Need help navigating "follow your dreams" vs. "follow the money" dichotomy!

Even that can be debated. If a system creates few losers, but the losers lose big, is that necessarily a good thing, particularly if there are also few winners or the winners win little?

It can also matter whether the distribution of “win” and “loss” is what people consider to be “fair”. E.g. some people may consider “win” and “loss” by one’s own ability and motivation to be “fair”, while “win” and “loss” by one’s inherited family wealth to be “unfair”, while other people may take the opposite viewpoint.