Learning and teaching practical wisdom

It’s not always obvious, but this newsletter is a place in which I am trying to teach you something unified. It’s just that the unified thing is very large, and I can only grasp pieces of it, so often it looks like I’m completely all over the place despite there being an underlying whole to it.¹

In the incomplete piece, “What every programming tutorial gets wrong”, I argued that programming tutorials suffer a major problem, which is the lack of integration between theory and examples: They either give you lots of examples, and expect you to be able to generalise from them on your own, or they give you lots of theory, and they expect you to be able to put it into practice on the basis of that. Effective teaching requires both: Examples are the core of learning, but theory allows you to generalise those examples into your own life.

I fear I have fallen afoul of my own critique in writing this newsletter, and I’ve given you all a great deal of examples of the thing I am trying to teach without telling you how it all fits together. In my defence, this is because telling you how it all fits together is very hard, and hasn’t always been clear to me either.

Anyway, let me have a try at explaining. What I am trying to teach you is practical wisdom - the ability to know what to do².

Other people I know who I think are trying to teach practical wisdom are David Chapman³ and Cedric Chin.⁴ We’re all working on some different aspect of the problem - Cedric is largely focused on practical wisdom in business, I’m largely focused on it in day to day living, and David Chapman is I think focused on a more top down view of how it shapes our lives writ large.

I think to a large degree most writing is in some sense sharing specific pieces of practical wisdom, but the thing that I think makes the three of us somewhat unusual (although far from unique), is that we’re actually trying to show what it’s like to have practical wisdom, and to teach people how to acquire it, rather than purely sharing the results of it.

What is practical wisdom?

Practical wisdom is the quality of knowing what to do in a particular practical context, and of being able to articulate why a particular action is the thing to do. The action is more important than the articulation of why it’s right, and is sufficient to count as practical wisdom in itself, but the ability to articulate its rightness is an important part as well, and shows greater wisdom than just the action.

Practical wisdom is particularly concerned with everyday contexts. A comparison that I find useful is that practical wisdom is the sort of wisdom you find in a car mechanic, not the sort of wisdom you find in a sage on a mountain top.⁵

It is not abstract or theoretical wisdom - someone might possess a great deal of practical wisdom without being able to properly articulate a general theory of the area - and it’s not the same thing as skill - someone may be very skilled in an area but utterly lacking in wisdom (you often see this with people who are young and brilliant, but it’s not at all confined to that category).

It’s also not “knowing what the right thing to do is” in an idealistic sense - someone who proposes a great plan that would work wonderfully if only everyone involved was perfect and self-sacrificing isn’t exhibiting practical wisdom. Practical wisdom works with the context in a way that actually gets results.

Almost every adult of remotely sound mind possesses some degree of practical wisdom - it’s very rare to meet someone who literally never knows what the right thing to do is - but some people clearly possess more than others, and the core of what I am trying to do is teach my audience how to develop more practical wisdom.

I’m doing this partly because I want other people to become wise, but also in large part because I, myself, am trying to develop more practical wisdom. Much of my writing consists of sharing particular applications of it as I’ve figured them out, but what I think is lacking is guidance on the general problem of developing it.

The wisdom generalisation problem

One way to learn practical wisdom is by building on other practical wisdom you already possess.

Everyone possesses practical wisdom, but often it fails to connect up. Our hypothetical car mechanic might possess a great deal of practical wisdom when it comes to repairing an engine, but it completely falls apart when he’s in the kitchen, or in the context of interpersonal relationships.

This is the wisdom generalisation problem: How can you use practical wisdom in one area of your life in order to develop wisdom in another area?

Ultimately the answer is annoyingly simple: You just do. It’s not actually that hard. It just requires learning to walk through walls, after which point it’s just hard work, not a difficult problem.

A great deal of how I got started on all of this was realising that I was miserable and that I should probably do something about that. Rather than treating it as a completely alien environment in which I had no practical wisdom, I brought most of my existing experience and knowledge to bear on the problems - I also had to acquire plenty of new skills, and new types of wisdom, but I could still fundamentally think of my life and its problems in terms familiar from a decade of software development experience which is, ultimately, a very good crash course in managing complex systems that interact with the real world.

