So Would You Quit Your Job if You Win the Lottery?

The guy who just sold me my hot ticket for the now $252 Mega Millions lottery asked if I’ll quit my job if I win. But before I could answer, the guy standing next to me said “Oh no! Never quit your job! A job keeps you from spending too much time thinking about your everyday problems.”

Funny…from the comments I get on this blog, for most people jobs seem to be a major source of their everyday problems. The stuff lottery dreams are made of!

But I also know I’ve had times in my life where I didn’t have a job and, to be honest,  although I love my days off more than I could ever express, when I wasn’t working at all I actually missed the challenge and regular social interaction. And I got cranky. Plus there’s just something about getting that paycheck…

I’ve seen stories about people who win the lottery and then stay in their jobs anyway, even if it isn’t a job you and I might call a dream job. Would that be you?

As for me…if you ask whether I’d quit my job – as wonderful as my current boss is (especially if he’s reading this) – I would most definitely quit my job. It’s been great having an extremely flexible part-time consulting gig and working with nice people, but since I’m thinking it may be time for a career change anyway, a spare 50 mill or so would be most welcome.

So let’s see…what would I do if I did win $50 million after taxes?  It’s fun to play with lottery dreams (and career dreams) as a spur-of-the-moment free-writing exercise and see what pops out. Here I go…

First I’d set aside about $5 million just for me so I’d never have to work again unless I wanted to. Then I would probably volunteer my time offering free individual coaching and/or business consulting to companies doing work I believe in. And I would take taxis everywhere (or hire my own driver) without even thinking twice about the cost. (I don’t like to drive.) I might also go back and do a little acting again or maybe even help manage a theater.

Oh hell…I could build my own small neighborhood theater!!! (Another few million for start-up costs and sustained operating capital should do nicely. It is small, after all.) My theater would have plays and readings (sometimes by me) and art from local artists on the wall and original music and classes and workshops and opportunities for people to hang out and express themselves creatively through all kinds of art. (Wheeee! This is fun.)

Plus of course, I would visit friends all over the country – and elsewhere.  Then I’d put another $15 million or so into a foundation I’d create to donate money to organizations I think are doing a great job – without them ever having to apply. Just a surprise donation. More fun! The rest I’d divide among friends and family and maybe invest in an environmental project or two I believe in. Oh yeah…and while I’m thinking about it, I’d use some of my original pot of money to buy myself a nice QUIET 2-bedroom apartment (it’s all I really want) and…most wonderfully…a full set of completely new undies that don’t have even one piece of fruit on the label!

Hey…I like all that. Cool stuff. Not bad for lottery dreams, huh? Hmmm…maybe I better go out and buy myself another lottery ticket right now. 😉

So what about you? What are your lottery dreams? Would you quit YOUR job if you win a big lottery prize? Why or why not? What else would you do if you won a cool $50 million or so after taxes?

Just for fun, please take a moment and try the exercise I just did…whether you share the results with us or not. (But I hope you do.) Just let your lottery dreams run free and wild without any self-censorship or even too much conscious directed thought based in the dreaded reality.  And remember to spend every penny of that $50 mill.

Like me, I hope you wind up seeing something wonderful pop out you never even realized was in there! (Luckily stuff we can pursue anyway.)

Good luck. See you in our dreams!


News flash…I didn’t win the giant lottery yesterday!!!

But it’s ok…I still have my rich dreams – and my friends. 😉

(And there’s always another ticket.)


About the author…

Ronnie Ann, founder of Work Coach Cafe, bases her real-world advice on her many years as an organizational consultant where she helped interview and hire people, added to a certificate from NYU in Career Planning & Development and her own adventures as a serial job seeker. She can also be found on her new blog, and on Google+.


  1. I’d do a lot of what I do already … developing Life Dreaming and SKIL2 are a huge part of my life at the moment … and I’m doing it unpaid.

    I haven’t had a 9 to 5 job in nearly 20 years … and love the unknowingness and freedom.

    I’d stay here in Ballinamore and go on a few more city breaks … but I have a feeling Life Dreaming might make that happen anyway … and flights are cheaper now.

