etc, and own it.
  7. Don’t ask what the world needs, ask what sets your soul on fire. And go do that.
  8. Don’t wait for people. Do epic shit. Your people will find you.
  9. Taste everything once. You never know what you may like until you try it yourself.
  10. Introduce yourself to everyone. First and last name.
  11. All you touch and all you see is all your life will ever be. Pet the dog/cat, smell the flower, ask the girl out, try the new food, watch the sunset, book the ticket, take the flight, ride the wave, jump off a snowboard, sing in karaoke, dance in the street.
  12. Exercise the mind. Come up with 10 new ideas a day. Become an idea machine by taking the quantity over quality approach.
  13. Tell stories. People don’t remember statistics or facts, but they buy into humans. To be human is to have your own story, your own thoughts, emotions, perspective, memories, and experiences. Share it with others.
  14. Take opposing viewpoints on the world and play them against each other, adopting whatever serves your purpose at the time. Examples:
    • When I want to work harder / do more, I tell myself: This is my one life, as far as I know it. I already won the lotto, being born a human, which is 400 Trillion to 1 odds. I have around 85 years of life, so I’m in my second quarter already. The first quarter of life was just learning the rules of this video game we call life, now I need to dominate life and defeat bosses. I need to squeeze the juice and do everything possible to live my best life. To avoid being on my deathbed and have “what if” floating around.
    • When I feel overwhelmed/stressed, I tell myself: This doesn’t matter. Nothing really matters. In a hundred years, I and everyone I know will be dead, and no one will remember anything. I could go on to create the world’s most valuable company, and then be 6 feet under the ground in 50 years. I could also play video games for the rest of my life, and it still doesn’t matter. Legacy doesn’t fucking matter when you’re dead. So no point in my stress. I have lived many a conflict in my life, and most of them never came to pass, but just lived in my head. So screw it, take the day off, and stop applying needless pressure.
  15. You catch more flies with honey. Often, the best way to win an argument is to avoid one altogether.
  16. Wealth comes from VALUE x LEVERAGE x SCALE. VALUE = Time / Money / Improvement in people’s lives. LEVERAGE = Capital x People x Systems. SCALE is derived from the number of people served. In today’s world, the quickest way to grow is with permissionless leverage. (Media or Code)
  17. In a world where everything is finite, play infinite games. My friends, business partners, hobbies, and passions should be lifetime pursuits. Perfection and winning the game is not the goal. The goal is to keep playing the game, and to get one day better, every day.
  18. You get more out of reading 1 book that’s great 5 times, than out of reading 5 mediocre books.
  19. Extraordinary accomplishments come from doing ordinary things for extraordinary periods of time.
  20. Focus time and energy on Multipliers. Multipliers are activities that compound and yield dividends. Once-in-a-lifetime experiences, goodwill to others, financial investments, and personal development are examples. Activities that are directly related to your time, and cannot be shortened in the future, should be avoided, unless you get real enjoyment from them. For this reason, since I don’t like cooking, I should avoid it and prioritize other activities.
  21. You gain status by giving more to the group than you get. Note: status is a tool that can help you accomplish your goals, but it should not be the top priority.
  22. Make sure the girl sitting next to you in the passenger seat is the same girl who would be waiting with you at a bus stop if life turned out differently.
  23. The current economic system is broken. We were not meant to just study things that don’t fascinate us, work a shitty job, retire in old age, and then die. Life is a marathon, but I like to live my life in short sprints. Ideally, I break life into 3 phases: Exploration, Deep Work, and Vacation. When I wake up, I would like to have options of different projects that I find 1) Meaningful 2) Play to my skill sets 3) Make me money 4) Give me the opportunity to grow. I then can pick what I find to be the best fit at the time, and work hard on it. After that, maybe I go dance my ass off in Ibiza, surf in Bali, or visit friends in the US. Once my system is cleared, I start thinking about the next thing, read more books, take more courses, and learn/hone more skills. The cycle repeats, burnout never happens, I still save for “raining days” or old age, but I don’t miss out on the present moment of my current age. Because, at the end of the day, the present is all we have.
  24. You don’t become confident by shouting affirmations in the mirror, you become it by having a stack of undeniable proof that you are who you say you are. Outwork your own self-doubt.
  25. Ready, Fire, Aim. when you see an opportunity, take the shot. If you miss, then you readjust and take another shot. If you end up waiting, aiming for the perfect shot, the opportunity is often already gone
  26. Understand that the 3 biggest decisions in life are 1) what you do 2) who you are with 3) where you live. Practically everything else is cheese.
  27. Time is the most valuable currency in the world. A Billionaire on his deathbed would give all of his net worth for one more year. Imagine how much he would trade to be in your shoes right now. You are worth more than a Billionaire, so act as such, and be resilient with what you trade your time with.
    • Taking into account a life expectancy of 85, and just turning 27, I have approximately 1.8 Billion seconds left. Time Billionaire > Monetary Billionaire, so wake up every day smiling.

