Life is like a huge, non-refundable purchase. We’re all kind of stuck with it, and most of us don’t know what to do. Why doesn’t it come with a manual?
Instead of simply giving us the instructions, each of us must go out into the world and figure it out for ourselves. If we get it right, it can be grand. But life is complicated, and it’s not exactly obvious how to get there.
If we pay close attention, however, we can find patterns in all the data. By observing our own lives and the lives of those around us, we can identify principles that serve as instructions for how to “win” at life.
Like French mathematician, Henri Poincaré, pointed out:
“The more general a fact, the more precious it is. Those which serve many times are better than those which have little chance of coming up again.”
I’m slightly obsessed with studying the lifestyles and choices of different people, myself included, and the outcomes they result in.
To me, it’s clear that our actions in every single moment determine whether we’ll be able to look back and say it was all worth it in the end — and if we don’t do everything in our power to make life the best it could have been, then what was it all for?
I’ve identified five cardinal principles for people who win at life, proven by my own successes and failures and by observing others succeed and fail. I fully expect to add to this list and update it over the coming decades.
Everything good in life starts with knowing who you are. It’s what defines your relationship with everything and everyone.
In contrast, most bad things in life start with betraying who you are.
We’re all born knowing exactly who we are. Then, sometime between childhood and early adulthood, the world comes along and beats it out of us. We get confused and doubtful about our place in it.
Your first job in life is to strip away all those doubts and outside influences and rediscover who you were born to be.
Then, you must figure out how you can show up as that person in a pragmatic and constructive way. Otherwise, you’ll just take up space.
It’s not a definitive process — the “self” is an elusive concept and it will change over time. This means knowing who you are is an ongoing investigation — and those who win at life constantly reflect on this.
Here are three things that can help you in this investigation:
Remember: the task at hand is to identify which of your beliefs are a genuine part of you, and which were created by the outside world.
The best way to do this is to use empirical data (experiences) and inductive reasoning to identify the patterns in your life that seem true.
Essentially, this makes life into a scientific experiment. In science, you want as many data points as possible to increase the probability of your conclusions. This is the value of foolishness: if you only test what you already know, you won’t learn anything new.
You need to have diverse experiences, especially those you don’t agree with.
As an example, I sometimes have a great time at parties, but in general, they make me anxious and bored and feel like a waste of time. At first, those feelings didn’t stop me from going to parties — for years, I kept on going to many parties, gathering data (for science, you know).
I have now observed enough data points (I’ve been to enough parties) to know that even if the outside world says, “parties are fun” — that’s not a core part of who I am.
I spent most of my life not considering therapy as a serious option. Yet, I was far from the person I wanted to be.
Twenty sessions later I can say it’s been one of the most important things I’ve done for myself — and research shows the majority of people have the same experience.
A trained professional, if they are good, can help reveal things you hadn’t even considered were standing in your way.
Writing your thoughts down creates clarity, and clarity is what you need to decide what parts of yourself to shed and what parts to keep.
Some people journal every day. I do it once a week. As long as you find consistency, you will reap the rewards.
If you need something concrete to get started, here is a popular journaling practice, praised by self-help guru Tim Ferriss and many others.
Many people see the world the way they wish it would be, not the way it actually is. They try to impose their will on it and delude themselves into thinking they can make up the rules. Such people have many desires, but somehow those desires never become reality. They’re stuck in a pleasant fairytale.
The few who see the world for how it is are the ones who get what they want. They do whatever the real world requires to make things happen. Therefore, they get real-world results.
To win at life, you must see what the world requires of you to succeed on its terms, not yours. The less you bullshit yourself, the better off you’ll be.
Life’s demands are not always pretty, and they may hurt your feelings — good, that means growth.
Indeed, the true nature of the world is sometimes deeply painful to learn.
“The source of wisdom is pain.”
– Naval Ravikant
Here are two questions you can ask yourself as a reality check:
Whatever you’re trying to accomplish, ask yourself if it’s something the world actually values. If it isn’t, you can still win — you just have to adapt and make the necessary compromises.
A good demonstration comes from my favorite film La La Land, where one of the main characters, Seb, is a struggling jazz musician.
Seb's dream is to convince the world of how great this lost art form is. He’s an amazing musician, but he’s obsessed and refuses to adapt to the rules set by the world. He even gets fired from his restaurant gig because he insists on playing complicated jazz songs instead of the Christmas songs he was hired to play.
Eventually, he joins a hip new band with some jazz influences. They achieve success and fame but the music they play is nowhere near true jazz. So despite the success, he feels dead inside. To him, this wasn’t a compromise — it was giving up.
In the end, he achieves his lifelong dream by opening a jazz bar. This bar holds true to his core purpose: bringing back the gift of true jazz. But everything else about the place fits the bill of what people already want in a classy, cool downtown LA bar.