    I’d set up a foundation along the same lines as you Ronnie … I’ve worked with so many community organisations and artists so I already have a fair idea who I’d give money to … and … I already give them a fair amount of my time free … and I gave money to artists a few years ago to support their dreams.

    I’d build a small passive solar home no more than 5 miles from Ballinamore.

    Massages would happen more often and I’d give my family and friends money.

    I’d buy my Citroen 2cv … but that will happen anyway in the next year or so.

    I don’t think my life would alter dramatically … I’d just have some extra money to fly to Oz to see my family … or fly them here to Ireland.

    So … I suppose I’m living the Lottery Dream …


  2. A cool, fun post, Ronnie Ann. Instead of what I’d do with the money, I’ll stick with the original question and answer it a couple of ways. First, I have a friend who took a vacation on some Caribbean island that had gambling. Every morning, she would go down to the casino and play blackjack until she’d won the cash to cover meals, drinks and entertainment for the day [yes, she’s that reliably good at it]. Then she’d go out to the beach or whatever and just have fun. A friend asked her why in the name of god she didn’t just do that for a living. She said because then it would be a job.

    I like my career as an advertising copywriter/creative director. And I used to be so focused on it, so defined by it, that when I played the lottery, I secretly hoped for a modest win, one that would make my family and me comfortable and secure, but would not allow me to give up working in advertising. Then I got laid off from an ad agency right around 9/11. It was a really stressful time, as you might imagine, and I spent most of my waking hours looking for work. But I also spent time doing things like hanging out at the library during the day—doing job hunting stuff, of course, but also doing some recreational reading. I spent more time in the kitchen, a real love for me. And I began feeling that there could be life after advertising, that I could find plenty of things to keep me not only occupied, but actively engaged in life.

    So yes, I’d quit my job, in a New York minute. And now when I play the lottery, I hope for the big win.

  3. Yes and no. Yes I would quit this current job BUT I would not quit working. Idle time is not a good thing, I need to keep busy doing something…anything.

    I’d imagine that I will keep the current lifestyle. Although not having to worry about mortgage and car payments will be magnificent. I wouldn’t turn a hobby into doing something for a living, as mentioned earlier it will then become a job.

    If I had the $50M I think I’d try many jobs. I’d like to see/experience new things that otherwise I couldn’t do because I had to make that paycheck twice a month.

  4. My brother-in-law was one of those Sargento Cheese employees who won the huge jackpot a few years ago. He’s a factory worker, and so is his wife…and neither of them quit their jobs.

    After the huge jackpot was split among the participants, and after the taxes were paid, they only got about $700K. They were both in their late 30s, so they didn’t feel it was wise to stop working on that much.

    They’re still as frugal as they always were–they bought a new car, but that’s about it. They shop at the same stores, eat at the same places, and their big vacation was to South Dakota. The money hasn’t changed them one iota. You have to admire that.

    My job is stay-at-home mom and blogger. I certainly wouldn’t quit the former; not sure if I’d keep the latter or not. I’d still plan to do SOME kind of work after my kids are both in school (although it wouldn’t be in HR).

  5. Dear Ronnie – What a great post! A marvelous exercise is unearthing our real desires and allowing ourselves the emotional freedom to do it! What is always so useful is to notice what beliefs (the disabling ones) show up when we do that. Even though we are talking lottery dreams here, the voices that shout out saying “stop, no that’s not possible, and in your dreams,” are not so far removed from the daily voices that try hard to keep us flying under the radar.
    As for my lottery dreams I share some of yours. Big money would underwrite one of my big dreams – giving money away to others. Some sort of vehicle or foundation to do that. I would certainly continue to do the work I love as a co-founder of Intentional Communication, but I’d be super choosey about who I would work for and what I would do.
    So the really important question that surfaces for me is – do I really need the BIG money to do these things? What stops me from living more of my lottery dreams – minus the lottery win!

