Enter Contests for a Living

Enter Contests for a Living

I would never have thought that you could actually enter contests for a living successfully, until I tried it. Just like any job, the amount of time you put into it is generally going to reflect in how well you get “paid,” and therefore how well of a living you can make.

Just like with gambling, you can get really lucky with contests and sweepstakes and maybe get a big one that you can live off of for a year, but that’s not common. I know people doing this full time who actually do nothing but enter contests and sweepstakes online, and they live quite well.

Read on if you’d like to learn how you can, too!



I spent two years putting in about an hour a day entering free sweepstakes and contests online. Anytime my family would sit and watch TV I’d have my laptop and just sit there entering. I came up with a system that made it fast, easy and helped me enter a lot of them in a little bit of time. As a result, in that time frame I won all the following (that I can recall):

Weekend trip to Las Vegas with tickets to see Mariah Carey and meet her backstage

4-days, 3-nights in Chicago, with flights, hotel and $500 spending money

3-days, 2-nights in NYC with flights, hotel and some food fully paid for

$1000 gift certificate to a jewelry store

Bowflex elliptical and weight set worth $3500 (sold it to pay rent)

$100 gift card to Bluefly.com

$100 Visa gift card (3 separate times)

XBOX 360 gaming system

$500 gift card to Home Shopping Network

A year’s supply of Tonnino Tuna

LED gaming computer monitor and accessories worth $250

Epson color printer and fax machine

Generic exercise bike

Yoga mat and bag

Lots of beauty products and accessories

Lots of DVDs and musical downloads

I didn’t document everything and there are a lot of little and even semi-decent wins I don’t remember. I sold almost everything I won, aside from the trips. I would say on average I won something 1-2 times a week.

Often my wins would be something small like a free candy bar or grocery item, but as you can see it was often something very worthwhile. Had I put more time into it I could have won a lot more. The point being, the more you enter the more opportunities you have to win.




Here are the basic steps I recommend that helped me make entering efficient:

1. WHERE TO ENTER: Find a contest and sweepstakes website that works for you and provides updated lists of contests to enter that is organized in a way that works for you. There are a ton out there and new ones pop up on blogs all the time. The one that I found and love is Contestgirl.com.

Contestgirl.com is organized well, with search options so you can find the specific type of contests or sweepstakes you’re looking for. You also have the option to save them to your own list so you can go back and enter again on the ones that allow repeated entries. I can’t provide any other suggestions on sites for this because this is hands-down the only one I will use. I’ve tried others, but the ads on their sites often make it confusing and hard to navigate.


2. EMAIL ACCOUNT: Create a separate email account for your entries. I highly recommend doing this as a lot of contests and sweepstakes entries require email sign-up. By having a separate email account you don’t have to worry about spam filling up your regular account. You also don’t risk losing winning notifications – I missed out on a few big wins (several hundred dollars worth of merchandise) by not having a dedicated email address.

You will need to take a few minutes daily to quickly delete all the spam on your new account and check for winning notifications. This is the most tedious part of the job, but it can be kind of exciting, too. It’s quite a rush getting that email that starts: CONGRATULATIONS!

I personally like Outlook, but you can also create free email accounts with Gmail and Yahoo. Whatever you want to use, just make sure it’s easy for you to organize and clear it out quickly.


3. FORM AUTO-FILLER: Get an auto-filler for quickly logging in to websites and filling out forms. Roboform is my favorite auto-filler and allows me to click one button and fill in my name, address, phone number, email, etc. All contests and sweepstakes entries require some sort of information like this, so it’s beneficial to have an auto-filler.

I promise you, this will speed up your entries by at least 100%. Even thought I type fast, after starting to use Roboform I went from entering about 20 a day to over 50 in the same amount of time. Remember the more entries you get in, the more chances you have to win. There are other auto-fillers out there, I use Roboform as the simplest and most popular option.

You can get a student account for pretty cheap form Roboform, that’s what I did. It was about $10 a year, and if you’re not a student it’s $19.95 for the entire year.

robo form small banner

And that’s my simple system for winning!



