Smile Now, Cry Later

Hello girls and boys (if there are any of you men-folk reading this),

I would like to have a chit-chat with you. This is a little awkward, so pull up a chair, grab a box of tissues, and make sure to draw on your eyebrows a little more sad today. I have something to tell you that is rarely discussed in Sweepstake Land.

Sweepstakes can cost you money.

Whaaaat? It's true. Sad hobo face.

Is it still worth it? Most of the time, yes.


The reason why winning sweepstakes can cost you money is this: TAXES. Most people wouldn't think about future costs of winning a free prize. I know I didn't until a saw a few sweepers online mention that they had turned down prizes (mostly vacations) because of the high dollar worth and the future consequences of accepting.

Most t.v. shows, news articles, blog posts, etc, will have you believing that not only is winning relatively easy, but that you can make a living off of it. It's not impossible, but it's definitely not easy and I am sure it will not make anyone a millionaire. Most you will get out of hardcore sweeping is a lack of friends due to being cray cray.

I am most definitely cray cray, but in a fun-loving, somewhat socially acceptable way. Don't you dare judge me... yes, you. Put those eyebrows away.

So, here's what happens: If you win a prize worth over $600 most likely (if it is a bigger, more responsible company) the givers of the prize will have you fill out paperwork (W-4), which will then be reported. This win will count against you as earnings/winnings and you will have to include it in your income taxes. I think most prizes are worth it because most of the things I enter for are things I really want or need and paying taxes on it is better than having to pay for it out of pocket. Remember, I am a cheapskate.

I am very careful about entering vacation sweeps. Most likely the value will be high and it's obviously not something you can sell if won. Maybe when my finances are better I will start entering for a trip to the moon.... oh man, which reminds me. I once found a trip into space that I wanted, but it was worth $100,000. ONE HUNDRED GRAND. How much would you owe on that at the end of the year? idied.

Most sweepstakes out there are for smaller, less expensive items and that is mostly what I win. I try to win cars, boats, and mansions... but most likely that will not happen for me. Dream big and be excited about the little things in life. Worst case scenario, if I win something I can't afford I can sell it.

And that brings up another subject. When you win larger items you plan on selling, you not only have to pay taxes on the full retail value, but you will not be able to sell that item for as much as it's worth. There's still free "money" somewhere in the sweeptastic equation, but it is sadly not as much as you would hope for.

Moral of the story: Don't be a greedy whoreder. Enter for what you want and what you can afford. Free is not always free.



Photo of Emmett Kelly as "Weary Willie"