Hustle · Lifestyle

How to Get Paid to Play

Last week, we analyzed the system of preparation and found out why the truly sensible never work. The conclusion of that article was to find a way to get paid to play. In this article, we will try and determine how you (yes, you!) can get paid to play. But first…

What is play?

“Play” is simply anything you do purely for enjoyment and not for any practical or serious purpose. The kinds of people we traditionally think of who play for a living are the professional athletes who play the field, talented musicians who play some instrument, and performers who play the part on stage.

However, someone whom we often don’t associate with “play” is the artist.

What do you consider play?

Your idea of play is likely different from mine. However, discovering (or rather acknowledging) your play can be tricky especially if you’ve gone so far into the system of preparation that you’ve forgotten what “play” means to you.

Here are some prompts to help you acknowledge your play:

  • What kinds of play did you do as a child?

My answer: From middle school to college, I was always tinkering. First by dissecting my toys, electronics, and then computers. Once, in 5th grade, I made a motorized bug-like contraption out of broken toys and a computer motherboard.

Takeaways: Inventive, Inquisitive, Resourceful, Hands-on, Technical, Creative

  • What do you find yourself doing in your free time?

My answer: Often when I have free time, I read a book or watch informative YouTube videos.

Takeaways: Always learning

  • What do you wish you had more time/money to do?

My answer: If I had a sudden lump of cash, I’d use it as startup capital for an e-commerce business.

Takeaways: Entrepreneurial, Risk taker, Investor

Take a moment and answer these questions for yourself. These are the things that bring (or you think will bring) a sense of satisfaction, or pleasure even when nobody is paying you to do them. However, these are not all necessarily play!

Delusions of Play


Play in its truest form has no purpose. Our minds are very skilled at fooling us to believe that we enjoy the things that bring us money, that feed us and make us comfortable. But play alone does none of these things

The dangers of living with such a delusion are many. Besides the fact that you are intentionally depriving yourself of much of what this life has to offer, stress, anxiety, and a general numbness to reality (also known as becoming boring) can be expected.

The true play never expires or gets old. It does not drain you; it energizes you.

So you’ve found your play…

Whether your play is drawing, snowboarding, parasailing, video games, the violin, crossword puzzles, or writing, there is a path to getting paid to do it. The play you have chosen (or that has chosen you), has a unique path to the first payoff. However, there are 3 general traits that apply to all of them:

I call these the 3 M’s.

  1. Merit
  2. Mastery
  3. Marketing

Merit (Value)

Futurama Shut Up and Take My Money GIF

Merit – “the quality of being particularly good or worthy, especially so as to deserve praise or reward.”

Put simply: Someone has to find your play valuable.

Your ability to craft value from your play is the single most important step to getting paid. If you are an artist, your value may come from the art you produce. If you are not an artist, try to think about yourself as an artist anyway. What is your art? What specifically, are people willing to pay for? Is it the product of your play or is it something more personal or abstract?

People will pay for value.

Find the areas of your play that produce value for others or find ways to shape your play so that it creates value.


Pug Playing Piano GIF

Mastery – “comprehensive knowledge or skill in a subject or accomplishment.”

Put simply: You have to be good at your play.

I may love to draw, but if my drawings are stick figures, then I may need to reconsider where the value is in my play. I could be like the highly successful XKCD who uses stick figures in a web comic.

The point is this: you create more merit by being more skilled at your play. Start playing now and don’t stop. Build your skill through deliberate practice.


Look at me GIF

Marketing – “the action of promoting and selling products or services, including market research and advertising.”

Put simply: Know who thinks your play is valuable and make sure they know about you.

Today, marketing is less about getting yourself out there and more about cutting through the noise. Anybody and everybody can start marketing on social media. The idea is to build an audience of people who regularly tune in to what you have to provide. Social media is a great beginner’s channel to reach your new audience.


Find your play. Discover where the value lies. Maximize that value by developing your skill. Find and interact with the people who find your play valuable and make sure they know you are open for business.

Again, these are general steps that apply to any kind of playful pursuit. There are infinite ways to play this game we call “life”. What is the best use of your turn?


The Truly Sensible Person Never Works

In western civilization, we have a very peculiar way of treating our youth. We could, for instance, say to the child, “Welcome to humanity! Here are the rules, and when you get older you may be able to create better rules.” Instead, we cultivate an eternal system of preparation.

The System of Preparation

So you go to pre-school which is preparation for kindergarten. You are going to kindergarten to prepare you for the first grade. You work your way up the ladder and if you find yourself fascinated with this system of living eternally in the future, you may go off to college. If you are smart, they recommend a graduate school and you go off and become a professor and live perpetually in this cycle.

“The most dangerous risk of all is the risk of spending your life not doing what you want on the bet you can buy yourself the freedom to do it later.” – Alan Watts

Now, of course, you can leave this system at some point and enter what they call “the World”. You go to your first sales meeting and find that they are under a very similar system. You have a quota and once you meet that quota, they give you a larger one.

Once you become middle aged, you begin to realize your life has been quite the same since you can remember. You have been conditioned to be in desperate need of a future. All in pursuit of this thing called “retirement” where they give you a discount at Hardees and you will have the time and money to do the things you’ve always wanted. At the same time, you will have no energy, rotten teeth, and aching joints. You begin to realize that this whole thing from start to finish is a hoax!

The Price of Living in the Future

You see, we live in a very bizarre human machine that creates a distinction between work and play. You go off and do your work because everyone else does and you get paid to do it because no one would care to do it otherwise. Your work is so boring, so dangerous, so dreadful that other people pay you to do it so they don’t have to. So you go to work to make money so you can leave work and enjoy this money that you’ve made. You see, “money can buy you pleasure”.

However, more often than not, you find yourself spending your hard earned money on TV dinners that save time cause you work so long, nice cars that get you to work and impress your coworkers, an expensive house that’s close to work, and Netflix/Hulu/HBO GO subscriptions so you can watch a manufactured life through a screen (or maybe you prefer to play pretend life using an Xbox or PlayStation) without engaging in life yourself. You see, you find your own life so dreadful and boring that you watch other’s to tickle that nerve. The same goes to social media.

You see, we have cultivated a culture of living in the future. We have a mindset that we are always on the move toward something bigger and better. No wonder anxiety is such an epidemic today!

A Solution

I am not proposing that we do away with money, or even the system entirely. Money is a fantastic tool for controlling behavior and it allows us access to pleasurable experiences and things through the division of labor. Likewise, we all depend on the people who faithfully go to work every day to deliver the mail, grow and prepare the food, and clean the streets.

But suppose for a moment that a person saw through this system early in life and decided he wanted no part of it. This person reasons that he’d rather spend his life playing than working. That is, he’d rather do things he liked than things he didn’t like. If he’s truly sensible he’ll see all the accessories, gadgets, frivolities, and distractions of life for what they are and he’ll have very little to do with them. As such, his cost of living is significantly less than his peers and now all he must do is to find a way to get paid to play. Of course, all this comes by first choosing to live in the present.

This, then, is the great question: “How does one get paid to play?”. I will attempt an answer in next week’s post.