In praise of rabbit holes

"When I grow up, I want to be just like

Chris Wong

." I know, I know coming from a nearly 60 year-old man this sounds facetious, but in a deep-but-not-literal way, this is how I feel.

I think of Chris as a pied piper but instead of a siren for children, he lures curious folks like me down rabbit holes. Amazingly, each of his magical rabbit hole is presented to me just at the time I am most receptive to appreciating it

The first Chris Wong article I read was How to Give Great Feedback. It presented a feedback framework in a classic biz school-ish 2x2 matrix. I thought it was a clever way to highlight that the most useful advice to give is whether the core concept is shining through. I read it when I first took Write of Passage. We were asked to give feedback to each other’s essays, so it felt immediately applicable.

Being a fresh Asian immigrant, I was then drawn to 100 Years of Gratitude, a piece commemorating how his grandfather came over from China a century ago. But the poignant part I took from it was how he related his grandfather’s journey with himself and his reflections. Was this the start of his own journey and awakening?

Throughout my life, I’ve wondered what my identity is.  I’ve also wondered why that matters.  I think it’s because I feel like I need to fit into other people’s conceptions.  Or because I needed a way to describe myself to other people.

It was when I started subscribing to his newsletter that the rabbit holes started appearing regularly. 

Chris has a knack of seeing things just slightly differently and connecting dots which I know about but in just a unique slant that gets my thinking juices flowing. His newsletter is generative, it’s always making me think of new ideas, even on familiar grounds.

Chris’ recent series on creativity is a beautiful example. He starts off by riffing off Daniel Pink’s three building blocks: autonomy, master and purpose. But instead of considering motivation, he applies it to creativity. 

These 3 elements are still rather abstract and hard to pin down, so he applies Munger’s inversion technique and asks, what is the opposite of these concepts?

Autonomy <-> Mimesis

Mastery <-> Rigidity

Purpose <-> Boredom

This is what I like about Chris. These are not antonyms in a literal dictionary sense, but they are inversions in revealing ways that made me contemplate.. 

If I were to come up with the opposite of autonomy, I would probably say imprisoned or enslaved. Fortunately none of us are physically locked up. So, mimesis is a more reflective term because we are all under the spell of mimetic behavior.

I like how Chris is also nuanced as in his piece on Finding Purpose.

It sounds counterintuitive.  Doing something 100 times sounds like a slog.  But it forced me to identify the important aspect - I wanted to know what ideas are interesting to me.  Doing something 100 times forces you to strip away everything you find painful and you find something interesting inside.

In doing something 100 times, it’s hard to avoid boredom or even pain. But if we’re mindful of what we put in and get out during each iteration, it could lead to finding what is meaningful and fulfilling for ourselves.

If you are an artist or creator, start with #86 - Liminal Creators and move up. The series proper starts at #94 - Via Negativa. I think you will gain much self-awareness on why you do what you do. Even if you are more of a dilettante like me, Chris’ newsletters will make you appear smarter. This literally just happened to me last week with a book recommendation that I learned, of course, from UnknownUnknows!

Congrats on your 100th newsletter, Chris! They have planted seedlings in my mind that have grown to become mind bombs. I look forward to making time for the next 100