Do people think that there is such a thing as too much money? The present research investigated this question in the context of hypothetical lottery wins. By employing a mental simulation approach, we were able to examine how people respond to increasing envisioned jackpot amounts, and whether there are individual differences in people’s reactions. Across five empirical studies (total N = 1,504), we consistently found that, overall, the relationship between imagined lottery wins and expected happiness is characterized by an inverted U-shaped curve, with expected happiness being highest around an envisioned win of roughly 10 million pounds. Both lower and higher envisioned wins reduced participants’ overall expected happiness. In addition to this overall pattern, we identified three clusters of participants who react differently to expected increases in wealth. These clusters mainly differed in terms of how soon the top of the expected happiness curve was reached, and if and when the curve started to drop. Finally, we also found some interesting cluster differences in terms of participants’ prosocial and proself motivations.