If money were no object...

Sometimes I like to play a game with myself called "What if I was rich?"  I mean, money-is-no-object, filthy rich. What would I do with all that money? I was raised in an upper-middle class family and although we lived comfortably, we were by no means wealthy. Now that I support myself on a teacher's income, I would say that I am financially stable, but not enough to even afford a one-bedroom apartment; not with students loans that need paying off and the everyday cost of living expenses. I eat out about once or twice a week and go through phases of shopping, but never anything extraordinary. I live well within my means and consider myself to be a saver. I am not quite sure what I am saving for (a house, a big vacation, etc...), but I like to have a little cushion that I pretend doesn't exist just in case of emergency.  With all that being said, I often wonder what I would do if I hit the jackpot and didn't have to worry about my finances anymore. Would I spend differently? How would my lifestyle change? These are the questions I sometimes ask myself if money were no object (and I planned to stay in NYC)...

1) Would I still work or would I become a "lady who lunches"?
I would probably quit my job initially and spend my days working out, playing tennis, getting massages, getting manicures and pedicures, and volunteering.

2) Would I get a doorman penthouse apartment on the UES/UWS or a townhouse in the West Village?
I would like having a doorman for safety and convenience and love the proximity to Central Park of the UES/UWS, but my own townhouse in the village would be pretty awesome.

3) Would I still shop at Target or head over to the three B's (Bloomies, Barney's, and Bergdorfs) now for all my shopping?
I would most def still go to Target often but would probably start buying some high end stuff as well. I  would def buy all my workout clothes at Lululemon ($90 for yoga pants is not in my budget now), would for sure splurge on a pair of black Louboutins, and would buy a really nice designer purse or two, but beyond that I just don't know.

4) Would I get myself a really nice car or just get a chauffeur?
Probably both. I want a black Range Rover with Spreewell rims, but I am not a fan of driving in NYC, so within the city, I would have driver, but beyond that, I would prob drive myself.

5) Would I summer in the Hamptons or the Shore?
I know the Hamptons is where all the rich, famous, and society people go. And although its gorgeous, I don't know if its "my scene." I am sure I could make it my scene if I needed to or just avoid that scene all together. On the other hand, some shore towns like Avon-by-the-Sea or Sea Girt have amazing houses right on the water with huge wraparound porches also and the people are not as pretentious. I know people "poo-poo" Jersey but its not as showy as the Hamptons and its less of a pain-in-the-ass to drive to. (But I guess if I am loaded, I would take a quick private helicopter/jet to where I am going anyway.)

6) Would I winter in a tropical locale or go skiing? 
Who am I kidding with this, I'd do both!! Winter is long and I want to hit the beach AND the slopes.

7) Would I send my kids in public or private school?
In the more wealthy neighborhoods, there is nothing wrong with the public schools. I would like my children to be well-adjusted and open-minded and I feel that a good public school is the way to go with this. I watch Gossip Girl and have read Schooled by Anisha Lakhani to  know what happens in those NYC private schools....

I do know that there are a few definite things I would do if I hit it big. I know I would pay off my student loans right away, take my parents on the vacation of their dreams and pay off any loans they have, get a year round personal trainer AND personal chef, travel to all the places I am dying to go to myself, and make a large donation to Breast Cancer research.  Beyond that, I am sure now that I am rich, I can find other things to spend my money on. Depending on where I end up in the future, New York or Chicago (or even somewhere else), this could all change. I do know one thing, money will NOT change who I am. I would never let it.