Could I Have it All if I Won Powerball?



I’d like to think I’m immune to the lure of Powerball jackpots.  All that hoping and dreaming feels naïve when you consider the odds.  Besides, I’m capable of making my own fortune and don’t want to spend my energy wishing, when I could be doing.  Just give me time, I’m sure it will pan out, right?  After all, I went to business school, read “The Secret” and made a vision board.

But did you hear that Powerball is up to $320 million?

Sure, the odds of winning are 1 in gazillion, but with stakes this high it’s practically my civic duty to play, no?

I doubt I’ll win, but it’s good to think about these things because no one wants to be caught off guard with $320 million dollars on their lap.

Lets get the boring stuff out of the way.  My first call would be to a financial advisor, who would likely tell me to withhold 65% for taxes, and of what’s left, set aside another $90 million to secure my entire family’s financial future and fund any charity work I would like to do.

Wow, that went fast. I’m now left with about $22 million in play money.

This is where the fun — or is it the anxiety — begins.   I’m fascinated by Graham Hill’s Life Edited concept.  In his NY Times story “Living With Less.  A Lot Less”, he wrote about how even after making his Internet millions, he found it exhausting to keep up with all of his stuff.

I get it.  When I open my closet and see a rainbow of stuff, I feel overwhelmed and heavy.   Been there done that on the Choo/Manolo/Louboutin shoe circuit and have gone thru enough “it” bags to lament that my $1000+ investment was nothing but a wasted trend that screams “I lived large in 2007”.


Inspired by Graham’s concept, my new standard for luxury is freedom, simplicity, and experiences with the people I love, so my $22 million dollar fantasy would look like this:

1) Three bedrooms, two and half baths and lots of feng shui.  $5 million.

Living in NYC, I’ve become used to small spaces.  But dinner for 12 in my current 2 bedroom pad feels liked more like eating in a clown car.  And lets face it, the fun of sleeping on Aero bed loses it’s charm once you turn 30.

I don’t need fancy, just a home that’s open, warm and hospitable, where friends, family can can comfortably crash when needed.   This looks like a sunny 3 bedroom/3 bath apartment with an office, washer dryer and open space kitchen, dining and living room.  And my friends, $5 million in NYC is middle of the road, not at all fancy.

An architect would feng shui the place and build a bangin’ kitchen with chrome appliances and a center island that people would gather round with wine in their hand while I cook and Miles Davis plays in the background.  You’re all invited, any time.

 2) A personal fairy godmother. $2 million ($100K for twenty years, full-time).

This comes in the form of Norma, my housekeeper and babysitter who’s been with me part-time for 17 years.   She makes a habit of telling me in a thick accent “Misses Rebecca, you look so tiny, like a magic princess” and does surprise tasks like rearranging my shoes by heel height or creating something delicious and stewy out of lentils.

While I’m not above paying for flattery, Norma is the underpaid wife my family and I desperately love and need.

 3) Family bonding, even if it kills us.  $8 million (over 30 years).

From my parents, cousins and in-laws, everyone complains that we never see each other enough, so we’ll throw money at that problem and wrangle the troops twice a year for a relaxing vacation.

We’ll start with my side of the family and take them on some Alpine adventures to Stowe, Aspen, Telluride or Whistler.   My mom insists she can’t ski due to some knee issues, but heck, that’s what snow boarding and helmets are for.  My mother in law lives for lying in the sun, so for her and her brood someplace beachy, warm and low key.  Where we can all learn to surf.  I’m thinking Surf Simply Coaching Resort in Nosara, Costa Rica.

Photo credit: Simply School

Next, I would treat my husband and son to one terrific international soccer match a year, wherever in the world it might be (please be Barcelona).  Tack onto that a month long immersion in France, Italy or Spain over the summer break where we rent a simple apartment, learn the language, eat the food and explore on foot or bikes.

And then at some point, we would squeeze in 10 days of glamping outdoors adventure travel to stay in touch with nature.  Maybe an RV trip thru New Zealand, hiking in Yellowstone, the Grand Canyon or the always popular, Mongolian Horse Trek in Asia.

Yes, I think this is possible and we could squeeze this in around the school holidays.

4) My new job: explorer of the world.  About $5 million (over 25 years)

OK, admittedly, I’m a little worn out at the thought of shepherding multiple generations around the world for family memories, but what’s a little jet lag when you have some rich girl time on your hands.

