Learning New Skills: A 3 Step Framework For Choosing Infinite Games

Choosing Work That Matters

In 2017, I quit my job at HPE because I hated being a cog in the wheel. Something about doing the same thing over and over again day after day was depressing. Outside of making money, this work had zero meaning to me. 

Like most other mid twenty something millennials — I wanted to do something “on my own.” So, over the course of the next year I moved to the mountains, started a coworking space, acquired another coworking space in Denver, and purchased equity in a coffee company

Building these companies for three years has been fun, and I’ve learned a lot. But as we approach the new year in 2022, I’m reflecting on an important lesson I’ve learned about the work I do. 

A Lesson From Entrepreneurship

When I quit my job, I thought that “doing my own thing” would be meaningful enough to scratch my itch. But after running two businesses for three years, I’ve learned one very important lesson: 

I have a consistent craving to learn new skills paired with a need to create things. 

When the pandemic struck and my businesses were forced to close doors, I couldn’t just sit and do nothing, so I spent my time researching skills I could learn that would add value to my current and future businesses. So I made the decision to spend the days working from home learning SEO and began implementing the principles and strategies by starting this blog. 

During this time period, I also experimented with extended fasting for productivity, and it just so happened to be my first article to rank on the first page of Google the “3 day fast” keyword. 

After learning the principles behind writing SEO focused articles, I’m ready for something new and exciting to learn and practice. I recently came across the concept of playing infinite games and it made me think…


What skill could I learn to play an infinite game? 

What is an Infinite Game? 

NY Times bestselling author and business leader, Simon Sinek, defines infinite games as the following:

“Finite games, like football or chess, have known players, fixed rules, and a clear endpoint. The winners and losers are easily identified. 

In infinite games, like business or politics or life itself, the players come and go, the rules are changeable, and there is no defined endpoint. There are no winners or losers in an infinite game, there is only ahead and behind.” 

"The rules are changeable, and there is no defined endpoint."

I’ve never liked being told what to do, and probably never will. It’s the reason I chose entrepreneurship as a path when I left corporate. In entrepreneurship, you get to create your own rules. And there’s really no defined endpoint if you have a long term mindset. There’s no winning or losing, just improving day after day and building upon what you already know. The real competition is with yourself in an infinite game. 

When deciding if a new skill is worth learning or not, I use the following framework to define whether or not the skill would lead to an infinite game.

What Skills Lead To An Infinite Game?

In order to determine whether or not a specific skill leads to an infinite game, I've developed a simple 3 question framework: 

1. Would you practice this skill on a Saturday morning for pure enjoyment?
2. Does this skill support opportunities with maximum flexibility? 
3. Does this skill create infinite wealth building opportunities? 

Let’s unpack each question.

Would you practice this skill on a Saturday morning for pure enjoyment?

To answer the first question, we have to first define: What constitutes enjoyment? 

My personal definition of enjoyment is something that:

1. Is challenging
2. Requires consistent learning and practice 
3. Lends itself to long periods of focused flow states
4. Is elevated by abstract thinking and creativity

Even when I have plans to do something fun on the weekends such as ski or mountain bike, I’ve noticed that my natural tendency to wake up early and scratch the itch to learn or create something doesn't go away.

Therefore, getting clear on whether or not I’d enjoy learning a specific skill to create something on a Saturday morning is important when choosing whether or not a skill leads to an infinite game.

In order for the game to be infinite, it has to be enjoyable enough to continue doing on consistent basis.

Does this skill support opportunities with maximum flexibility? 

Flexibility in this context is defined as: 

1. Location independent - i.e. can be done remotely from anywhere in the world
2. Supports your natural schedule - can work during most productive time of day
3. Allows time for exercise & hobbies 

Location Independence

Being able to choose where you want to live without the constraints of a job is one of the best perks of learning skills that support remote work opportunities. You get to choose to be close to your family, friends, favorite activities — or a mix of all the above. 

When deciding to learn a new professional skill, it’s important to me that the skill supports remote work opportunities. I plan to raise my family in the mountains of Colorado, therefore having the ability to put the skill into action from anywhere in the world is high on my priority list. 

Will learning this new skill support a remote work lifestyle? 

