Category Archives: Essays

The Infinite Game

I wrote an essay I wish I had been given when I graduated from college, retired from tennis, and began the transition from student-athlete to the “real world.”

Through this essay, I hope to provide some awareness and tools, namely around self-reflection and self-awareness, how to think about how to spend your time, what to look for in a job, and the importance of coaches and mentors.

While written through the lens of a student-athlete, hopefully some of these principles and tools apply to a broader audience.

What that, let’s jump into this rabbit hole…

*Update as of 10/26/20. Within the essay, I reflect on the importance of defining your life dimensions – areas of life that you deem important enough to prioritize. For me, those are health, family, friends, work, community service, personal growth, and spiritual growth. I’ve put together this simple spreadsheet to help keep me accountable in each of these various realms. (Just FYI – An excel file will download if you click the link below)

The Ripple Effects of Pursuing Mastery

I’ve had the privilege of being able to pursue several different skills to a high-level and now that I’m a father (and soon to a second!), the ripple effects of pursuing mastery are becoming increasingly apparent and important.

One of the key ripple effects of pursuing mastery is that it has extended my “difficulty spectrum.” By pushing myself to the edges of my abilities, I’ve enhanced my skills, mindsets, and habits to endure difficult situations and these traits are universally valuable and accessible to those who pursue something, anything, to the highest degree they can bear.

The price for admission is high (time, failure, effort, embarrassment) and it is terrifying to consistently put yourself on the line, but you come to learn and trust that the pay-off is worthwhile even if the goal isn’t always clear or attainable. This is where compounding kicks in, especially if you can take the skills and mindset and apply it to your “learning OS”, rather than simply your current craft. If you can do this, every additional skill you attempt to master becomes marginally easier and it impacts every other area of your life too.

Lessons at 30

As I reflect back on my first 30 years, I wanted gather some quick sound bites on things that have proven valuable to me.

Incomplete and imperfect, but hopefully some of these spark something in you too.

Challenging * Mattering = Meaningful

This essay helped me discover a deeper connection between challenge and meaning than I previously appreciated. This seems obvious in hindsight, but it wasn’t before, and I think that’s the key to an interesting essay.

Distilled, the “meaningful” results from the combination of something challenging (PIPER in something that interests you) with something that matters (creating; doing something difficult that others find even more difficult than).

When these circumstances come together and form something meaningful, it’s like blending tin and copper. The result is bronze, an alloy so much harder than would be expected that it appears a different metal.

My Learning Process

I’ve gotten a lot of questions on my learning process and this essay briefly shares some big picture strategies and concrete tactics that I’ve found helpful. This is by no means the “right” way, simply what has seemed to work for me so far.

The Opportunity Paradox

The Opportunity Paradox


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You can also find more of my articles in audio version at Listle

Meditations on Meditation

V > Λ: The Inverted Hierarchy



If you’d prefer to listen to this article, use the player below.

You can also find more of my articles in audio version at Listle

The Industrialists

The Industrialists

The Best Product? A Great Team

The Best Product? A Great Team