When left to their own devices, people could choose to enjoy their own thoughts. But recent work suggests they don’t. When given the freedom, people do not spontaneously choose to think for pleasure, and when directed to do so, struggle to concentrate successfully. And, people find it somewhat boring and much less enjoyable than other solitary activities. One reason for this is that people may not know how to think for pleasure. Specifically, they may not know what to think about to make this both a meaningful and pleasant experience. We tested this prediction in two preregistered studies, by providing specific examples of meaningful topics (Study 1) or instructing participants to think “meaningful” thoughts (Study 2). Although providing specific examples of meaningful topics boosted how meaningful and enjoyable people found thinking for pleasure (Study 1), asking people to think “meaningful” thoughts (as compared to pleasurable ones) did not, because some of the meaningful topics people thought about were negative (Study 2). In order for thinking for pleasure to be pleasurable, people need to focus on topics that are both meaningful and positive.