23 Lessons for 23 Years

I turned 23 over a month ago.

I wanted to share 23 lessons that I have learned over my past 23 years. These are ideas from people that I have been lucky enough to spend time with, to listen to, and learn from.

I hope you enjoy this collection of ideas. One of the biggest things that I learned this year is that none of this is about us.

It’s about so much more than that. Life is very short, and it’s startling when we are faced with that brevity.

Life is about what you do with your time here. About creating a learning loop, upcycling creativity, creating connections across the world, and absorbing as much as possible along the way.

“I began to realize how important it was to be an enthusiast in life… if you are interested in something, no matter what it is, go at it at full speed ahead. Embrace it with both arms, hug it, love it and above all become passionate about it. … White hot and passionate is the only thing to be.” – Roald Dahl

1) Opportunity Costs

“The dream is free…but the journey will cost you something.” – John C. Maxwell

Life is a series of tradeoffs. Every decision that we make has essentially two different paths – the one we took, and the one that we didn’t. Reading this book, or not reading this book. Eating the salad or the burger. When we decide to do something, there is an inherent cost to making that choice.

There are always sacrifices. The true cost of something is never the absolute number that we see – it’s always higher, sometimes immeasurably so. It’s a game of allocation. Make sure that you allocate well.

2) Forgive Yourself

“Embrace your vulnerabilities, accept them, and forgive yourself” – Angelica Monroy

Keep moving forward, one step at a time. If you trip along the way, learn from the fall. Things are always going to be complicated. They are always going to be confusing and messy.

It’s easy to throw our hands up to the sky and ask, “Why me?” It is tempting to fall into a pattern of self-hatred and guilt. Do not do that. You achieve nothing by hating yourself and feeling guilty. Give yourself the space to try things, and maybe fail. Give yourself the space to take chances. Give yourself some love when something goes wrong. Don’t hold grudges against yourself. It is not worth it.  

3) Outcome vs Systems Mindset

“A system is a set of related components that work together in a particular environment to perform whatever functions are required to achieve the system’s objective” – Donella Meadows

When you fall down, which will inevitably happen, think about how you frame things. If you make a mistake, do you completely give up? Do you toss the effort aside entirely, mark it off as a useless endeavor, and forget all about it? This is the difference between an outcome and a system mindset.

  • Outcome Mindset: I made a mistake doing this; thus, I will never do it again
  • Systems Mindset: Why did I make this mistake? What was the underlying cause, and how can I avoid it next time? How can I learn from this?

An outcome mindset focuses on the tangible – on the mistake that happened. A systems mindset helps to frame that mistake into an opportunity to learn. It addresses the actual thought process that occurred.

When you address your thought process, the learning becomes that much more valuable. It’s like pulling the weed up from the root, rather than just yanking at the stem. Seeing where things connect teaches you how it functions – and once you understand the root of your weed, it is that much easier to eradicate it.  

4) Reframe Curiousity

“Study hard what interests you the most in the most undisciplined, irreverent and original manner possible.” ― Richard Feynmann

Think about what you love to do. Think about what makes that work meaningful. Think about how it applies to the world. Talk to people. Learn from others. Ask the big questions and figure out how those who do what you love to do have become successful.

Life is really about leaping before you can see the ground. Some leaps are well-timed and graceful, while others leave us with a few scratches and a story to tell. But really think about what makes you hungry. What are you willing to have a few bumps and bruises for?

What is the thing that will drive you into late nights and early morning? What do you geek out on? What do you enjoy spending time learning about? That’s the thing. It doesn’t have to just be a hobby. Curiosity is the reason that we grow as humans, as people, the reason that we innovate and accelerate.

Give yourself the chance to be curious.

5) Think about Others

“It is an absolute human certainty that no one can know his own beauty or perceive a sense of his own worth until it has been reflected back to him in the mirror of another loving, caring human being.”- John Joseph Powell

If you can show a person that you care about them, that goes a long way. Showing that we care is one of the best things that we can do for one another.

