I don’t think it’s silly to restrict it at all because you can still give a good answer even with restricting the fantasy. Honestly, I look at it this way. I have about $275k in debt I’d like to get rid of. I’d like to have $125k put away for my son’s college. I’d like to put 100k into repairs into this house. That’s ½ a million. If I did that, eventually I’d probably like a different house that would cost about $500k more than mine would, so that’s a million. I’d like to ensure that if the impossible happened and my wife and I both lived to be 100 years old, we could live in comfort until then. My definition of “as much money as I would be able to spend without being greedy” would be about 250k a year for 60 years. So, I’m up to $16 million. I’d like to have some cushion if for no other reason than I’m going to have to maintain my own health insurance, which can be expensive for a diabetic., and be able to give some money to friends, family and parents, bump that up 9 million to make an even $25 million. Double that because half would go to taxes. Bam, $50 million is my answer, it would give me way more than I would ever need, but wouldn’t make me so ridiculously wealthy that I’d be having 7 vacation homes, a fleet of private jets and a mansion of toadying manservants. I’d be able to live well and debt free, and I’d be able to spend money on things like a personal trainer and a nutritionist to improve my health so maybe I would live to be 100. I’d have the toys and fun things I’d want, I’d be able to travel, I’d have freedom from working for a living, but could volunteer my time however I wanted, I could be generous, I could support charities I believe in, I could leave my son well equipped to meet the world head on, I could finally write that book and when there was something I didn’t know how to do, I could pay someone who needs the money to do it…that would be perfect, that would be more than enough to meet any eventuality and to give me the tools to seek happiness and fulfillment. Now, tell me how to do it.