This is a compromise.
“Remember: we all get what we tolerate.”
– Tony Robbins
I’m sitting here in a small mountain village in the Swiss Alps.
During the day I go skiing with friends and in the mornings and at night I work on my businesses. I run an early-stage remote startup and I make good money on the side as a consultant, with complete autonomy in my work and private life.
I don’t have a college degree.
My life is a testament to the fact that you get exactly what you’re willing to accept. Of course, what you’re willing to accept is highly dependent on your circumstances; if you have a family, if you have debt etc.
Whatever your situation is right now, ask yourself:
To improve my work as a designer, I enjoy reading old books about design. I don’t focus on the newest technologies or the latest workflow hacks. They come and go — and when they do the resources I invested in them will go to waste.
The fundamentals of design, however, stay the same. By investing in them, I both ensure and compound my returns.
Human nature is one of the few things in life that doesn’t change significantly. Only the surface-level stuff does.
One of my best-performing Medium articles so far talks about why we compare ourselves to others and how we can combat that tendency. The article did well because the problem of status is a core part of the human condition.
If you can understand human nature, you will have a superpower. You’ll be able to give people what they want. And in return, they’ll give you what you want.
This is what author Robert Greene’s iconic book The 48 Laws of Power is all about — throughout history, those who truly understood human nature have always ended up in powerful positions, no matter where they came from.
Knowing how humans work is also key to knowing yourself. It’s therefore crucial to your own happiness, and to your relationship with others.
So, how do you learn to understand human nature?
Every problem we face today existed in some form in the past. No situation is completely new. Studying what happened in the past can tell you why something is happening today.
This is because our behavior is rooted in deep evolutionary patterns.
“Biology sets the basic parameters for the behavior and capacities of Homo sapiens. The whole of history takes place within the bounds of this biological arena.”
– Yuval Noah Harari
If you can understand humans from an evolutionary perspective, you can understand the drivers behind literally everything in life.
The above-quoted book Sapiens by Yuval Noah Harari is a great resource to start thinking in these terms, as well as The 48 Laws of Power by Robert Greene, also mentioned above.
All successful marketing taps into the same evolutionary patterns. Whenever you see an advertisement or marketing tactic that works, ask yourself what part of human nature it successfully targets.
Marketing can teach you about human nature and how it interacts with the world today.
The best thing about studying humans is that they’re all around you. Learn to pay close attention to your interactions with them.
If someone you care about acts in a way you can’t understand, ask yourself what could be driving this behavior. Put yourself in their shoes. Go deep.
Those who produce more than they consume tend to accumulate assets, and owning assets is what separates free women and men from those in shackles.
To win at life in the modern socio-economic landscape, you have two options: be on the right side of capitalism, or get out.
By “getting out”, I mean move to a cheap part of the world, learn to live with less, and hope it stays cheap forever.
There’s something to be said for the mindset of needing less. But owning assets doesn’t prevent you from developing this mindset — you can have both, which only increases your freedom.
The majority of people choose the third option, which is to be a consumer in all things.
In order to win at life, you must produce more than you consume.
Otherwise, you too will live in shackles.
We all come from different backgrounds. Some people start with nothing. Others inherit the world. Regardless of circumstances, everyone can find a way to stick to the rule: produce, don’t consume.
Right now, content is king. The internet gobbles it up. This will change eventually (and you remember what we said about things that change, don’t you?).
But it’s a good example: Don’t be the person who binge-watches all of the latest YouTube content. Be the person who created that content.
The final principle is a bit counterintuitive. Hard things just suck, don’t they?
Well, yes and no.
Hard things aren’t inherently valuable. But since they are hard, few people do them.
An asset is relatively exclusive access to something valuable. The more exclusive and valuable — the bigger the asset.
So if something is hard to do and also has a utility to others, it can become an asset (and you remember what we said about assets, don’t you?).
For example, becoming one of the best golf players in the world is impossibly hard. Golf also happens to be entertaining to enough people to generate lots of commercial interest in the best players, since they are the most powerful marketing channels through which brands can sell golf products.
Because golf products are expensive and generate lots of revenue for the brands, and because many people watch the competitions, the best golf players are among the most well-paid and rewarded athletes in the world.
Being the best golf player in the world is a large asset created by doing something hard that has a utility to others.
The same applies to building a company, getting a degree in a difficult subject, or becoming a good writer.
Life generally gives us back what we put into it. Some people want to put in as little as possible so they can just relax and pass the time. But that’s also what they’ll get out of life: little.
The more you put in, the more you’ll discover how much life has to give.
“Far and away the best prize that life has to offer is the chance to work hard at work worth doing.”
– Theodore Roosevelt
Do hard things that matter.
“Winning at life” is completely subjective. Yet, everyone knows what it means. If you follow these five cardinal principles you will increase your chances of turning your own definition into reality: