Much like pain, boredom provides unpleasant but important feedback, propelling us to action when we do not (or cannot) engage meaningfully in our lives. But what happens when bored people make the “wrong” choice? Enjoyable alternatives may alleviate boredom in the short-run, but perpetuate boredom in the long-run if they do nothing to solve boredom’s underlying deficits in meaning and attention. We present new experimental evidence (n = 79) that people prefer such enjoyable activities when bored by tasks that are too hard, but prefer interesting activities when bored by tasks that are too easy. Environments with limited opportunity may thus not only lead to greater boredom, but also limit good alternatives to alleviating it. Does this matter? Using big data from Google and public records for all 50 U.S. states, we show that states with lower diversity and opportunities for meaning-making experience more boredom, and that state-level boredom is predictive of self-harm, alcohol, and drug use, including drug-related deaths. While boredom is adaptive, it may go awry when people are placed in environments that limit their motivation or ability to choose emotion regulation strategies that address boredom’s underlying meaning and attention deficits.