(Many software developers go wrong when they try to generalise from software development to other disciplines. My impression is that part of this is because they weren’t very good at practical wisdom in the software context either. Software development complexity involves a lot of messy social reality problems, and many people try to ignore that).

When you are in a new area, and you want to be good at it, you of course need to learn new skills for that area. But I think equally importantly, you need to learn new wisdom for that area, and the best way to start doing that is by analogy making: Consider what you would do in an analogous situation in an existing area where you have wisdom, and try doing that. It may or may not work, but either way you’ll have learned something.

Developing practical foundations

Learning practical wisdom from other practical wisdom is all very well, but you do need somewhere to start. That place is work. It doesn’t have to be formal paid employment (for example running a household is if anything likely to be a better training ground for this), but it does have to be some sort of engagement with the real world, ideally one that involves other people and can fail.

Practical wisdom involves knowing what to do, and the best place to learn the basics of this is in an environment with reasonably well defined goals, because this gives you the experience of knowing what to do when you are trying to achieve a particular result. This provides a good training ground for the foundational skills needed.

Many actual sources of work are not actually very good for this, because they do not give you autonomy. If you never have the opportunity to make decisions, you will never actually need to exercise the skill of knowing what the right thing to do is - you just do what you’re told. The more you are required to exercise wisdom in your work, the better training it is for that.

As a result, formal education is also not very good at teaching wisdom (if anything it’s actively deleterious to the process of acquiring wisdom) because it’s so regimented: At no point are you really autonomously trying to achieve something, you are just trying to show to an authority figure that you know how to do the exact thing they want you to do.

Games are another environment that I think are quite poor for developing practical wisdom. You develop some in them, especially the more complicated ones⁶ in that you are at least autonomously working to achieve a goal, but the environment of a game is too simplified and involves too few of the messy realities of the real world.

An archetypal example of someone who has missed out on this sort of experience is the trust fund kid, and I think stereotypes about them show what a lack of wisdom looks like: Not necessarily bad people as such, but with a certain ineffectiveness to their character.

The art of the obvious

I think one of the ways in which you know practical wisdom is present is that you get stuck, and then someone wiser (or differently wise) comes along and shows you what to do, and you feel like an idiot for not having thought of that.

A lot of the advice I provide in coaching is like this. “Have you tried solving the problem?” (followed closely by “OK, what have you tried?”) is a running joke for a reason.

(Obligatory plug for my consulting services, in which I do this for people in their jobs at software companies. Learn more about this on my consulting site.)

One of the things I’ve learned from Cedric and his work on skill and decision making in business is to read up on the Naturalistic Decision Making literature. What people tend to do is recognition-primed decision making. They look at what's in front of them, they reason by analogy, thinking "Oh, this looks like that thing I saw before, let me see what happens if I do the same thing that I did there...", and then they do the thing. If that works, they now have another analogous situation to draw upon. If it doesn’t, they understand better why the situation wasn’t analogous and know not to do it next time.

This is precisely the thing I am calling “practical wisdom” - knowing what to do.

Generally speaking, the action they chose is one that anyone reasonably competent in the area could have done, the hard part was developing their intuition to the point where that action was what came to mind. Much of expertise consists of refining your pattern matching until the obvious-in-retrospect thing to do is also obvious in advance. Thus, practical wisdom is often the art of the obvious.

This leads to two major features of wisdom:

The first is that wisdom out of context often sounds like platitudes. “Have you tried solving the problem?” sounds like a joke until you hear it in the specific context of a problem you haven’t tried solving. “Go for a walk each day” is obvious advice to the point of being trite - something you roll your eyes when your parents tell you - but also often actually is the solution to your problem. “But going for a walk is hard and I don’t wanna” you say? Yeah, that does sound like a problem. Have you tried solving it?

The second is that because practical wisdom is the art of the obvious, it’s very easy to rely on other people’s wisdom. Instead of figuring out what to do yourself, you just go and find some convenient guru and ask them what to do and then do it. This works pretty well, but naively implemented will tend to lead to you never developing your own wisdom broadly - instead you’ll implement the very narrow “wisdom” that the thing to do when you’re stuck is to go ask your guru.

