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The Game of Life
Consider if life was a game. You are spawned and given one life only. Your body demands 8 hours of sleep each night to function during the day, and for the first 18-22 years, you’re mostly sheltered from most of the decision making around where you sleep, where you’re going, what you’re doing and acquiring the resources to support yourself.
Finally, after those first 22 years, you are given the controls. You are given a limited amount of time, energy and resources to accomplish a single mission. To live a fulfilled life.
Fulfilled - to develop to the full potential of.
You may have differing tools in your toolbox (family connections, financial support, a diploma) or you may not. But what matters is that you exercise the tools to fill the buckets ahead of you to live a fulfilled life.
These are
1. Financial Wealth
2. Meaningful Work
3. Relationships (Romantic, Familial, Friends)
4. Health
Having each of these buckets at least partially full is necessary for a fulfilling life. Without money, you cannot afford the basic necessities of food, shelter and water. Doing work you don’t enjoy is soul crushing and no one prescribes being lonely, or having poor health.
Also, filling one bucket does not necessary fill the others, but it can. You can go on a run with a friend and develop a better relationship with your buddy plus get in something for your health.
Most people intuitively understand these concepts. This is the “well balanced” life and most noticeably, it’s a kind of life people turn to when given a large amount of leisure time.
Climb, American, climb.
As accurate of a American flag as I can make in Illustrator 🙂
The promise of America is the American Dream:
“a set of ideals including representative democracy, rights, liberty, and equality, in which freedom is interpreted as the opportunity for individual prosperity and success, as well as upward social mobility for oneself and their children, achieved through hard work in a capitalist society with few barriers.”1
For anyone who wishes to climb the socioeconomic ladder, from those who immigrated here from other countries where access to education or business was limited by their social or political status, race, or even for those of us born & raised here, the open markets, a strong sense of individualism, and a can-do attitude are a blessing. As long as you can make the ends meet, America leaves you alone.
Take it from Spanky Rigor, the Filipino-rock-star who gave up his wealth and fame at the height of Filipino society to live in the Bay Area, working as a airport worker in SFO.
Albert (Spanky’s Nephew): Was it really worth it to leave all that behind?
Spanky: I don’t know if I would be able to give to them what they have now if it were in the Phillipines.
Albert: Why?
Spanky: Whatever successes you do in the Philipines, there’s always a price to pay.
…
Spanky: Whereas here in the States? At least they leave you alone to do your thing to the best of your ability.
However, this work culture can have a toxic side to it too. We’ve internalized it to the point where to not work is equated to being lazy; if you are not working a job or building a business, then what are you doing? What is your life for? Who even are you?
In America, Job = Identity.
It’s no secret that a common question to ask American children is “What do you want to be when you grow up?” From a young age, we condition children to fit into a neat economic role in our society.
Then, it’s no surprise that as adults, we respond to the question of “What do you do?” with “I am a X.” It’s who I am, not what I work as.
However, this obsession with work is not universal.
I’m sitting at the Universidad de Navarra’s research housing lunch hall in San Sebastian, Spain, visiting my brother while he’s doing postgraduate research. My family and I were invited to dine with the research residents of the Catholic university and what I’m seeing shocks me.
Everyone is intensely engaged in talking to people around them and there’s not a phone or laptop in sight; everyone is fully present. What’s more is that lunch drags on for a whole hour. And afterwards, everyone moves to another room where they sit and chat for another hour.
Sacre bleu! When are you working? Surely this is a uniquely university phenomenon!
As I am a guest, I am excused from the after-lunch discussions and when I step out onto the streets of San Sebastian. I see, all major restaurants and business are ….closed?
Signs next to each of them signal they are re-opening later in the evening and a sleepy ambience fills the city. Stunned, I think, What of work? What will their bosses say? Who gave them permission to live like this??!
This gave meaning to a phrase I’d heard before: “Americans live to work. Europeans work to live.” Their jobs exist so they can live the life they want to live. And their lives are centered around friends & family first and jobs second. In America, we possess a completely different approach; you’ll never catch an American without a phone in their hand, a sandwich in the other while walking to “optimize productivity”.
In place of certain values such as being present with our family & friends, we’ve replaced them with work.
From there, everything that relates to a job, from compensation to titles to connections, becomes the starter of every conversation.
Why is that?
Company Man vs. Companies Person
In his piece, How to Legally Own Another Person, Nassim Nicholas Taleb argues that in the twentieth century, the so-called “company man” emerged. This is the man who graduates college and works at the same company for 40 years straight.
The company man -which dominated the twentieth Century -is best defined as someone whose identity is impregnated with the stamp the firm wants to give him. He dresses the part, even uses the language the company expects him to have. His social life is so invested in the company that leaving it inflicts a huge penalty…Saturday nights, he goes out with other company men and spouses sharing company jokes…
How to Legally Own Another Person by Nassim Nicholas Taleb
However, he continues to argue that as upstarts usurped legacy companies in the 1990s, the company man became a dying breed and the present “companies person” emerged.
