Make Sure That You’re Optimizing for What’s Important (to you)

What are you optimizing for? Are you sure that’s what you want?

I recently listened to an episode of Revisionist History (my favorite podcast of late) in which Malcolm Gladwell spends much of the episode elaborating on his ‘life-rule’ of “Pull the Goalie”.

Gladwell is referencing an academic article Pulling the Goalie: Hockey and Investment Implications that uses pulling the goalie at the end of a hockey game to talk about risk management. I was almost scared off by the ‘academic’ orientation of the article (so many footnotes!) and that it’s mostly concerned with investment, which isn’t a particularity interesting topic to me, but the article’s authors did an amazing job of making the concepts easily accessible through the lens of professional hockey.

You don’t need to know much about hockey to follow the arguments, just these 2 points will do:

The concepts in this article are so accessible and well put, I’m going to liberally reference it (read: copy/paste!) in the remainder of this post rather than try to summarize, as there’s no way I can do any better.

Here’s one of my favorite bits:

This reminds me of an issue that I think about all the time, both in work and in life more generally, and gets us to the subject of this post (finally!), what we’re “Optimizing” for.

So in this case the authors are pointing out that, in the choices that they make at the end of games where their team is losing, coaches are not optimizing for what most people might argue is “point of hockey”, which is “points”. I’d argue that they’re optimizing for something else, either intentionally or unintentionally

If you choose to read the entire article, you’ll probably be convinced as I was that coaches should change their behavior and pull their goalies earlier when they’re losing at the end of a game. The authors point out 2 compelling reasons why coaches fail to act in this way:

Wow! I love these reasons in that they illustrate out that hockey coaches might actually be primarily concerned with something else besides winning, and it basically boils down to how well they appear to be doing in their goal of ‘winning’, and not how well they are actually accomplishing that goal.

However, the article mentions one more possibility toward the end, which I think is probably the most salient point:

Is this possible? Is this giving hockey coaches too much credit? Perhaps, but perhaps not.

Even if the hockey coaches are completely informed and rational (not a given by any means), I’d even go so far as to argue that they are behaving exactly as they should by not pulling their goalies earlier, even though these decisions to leave their goalies in mean that they’re going to lose more games. In other words, I’m arguing that the coaches should not care most about winning (or tying) games. Their most important job is the same as that of the players, to support the goal of professional hockey to provide entertainment.

Let’s say for the sake of argument that this is true, that hockey teams (including their coaches) are optimizing for entertainment, and not for winning games, making the playoffs, or wining the Stanley Cup. If you’re a hockey fan, would that matter you? Does that change your expectation of hockey or the way that you engage with hockey? Would you stop watching hockey altogether as it ceases to be entertaining to you if your favorite team’s end-goal is entertainment (and not competing or wining)? Can entertainment in professional sport only be fully realized when entertainment is not the end-goal?

So I don’t really care about hockey, and maybe you don’t either, and even if you do maybe this entire argument isn’t a big deal to you and feels like splitting hairs, and that’s fine. But regardless of how you feel about hockey, hopefully you can see how in other areas subtle distinctions in optimization choices could have important consequences.

I’m not arguing here for any of these over the other (that would be another post!), and not all of these choices mutually exclusive (but at least some of them are). What I am arguing for is that we need to be asking these questions both of our ourselves and the organizations what we’re involved with.

Take the tech company example. It should matter to us what these companies are all about. That information should have an impact on which services we use and how we engage with them. Will we optimize for our convenience by using the given service, trading off our privacy for that convenience?

Yes, the privacy/convenience trade-off is a real thing and it’s nothing new. In the book World Without Mind: The Existential Threat of Big Tech, Franklin Foer points out that Louis Brandeis was concerned about this back in the early 20th century:

I think we’re starting to learn this lesson, but we still have a long way to go. We can start by asking, even if just to yourself: “What as a company are they optimizing for?”.

But the next question is just as important, if not more so: “What are we optimizing for”. Is it price? Or convenience? And at some point, we’re going to cross a threshold where the cost of what we’ve been prioritizing has become too great and we going to have to change what we’re optimizing for.

The same goes with anything you care about personally or professionally: work, money, politics, whatever. Upon reflection, we can sometimes discover that, without knowing it, we’ve been acting in a way that prioritizes X when we really care more about Y, and that we need to reprioritize. This isn’t really anything new, but it does take a conscious effort, it doesn’t happen on it’s own.

Make Sure That You’re Optimizing for What’s Important (to you)

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