The community of species, human institutions, and human activities at a given location have been shaped by historical conditions (both mean and variability) at that location. Anthropogenic climate change is now adding strong trends on top of existing natural variability. These trends elevate the frequency of "surprises"—conditions that are unexpected based on recent history. Here, we show that the frequency of surprising ocean temperatures has increased even faster than expected based on recent temperature trends. Using a simple model of human adaptation, we show that these surprises will increasingly challenge natural modes of adaptation that rely on historical experience. We also show that warming rates are likely to shift natural communities toward generalist species, reducing their productivity and diversity. Our work demonstrates increasing benefits for individuals and institutions from betting that trends will continue, but this strategy represents a radical shift that will be difficult for many to make.