Recently, the Powerball jackpot grew to one of its largest ever. The thought of actually winning such an ungodly amount of money doesn’t appeal much to me – I can easily see it creating problems I don’t want to have. But what about a reasonable amount, say, $20 million? Enough to be charitable, help out family, and live a comfortable life without completely going bonkers or carrying the burdens of the world. (Yeah, I kind of selfishly don’t want to win enough money to also win responsibility for solving systemic problems). I came up with a list of ways I would use my lottery winnings – a fun exercise I recommend you try!
Then I decided to add the constraint of keeping my $20 million win completely private. (Well, aside from my financial planner and/or attorney). How would that change things? Or rather, keep things from changing too much?
I realized that it would be a little difficult to purchase multiple homes and live in them if I wanted to keep my secret, but there are ways I could make life nicer for me and others while staying under the radar:
First, I’d find a part-time or flexible job, so I could continue to have the structure of working, which I really enjoy, but also the ability to do other things more easily.
I would pay for the following services:
-Personal shopper (and the clothes of course). I am not very high maintenance but I do like nice things and it would be nice to have someone tie together the look I want.
-Personal trainer. Exercise has always been a struggle for me, I just don’t stick with it or enjoy it. But maybe if I had someone really customizing a workout to my level and needs, it could work.
-Private chef or catering (by delivery, not in my house). Someone to make a variety of wholesome, flavorful, FUN breakfasts, lunches, snacks, and dinners for me each week.
-Standing appointments at a hair salon for blowouts, or maybe a stylist can come to me.
-Regular massages. Twice a month?
-Hire a driver as needed! I HATE DRIVING. And don’t do it on highways. Or in Lakewood. Or many other places. This would be a big help.
I would also like to take some customized, thoughtfully-planned longer trips (with the assistance of someone on the ground to provide transportation to hard-to-reach locations, or arrange kosher food delivery, for example). I can vaguely cite credit card points if the need for explanations arises. And I am not that interested in luxury travel!
I could have my attorney arrange for some anonymous philanthropy. Based on my work experience, the needs I would most like to fill are honestly paying people’s utility and grocery bills and meeting other basic needs. That would mean so much to me. I would also like to anonymously fund something arts-related, I would need to explore this further.
The one thing it would be hard to do anonymously would be to give sizable gifts to family or friends. I am not sure how to go about doing that. But I would be able to give smaller amounts in the form of treating them to trips, meals, gifts etc.
Upon reviewing this list, it does occur to me that I don’t need $20 million for this, not really, and I could do many of these things on a smaller scale (perhaps on a rotation) starting now! Some things will have to wait until I have a higher income (or yes, win a reasonably-sized lottery jackpot), but it does seem that bits of these can become real relatively easily.
I need to add that I am so very grateful for that, and do not take that for granted!!
What would you do with your lottery winnings?
(Photo credit: Viviana Ceballos/Pexels)




Lol none of those things require a lottery if you do them occasionally.
I bet I could challenge you to do each of them for a month for under $3,000. New goal for 2026?
Haha that’s exactly it, I realized as I wrote this list that it wouldn’t cost THAT much to treat myself to these things at least some of the time! Hmm, is that $3000 for the year ie $250/month? Let me take another look!