Enter my second act, where I transform into a globe trotting, story telling semi-soft adrenaline junkie.  With world class guides like Abercrombie & Kent or National Geographic Explorer to help me chart my course, I would see, eat, write, shoot and post my adventures on the Internet to who ever cares.

Photo Credit: National Geographic Expeditions

My map of adventure might include a sidecar motorcycle trip thru India for the Holi Festival, a hot air balloon ride in Bagan, Myanmar, exploring Indochina and Angkor Wat, or taking in the cherry blossom festival in Kyoto, Japan.   I might grab a few girlfriends and hit Martha Beck’s African STAR retreat where we can make more vision boards, watch giraffes, drink wine and get coached into full self actualization.

To prepare I would take my new Nikon D3 and head off to photography school at the School of Visual Arts and writing classes at the New School, just to get better at my craft (no diplomas needed here folks, remember I’m rich).

5) Finally, I would buy eternal loveliness.  About $1 million (over 45 years)

Being rich is going to be exhausting so I’ll need to keep up my stamina.  To do that, I’m going to get super fit with a $25K annual membership to E @ Equinox which is the bulk of the expense.   A full time personal trainer, nutritionist, physical therapist will ensure I’m a mighty ball of muscle with a core made of steel.  Plus, they have private changing cabanas to spare one from any unnecessary full-monty.

When it comes to “getting stuff done”, I’ll be too busy for any kind of downtime, so I’ll map out a long-term anti-aging plan with my doctor to keep me looking great, but also looking real.  For now I would continue what I normally do (Botox 2x a year, fillers 1x a year, plus chemical peels) but consider the following:

  • Thermage CPT for tightening the sag around my eyes and jowls.  (This might happen anyway, Lotto or not).   About $2500 once every two to three years.
  • Possibly a series of Fraxel Restore for zapping my melasma and sun spots.  About $2000.
  •  Invisalign to straighten my slightly crooked teeth.  This is purely a nice to have, but I can’t help but notice my formerly straight teeth seemed to have gotten more crowded since I’ve hit the other side of 40.  About $7000 for upper and bottom teeth.
  • And screw it, if I’m spending $25K a year at the gym, I want to look super hot so why not throw in some lipo-sculpting or Coolsculpting for my waist.   I might even get brave enough to try Cellulaze.  Huge guestimate of about $10,000.
  •  Maybe an upper and lower blepharoplasty.  Not sure if I need I need this, a laser treatment or filler, but I have a feeling a bleph is somewhere in my future at some point.

If I stay on course, I’ll have blown thru $21 million of my mad money and comfortably retire until about the age of 105 and die with my family financially in tact.

But at some point, I would want to comfortably slow down and just breathe, maybe in my 80s.  Money or not, I hope by then I’m surrounded by people who love me, call me grandma and put up with my stories of adventure, whether they’re from the base camp of Kilimanjaro, the streets of New York of just from my own mind.  Which diminishes all the stuff in between, doesn’t it?


Reposted from March 2013, the last time I succumbed to Powerball fever.  


  • Reply
    March 23, 2013 at 11:47 PM

    Ok I have came up with the “what if I won the lottery” lists but I love yours and how you break it down and put so much thought into it! Good luck. I forgot about it until tonight at a birthday party and was with some of my coworkers so we all threw out $2 bucks in. I know the only way to really make money is working ( I work three jobs and am not near being “set”) inheritance (those odds are as high as the winning the lottery) and investment. But all you need is a $2 and a dream and that is a good investment!

    • Reply
      March 24, 2013 at 10:38 AM

      And of course I didn’t win:( But it was nice to dream for a while.

  • Reply
    March 25, 2013 at 10:24 AM

    I read the article about how to live with less. He has millions, but he has 8 dress shirts or something. Now THAT’s impressive restraint. I would pay off all debts and then go NUTS. New car, new clothes, my kids’ college tuition would be paid, some sucker would be cooking for us all–ahh the good life 😉

    • Reply
      March 25, 2013 at 10:27 AM

      I forgot to leave my name on that last comment–sorry!

    • Reply
      March 25, 2013 at 7:49 PM

      I also realized he’s also single without kids. I want to see Graham write this piece when he has a family.

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