Win The Lottery, Lose The Job?

Life is pretty good here in Canada.  Things are generally pretty quiet, so much so that a lottery jackpot going unclaimed for three weeks in a row is newsworthy.  Very newsworthy.

LottoMax is a weekly lottery where you pick seven numbers, from 1 to 49, for your chance to win.  The pot starts at $10 million, and once it hits $50 million it goes into super-fancy “maxmillions” mode, with additional $1 million draws on top of the main jackpot.   The other night there was one draw for the $50 million prize, and an additional 45 – $1 million draws.  No one won the $50 million.

The odds of winning are 1 in 28 million, but considering that there are only 33 million people in Canada – it’s surprising that it hasn’t been won yet, but not that surprising that it’s featured prominently in the news.

So what does this have to do with WorkAwesome?  I’m sure I’m not the only one to play the “what if?” game:

“What would I do if I won the big jackpot?”

How much would you need to win in order to quit your job?  Or would you keep working where you are if you had an extra $50 million in the bank?  Would you move on to something else altogether – something you truly love?

What would you do if you won the big jackpot? 

After spending way too long in the corporate world, Jason has switched to full-time freelancing. With any luck you enjoyed this article - and if you need one of your very own, give him a shout! @brandscaping on the twitter, or at


  1. Colin on the 19th June

    I’d go back to school.

    I already do what I love but I also love to learn.

    Most of the depts in my work place have pooled money to buy tickets for this draw.

  2. rorschachdesign on the 19th June

    I’d make sure my family was set up, then travel, upon returning I would set up a design studio, go to school for industrial design, and continue working, just not where I am…oh and I’d start that music magazine I’ve always dreamed of.

  3. InkSketch on the 19th June

    I’d take care of the family of course, I think that’s everyone’s no.1. Go back to school (may be for a while cause I love to learn). open a bookstore (franchise b&n) and design studio. Also, tossing around idea of designing green apartments/condos (to lease) as a source of income for my kid so he’ll be setup when I’m no longer here. I’d be damn busy if I won the lottery. very little laying around and relaxing.

  4. Enrique Ramírez on the 19th June

    I’d use around 80% of the money buying as many properties as possible to get them rented. Mostly to ensure my financial future (and buy a nice place for my family while I’m at it).

    Rest 20% would be used to pay my debts (which aren’t really that huge), get a nice appartment and furniture to fill it (nothing too fancy). Remaining would go to the bank as a backup in case things go wrong.

    I’d continue to work for a while, but mostly for enjoyment (I love my job). I’d definitely seek financial safety with my newly acquired properties.

  5. Salim on the 20th June

    I would donate 80% of the win to the poor. I think that the rest would be enough to bring my family and me trough life (a very good life).

    We would be traveling around the world visiting places that we want to see and learning the culture and the habits of the people.

    Another dream of mine would to go back to school and learn more about design and maybe freelance building websites but on the otherside, people playing the lottery are winners already because everybody playing is, aware ore not, buying them selfs a dream that they live untill the lottery gets pulled. The question is, is the dream worth paying for or is some immagination enough?

  6. Andrew on the 20th June

    I’d buy into the company I work for so that I’d be one of the directors.

    That way I can have as much time off as I need/want. I’d make sure I finished my current project first though as the client always should come first.

  7. Mário Andrade on the 20th June

    A friend of mine had a similar experience in the past. He didn’t won millions but won a considerable amount of money and eventually he moved to another country where he founded a company, that he later for an even bigger amount of money. Today he travels, takes photos as an amateur photographer and makes some interesting money by selling them. He was truly blessed and smart enough to get his life to this point.

    As for me, 50 million dollars…. a part of it I would invest in several places and live from the profits, eventually donate some money to help humanitarian causes. other part would be for my retirement and the rest would be for fun and education 🙂

  8. I would buy properties and have them rented out.

    Also, I would be making investments in other places.

    Basically, I would no longer need to work, even in a business.

  9. Tadd on the 20th June

    I’d give a chunk away first. Support organizations that I’ve backed for years (BTW, NEVER give large lump funds to non-profits – always set up trickle accounts so they get decent draw but not so much they go crazy).

    Then I’d pay off debts. Pay off most of my family’s debts.

    Put a large bit in some stable investments. Mutual funds for the kids college funds, etc. Basically, plan out some for the future.

    Then, move to the country, build a modest house. Start a working more actively on my projects (film & print) that I’d not been able to do since I have to work (no time!).

    Basically, a heck of a lot. Take care of people around me first, then start looking at my dreams being fed. I have a lot of projects on the side that have been neglected. I’d work for myself. I’d be my client. Do what I love .. imagine and create.

  10. Mike on the 21st June

    I used to always say “I’d keep working…” But now I think I can honestly say I would probably invest the majority of the money and live off that and get a bunch of cool hobbies and travel. I love my job, but if I don’t know If I would be able to work 40 hours a week knowing my salary was mere pennies compared to the interest I was earning on investments. 🙂

  11. Sophie on the 21st June

    I’d buy into the company I work for so that I’d be one of the directors.

    That way I can have as much time off as I need/want. I’d make sure I finished my current project first though as the client always should come first.

  12. Thera on the 21st June

    For starter, I would allow myself a whole week of holiday (because I didn’t have one this century).

  13. Reeder on the 21st June

    I think i would help other people. Nobody needs 50 Million. Spend some money on Organisations like Doktors without borders or something like that.

  14. Ron on the 28th June

    If I won $50 million, outside of traveling more and perhaps spending some time living abroad (either for work or service), I would probably not change my lifestyle that much. #1, I’m only in my 20s, so that jackpot would need to last me a while (40-50 years if I live to my 70s). #2, I’m still in the early stages of my career, so I’m not exactly itching to retire or get out of the race yet.

    I would use at least $5 million to start a charitable foundation, pay off my $20k in student loans, and put as much as possible in low-cost index funds. After seeing to those essentials, I would consider using my wealth to re-orient my potential in my career (by returning to school or investing in a startup).

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