A simple text or email or call can make a world of difference. Reach out to your friends. Reach out to your family. Nurture these connections and realize that it might feel simple, but that simple hello can compound into something far greater.

6) Normalcy is Overrated

“I have never seen a normal man or woman, or even a normal dog. I have never experienced an average day or an ordinary sunset. The normal, the average, the ordinary describe that which we never encounter outside mathematics, i.e., imagination, the human mindscape.”- Tim Finnegan

When we think about how astounding this life is, we realize that nothing is ever normal. We are all living in our own little worlds, with our own hopes and worries, and the mere existence of other humans is a radical concept within itself.

Things might feel mundane sometimes, but we must realize that our existence defies the laws of “normalcy”. If we live as if each day is a new opportunity to discover something incredible, it becomes so. It’s self-fulfilling.

One of my favorite things to do is watch the sunrise. I was inspired by one of my mentors, who takes pictures of the sunset every day. The sun is here, circling around this Earth, providing an incredible show, twice a day. It is such a gift to watch it wake up. Every single day it is different. Sometimes, the clouds are wispy, sometimes the sky is more pink than orange, and every single time, I’m reminded of how extraordinary this life can be.

7) Life is Never Easy

“I often tell the story of a person walking in the woods and coming upon a little dog. The dog seems harmless enough, but when they reach out to pet the dog, it growls and lunges at them. The immediate response is fear and anger, but then they notice that the dog has its leg caught in a trap and compassion begins to rise up in the place of the anger. Once we see how our own leg is in a trap and hold our experience with self-compassion, it becomes easier to see how others might be caught, too—causing suffering, because they are suffering.” – Tara Brach

Life may be extraordinary, but it can be hard. Be compassionate for those around you. Some battles are too heavy to carry alone, such as sickness, injury, and abuse, and many others. Recognize that these battles are often hidden as well. Mental health is a challenge that we are facing. Anxiety, depression, and other mental health conditions are on the rise. We have to take care of each other.

Do what you can to help others heal and allow yourself to seek help in your own healing. No one should ever be the only soldier on their battlefield.

8) Be With Those Who Build You

“There are two types of people in this world — those who build sandcastles and those who smush them. I try to surround myself with people who are builders, not smushers.” – Mary Lou Jepsen

There are some people who are going to have your back, and support you, no matter what. When you say something dumb in a meeting, they are the people that you can go to and talk it through. They are the people that will look over your projects or give you a chance to share ideas. They are the builders.

Then there are the smushers.

Some people are simply not interested in you. You will come to them with an idea, and they will completely shut it down. They will discourage you from trying new things. They will give you a destination with no directions, or even worse, directions with no destination. Nothing is wrong with this – it is just how things are. The smushers make us that more appreciative of the builder.

9) Proactive vs Reactive

“If we wait until the problem develops and then react to it, there may not be time for any good solutions before a crisis point is reached” – Draper Kaufmann

If you wait until you’re ready, you’ll be waiting your whole life. A lot of the things that we experience require a response. We can either prepare ahead of time, or we can react in the moment.

If we can somehow prepare ourselves for the range of outcomes that can occur, we are that much more prepared for uncertainty. If things feel less uncertain, we feel more stable. And if we feel more stable, we feel happier. Of course, it’s never that simple. But the way that we operate now can be simplified. Proactivity is one of the ways to do that.

10) Prepare for the Future

“Failure comes from failure to imagine failure” – Josh Wolfe

Always visualize the conversation that you are going to have. If you are going to sit down and talk with someone about your work, think about the absolute worst thing that they could say to you – “I hate what you do, you’re terrible at everything, goodbye forever”. Now, think about the best possible thing that they could say – “You’ve really done a good job, you work hard, and we see that”.

When we imagine what success and failure looks like, it becomes easier to accept both of them. When you have prepared for the worst, it’s hard to get caught off guard when the worst really does occur. When you’ve prepared for the best, it helps frame what you really want to achieve, and what YOU really want out of the conversation.