  6. AHHHHHH Ronnie—loved the post. As for me—hmmmmm let’s see—-if I hit the big one. Well, after getting up off the floor, just kidding…..I think I’d just do a little traveling, but in style. No more airplanes for me—–a land cruise would do the trick. Amtrack here I come, luxury compartment all the way. Since I’m retired, there’s no job to worry about, although the thought of going back to school lurks in the dark recesses of my mind. Nothing dramatic like becoming a lawyer at my age, but something fun for me, maybe a few writing courses. As for charities a definite yes. Something for all creatures great & small to be sure. Money to family & friends of course is up there too. Would I move back to the Big Apple, hmmmm, that’s a tough one. I love the tranquility of Niagara Falls, but in a way I do miss New York a bit. It’s fun to dream, better if you win, but if it’s not in the cards, oh well, I still have my imagination!!!!

  7. i would not quit my job… yet! i agree with the guy, a job keeps my mind off my other troubles. yet it is true that my job does take a lot out of me and is my major source of problems in the first place! the irony. 😀

    i’ll do the requisite stuff to ensure i’m financially taken care of for the rest of my life… probably throw in a few luxury things like having my own driver, like you! 😆 and splurge on a house with my own private library, etc…

    meanwhile, what do i do with myself? do i still stay on with my job? yes, but only on a part-time basis. that way i have the freedom to do the things i want to do with money, like travelling, and at the same time have something to come back to. part-time positions are less stressful and therefore more fun because you’re not dependent on the income. 🙂

    that’s what i’d do if i win the lottery!

  8. Hmmm, very provocative post Ronnie! Here’s my financial fantasy plan: Pay off my mortgage, fully fund my kids’ college accounts (after all, there would be no more financial aid), drop a few mill into the retirement fund, and donate to worthy causes.

    If there’s anything left over, I’d buy a majority share of a professional sports franchise. But given their current pricetags, I might have to settle for something like a 2-5% stake.

    But I’d probably still work because I get bored easily.

  9. Provocative, and a wonderful exercise in examining ones dreams. Obviously, the right “counseling” thing to say, after completing the exercise is “let’s work on how we can accomplish those things on our way to having all that money!” This kind of planning, alone, can spunk up ones life a great deal!
    As for me: I would not quit my job because I already have done! Because of this and that in my life, it is not advisable for me to work full time for an employer, so I’ve gradually carved out my own way of being in the world without doing that.
    What the $50 mil or so would do is firstly, remove some of the anxiety about that! (hehe) I’d still do most of the same things I do now, with, perhaps, a bit more zest! I would fund the arts in ways that are meaningful (to me), I’d fund a few family members’ projects (these family folks already have started small businesses, so it would be fun to invest in them), and I’d start a foundation engaged in research in arts, consciousness, and science, and how that mix helps us to understand and enhance the human condition.
    Personally, I’ll bet I’d travel a bit more: To the east coast to see that part of the fam; to the west, likewise. It would be fun to pick a new country each year to visit. I would study the culture, not just observe it.
    I like my house, and my neighborhood, and the mountains, so I’d stay, I believe. I’d replace the carpet with Bamboo floors! I’d hire a gardener and a housecleaner, each once a week. (I wouldn’t want them around TOO much!) I’d very likely buy a new car, or perhaps a light truck.
    I’d pay myself a salary, and donate to causes I believe in every month.
    I’d set up a trust, for after my demise, so that my family and the research could benefit. I think…I’d write just a bit more. I don’t know why I say that; it seems having the bills paid would be less of a distraction.
    In short, I’m living pretty much as I wish to. Still, a few modifications would go a long way! 🙂

  10. Thank you everyone! Wow. These are great. I love how many people are basically happy with what they’re doing and would only change a few things. Very cool. Also cool if this exercise shoots you in a new direction. For me, life always offers possibilities – even w/o the Mega Million win.

    And just as MusEditions suggested, anyone who tries this just for fun can also use it as a good self-coaching tool to set their own short- and long-term goals. I’ve already been moving toward most of what I wrote without the big win – but seeing what I wrote, I feel even stronger about the new direction I’ve chosen. (I’m still dreaming of someone to drive me around – but maybe that will come in a very different but equally lovely way. 😉 )

    Thanks again to everyone. And please add your own lottery dreams. I’m nosy and would love to read them!

  11. Always thought provoking Ronnie!

    What would I do? Hmmm, I should preface this as the original S.E. voice as I’m starting to add more voices to the site (stay tuned).