1. TAKE ADVANTAGE OF REFERRALS: A lot of contests and sweepstakes will provide referral links and give you extra entries by getting others to enter. On Contestgirl.com there will be a referral chain attached to contests like this so you can use someone else’s referral link and then share your own for others to use. I also have created my own Facebook page and share the best contests there and on Pinterest and Twitter.


2. CASH FOR PRIZES: Anytime I win a prize that I won’t personally use, I always ask if there is a cash option. This will usually by noted in the terms and conditions for the bigger prizes. Unless it’s something special, like meeting Mariah Carey, I will try to take the cash option before the flights and hotel stays because they will always be valued more than you could pay for them yourself. This is also a key part of making a living on this. If you do nothing but take all the trips then you’ll be spending money. I have a day job, too, so the trips were great for me. But if you’re looking to make a looking on this you’ll want to see what trips you can turn into a paycheck instead.

With physical prizes, you can also sell them. I paid my rent one month with my Bowflex elliptical win.



You will have to pay federal taxes on your winnings over a certain dollar amount, and you may have to pay state taxes depending on the laws in your state. I live in Nevada so I don’t pay state income tax, but I did pay federal tax on anything I won that was valued over $2000. The sponsors had me fill out a tax form to claim the prize and then provided me the form I needed when I filed my taxes. How much you are taxed is going to depend on your tax bracket, so it’s helpful to keep track of your bigger winnings throughout the year so you’re not blindsided.

If you win enough, you have the option to itemize deductions. Since your winnings are income, basically any money you spend in relation is going to be deductible. I was able to get deductions for purchasing my laptop, my Roboform subscription, and even the food I paid for on my trips. It’s all a part of the “business expense” of entering contests. So if you keep track of your expenses and winnings well enough you can end up paying very little in taxes for your winnings.



We’ve got a little page going where we like to post some of our favorite contests and sweepstakes we feel are worth entering, big prize amounts or just awesome prizes and easy entry.




I’m documenting further as I get into entering contests and sweepstakes full time, but if you have any questions on the subject I’m happy to help. Please feel free to comment below.

12 Replies on “Enter Contests for a Living

  1. Hi there!
    Thank you, for putting this info together – hey, we can ALL use some extra cash and winning
    prizes! Have you heard of Helene Hadsell? She was a sweet, American lady that’s won over
    5,000 prizes in her lifetime – all prizes ranging from household appliances to exclusive, first
    class trips all over the world!
    I appreciate all the tips given in your post – I will def bookmark this page and refer to it for
    future endeavors!
    And of course, the WINNING part all lies in your mind and beliefs – so stay positive and know
    its already coming to you!

    1. Helene Hadsell – The Contest Queen. She has some great advice on the subject, too. I agree that state of mind plays a lot into winning. Staying positive and having a winning attitude all lead to wins. It took me a few weeks to get my first win, and that made me feel so good that it just started rolling downhill from there.

  2. Wow, this is such an interesting article. I would have never thought that this was even
    possible…well not do to it as a living anyway. I bet it does take an awful long time to enter the
    contests and receive your winnings, but at least you won’t have to work a normal J.O.B. I’m a
    big fan and will be back for more 🙂

    1. It’s definitely a fun job, a huge benefit being you can do it from anywhere. It actually doesn’t take too long to get your winnings and entering is fast if you follow the tips with Roboform. When I can put in a good 4 hours a day I can enter up to 500 contests or sweepstakes (some small, some big) and I have about a .05% win rate and growing.

  3. Very interesting concept here. I have entered surveys before, but often back out at the end
    when it asks for credit card info on something free. But the ones I have entered you always
    have to put a phone number then I am constantly harassed by these companies, so i don’t do
    that anymore. Do you encounter this type of thing as well?

    1. I know what you’re talking about because I’ve done those survey sites or followed an alert that said I won something but have to complete an action first. Contestgirl provides complete lists of actual contests and sweepstakes that are all free and easy to enter. It’s mostly businesses wanting you to sign up for emails or like their Facebook page, etc. but you don’t always even have to do that. I DO recommend getting a separate email as you will get a lot of email subscriptions and spam.

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