The older you are, the more realistic you have be (and that doesn't just apply to aviation). If you want to do it and can afford to 'write off' the investment in time and money, then why not - you only live once, and all that.
Also, as you get you older, you become more philosophical and understand what is possible and what isn't. One thing I don't buy into is age making it more difficult to re-train and learn new skills etc. Yes, there is a bit of truth in that but I've got an engineering background where you effectively retrain your whole career learning new techniques, software and more. It's more to do with the individual than any arbitrary age.