    Stream of consciousness….

    1. live each day openly and freely. when spending time with the family, not be stressed that I need to spend more time working and when working, not be stressed about wanting more uninterrupted time with my family; and
    2. as long as I would be working in some sense or another, i don’t sit still unless to read, i would want my mental energy to be spent on finding a real, tangible way to make a difference with my efforts, to put more positive energy out into the world to create a chain link effect of good; and
    3. Help children and families. How? Not sure, but I would have the time to think about it; and
    4. Really, really learn more about other cultures and people, individuals, not just the generic “children and family” term; and
    5. Paint; and
    6. Make up lots of modern day fairytale stories; and
    7. Have time to put all the crazy thoughts in my head on paper or canvas; and
    8. Suprise my friends with time & things; just doing things because you can and want to; and’
    9. Making a bunch of people’s lives better and enabling them to enable others and so on.

    Oops, is that enough? I got carried away!

  12. That was wonderful S.E. I’m so sorry I lost the $333 million (it grew). I would definitely have given you some for your chain of good! 😉

  13. I would NOT quit if I won the lottery. I asked myself that question 12 years ago…..answered yes…..and totally shifted gears.

  14. Hey Ronnie Ann,

    Loved this question and the great answers you and everyone else have shared here too!

    As for what I would do with a big lottery win, I think I would carry on but with a greatly improved ability to support people who are pondering the big career questions. I think that foundations, investments, inspiration from the arts and community work would all play their part too!

    What a wonderful way you have helped us to dream.

    All my best for now,


    P.S. Save me a seat at your theater 😉

  15. Jim Variable says:

    Hello!!!!? Yes, I would quit my job! Are you people nuts!!?? Working with idiots is the worst!

  16. Hi Johanna! Congratulations on making the decision to pursue a career you love. Best of luck!

    Good to hear from you Paul! Welcome back from vacation. Hope you had a terrific time. You too are someone who made the move to pursue your dreams. May the lottery gods smile on you. 😉

    Hi Jim! Had to laugh when I read your comment. I know you’re not alone in your feelings about work. In fact, I’ve had jobs in the past that felt like that MANY times. But truth is there are people who love their jobs/ careers and some who actually enjoy the folks they work with.

    I found as I changed my own attitude toward work and toward the people I work with (looking for commonality and trying to see where they have something to offer I might not have noticed before), it didn’t make the job perfect all of a sudden – but slowly I started to find more people and things I enjoyed.

    On the other hand, this may be a call for you to find a career (and co-workers) you can enjoy – or maybe even start your own business like I did. Seriously…we aren’t all idiots. Please think about whether it might be time for you to say good-bye to jobs you hate and go look for something you could actually feel good about.

    I wish you the best!

  17. Isn’t anyone afraid their supervisors might be reading this? There seems to be no place a person can be themselves anymore.

  18. Hi Marsha!

    Thanks for the comment. Fear not. I don’t see any way to connect the dots from the one comment that you might want to keep private. And if a supervisor is reading this blog, most likely it’s because they too are looking for a new job or at least some answers! As long as you keep it anonymous and fairly civil, there are a lot of places on the internet to share your thoughts. At least in my experience.

    One more thought (of mine)…most people I know have found ways to be themselves most of the time. If you really feel you can’t be yourself (say in your job), that might be a great reason to start looking for places where you can be yourself. Maybe there are things you want to be and do that you haven’t even let yourself explore. If so…I hope you do. Then again, maybe not. Just a thought that popped up that I dared to share. 😉

    Ronnie Ann

    Oh…btw. I removed the link you left since it seems to be a place of business and that could be incriminating for you. I try to do that to protect my readers. 🙂

  19. Honestly? There are so many people who need jobs today – it would be very selfish to take away a chance for someone to earn money to support a family if I didn’t need it. Rather, I would find a cause that I believed in and felt passionate about and would pursue that. Perhaps I start a business or I volunteer for a worthy charity – either of those two options would free up a job for someone who needs it and keep me satisfied emotionally.

  20. What a caring and thoughtful comment, Sandra.

    Thanks for adding to the conversation!

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