Someone who hops from company to company, climbing the career ladder and trying new positions. Loyalty to a particular company is valued far less than say, having the particular skills for a role. If the company man strived for loyalty and conformity, the companies person strives for employability.
But what’s driving our desire for employability?
The Default is More
From a young age, we’re bombarded with commercials showcasing lives we’re told we should be living. We’re subconsciously convinced that one day, we’ll be rich and living the proverbial “the life.”
If it’s a beat up car we’re driving, we’re pitched the Toyota Camry. If it’s the Toyota Camry, then the Cadillac. If it’s the Cadillac, its the Benz next. If you have a Benz, then why not a Porsche? And if you have a Porsche, you’re told Rolls Royce is what’s in. And if you’re driving a Royce, shouldn’t you be flying? Flying first class that is?
This constant upselling culture leads to a sensation that John Steinbeck once put eloquently, “We are all temporarily embarrassed millionaires.”2
We’re taught to always get more. More money. More status. More fame. More is better; more is king.
But when this constant pursuit of more comes at the cost of being present for our friends, family, and even pursuing our own interests and hobbies, a question emerges:
Would the pursuit of more be worth it if it was Game Over in 10 years? How about 5 years? 1 year? 3 months? 2 weeks? Tomorrow?
Would you prioritize that shareholder meeting or go on dates to find that special someone? Would you spend that time on those Powerpoint slides or talking to your siblings? Would you stay late at the office, crunching out that last bug or would you head out to dance with friends for the night?
When each day becomes precious, the financial payouts don’t seem so appealing anymore.
Why is that?
The reason is money is optionality!
It provides you a wider array of options to choose from whether it be what city you live in, where you can travel to and what experiences you may get to have.
However, the true optionality of money declines once a few other vectors are tweaked.
Amount
What can $100,000 buy you over $1,000?
A room in home with heating and A/C over struggling to retain housing, living paycheck-to-paycheck. A set of wonderfully warm winter clothes over some from a Goodwill donation pile. Great, private healthcare coverage over the default of Medicaid.
In each of these cases, the value added is immense and you are experiencing a significant jump in the quality of life.
What can $1 billion buy you over $100,000?
Your own private jet instead of a plane ticket. The entire restaurant instead of a meal there. Your own estate instead of a comfy home.
But, doesn’t a plane ticket get you to the same destination as your own plane? Doesn’t eating at a restaurant fill your belly with food the same way that owning that restaurant does? Doesn’t a nice home keep you warm & safe and provide a place to rest your head at night, the same way an estate does?
For our human needs, the impact money provides declines significantly as the amount increases; there simply isn’t as great utility in it.
Time
Once you are of old age, of what use is it being incredibly wealthy? You can’t buy time no matter how much money you have.
Are your 20s & 30s meant to be spent working towards payout later in life at a time where you’ll struggle to enjoy the fruits of your labor? After all, how many 70 or 80 year olds are healthy enough to travel the world, climb distant mountains and forge new relationships?
Health
If you are in poor health, you cannot enjoy the optionality that you have generated. None of us really know when we’re gonna go; we’re not born with expiration dates on our bottoms.
A healthy man wants a thousand things, a sick man only wants one.
Confucius
So what real optionality are you generating by going for more?
But if we are not generating optionality, what then is the antithesis to this way of living and conversely, a path to a non-work centered life?
Defining Enough
As Paul Millerd puts it in The Pathless Path, “If we don’t define enough, we default to more, which makes it impossible to understand when to say no.”
Paul Jarvis puts it a better way in his book Company of One, “Enough is the antithesis of unchecked growth because growth encourages mindless consumption and enough requires constant questioning and awareness. Enough is when we reach the upper bound of what’s required.”
Effectively, when you don’t define an enough, you are defaulting to getting more. And going for more can mean denying time & energy for your other buckets.
How Much Is Enough?
What is your enough?
No, I am not saying how much do you want to stunt or what would be a n idealistic lifestyle. How much do you need? Some money for basic expenses (food, water, a roof over your head), savings (for those future emergencies), fun activities (restaurants, bars, vacations), retirement and maybe a future college fund for a kid or two.
What does that number look like for you?
After you’ve chosen your amount, by when do you want it by?
What will it take to make that much money in that short of a timeline?
Do the same with your wants. I’m not asking how much a person needs or how much a person should have. Those are moral arguments and each person’s morals are different. How much do YOU want? Is it $1 million? $100 million? $1 billion? It’s OK to be as wild and dreamy about the number as possible. You can say, “Yeah I want to be a multi-billionaire.”
Be honest with yourself. If you intend to make a billion dollars by the age of 30, it’ll definitely involve some hustle and grind.