It may feel silly, but once you get into the habit of thinking about either end of the tail of occurrences, you become better at processing and better at executing. Most of the time, interactions will be in the middle of the distribution, with no surprises. But visualizing the worst and the best will help to outline what the worst and the best means to you, and there is a lot of power with that information.

When you realize what you really want (“the best”) work towards that. Avoid the worst.

11) Practice Inversion

“Inversion is a powerful thinking tool because it puts a spotlight on errors and roadblocks that are not obvious at first glance.” – James Clear

Avoiding the worst is also known as inversion. Think about what you don’t want to have happen. It seems counterintuitive, right? We should focus on our goals, what we want to achieve – but there is a lot of power in visualizing the reverse too.

As Charlie Munger said:

“Problems frequently get easier if you turn them around in reverse. In other words, if you want to help India, the question you should ask is not ‘how can I help India,’ it’s ‘what is doing the worst damage in India and how do I avoid it? A lot of success in life and business comes from knowing what you want to avoid: early death, a bad marriage, etc.”

Source: Charlie Munger

Think about the worst possible outcome. With Charlie’s example above – how do you avoid early death? You eat healthy, you exercise, avoid excessive stress.  Create a plan to avoid failure. It’s a lot easier to avoid failing than it is to achieve success. Most of success actually comes from simply avoiding failure.

Challenge your own thoughts. Think about why you think things and think about why you don’t think other things. Step outside of your own bubble and consider the world from the opposite lens.

12) Defining Success

‘The most damaging thing you learned in school wasn’t something you learned in any specific class. It was learning to get good grades.’ – Paul Graham

Think about what success means to you. In school, we were taught that good grades equates to success. Good test scores are success. All A’s are success. One thing that is not taught is that learning equates to success.

If you can spend a lifetime learning, you will be the most successful person in the world. When you can detach success from a tangible, external reward, and create an intrinsic feedback system within yourself, that is truly infinitely rewarding. When you realize that this life is a learning loop allowing you to pass your knowledge along to others, that is also success.

When you approach a project, ask the person (or yourself) what does success look like here?

13) Be Intentionally Concise

“I have only made this letter longer because I have not had the time to make it shorter.” – Blaise Pascal, The Provincial Letters

It’s a lot easier to write long sentences and talk and talk and talk (I am bad about this). But the real power comes when you can explain things in one sentence. Think of the “Three Bulletpoints” method. For everything that you present or talk about, you should have three key takeaways that people can walk away with.

Just three.

  • Just
  • Three
  • Points

If you can make things easier for others, do it. People don’t really care too about  what it took you to create something – hours and hours of work is always so important to us, but to others? They just want to know what value it provides to them. Show them that. And one of the best ways to do that is to be concise (I say, as I write a 8,000 word post)

14) Explain it Out Loud

“You know, I couldn’t do it. I couldn’t reduce it to the freshman level. That means we really don’t understand it.”- Richard Feynman

One of the best tests of brevity is trying to explain something to a 6-year old. If you cannot distill that information down into an easily digestible format, then you probably don’t really know what you’re talking about. It is challenging to simplify complex concepts. But ideas are that much more valuable when they are tangible. The more complex a general idea becomes, the less useful that it is to the average person.  

15) All Models are Wrong, But You Should Still Build Them

“All models are wrong, but some are useful” – George Box

Nothing is exactly true. To expand on the full context of the quote, Box wrote:

“The law PV = RT relating pressure P, volume V, and temperature T of an ‘ideal’ gas via a constant R is not exactly true for any real gas, but it frequently provides a useful approximation. Everything is an educated guess, some things more educated than others. The big question is how good the model is for the application at hand– that tells us the usefulness of the model.”

George Box

Things aren’t true, but they are useful. The goal is not to seek an exact answer. The goal is to provide a framework that is useful and applicable.

