I remember hearing somewhere about a guy who resolved never to buy a bottle of wine costing more than $10—not because the more expensive wine didn’t taste better, but because he didn’t want his own taste to develop to the point that he had to buy expensive wine if he wanted to enjoy it at all. Clara and I decided to call this opposition to acquiring a taste “curated contentment,” because it’s about deciding that you’ll be content with something (in this case, your taste in wine) that could in principle be improved.
But the phrase curated contentment immediately suggests the question “With which things should I be content, and with which should I not?” Everything? Nothing? An amount in between that maximizes some metric?
There’s an obvious case for being content with everything: it’s happier! Consider a perfectionist for whom nearly every area of their life fails to measure up:

Red area below baseline = disappointment
All they need to feel better is… lower standards!

But there’s a problem with being content about everything. Looking at that picture I’ve labeled “contentment,” I see those little red areas and think “Oh, I should have either raised them up a little to be green, or just made the baseline a little lower so everything would be satisfactory.” In particular, I lose focus on the rest of the columns that are already above the baseline: in principle, a gain there is just as worthwhile to the total as a gain anywhere else, but that doesn’t seem to matter as much as trying to make every column come out positive.
So when is it good to be content with something, and when does contentment turn into complacency? I can’t answer for everyone—like any “should”-type question, it depends on what you want from your contentment—but I do think it’s a question everyone might benefit from asking themselves, and I want to showcase a few different approaches I’ve come across.
1. Be content when improvement is too costly
This is strategy of the person from the introduction who decided never to buy expensive wine. The problem with developing good taste is partially that lower-quality wine becomes unenjoyable (and you risk being called a snob at dinner parties), but partially that there’s no upper limit to how much you can spend for nicer and nicer bottles. Nice clothing, quality coffee, and luxury yarn all have the same problem: As your taste heightens, it becomes more and more expensive to please yourself.
More generally, sometimes improvement takes too much time or effort—running experiments, gathering data, controlling for confounding variables—and it just isn’t enough of a priority to be worth it. In these circumstances, given that you’ve decided not to change them, it does seem to make sense to be content with the way things are, rather than continually frustrated.
2. Be content with what’s out of your hands
There are some things in life that I just do not have control over, from where natural disasters strike to whether the bread will be on sale at the grocery store. Again, given that there’s nothing I can do about these things, it makes sense to accept them and be content.
But I worry that some things that seem impossible aren’t really, and by choosing contentment I am choosing not even to try. What if, by chipping away at a seemingly insurmountable problem, little by little it becomes solvable? This suggests not merely being content with the things you can’t change, because it may be only that you can’t change them yet, but I don’t know what else to do in the meantime.
3. Be content with what stretches you
What about those things for which change is possible? Sometimes we can meet our own standards—does that mean we should raise them? Perhaps the bar should be set just above our current abilities, in order to maximize the impetus to grow. Ultimately, then, is contentment about gradually setting the bar as high as possible, but no higher? Is it about understanding the range of possibilities, and being satisfied as long as you’re at the upper limit?
4. Be content with what is done for you
Perhaps, rather than optimizing for growth, you’re optimizing for graciousness, and want to be content with the things other people do for you. Often I see this borne out in two ways: being much more demanding of yourself than you are of other people, and being much less demanding of anything that only matters to you than of things that matter to other people. Problematically, this can result in a kind of extreme self-ungraciousness in which you have unreasonably high standards for anything you do for other people, but in principle you could fill in the four squares in this grid arbitrarily:

High standards for the left column, low standards for the right?
I’d love to know your thoughts on contentment, where you struggle with perfectionism or complacency, and what helps you decide whether to be satisfied. Let me know in the comments!
One can reduce a question of “should I ask for more” to “what do I value” in the end, but this maybe too simplistic. (My true question is, how to make such nice figure/plot?)
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You’re right, and I think any “should I…?” question similarly boils down to a question of values. The interesting thing about contentment, though, is that it’s a question of how much you value having certain values: “Should I have high standards?” can be rephrased “Do I value putting value on quality?” The cheap wine purchaser, even though (and perhaps because) he values high-quality expensive wine, decides that this valuing is not important enough to act on, that this valuing is not itself valuable.
As for the diagrams, I’m so glad you like them! I use an iPad app called “Paper by 53” that does a very nice job emulating different kinds of strokes (mostly I use the pen), and has a tool for filling regions with a transparent layer color (which I used to create the red/green areas). It’s a great app that I am definitely not using to its full potential!
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