20s are a wash

I want to treat the rest of my 20s like they are a wash.

Now is not the time to get a safe job. I already did that.

Now is the time to be as risk focused as possible.

I will never be as “free” as I am now.

I have no baggage. No college debt left, no significant other, no parents I need to take care of, no children, nothing.

I can eat like shit and still be ok.

I can barely sleep and be fine.

Not saying I shouldn’t eat and sleep well, but I could survive. And on top of that, it’s not that hard to still eat and sleep well.

I can sleep anywhere (couches, beds without a bed frame, floor) and cook cheaply.

I can live for free with friends or my family.

I can stay in hostels for cheap all around the world.

I’m 26 now, so I have 4 years left.

So let’s think about the worst-case scenario: I wake up broke at 30. I have to move back home with the parents. I have to get the “safe job.”

Most likely scenario: I wake up broke at 30. But I’ve traveled the world, met incredible people, tried starting businesses, tried learning a new language, tried getting jacked in the gym, and learned about all these things I do/do not like. And then I can still use my college education and friends to get the “safe job.”

I understand this “20s are a wash” is a privilege. I am a college grad, I grew up / still have a somewhat stable family household, I have good friends/mentors, my body is fully functional, and I was born with a good mental state. But one thing I have learned in the last couple of years is it’s foolish to not recognize the privilege, but even more foolish to not use it. It would be selfish of me to not go for it. To not try and live my best possible life. If I was to just coast on my privilege, then I would be just taking it for granted. I owe it to my family and friends to go for it.

And the best-case scenario? I think we can all realize how good life can get.

But I think the best will be to look back on my life and not wonder: “what if…”

To know that I went for it.

And the chips fell where they did. But I went all in.

Hell, I was born with pocket Aces.

What a foolish thing to go silently, tiptoeing, safely to my deathbed.

I want scars.

I want the lessons, the failures, the struggles.

I want to point to the scar tissue on my body and say: Got this playing basketball with friends, this from snowboarding, this from longboarding, this from surfing…

When I was studying at Uni, I heard a quote from Peter Thiel that has stuck with me since. He said, “In a world that’s changing so quickly, the biggest risk you can take is not taking any risk.”

What a sad day it would be if I woke up and realized there was no time to try out / risk / do the things I always wanted. (Paulo Coehlo paraphrase)

The happiest I’ve been in my life has always been when I’m doing what I deem “epic shit.”

That’s often when adrenaline and risk are involved.

I could get hurt doing this. I could lose money, get my heart broken, fall off a cliff, get shattered by a wave.

But it’s all risky.

None of us are making it out of this alive.

Nietzsche said: “I know of no better life purpose than to perish in attempting the great and the impossible.”

That makes sense. Why be satisfied with average?

But the key is to listen to my own internal dialogue about what I deem ”great and impossible.”

My definition of “epic shit.”

I don’t need to surf Nazare waves.

But maybe I don’t go back to working in Corporate America for now.

Maybe I don’t play the status games of a high-paying job and instead take the zero pay of startup life.

Follow the “epic shit” and happiness model, cut out the status games and flexing that is engrained in me.

When in doubt about what to do, I should do what scares me.

Because if my dreams and plans don’t scare me, I’m not dreaming big enough.