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The Games of Life

I think about games a lot.

In a meta way, working on games does not feel like work to me. It feels like play. Like a game. Of games. And I love it. I love the challenge, the excitement, the process of creation, iteration, and knowing that I’m bringing joy and fun to someone else.

In an even more meta way, I think of myself as a player in the Game of Life. What are the objectives in this game? How do I optimize my strategy to generate the most rewards? Which rewards are actually valuable and which aren’t? Can I even change the cards I am dealt with?

Wisdom from my younger self: This takes practice. Also, throwing cards is super fun.

Life as a Game of Games

I was driving back home after dance class when something clicked: Life is a Game. A Game of games. Academics, work, investing, self-improvement, relationships, health, politics — all games. You choose which games you want to play. Each game has their own rules, their own players, community, difficulty, rewards, costs, etc. Some games earn you money, others upgrade your skills, gain you status and power, or bring you joy.

Some games you play for fun, others you play to win. Perhaps even pay to win. It doesn’t matter how everyone else is playing; maybe they are taking it super seriously, but you just want to enjoy it. So be it! Its your own game. You decide what you want from it.

Let’s take dance as an example. Some dancers want to compete in battles, perform on the big stage. Others just see it as a way to keep fit or flexible. Another group may just like it for its own sake: a medium of creative expression. Or maybe they really like the dance community. Your motivations could fall into any of these, or be a combination. Its all good. If it’s a game you want to win, how you win is also entirely up to you. So what if everyone is playing a certain way? If that way to win was so good, they would all be super successful, right? But noooooo. Chances are, following the crowd would only get you the returns of the crowd. If you want to win, you need to develop your own unique strategy, or find pathways or glitches or loopholes that enable you to ‘hack’ the game and win.

One hack I’ve found is that creativity rarely comes in meeting rooms or brainstorming sessions. Those are probably the worst places for creative ideas. I’m most creative at weird times like in the shower, or swimming or on a walk, or even driving (which is how the idea for this blog entry even came about). We’ll discuss strategies in a bit.

Whichever game you choose to play, you will also have to recognize the costs that come with it. The main currency we trade here is time. But there are other costs like your money, your energy, or your relationships. Sometimes this cost is upfront, sometimes its a passive drain. That being said, not all games are equal. There will be games with massive upside and little cost, and others that are nearly pure cost, leaving you wondering why you are even still playing them. And again, ‘cost and upside’ are subjective. If you hold some things more dearly than others, naturally you would perceive the same game differently from others. Lastly, and perhaps most importantly, you are not the avatar in these games, you are the person sitting behind the console, pressing the buttons. You are the puppet master, not the puppet. This is a perspective that was inspired by Steven Bartlett, a modern day thought leader and entrepreneur.

You are not your labels. You are just a person with a bunch of skills and experiences. - Steven Bartlett

This is important to digest. So many of us live your lives way too seriously, unable to realize that we are not the roles we play. We are much more than that. And there is a distinct distance and separation between our avatars and us. Steven calls this the ‘video game state of mind’, going through life as if you are playing a video game: free from others opinions, free from the fear of failure.

Looking at life this way also means that you can quit these games anytime. This may sound like bad advice, telling people to be quitters. But continuing to play a game even when your odds of winning are near impossible, and the rewards aren’t even valuable to you anymore, or its costs are way too high — now that’s a foolish thing to do. Its true that perseverance is a virtue. The ability to stay steady, hustle hard and be determined all the way is admirable. But you also have to recognize the times when you should quit; when its time to cut losses and play another game with rewards that are more valuable and meaningful to you.

We start games with imperfect information: we may not know what the community is like, how difficult it really is, whether we have the skillsets to excel at it, whether we would enjoy it. So the more time you invest in a game, the more you will find out about it. Its like poker, where you essentially are paying for information: information on your opponent, on the cards in play, etc. So once you have gathered the information you need, you can revisit the idea of staying on in the game, and decide accordingly.


Some rewards are meaningful in ways you can’t quantify :)

The Big Game

If Life is a Game of Games, then what is THE Game? The ultimate game that all these other small games are subordinate to? What are we choosing between all these games for?

This could also read as: ‘what is the purpose of life?’ To which I shared a little bit about in a previous blog entry here. Although since going back to read it again, I’m pretty embarrassed by it, as we all usually are by our past works and past selves. Also, my answer has changed.

Back then, I said that the purpose of life was Growth. That we shouldn’t think of life has having an end point, but rather to see everything as constantly changing. A process.

While I do still think very highly of this idea, and try to embody it as much as possible, I’ve come to the conclusion (with the help of others who shared their own views on this with me, thank you) that Growth isn’t the purpose of life, its simply the way life manifests itself. A fact of life, not our objective in it.

So as of the time of writing this, my new answer is…


Peace in the deep, internal sense of being truly content, assured and free. In the sense that the present moment is complete, in and of itself. When we stop sacrificing today for tomorrow.

There are 2 quotes that capture the point I want to bring across:

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone.” — Blaise Pascal
“Enlightenment is the space between your thoughts.” — Eckhart Tolle

The first sounds quite extreme at first reading, but when you really think about it, it doesn’t seem that crazy. It is immensely difficult to sit in silence alone with your own thoughts. Yet, it is in pushing through that discomfort that we achieve clarity: about ourselves, and about the world. And what do we get clear about?

  1. That so many of the things we think are important, like money or status or approval, are illusions. Games. Stories that we collectively believe in and get sucked into.

  2. That we already have everything we need. This is where the second quote comes in.

Enlightenment isn’t something you achieve after thirty years sitting on a mountaintop. It’s something you can achieve moment to moment, and you can be enlightened to a certain percent every single day.