Life is like this too. Nothing is exact. Even in our chemical makeup, we are never exactly touching anything- our electrons never actually touch another electron because of electron repulsion. That means that we are always sort of floating. The sensation of touch is an illusion.

In this same line of thought, models are somewhat of an illusion too. The whole process of statistics is maximizing the usefulness of a given model – searching for better ones along the way and realizing that an exact truth will never be achieved.

There are no truths, just best approximations to the real world. We are never actually touching the ground. Just really, really close to it.

16) Ask the Question

“The art and science of asking questions is the source of all knowledge” – Thomas Berger

When we ask for feedback or direction, it is not a sign of weakness. Rather, it’s a superpower. If you can figure out what people want without them directly saying it, you’re a mind reader. Most of us need to ask.

It’s hard to ask for help sometimes. You want to show your prowess or skills, to show that you don’t need direction. But asking questions saves a lot of headache. It gives you an outline of a path to follow. You can also learn a lot from how others have tackled similar issues. You don’t need to reinvent the wheel – just make some modifications to it.

However, this comes with a caveat: sometimes, you shouldn’t ask the question. Sometimes, you should forge ahead. Make a mess. If you have the space, see what you can do. Then, show it to someone. Then, ask the questions (always ask eventually).

17) Making a Mess

“Nobody has eaten their way to opening a Michelin Star restaurant.” – George Mack

Forging ahead can feel a bit like making a mess. Especially if you have no idea what you are doing. But, what is the best way to learn how to do something? Make a mess.

For example, when learning how to cook, you don’t sit back and watch. You dive in. You combine ingredients, test ideas, modify recipes – you make a mess. That’s the best way to learn. You will only learn if you try.

But you can only learn these things by making dishes that taste bad. Not everything that you cook is going to be good. But you can take the lessons learned from the dishes that taste terrible, and apply it moving forward. Don’t punish yourself for making a mess at first. That mess is going to teach you how to make a beautiful creation.

18) Create a Margin of Safety

“Practically all models for pricing vanilla options are based on the Black-Scholes-Merton paradigm. This assumes a log-normal price distribution, which has a lower bound of zero.” – Darren, @ReformedTrader

Oil prices went negative for the first time in history in April 2020. That defies a lot of the laws’ of finance. The idea that prices can go below zero is astounding. Paying buyers to take product is not a business at all.

The lack of demand for oil drove the price down. The lower price squeezed the sellers. There were more barrels of oil than we have storage for, and that glut of supply caused the price to go below zero – something that a lot of people never thought could happen.

The impossible can always happen. Have a margin of safety built into your decisions so you aren’t caught on the wrong side.

19) Shout into the Void

“Ideas don’t make you rich. The execution of ideas does. Good ideas are like Nike sportshoes. They may facilitate an athlete who possesses them, but on their own are nothing but an overpriced pair of plimsolls.” – Felix Dennis

We are on the cusp of a creative revolution. Gen Z is shaking up content creation. They upcycling creativity, constantly learning through trial and error. They are figuring things out along the way. There is no “School of Content Creation”. You have to shout into the void for a while to calibrate to what people want. But if you keep shouting (intentionally) eventually, someone will listen.

The first Disney studio went bankrupt. Running an animation studio is an expensive operation. The company had produced nearly 400 cartoons by the mid-1930s. Most of them flopped. There was no money left.

But then Snow White and the Seven Dwarfs happened, earning $8M in the first half of 1938.

This is the long tail. This is the power of occurrences. The more you do something, the more likely it is that you will succeed. But a lot of the time, you will fail. But you will only succeed if you try.

There is a lot of power in writing. A lot of power in audio. A lot of power in video. All of those things are easily accessible to us now. Creating a platform for yourself is one of the most valuable things that you can do.

It aligns you with an identity and creates a place for you to be a unique version of yourself. It’s a living, breathing portfolio. Focus on doing something, focus on the work, and create the results.

Then, keep doing that. Over and over again. Upcycle.

