Scott Hardie | December 12, 2008
Lately Kelly and I have been on a winning streak, from the Halloween costume contest at work, to a graphic design contest that netted Kelly a PS3 game, to a trivia game at work that just bought us Lobster Pot for dinner tonight.

I don't believe in luck, or that this streak will necessarily continue, but all this has gotten me wondering if I should enter more contests. I must have dangled that Snickers wrapper over the trash can for a good minute, pondering whether I should take that code to the website and register for their spam mailing list, just in case it wins me a trip to the Super Bowl. What would I even do with a trip to the Super Bowl, since I don't really like football and I live right next to the city where it will be played?

Anyway, there are people who make a point of entering every contest they can, turning sweepstakes-entering into a hobby, and they take full advantage of the no-purchase-necessary clause by doing it all for free. These people don't become millionaires, but they do seem to win some cool things for their effort sometimes, more than the average schmoe does, and they get some neat stories out of it. This idea appeals to me, but it might be a lot of effort for nothing, and I've got enough to do already.

Does making a hobby out of entering lots of contests appeal to you?

Steve West | December 12, 2008
I do a lot of phone dialing for radio contests and win about once every two years. Last thing I won was concert tickets to see Earth Wind and Fire .

Steve Dunn | December 12, 2008
First, create a reasonable valuation of your time, per hour. A simple way to do this is to divide your annual pre-tax salary by 2000 (representing 50 weeks per year at 40 hours per week). It's not really accurate as a valuation of your leisure time (I could expound on this all day) but at least it's a start for a rough idea. It's higher than most people think, especially if you throw in benefits, retirement account matching, etc.

The next step is determining whether entering contests or raffles is worth it based on the time it takes vs. the odds of winning. In my humble opinion, the answer is almost always no. The odds of winning are so low, and the prizes almost always so modest, that the cost to you in time is almost never worth it.

Nonetheless, I will occasionally enter a "100 words or less" writing contest, but I justify that as having a certain entertainment value.

The case against entering contests and raffles is, I think, pretty easy no matter how you value your time. The harder questions, and ones I don't think most people think through logically, are: should I mow my own lawn? Should I clean my own house? Repair my own car? Paint my own living room?

I encourage everyone to think hard about valuing their time and be VERY careful not to sell yourself short. I think a solid case can be made that your leisure time is worth a LOT more than your working time (remember, sleeping eats up a lot of your free time, and anyway, between work and play time, which do you enjoy more?) If you can find someone to do certain unenjoyable tasks significantly less expensively than you value your own time, AND they can bring to bear greater professional expertise than you possess.... often times even apparently "expensive" decisions make perfect rational economic sense.

Don't enter Publishers Clearinghouse Sweepstakes. And let someone else wash your car.

Lori Lancaster | December 12, 2008
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Aaron Shurtleff | December 12, 2008
Man, I can barely find the effort to clip coupons out of the newspaper, and that's guaranteed money in my pocket!

I enter contests like this only if they are totally for fun only (like trivia contests at bars and that kind of thing...). Sure, I don't win anything, but I don't lose anything, either. I have a hard time winning anything. I always feel bad about the people who lost, who might need the prize more than I did.

Denise Sawicki | December 12, 2008
Well in general I don't find it worthwhile to enter contest purely based on luck, unless the odds are better than like 1 in 10 :P. As for skills, I don't think I really have any... Phil the dog has won a couple contests though because he is very talented.

I do make a hobby of getting free stuff where if you put in the time you are guaranteed a reward, but then again, that's kind of like working isn't it. But fun for me, for some reason...


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