How Favorite Problems Evolve: A Case Study

Your favorite problems will likely stay consistent over many years, but that doesn’t mean they can’t evolve. 

I’ve found that in most cases I never actually arrive at a final, definitive answer to a question. Instead, the question changes as I learn more.

Let me illustrate this with a case study. I’ll show you how one of my favorite problems – teaching – changed over time as my life went through different stages. 

The 15-year evolution of my favorite problem

When I first started teaching English as a volunteer at my local community college in Orange County, California, my open question was very specific to the challenge at hand: “How do I teach English to recent immigrants who have no background in the language?” 

That question led me to seek out specialized learning resources that used images and games to bridge the gap from their native language to English.

I soon fell in love with teaching, and when I moved overseas to study abroad in Brazil during my senior year of college, I started a side job teaching English at a small private school in Curitiba where I lived. 

My open question changed a little: “How do I most effectively teach English to working professionals who are tired after work and only have an hour of instruction per week?” 

Notice how this question introduced the element of effectiveness for the first time. This was now a job, and I had to think about how my work would be evaluated. Not only that, but I was charged with making a difference for my students in only one session per week, forcing me to come up with easy ways to help them practice speaking throughout the rest of the week.

A couple years later, I joined the Peace Corps, a U.S. government program that sends American volunteers to serve abroad. I found myself stationed in a small town in Eastern Ukraine, the lone American for many miles around, and responsible for about 8 classes of students ranging from 3rd to 11th grade. 

My question suddenly became “How do I keep Ukrainian students of all ages engaged and interested in English?” I looked for ways to use games, role play, and improv activities to make learning English an interactive, and even fun, experience. 

For example, we painted a large map of the world on a classroom wall, labeling each country in English. We made up adventure stories, narrated, of course, in English. I showed them pictures from my life in the U.S. and asked them to point out words they knew. 

When I returned to the U.S. after two years of service, I wanted teaching to remain a part of my life. And after two years working in consulting, I decided to try teaching online as a freelancer. Once again, my attitude toward teaching had to adapt in line with my changing life. 

My new question became “What do I know how to teach that could become a profitable business?” I had to think about the economics of teaching for the first time, which eventually led me to a model of “cohort-based” courses that combined online content with live interaction on Zoom.

As that business has grown and evolved, my question has continued to change. I’m no longer directly responsible for most aspects of our programs. I don’t make most decisions, don’t answer most questions, and am not in direct contact with students most of the time. My job is instead to build the team that does all those things, and to keep them productive and happy. 

My questions these days include:

• How can I design an effective online learning community that sustains itself?
• How do I build and maintain a high-performing remote team to run the best training program on personal knowledge management in the world?
• How do I use free content on our blog, YouTube channel, and social media platforms to serve people even if they never take our course, but prepare them better for the course if they do?
• What new formats, mediums, and platforms can we use to reach more people more effectively with the Second Brain message, without overtaxing our resources or bandwidth?
• What kind of company are we? Are we a media company, a professional development company, a tech-enabled services firm, or something else? What should our model of success be?
• How do we make our community bottom-up instead of top-down? How can we enable others to unlock their potential using our community as a platform?
• How can I be the kind of leader and manager that inspires people to greatness without me needing to be there?

These questions have led me to such unexpected places. In pursuit of answers, I’ve unexpectedly found myself learning the art of recruiting, figuring out how to structure an organization, designing salary ranges and benefits, and spending time doing financial planning, among many others.

These are topics I never imagined would have anything to do with teaching. And yet they are the natural consequence of an underlying, insistent question that has been with me for as long as I can remember: “How can teaching change people’s lives?”

Your favorite problems are always a “draft”

As you formulate your own favorite problems, keep in mind that they are always just a first draft. They can and will evolve as you uncover deeper and more subtle layers of your initial curiosities. 

Not only should you be open to this change, it is the entire point of this exercise: to immerse yourself in the inherent uncertainty that comes with asking questions with an open mind, and embracing the unknowns that will inevitably come into your life as a result.

The information you consume is ultimately a result of the questions you are trying to answer. Change the question, and you’ll begin to notice entirely new kinds of answers you never imagined existed.

The quality of your life depends on the quality of the questions you ask. Ask wisely.

In Part 5, I’ll revisit Feynman’s life and work one last time for a look into the heart of how he viewed the world – as a place of fundamental uncertainty – and the principles he used to navigate that uncertainty effectively and even joyfully.

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