There is a nasty catch-22 when it comes to happiness: you want to be happy, but explicitly trying to be happy often makes you less happy, not more happy.

Consider the example described in this article:

I saw it happen to Tom, a savant who speaks half a dozen languages, from Chinese to Welsh. In college, Tom declared a major in computer science but found it dissatisfying. He became obsessed with happiness, longing for a career and a culture that would provide the perfect match for his interests and values. Within two years of graduating from college, he had bounced from working at the United Nations to an internet startup in New York, applied for jobs as a supermarket manager, consultant, and venture capitalist, and considered moving to Puerto Rico, Trinidad, Colombia, or Canada.

These careers and countries didn’t fulfill him. After another year, he was doing standup comedy, contemplating a move to London to pursue an advanced degree in education, philosophy of science, management, or psychology. But none of these paths made him happy. Dissatisfied with his own lack of progress toward happiness, he created an online tool to help people develop more productive habits. That wasn’t satisfying either, so he moved to Beijing. He lasted two years there but didn’t find the right cultural fit, so he moved to Germany and considered starting a college dorm for adults and a bar for nerds. In the next two years, he was off to Montreal and Pittsburgh, then back to Germany working on a website to help couples spend more quality time together. Still not happy, he abandoned that plan and returned to Beijing to sell office furniture. One year and two more moves across two continents later, he admitted to his friends, “I’m harder to find than Carmen San Diego.”

The article goes on to describe the mistakes that Tom made. Here is the first:

The first blunder was in trying to figure out if he was happy. When we pursue happiness, our goal is to experience more joy and contentment. To find out if we’re making progress, we need to compare our past happiness to our current happiness. This creates a problem: The moment we make that comparison, we shift from an experiencing mode to an evaluating mode.

Something similar is often true with rationality.

Consider epistemic rationality. Learning about biases can hurt people.

Consider instrumental rationality. Optimizing how you spend your time can backfire by making you feel guilty when you are doing "unproductive" things like hanging out with friends.

This has been discussed before. I think people generally agree that rationality faces a similar catch-22: incremental steps in the direction of rationality don't always lead to forward progress.

But does this mean that we should abandon the Art? Does it mean that we should hold off on applying what we've discovered?

Well, when I think about such questions, I think back to happiness. Trying to be happy can and often does backfire. This is even true for people who apply the virtue of scholarship and investigate what the study of happiness has found.

But at the same time, I think there is still a fair amount of useful stuff in the literature. And I definitely don't think things are grim enough where we should abandon the study of happiness. No. It is an important and promising field that we should continue to develop.

Same with rationality. Maintain a healthy amount of skepticism, anchor towards things that actually work, but don't close the door. Open the door, walk in, see what sorts of fun trinkets you discover. And if you're feeling generous, maybe contribute a few trinkets of your own.