And depending on the number, it might mean saving up modestly over a 30 year career on one end of the spectrum or it might mean starting a startup and swinging big on the other. It’s also exceedingly unlikely that you’ll be able to save up to, say, $10 million dollars without some form of business or very fortunate investment vehicle.
“And in the end, why should you expect, I mean, you’ll get a very perfectly decent return over a 30 or 40 year period by doing what I suggest. And, and why should you expect more than that when you, you don’t bring anything to the party? The salesman’ll tell you you’ll get it but you won’t.”
Warren Buffet on investing in index funds when asked by Tim Ferris in 2008.
Finally ask yourself, Is it worth trading all that extra time & energy, to acquire wealth beyond your needs in order to achieve your wants?
Remember The Fisherman & the Investment Banker Parable.
Play the Infinite Game
What’s the alternative?
First, expand your timeline.
You don’t have to be a billionaire by age 30 to live a great life.3 Also, with a longer view, you have the time to go on those dates and hang out with your friends. Life is not something to be optimized away; you can take the time & fill the different buckets of your life.
Second, find the game in life that you want to keep playing; the infinite game.
Unlike games that result in winners & losers, the infinite game is the game you play simply for the purpose of continuing to play, kind of like a great round of pool with friends.
It’s not so much about winning of it, rather the experience along the way.
On average, people born in 1990s to early 2000s will live to be around ~80 years old. Take 60-70 years of those to likely be in decent health. The first 22 years of life are generally education. So really, you are entering the part of life centered around adulthood for the next 38 years, in good functioning health.
What kind of game is worth playing for those 38 years?
So does this mean we should throw our financial dreams to the wind and leap away from starting companies and simply hang out with friends?
It depends.
What are you building this company for? If it’s solely a financial payout, then it may not be worth it.
And if it’s something larger, a personal dream or deep interest in a subject matter, then it really might be worth it.
Something that I’ve realized from seeing founders in Silicon Valley who have stuck around for years on the same company, tuning their personal lives to the needs of the company, is that they have a deep interest and a personal stake in the cause of the company. They are true nerds and believers. They will grab textbooks & research papers and discuss passionately around how a technology will impact the world. They’ll spend weekends and late nights, working obscene hours to fulfill their innermost visions.
That’s what they love! And it’s OK that they love that. To them, their companies fulfill the buckets of Financial and Meaningful Work and they are OK with their Relationships & Health buckets suffering at times.
But is it what you truly love?
Can you be OK with excelling in one or two buckets and having diminished or even empty buckets in other areas?
And, if you can accept that working on a company or project is worth it to you, then go for it!
Do that thing.
And if you don’t, then isn’t your time better spent figuring out what you do like?
Instead of jumping on the latest no-code-machine-learning-platform or integrated-chatgpt-ai-wrapper hype, wouldn’t it be best to try discovering the things that excite you?
How To Discover What Interests You.
For me, it’s writing. Each morning I wake up, go to the bathroom, sit at my desk and just write. It’s a habit now. A habit that I am coming to love and truly enjoy fully.
But I didn’t start out enjoying writing. No, writing was something that I had to learn to love. And for that to occur, for me to try, I started checking out a writing club in San Francisco. I go each weekend to SF and spend the time there for 1 hour, writing about whatever.
Why? Just to see what comes up, to see what arises for me.
And over time, my interest in writing shifted. From small poems to short stories, to personal blog posts, to a anime newsletter and now something else entirely. My interests are still evolving and will continue to in the future.
What matters is not the particular activity itself (writing) but rather the continual experimentation. The checking in with yourself, and asking, “What do I like? What do I want to do next?”
It’s entirely possible that 10 years from now, I’ll create a company of some sort around some technology. It’s also entirely possible that I won’t.
In his book the Pathless Path, Paul Millerd says, “On the pathless path, the goal is not to find a job, make money, build a business or achieve any other metric. It’s to actively and consciously search for the work that you want to keep doing.
And you accomplish this just as you would with any other form of discovery: experimentation.”
Here’s to the infinite game. 🍻
-Kiran
The quote was likely summarized from A Short History of Progress by Ronald Wright: “John Steinbeck once said that socialism never took root in America because the poor see themselves not as an exploited proletariat but as temporarily embarrassed millionaires.” Mr. Wright was likely paraphrasing from John Steinbeck’s article A Primer in the ‘30s in Esquire: “I guess the trouble was that we didn’t have any self-admitted proletarians. Everyone was a temporarily embarrassed capitalist.”
In fact, you probably shouldn’t. Achieving success at a young age can warp your experience of friendships, relationships, money, purpose among other things.
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Kiran’s Gems 💎
An insightful read from Harvard Business School Professor Mihir Desai’s The Trouble With Optionality.
A moving story from Morgan Hausel on risk and avalanches.
What would a life of total work look like?