Supports Your Natural Schedule

Are you naturally more productive in the morning, afternoon, or evening? 

I’m hands down a morning person. It’s when I have the most natural drive to learn and create. And as long as I get to choose, I’d rather spend afternoons outside in the fresh air doing something active rather than sitting at my computer. 

Most mornings (when I’ve slept well), I’m awake sometime before 6am with a relentless stream of energy to learn and create. But guess what? My brain will likely be fried by the afternoon. 

I’m naturally productive in the morning and not productive in the afternoon. Therefore, I’m going to define the rules for the game in my favor by creating a work schedule that meshes well with my natural schedule. 

If I was working a corporate job, I’d likely be held to an office chair by some boomer’s old school expectations. But learning a skill that supports maximum schedule flexibility allows me to work when I’m naturally productive and hit the trails after lunch. After all, I’ve already checked the “8 hour” box, right?

Allows Time For Exercise And Hobbies

As mentioned above, I love outdoor activities. Especially if it involves some sort of cardio exercise. It’s what keeps me sane. Oftentimes, this endorphin induced brain state is when I do my best strategic planning and problem solving for work. So I guess I could argue to the boomer that I’m still working while I’m on the trails ;) 

On top of achieving a different level of abstract thinking, outdoor activities also support a healthy body. Healthy body = healthy mind. It’s an infinite loop. 

In order for me to perform my best at work, it’s important that whatever skill I learn lends itself to a flexible work schedule that supports my ability to get outside in the afternoon. 

Does this skill create infinite wealth building opportunities?

Last but not least, it’s important to answer if this skill will create infinite opportunities to build wealth. Yes, I wrote “infinite opportunities to build wealth” and not “make money” for a specific reason. 

If you wanted to simply make money and check the “enjoyable” and “flexible” boxes, you could take an entry level customer success or sales development job at any tech company with little to no experience. 

Good enough salary to pay the bills, flexible schedule, great benefits.... Making money and checking the remote & flexible boxes, right? 

That's great for a lot of people, but if you're still reading this article you're probably driven to build long term wealth. And that requires learning a compounding skill.

What Defines A Compounding Skill? 

There’s a difference between learning a compounding skill and a regular skill. Compounding skills provide you with knowledge that can both make you money in the short term while also creating infinite future opportunities to build wealth. 

Take SEO for example. If you learn the fundamentals of how to write high ranking blog articles you could easily get hired on at a remote tech company making a similar salary to the customer success or sales role. While getting paid from a company to write their content you also get to hone your SEO skills. In your free time, you could use your new skills to create a personal blog.

With some time and work, you could benefit from a new website that gets ongoing organic traffic from Google. In turn, you could monetize the traffic to your website through building an email list, offering paid courses, or embedding affiliate links. 

Or, you could start freelance writing high ranking articles for other companies and get paid well to do it. Once you define processes, you could even turn this into an agency and hire other writers to write the articles for your clients while you take a management role. 

One of my friends at the coworking space did this and scaled to 1mm revenue in 12 months. He’s since hired a CEO to operate the agency and is working on another project while the agency is still printing cash into his bank account. 

This is why SEO is a compounding skill. Learn SEO and you can get paid in the short term while also creating opportunities to build personal wealth in the long term. 

Deciding What Compounding Skill Is Right For You

Through starting this blog, I’ve found a love for writing and have also had thoughts of doubling down on this blog, a newsletter, or building an SEO agency. But writing is a creative processing tool for me. It’s basically free therapy. 

Over the past couple years, I’ve tried the consistent newsletter & blog publishing thing but it felt like it was forced. I’d rather write genuine content sporadically throughout the year as a tool to help me process my thoughts — just like this article I’m writing. 

For example, I’ve been tinkering with the idea of learning some JavaScript to enhance my knowledge of no code automation tools. So I started writing about it, and this article is a product of my thought process.

Through writing, I’ve developed a logical framework to one of my real world situations. And I’ll be able to reference this in the future for deciding whether or not to allocate time to learning a new skill. For now, I’m going to keep writing as a way to process my thoughts and develop frameworks and explore other compounding skills like learning SEO, coding, and real estate investment.

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