Entering contests and sweepstakes is an easy hobby that offers the potential for huge rewards. You can see my win list here. Since I have been enjoying (and reaping the benefits from) this hobby for many years, I have found several things that make entering a whole lot easier and faster for me.
The first thing to do is to make sure you have good Anti Spyware and Anti Virus protection. I personally use Ad-Aware, Spybot Search and Destroy and AVG AntiVirus and don't have any problems. All of these have free versions. If you want to see what else is available, look up Anti Spyware or Anti Virus software in any search engine.
Next thing is to download RoboForm, a form filler that also saves your passwords and protects your information. I love RoboForm and can't imagine entering nearly as much as I do without it. It speeds up the process and once you use it you will see why it is so highly recommended by serious sweepers everywhere. It will also help you fill out freebie forms and you can use it for several different family members. There is a free version of RoboForm as well.
Join a site dedicated to sweepstaking and contesting. The only one I will personally recommend is Online-Sweepstakes also known as OLS because after months of research, that is the only site I use and I find it meets my needs. You can join as a free member then read the forums to decide if subscribing is right for you. For me the $30. a year, mere pennies per day is well worth it for the organizational abilities alone, not to mention access to the harder to find sweeps and contests. Naturally, you can use any search engine to find contests and sweepstakes on your own or even to find a site more suited to your own particular needs.
Now it's on to the fun stuff. At first it can be overwhelming, but you can avoid a lot of mistakes newbies make by doing a few simple things.
Decide what types of prizes you want to win. A lot of people new to contesting and sweepstaking enter everything they are eligible for, and that is fine, but there are a LOT of contests and sweepstakes and there just isn't time to enter every one.
Realize that you are responsible for paying taxes on your wins. If you can't afford the hundreds of dollars you will pay on that two thousand dollar purse don't enter for it and have to turn it down. While some sponsors will move on to the next name on the list, many will not and everyone loses. An easy way to determine your taxes for next year assuming you are making approximately the same salary is to add the fair market value of the prize to your salary and see what your taxes would be, then you can decide if that is worth it to you. To me, getting a great purse at a fraction of the cost is worth it as we can afford the taxes, but you may feel differently.
Read the rules to determine if you are eligible for a particular contest or not. While OLS and other sites make it fairly easy to tell at a glance, it is always good to read the rules for each particular contest at least once. You will eventually become fairly proficient at knowing what certain sponsors are looking for, but at least at first I always try to read the rules. It is heartbreaking to receive a win notification only to have it be determined later you are ineligible for one reason or another.
Keep track of what you have entered and when so that you don't disqualify yourself. Contests and Sweepstakes can have different frequencies to enter, some of the options are once, once a month, once a week, once a day, every 24 hours, every hour, unlimited, once per code or really anything the sponsor determines. OLS makes this very easy.
Find a strategy that works for you. I don't want to spend all of my time on my hobby, I enjoy doing other things too much and if it feels too much like work I won't do it. I do have a strategy that works for when I do enter, though, and if you saw my prize list you know I win fairly consistently.
After logging onto OLS I go through the new sweeps that have been added since the last time I went through them whether that was the day before or a month ago and add the ones I want to enter to my sweeps. I do not enter them as I add them, although I know that some do. I then go through the expiring soon sweeps, and while the plan is to keep several days or even a week or so ahead I usually get to them the day they expire or maybe two days before.
Depending on how much time I have I might hit a category that I really want to win such as trips and enter those or if I have no other plans and just want a lazy day entering sweeps, I will go to my daily sweeps and enter like a madwoman.
There is an option on OLS to organize the sweeps by ratings, but I don't like this at all because it is user rated and some people rate everything one star just to have a record that they entered it and it does not go by the value of the prizes or how easy they are to enter. If there are some sweepstakes or contests that you really really want to win, put them somewhere else on your computer- I have a favorites folder- so when your time is very limited you can make sure to enter for the things that are most important to you.
Remember that the time put in does not guarantee you will win big or even at all. I have been fortunate and I admit it, but I don't think it is all a numbers game. Having a positive attitude helps. As do patience and persistence. Some contests and sweepstakes run for months or even a year. Sometimes you will find out you won then have to wait what seems like forever to get your prize. You never know which entry will pay off, though, so if a prize is worth having, it is worth entering for. I know it isn't funny to them, but you will a lot of times see someone whining because they haven't won anything yet then realize they have only been entering for a few weeks. Sorry, but if you don't have patience, this probably isn't a hobby you will be happy with. If you are going to give up easily, ditto.
I know, I know you're impatient and want shortcuts- that first win would really help to show you it's all real and you aren't giving out your information for nothing. I don't blame you, and here is the advice I give to newbies who are getting discouraged. Enter contests and sweepstakes that have lots of prizes. Enter local/regional contests- radio stations, drop boxes in the stores you frequent and the like. The harder it is to enter the less competition you will have, so enter those recipe or essay or skill contests and you will have better odds of winning.
Okay good, you stuck with it even when it seemed like a waste of time. How are you going to find out you won? Good question, and the answer is... it depends. You can find out in any number of ways, the most common being instant win screens, email (check your spam folder), postal mail, UPS, Fed-Ex, DHL, your name being shown on a website, hearing it on the radio or tv and having a certain amount of time to respond or a phone call. Sometimes you will receive an affy (affidavit) to fill in and send back to make sure you are eligible and sometimes you will receive the prize by one of the carriers with no prior notice. All are exciting.
Why would sponsors give away everything from houses, cash and cars to candy bars and wallpapers and I-tunes? Advertising. And it works. I know I am loyal to sponsors that hold contests whenever possible, to show my appreciation. I have also found out about a lot of new sites, products, artists and whatnot that I never would have found on my own, and whether I win from them or not, I do support them when I can.
Keep at it and you will soon have all the T-shirts you can ever use and lots of presents to give away. I hope you enjoy your new hobby and wish you wins galore.