I agree you need rewards... Otherwise why is it worth saving at all! But in moderation.
Probably the coolest thing I have ever seen was a Lambo Muria driving in South Beach like it was nothing... That man has brass balls! You are talking about a super rare car probably worth a Mil+ and on the streets just cruising... Blew my mind.
I am only 35, married 3 kids and still party pretty hard... But my motto is work hard, play harder.
I have too many toys. I need to clean house. They are fun but get old quick. The one toy I still need to get is an old 50's Spartan travel trailer, laugh all you want but the semi art deco design is top notch and it is Rolls Royce quality.
Also I still have fun. In fact I will be leaving for New Orleans soon and hope to be surrounded by bare breasts at least half the time :) Actually it is my wifes business conference and I get to "play" while she gives seminars and such. Check it out if you are bored: www.slumberpartiesbyheather.com
In a round about way what I am trying to say is that being old, conservative with $, and an entrepreneur does not mean you have to give up all the fun in your life either. I seem to have more fun with PEOPLE than any of the toys I have ever purchased. Think about it.