Going back to our games analogy, it means knowing that we are free from the games we play. Like a rat that finally gets off the hamster wheel, out of the rat race, there is a deep peace that comes from realizing we have the power to choose. We can play these games, sure, but there is that agency in deciding whether to play, which to play, when to play, and how to play.


Escaping the rat race by making a game about the rat race. Fate loves irony.

How to Play

So we’ve gone through the broad philosophy, the whole Game of Games idea. But now what? How do we go about playing? How do we make this philosophy ‘actionable’?

At this juncture I want to say that the following ideas are largely inspired by stoicism (the small bits of stoicism that I have read thus far) and Naval Ravikant. Like Steven, Naval is a modern day thought leader, philosopher, investor, entrepreneur. Awesome guy. Full of wisdom.

Quotes, all from Naval:

“Do the things that feel like play to you but look like work to others.”

This follows up on a previous point on costs and rewards in games. If something feels natural to you, feels fun and comfortable and easy, yet to others feels like a chore or really difficult to do, then that is probably a good game for you to play. And by game in this case I mean like career/work/side hustle. I understand and resonate with the fact that these areas that feel like play also don’t generate much tangible rewards, and thus many of us leave them as hobbies. But keep searching, because chances are, you are going to find something that feels like play to you that the world would gladly pay for. Something like an Ikigai intersection of multiple circles kind of thing. Also remember that not all games are played for the same reasons. Some you play for the tangible rewards, others simply because you like it. That’s totally fine. Embrace it.

“No one can compete with you on being you. Most of life is a search for who and what needs you the most.”

Essentially, when you compete with others, you are trying to copy them, trying to do the same thing, maybe optimize a little bit. But all of us are unique. Nobody can copy you, nor can you copy others. So the way to win at the games of life is to understand yourself, make your own rules, and play it your own way.

“If you can’t see yourself working with someone for life, don’t work with them for a day.”

Now this quote sounds pretty brutal and extreme and perhaps even egotistic. And I agree that it is all those things. Yet, we can definitely see the truth in this quote: time is precious, both yours and everyone else’s. So the last thing we want is to waste both parties’ time in a relationship that you can’t see working for a long time. This quote isn’t saying to not have short term contracts or to not make friends at events. Its more of a mindset — a guidance that you take towards selecting people to join you on your journey. And it's about being more respectful of your own time and guarding it with increased fervor. Simon Sinek echoes this idea in his book, The Infinite Game. Essentially, the idea is to play the games of life as though they last forever.

Most games don’t have a set finish line where you go ‘okay I’m done, time to relax and celebrate and enjoy my trophy’. Yet from young, this is the idea we have been taught. ‘I got 270 in PSLE’ or ‘I got a first class honors.’ Uhhhh so…? Did u win? What exactly did you win at? Does it even matter?

In business, do you ‘win’ at marketing? No. Marketing or sales or supply chain or product development is an infinite game. You can decide when to tap out, or when to hand the baton over to the next guy in your team, but the game never ends.

Now back to the initial quote. Yes, it was specifically about people, but the essence of the quote can be applied to many other areas/games in life too. “If you can’t see yourself behaving in a certain manner for life, don’t behave that way for a day.” I suppose this could be seen as a variation of the Categorical Imperative: “Act only on that maxim through which you can at the same time will that it should become a universal law.” Except that in our case, rather than universal law for everyone else, its just a universal law for you.


I love bowling as a game. But its when I got into competitive bowling in school that I really disliked the sport.


That brings us to the final part of this blog entry: a way to bring all the strategies into one big strategy. A strategy of strategies, if you will.

Disruption, in the business world, is when a new business or technology comes in to overturn the old businesses or old way of doing things. A big part of why it’s ‘disruptive’ is because the old companies are so stuck in their ways of thinking, their ways of seeing the world, that by the time the new innovator disrupts them and takes all their market share, its too late for these old companies to change, and they are completely ruined. Take Nokia vs smartphones, Kodak vs digital cameras, Blockbuster vs Netflix.

Self-Disruption is about taking this concept and applying it to your own personal life. Change is nature, nature is change. So if you don’t disrupt yourself, life will disrupt you. Think like Covid, or losing a job or a loved one.

What are we disrupting? Our habits: patterns of behavior that you grew up with. And our mental models: narrow, outdated world views. An important caveat here is that we are not just changing the ‘what’; we are changing the ‘why’. Why have we been acting in this way? Why do we see the world in this way?

It’s really important to be able to uncondition yourself, to be able to take your habits apart and say, “Okay, this is a habit I probably picked up when I was a toddler trying to get my parent’s attention. Now I’ve reinforced it and reinforced it, and I call it a part of my identity. Does it still serve me? Does it make me happier? Does it make me healthier? Does it make me accomplish whatever I set out to accomplish?” — Naval

Take the time to have a good, honest, open-minded look at yourself. Maybe even do it sitting in a quite room alone, listening to your mental chatter, the thoughts that dominate your mind. There will definitely be all kinds of inconsistencies or unhealthy thoughts or habits that you can uncover. And know that you have the power to change them.

“We think of ourselves as fixed and the world as malleable, but it’s really we who are malleable and the world that is largely fixed.” — Naval

Remember the distance and separation that you as the player have from the games you play? Puppet master vs puppet? A similar thing is happening here too. We need to distance ourselves from our thoughts.

You are not your thoughts. You are not your habits.

As you disrupt yourself, you might even start to find odd habits and norms that other people have. Matthew McConaughey said on Tim Ferris’ podcast:

“Why do we go to air-conditioned gyms? Isn’t the whole point of training your body to put it in an uncomfortable place so it can grow stronger?”

I found that just really hilarious, and fascinating.

And in playing the Games of Life, I suppose that’s exactly how the journey is going to be.

Hilarious, and Fascinating.


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