Taking advantage of serendipity

Status: Notes/early draft
Confidence: Likely

A useful mental model: we live in a very complicated world. If there is a smooth, almost ballistic trajectory to somewhere you want to be, there’s good chance that it is 1) being smoothed by someone who will profit from you following it (meaning it will pay off less well for you) and 2) full of lots of people following it (meaning that it’s competitive to get there despite the apparently smoothness of it).

So if you want to follow a trajectory that will pay off for you without someone skimming and without having to fight tooth and nail with others for limited space, you need to be able to follow trajectories are not at all obviously going anywhere but will take you somewhere you will be happy to be.

A few physical analogies:

For life trajectories, this is largely about taking advantage of serendipity.

Taking advantage of serendipity has four parts:

  1. Being likely to have it appear.
  2. Being able to recognize it.
  3. Having the skills, abilities, and resources to take advantage of it.
  4. Having the time, mental space, and slack to take advantage of it.

Make it likely to appear

What is coming into your life, and who from? If you are seeing the same stream of things as everyone else, you’re probably not seeing much that they aren’t. Especially since streams that are dessiminated that widely are usually managed by someone…who is unlikely to be passing out serendipities on that stream when they could keep them for themselves. The producers of Days of our lives are not trying to pass on profound opportunities for serendipity to their viewers. Nor is Facebook’s newsfeed algorithm trying to encourage you to go, “Oh, hey, I’m going to go think about that for a couple hours. There might be something cool there.”

If you have multiple streams, you are more likely to get overlaps that others don’t see. If you have chaotic streams that aren’t curated by a single entity and mass broadcast, you are more likely to get opportunities in it. If you have streams that are curated by an entity that has your welfare at heart and is meant just for you (friends telling you things) you’re more likely to get things.

So: you need multiple streams, ideally ones that are somewhat chaotic. And you need to have relationships with lots of people where you feed them stuff and they feed you stuff. Think of it as a small world graph for knowledge flow.

Make yourself likely to recognize it

Hamming talks about having “big idea team” when he tried to think about what his field, at a large scale, would look like, and what that meant for what he should be working on.

There’s a scene from Mighty Ducks II where the coach talks about “garbage hockey.” Stuff shows up in the randomness of play and you have to take advantage of it.

There’s a formal structure to this, John Boyd’s OODA (Observe-Orient-Decide-Act) loop. You can also use it as the basis to put together strategy. In Leadership and Training for the Fight (check reference) the author describes specifically training people’s observe and orient phases in targeted way.

So how do you train yourself to observe opportunity? There’s a useful framework in The Last Word on Power of the default lens you look at the world through, your default strategy. When you see the world, you pattern match it against templates and see which templates get enough support to resonate into your conscious mind. If you don’t have an organizing pattern, you see disconnected bits. If an organizing pattern resonates up, you see an organized structure, potentially with gaps. Which patterns you have in your mind matters. Poor pattern libraries are how you end up with conspiracy theorists and crackpots, especially if your patterns don’t come with large hunks that disprove it and force it back out of consciousness.

Zwicky had a whole system for trying to recognize these gaps via morphological boxes.

The vast majority of what comes through will not be an opportunity. It will just be a thing. How do you know? The best heuristic I’ve seen comes from Cal Newport’s So Good They Can’t Ignore You: what will give you ‘career capital.’ It’s a good book. Go read it.

It may also be an opportunity that you choose to disregard. In choosing what to work on in companies, I have gotten to the point where I have criteria for discarding things, usually around whether they are clear to other people and something that other people could do without me there. But if you can’t see it, you don’t get that choice.

Have the skills, abilities, and resources

Skills compound and transfer. David Epstein’s Range is a good compendium of information, but it turns out that for wicked problems, which are most of the world, you do better if you have ever broader mental resources to draw on.

When I started in historical dance reconstruction, I had several skills already to hand: I could fluently read Renaissance French and Italian; I could fluently read and play pre-modern music notation; and I was an experienced martial artist and so comfortable moving my body precisely through space. I had to learn new skills, but not the hard ones. When reading your historical source materials is as easy as reading a light novel at bedtime, you can become quite well versed quite fast.

And the skills I needed? I didn’t just do that period of dance. I did everything I could get my hands on. Details of styling, which foot you step off with, where your toes are pointed, etc. are all much easier to keep track of if they’re linked into a whole historical evolution from the 14th to the 20th century. Can’t remember what it was in the late 18th century? Just fill in from before and after.

So you keep learning new things and transferring some skills, and you keep ending up with more probably transferrable skills.

There’s also how you learn something. I studied physics at university. By classroom standards I was excellent. But there are parts of physics where I pulled the subject apart, went back to its foundations, and then pieced it back together. Often it went back together idiosyncratically, but in those fields (mostly classical mechanics of point particles and certain aspects of quantum mechanics) I have giant masses of patterns that I can more easily transfer. In other areas, like electromagnetism or special relativity, I can solve the problems and rough out how things go, but there is nothing generative in them for me.

Nor was I comprehensive. I don’t know general relativity. And my friend who is a professional thermodynamicist is the only person in my world whose work seems like magic to me. You do not have time to learn everything. So it’s better to pull apart a few areas and reconstruct them, and if you’re going to do so, it’s better to pull apart areas that are not all clustered together.

And sometimes you don’t have the knowledge yourself, but you have a friend you can call who’s an expert. Or you know you saw half the solution to this in that book on the third shelf of the back room of the library. Novelists are familiar with this kind of thing. They accumulate bits of human experience and peculiarity like magpies, and sort through it for shiny bits to patchwork into their stories.

Having space and time

If you are working full tilt, all your attention and effort always allocated, you can’t take advantage of what shows up. Many organizations get this horrible wrong and drive everyone in them to “full utilization.” Which is foolish, since being busy is not a good predictor of outcomes. People sometimes will say things like “work smarter, not harder” but that’s all just trying to talk around the true point: “cut yourself some slack.”

Mindfulness meditation is useful. It lets you generate space. Denying people rent-free space in your head is useful. You can use that space for things that you value. If you don’t have time to take in chaotic, varied inputs, time to isolate yourself from input and reflect and structure your thoughts, time to explore a little way down what shows up in your reflections, and, if you like what you find, time to allocate to really diving in, then you can’t take advantage of serendipity. Cal Newport talks about deep works and small bets as a way to effectively deal with this, and that takes lots of time and mental space.