Willfulness

I want to live a virtuous life, and I want to have a positive impact on the world. In practice, these are 2 very different goals.

The former is intrinsic — the act is its own reward, and I don’t have to claim responsibility for any external outcomes. The latter is results-oriented, so my noble intentions must clash with the messy compromise of reality. For this reason, high-impact people often seem less virtuous... especially in the "humility" department.

Most of my high-impact friends have this in common. They can just shamelessly project their own expectations onto the environment around them & rely on others to reconcile the difference, rather than contorting themselves into a pre-determined slot. They’re not merely selfish with their time — they're assertive with their will.

For instance, let's say we're at a restaurant. Personally, having worked briefly in food service, it is my goal to be as easy a customer as possible, and for the wait staff to enjoy my presence & be glad that it was me, and not some more difficult customer, that sat at their table. Even if they bring me the wrong dish, I'll usually just eat it.

My willful friends are different. They’re not mean or aggressive in the “let me speak to your manager” sense... but they'll ask the wait staff some weird questions before ordering something with a lot of modifications. This is a more difficult dining experience for everyone, but it often results in more enjoyable meals for them (and me, when I ride their coattails with a quick "make that 2").

Until recently, my personal strategy was to only raise hell for important situations. For the other 99% of life, I'd just shut up and enjoy the ride. I'm now starting to notice a negative consequence of this approach, though. When important situations finally arise, I actually have a hard time being assertive, possibly because I'm out of practice.

For the longest time, I thought there was some spectrum between the character traits of "willfulness" <-> "humility", and that lowering one will increase the other. The problem here is that it assumed, for every situation, that I'd usually sit at the same place on that spectrum. The trick is not to have a default 1 way or the other, but rather consider each situation from first principles. I am not "a willful person" nor "a humble person" nor "a slightly-willful person". I'm whatever person the situation calls for.

Here are a few situations that call for different things:

• At work, my team is adding complexity to a project that will be killed next year. My boss is under a lot of pressure to deliver short-term results, but I think we should focus on longer-term value creation that's more difficult to measure. There is a spectrum between "build what I'm told" ↔ "raise hell."
• My son has a medical issue. The doctor listens, looks at data, and explains a treatment plan. I think he's overlooking something important, but he mostly just repeats his initial response, and it feels very generic. There is a spectrum between "smile & thank him" ↔ "raise hell."
• A younger friend is working hard at a dead-end job. I'm confident they could double their salary, work with more interesting people, learn more, and improve their work-life balance. There is a spectrum between "don’t meddle" ↔ "hound them about it."

It's intellectually dishonest to coast through each situation with the same pre-disposition to agree or disagree. In these examples, that would hurt my friends, family, and co-workers. I should be consistent to my values, not to conversational momentum.

Men who believe that they are accomplishing something by speaking speak in a different way from men who believe that speaking is a waste of time. \ Neal Stephenson, Seveneves

Afterthoughts

The "willful" options above generally involve persuading other people. I've noticed that people like me, who consider themselves both introverted & ambitious, will under-develop this skill. The ramifications of this conflict-avoidance start small but compound dangerously over time, especially when we keep our ambitions secret.

I used to have some big dreams about getting rich and then becoming a teacher, but I would get a lot of criticism whenever I voiced it out loud. Rather than adapting the idea, or learning to defend it, I instead chose to stop talking about it entirely. The plan was just get so rich that I wouldn't have to persuade anyone else, and then become a teacher.

This isn't a terrible strategy -- money talks, after all. But it's certainly not optimal. Many of my friends have similar altruistic ideas, developed within the echo-chamber of their own mind, and they become increasingly specific and ridiculous over time. If this is you, then just start talking about your big altruistic idea today. Drag that thing into the light & see how sane it can be without your hypothetical future fortune behind it. In many cases, you'll find that you can accomplish something similar to your original goal before completing the capitalism side-quest.

In my case, I've realized that I wanted to be a teacher so that I can help people grow into the best versions of themselves. To that end, I've now helped 4 non-traditional software engineering candidates bridge the gap to their first full-time programming jobs. This feels great, and the experience has helped me refine my ideas through practice.

It's also revealed that I have no idea how to measure altruistic impact. Startup companies are commonly advised to chase 10 users that LOVE their product before trying to get 1000 users that like it. I think a similar pattern applies here, where deeply impacting a few people is actually better than slightly impacting many.

By this reasoning, it's entirely possible that the most positive impact I can have on the world is to quietly lead a virtuous life as an example to the few people I see every day. Thinking otherwise leans heavily on my own understanding, which has significant limits... but anyways...

If you want to have an impact, start now. You're more likely to hit a home-run if you've had a few practice swings first.

Whoever can be trusted with very little can also be trusted with much. \ Luke 16:10

// TODO: consider renaming this to "courage"?