The wise get wiser

One of the big problems with the guru algorithm (go ask your local guru what to do when you’re stuck) is that one of the best ways to develop your practical wisdom is to help other people figure out what to do. It’s a much better feedback loop for developing your wisdom than merely doing the thing (although hard to do well without at least some practical experience), because explaining things to people deepens your understanding of them. Additionally, it’s a much tighter feedback loop than merely acting, because you get to skip the slow and hard bits of actually doing the work, and focus on the interesting bits of what to do. Someone who regularly gives advice is spending a much larger fraction of their time figuring out what to do than someone who spends most of their time actually doing things.

This creates a problem: If you automatically go to the wisest person around and ask them what to do, you are creating a feedback loop which only widens the gap between them and others. If someone has a slight wisdom advantage which leads to people going to them for questions, they get good at answering those questions, and as a result get transformed into the local guru, and soon everyone relies on them as the question answerer.

I’ve seen this most at work (both happening to me and to others), where someone gets enshrined as the local expert that everyone can go to for answers. This is usually frustrating for them because it gets in the way of their own work that they’d acquired all this wisdom to be able to do in the first place.

In general, being an actual guru who acts as a source of wisdom mostly sucks. Don’t get me wrong, many gurus seem to have a great time, but this is mostly for bad reasons of enjoying the power over others it gives them. If you actually want to help people, being this sort of guru is mostly thankless labour, because there’s no capability building - people just keep relying on you, and as your influence grows so does the number of people coming to you with the same sorts of questions over and over again.

It’s also a problem because it infantilises the people coming to the guru for help. If you rely constantly on external sources of wisdom, you never develop your own.

The solution from the guru’s point of view is to try to teach people wisdom. Rather than just handing people the answers, show them how to arrive at them themselves.

The problem is, many people hate it when you do that. They wouldn’t be coming to you if they wanted to develop wisdom. They’d like the answers handed to them on a plate. It’s particularly hard if you’ve been giving them wisdom and then one day start trying to teach it to them - yesterday’s favour has become today’s obligation, and people get upset when you ask them to work for something that they were previously getting for free.

The way out

A large part of me believes that the solution is for the supplicants to grow the fuck up and the gurus to make like a Zen master and hit them with a stick when they don’t.

The rest of me believes a slightly politer version of that.

The responsibility is on all of us to develop wisdom, and part of that responsibility lies in helping each other develop wisdom. This requires helping each other out - don’t necessarily go to the wisest person in the room. Instead, talk it out amongst yourselves. Learn to give good advice, and thereby become one of the people others can come to. Advice-giving is only burdensome if a small number of people do it for a large number. If everyone does it for everyone, it’s freeing.

If you’re still stuck, then go to the guru. Try to learn more from them than just the answer - ask how they arrived at the answer, talk again amongst yourselves about that. Try to learn more than the surface level from them - ask them how they came to their suggestion and, if you can, elicit stories from them about how they learned that.

In the other direction, when you are the guru in the room, if someone comes to you and asks for answers, try to provide that additional context. Show your working, and try to guide them to properly understand it themselves. Give people stories they can learn from, not just answers.

They might not want you to do that, and in those cases you should push back on it, or just tell them to go away. If you don’t, you are creating an Asshole Filter, and will spend all your time on people who will keep asking for more of it no matter how much you give.

The only way out of this is to tell them no, and to come back when they are willing to learn wisdom. You probably shouldn’t literally hit them with a stick, but you should tell them that they are not yet ready to walk the path.

Postscript

If you’re a software developer, or work with software developers, looking to learn some practical wisdom in a work context, check out some of the new classes I’m offering, which are designed to help people develop crucial skills for becoming senior software developers.

The cover image is a mechanic in Tanzania performing car repair, kindly made available by wikimedia user Azazelk.

1. And, truthfully, sometimes I just actually am completely all over the place.

2. From the Greek “phronesis” where it is most often referred to in the context of virtue ethics, but that’s not important here.

3. I originally came up with the label “Practical Wisdom” to try and define what the thing David Chapman and I are both doing is. This was made complicated by the fact that we’re not actually doing the same thing, except when we are.

4. Also, thanks to both David and Cedric for reviewing a draft of this piece and helping me improve upon it.

5. Hence the appearance of the final master in A good start.

6. There’s a reason Slay the Spire has played a significant role in my thinking.