I’m not exactly the Prize Winner of Defiance, Ohio, but occasionally I suspend my I’ll-never-win cynicism and enter a contest or two. Of course, entering contests has changed a lot since the subject of that memoir was collecting her winnings. Today, it means entering contests online.

Although there are lots of awesome prizes out there, the reality is that most of the time you aren’t going to be the winner. If you never win, it is definitely a waste of time, so you have to try and optimize your chances. I recently started entering giveaways more frequently, and I’ve had some good luck. But I always try to remind myself that more often than not, I will walk away empty-handed.

While you can’t influence the outcome of any particular giveaway, you can improve your time spent to items won ratio by strategically picking what contests you enter.

1. The fewer the entries, the better your chances

I avoid large sweepstakes and anything sponsored by a major corporation. Sure I could win, but it’s not likely. I prefer to enter blog or Instagram giveaways, because unless their readership is massive, the odds could be one in 1,000 or better.

I recently won $1750 in gift cards for Cost Plus World Market (from the awesome Pretty Providence). There were around 1,200 entrants, so winning wasn’t likely, but at least I knew I had a chance. One of the few big contests I actually enter is the HGTV Dream Home, and I know that my chances are next-to-nothing. I enter anyway since it takes almost no time.

2. Maximize your time

The one thing I don’t like about the Rafflecopter (or similar) contest entries on blogs is that they can be time consuming. Sometimes you have to follow a a bunch of accounts on Pinterest, Facebook, Instagram, and/or Twitter. For each account you follow, you receive a set number of entries. You may also have to tweet about the contest or post a comment. So I try to balance how much I want the prize with how much time it takes to complete all the entries.

Sometimes I quit in the middle and only get a few entries because there are way too many people to follow. There is a good reason for having so many entry options, which is that when a bunch of blogs sponsor a contest, the bloggers are often putting their own money toward the prize. So the likes and follows are what they get out of participating. It makes sense and I don’t begrudge them those likes. Nevertheless, if the prize isn’t something I would love to have, I won’t take the time. It is a good way to find other blogs you might be interested in, however.

3. Know where to look

One way to find smaller giveaways is simply to find and follow blogs on topics you are interested in. If you subscribe to a blog’s newsletter, you should receive notifications about new giveaways. There are also some websites that can help you find blog giveaways. Many of the sites that used to only list large sweepstakes now include a section for blog giveaways, such as Online-Sweepstakes. Some, like the Blog Giveaway Directory solely list prizes offered by blogs.

You can often also find great contests on social media including Instagram and Twitter. I impulsively entered a contest on Instagram where I had to share a picture and tag a friend. I wouldn’t tag a friend if the contest were sponsored by a huge corporation, but in this case it was a new, small company I was already familiar with, Passion Planner. I really wanted one of their planners, so I was thrilled to win. If you need to re-post (“regram”) a photo on Instagram, you generally need to use an app or another website to save the image, as screen shotting it can be kind of a pain. I use Iconosquare for this purpose.

4. Make sure the contest is legit & avoid spam

Some contests are for the sole purpose of collecting email addresses for spammers. If you sign up for a contest and you find yourself in the middle of a series of webpages asking you to sign up for special offers, it’s probably not legit.

I recommend setting up a special email address or two solely for entering contests. It’s not so necessary for blog giveaways where you are signing up with social media follows, but for any big company or contest with questionable legitimacy, I use a dedicated email address.

5. Say thank you!

If you win a contest on a blog or an Instagram account, say thank you. When I won the World Market prize, I emailed all the bloggers who sponsored the contest (and put their own money toward the prize) to say thank you. Several seemed surprised that I had taken the time to say thank you and one even told me outright that they rarely hear back from the winners. That seriously shocked me. If you win, take the time to say thank you.


Another thing I do to say thank you is to share posts from the sponsoring blogs on my social media accounts. This is quick and easy to do, and potentially driving some traffic to their websites is a great way to show your appreciation.

Entering contests is probably not going to line your pockets or fill your home with wonderful treasures. I recently had a week where I won three contests, but I haven’t won a single thing since then. It can be a fun way to win things you normally wouldn’t buy if you don’t spend too time at it or expect too much. What is the best prize you’ve ever won in a giveaway? Do you enter contests often?