Predicting the future is hard. You were both right. You only have the outcome to judge the decision, not the full probability distribution.
As in - perhaps OP and 40+ year person had the same, accurate mental model of the probability distribution of success, but OP and 40+ had different attitudes towards risk/reward.
Or perhaps the OP happened to have a much more realistic picture of the probability of success, and 40+ was unnecessarily pessimistic.
So hard to evaluate these things, and to internalise the fact that other people don't have the information you have all the time.