Checkbox Minds and Deep Souls

I was discussing life with a friend of a similar age, and they brought up the desire to cultivate virtue – deep, innate character. This led to a discussion about how some people’s morality is just checkboxes, while others is a deep sense of right and wrong inseparable from their personality. Between that conversation and speculation later, I wanted to share some thoughts.

(And yes, this is carrying on a conversation by other means.)

The idea of virtue is something I’ve thought of because of its depth, the idea of having some inherent deep goodness and quality. In my Taoist interests it stands out, a quality (“Te”) one obtains through contemplation and meditation, a kind of mystical-moral gravity. My recent readings on Neoplatonic and Stoic philosophy and mysticism led me to similar ideas as well, of one cultivating some kind of depth of character. There’s something that happens when we cultivate or find an inherent force of character, being “good” so we act “good.”

The “checkbox” idea of morality is the opposite. You are good because you can check off these things, like a car maintenance list or an order form. Things are done because they’re on the list not because of ones character or any depth of contemplation.

After this discussion I realized that “checkbox morality” is no kind of morality at all. It’s doing some signifiers, not even a minimal effort. It invites cheating the checkboxes with games of language, like some kind of tax code of morality. It has nothing to do with the actor, why they do things, and what led them to their actions.

And of course, checkbox morality invites people to say “I did all these checkboxes” then still go on being a colossal asshole. I’m sure a quick look at the world will allow you to name several public figures that fit this . . . then several more . . . then several more . . .

Checkbox morality is shallow, not really moral – and is empty. Also honestly sort of boring and pretentious.

This helped me understand my desire better, and that of other thinkers whose writings inspire me. I wasn’t interested in checklists, I was interested in evolving, like some kind of moral Pokemon (steal this idea, Nintendo). The drive to virtue is a drive to grow, sometimes driven be a delightful unsettling sense that one can be better.

The quest for virtue is something real, it has depth, it’s even a bit dangerous. It’s not a list, it’s both being and an adventure.

This also helps me understand some of legends of past sages and holy men and artists I saw in the Taoist cannon and elsewhere. Groups of informal mystics and philosophers and outright weirdos gathering to discuss virtue and morality and life, and of course sometimes get completely shitfaced while hanging out. There’s a delight in exploring one’s depths with friends – like this friend and I did.

I hope this column inspires you – and I’d like to hear your own thoughts on virtue.