20) Keep the Mind of a Child

“Knock knock

Who’s there


Fork who

FORK OF JULY” – Kids Write Jokes, Twitter

There is an account on Twitter that takes jokes submissions from kids around the world. All of them are hilarious and provide great insight into the mind of a child.

Children are unabashedly creative. They allow themselves the freedom of failure. Think about all the things that they need to learn – how to ride a bike, how to tie their shoes, how to write and read. The learning curve is steep those first few years.

But they approach it with enthusiasm. They are trying out things that they see adults do and say (we’ve all heard a kid drop the f-bomb in a grocery store) and connecting the dots in life. Their process of living is so well-rounded, primarily because they have the freedom to be a child.

They are learning through trial-and-error, through testing the limits, and through challenging ideas. We tend to lose some of this enthusiasm and curiosity as we age. We all have to grow up eventually. But that doesn’t mean that we shouldn’t wonder about the world.

21) Mistakes are the Currency of Learning

“The secret to being wrong isn’t to avoid being wrong! The secret is willing to be wrong. The secret is realizing that wrong isn’t fatal.” – Seth Godin

The other nice thing about being a child is that you have so much room to be wrong. People understand when you point at the sky and call it green. They will say, “they’re just a kid!”

When you’re an adult, things change. Life is not math, much to my chagrin. If I could simply apply a regression model to all my problems, things would be much simpler. But that is not the case.

Often times, the formulas that we seek don’t give us the answers that we need. The self-help books, the thought-blogs, the threads – all of them are ideas from someone else trying to provide perspective on our own unique situation. And that’s valuable in certain applications, definitely.

But it is also impersonal. Unagile. It’s separated from our own reality. We all have our own unique variables that shape our own unique journey, and it is tough to navigate those specifications when looking through the lens of someone else’s glasses.

The uniqueness of our journeys means that we’re going to be wrong. A lot.

No one is right all the time. It’s statistically impossible (there’s the math!) Think about comedians – they come to small clubs with rough-draft sets, see what flops, and then pull the better stuff along to the bigger club.

Life is a filter. We see what works. What doesn’t work will sometimes teach us what does work.

22) Always be Beginning

“The genuine love for reading itself, when cultivated, is a superpower…The means of learning are abundant—it’s the desire to learn that’s scarce.” – Naval

There is always something new to learn. It has never been more accessible or available to us. The universe of knowledge is infinite.  

It is up to us to take advantage of these opportunities to learn. It is easy to get caught up in the mundanity of everyday life. But when you take time to explore new avenues, to learn about different things, you also learn about yourself.

You learn what you love to do. You learn how you can help others. You learn deeply. Sometimes we think that if someone doesn’t get good grades, they are a bad learner. That is simply not true. There is a large difference between how schools teach and how some people learn.

Once you are given the opportunity to ask why, to question, to critically think about things, it changes you – all things that you can learn at your own pace, in your own style. The experience of learning is one that should be cherished. Keep asking why.

And finally –

23) There are No Final Answers

If all environments were stable, the well-adapted would simply take over the earth and the evolutionary process would stop. In a period of environmental change, however, it is the adaptable, not the well-adapted, who survive.” – Ken Boudling

Remain curious and seek insight where you can. You can keep asking why, and keep searching, but an important thing to keep in mind, is that there are no final answers in life.

Life is not a series of equations, with strictly defined variables and values. Life is something that is messy, and it is pieced together the best we can, with all that we have.

But when we begin to search for finality, that is when we make an error. Finality in life is not something that can be accomplished, unless we die, and only then is it final because it has ended. When we finally find the ‘answer’ to life, there is always a caveat, an asterisk after the fact. There is no true solving of the formula, or equating x to y to deliver z.

When we look at it from that lens, the idea that nothing is final, that this is a line that never really ends, it becomes much simpler to accept the bumps in the road. We are taught that solving the equation will deliver the final answer, but really, life is made up of a bunch of little guesses, strung together. This is life.

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