If I was in the position that I never had to worry about money I would do as follows...
1. 
Chauffeur. I would never drive myself around anywhere, and when you never have to worry about money, you are never late for any appointment. I hate driving.
2. Personal Assistant. I would love to have someone around to help me with my daily affairs. This person would be in charge of packing my luggage for trips as well as arranging the 
accommodations, etc. It would also be nice to have someone available to spend time with when I needed a cool friend. While I know it is shallow to be paying someone to be a friend, it is nice to know that they are there.
3. Travel. Exploring the world is a big 
durr. Who wouldn't see the world?
4. 
Philanthropy. Having an 
unexhaustible income would allow me to do the 
ultimate good to mankind. I have always loved charity and 
philanthropy organizations. I would be able to employ and help those less fortunate. I think this would be my life 
endeavor. I even what it to be my life 
endeavor now.
I once watched a documentary called, "Born Rich." It was made by one of the Johnson and Johnson heirs. He wanted to show the challenges, lifestyle and over all callowness that can result. Kind of a Micheal Moore film.
There is one scene where he is talking to his father asking him what his career should be. His father 
replies with and answer of the sky being the limit. He can do anything he chooses. He can go to the best schools, etc. The son asks further into what he should choose to "do" as a career. He father 
repels with ideas such as, collecting cars, painting, collecting artifacts, etc. The son laughs and comments that those are really careers.
The point of that story is that if you are in a position with 
expendable income, it is your 
responsibility to use that 
wealth to create as much good and comfort for mankind as you can. I am not talking about free hand outs, but helping others to progress.
5. Make sure my family truly understands the value of money. I am really grateful that my parents never let on the we had some money. I grew up middle class, and one summer I worked three jobs to buy a car. I had found the car I wanted a nice little BMW. Looking back it was a 
piece of crap on wheels, but as a teenager it was awesome.
When my father and I went to go look at the car, I was very doubtful of me having it. Then my dad did something 
surprising. He wrote a check for the car and then had me owe him money. I remember as he wrote the check thinking to myself, "We don't have that kind of money laying around to just write a check for a car," then I realized, "or maybe we do."
Children should always know that money has a direct value to your time. Anytime I asked for money from my father he always said, "This is time that I spent at work, here you go." $20 is so much more than just $20.
Well, there you have it. That is what I would do with a bunch of money. Now if I could just find a bunch of money.