I don’t think happiness is a real catch-22. A catch-22 is a structural deadlock; here it’s more a matter of skill. People often get less happy when they pursue happiness because they use counterproductive methods — constant self-checking, chasing novelty, or looking only to external fixes, instead of, say, finding a therapist or working out what’s actually making them unhappy. Theravāda Buddhism frames this well: Right Effort uses wholesome desire (chanda) early on to let go of attachments and build skill, and only later releases even that desire. Likewise, early pursuit of happiness can work if guided by good methods and awareness of failure modes — and rationality also shouldn’t backfire if you read about those failure modes and know why you’re doing it.
I agree that—for happiness and rationality—the problem is often that people are “doing it wrong”. However, at the same time, I think that people who “do it right” often also end up worse off, and so I think the catch-22 in both contexts is in fact real.
I don’t think happiness is a real catch-22. A catch-22 is a structural deadlock; here it’s more a matter of skill. People often get less happy when they pursue happiness because they use counterproductive methods — constant self-checking, chasing novelty, or looking only to external fixes, instead of, say, finding a therapist or working out what’s actually making them unhappy. Theravāda Buddhism frames this well: Right Effort uses wholesome desire (chanda) early on to let go of attachments and build skill, and only later releases even that desire. Likewise, early pursuit of happiness can work if guided by good methods and awareness of failure modes — and rationality also shouldn’t backfire if you read about those failure modes and know why you’re doing it.
I agree that—for happiness and rationality—the problem is often that people are “doing it wrong”. However, at the same time, I think that people who “do it right” often also end up worse off, and so I think the catch-22 in both contexts is in fact real.