1. Enter sweepstakes offering smaller prizes. Many people focus on contests giving away cash, cars, and trips, overlooking those with smaller prizes.
2. Repurpose old calendars. Instead of discarding your calendar at the end of the year, use the pages to create sturdy envelopes. Use an existing envelope as a template, trace it onto the calendar page, cut, fold, and glue. You can also use magazine pages, flyers, construction paper, wallpaper, or shopping bags. If the envelope is dark or busy, use white labels to address it.
3. Utilize local print shops. Check with places like Staples or UPS Store to see if you can use their paper cutters and other equipment. They often allow this for a small fee or even for free.
4. Target challenging sweepstakes. The harder a sweepstakes is to enter, the less competition you’ll face. For instance, if a sweepstake requires entries to be written in block letters (all capitals), enter it more often, as many people skip these.
5. Create postcards from cereal boxes. The cardboard is sturdy and often matches current promotions. For example, use a Kellogg’s Frosted Flakes box to make postcards for a Kellogg’s sweepstakes.
6. Use a glue stick. A glue stick is easy to use and avoids spills when sealing envelopes or applying non-self-adhesive stamps.
7. Make your postcards stand out. Use pinking shears or craft scissors to give your heavy postcard entries a unique edge.
8. Provide a comfortable phone number. If a sweepstakes requires your daytime phone number and you’re uncomfortable giving your work number, use a friend’s or neighbor’s number; just indicate whose number it is on your entry.
9. Enter sweepstakes requiring unique-sized entries. Keep larger papers and cards on hand to cut down to size. Sweepstakes requiring odd-sized entries usually have less competition.
10. Evaluate second-chance sweepstakes. Match-and-win or collect-and-win types require more effort but may have more available prizes than instant-win types. Adjust the number of entries you send accordingly.
11. Enter every sweepstakes once. Many grand prize winners enter each sweepstakes only once, ensuring they’re in the running for the prizes they want.
12. Pace yourself. It’s better to enter sweepstakes consistently throughout the year rather than in short, intense bursts.
13. Provide all requested information. If a sweepstakes asks for your email and you don’t have one, state that on your entry to avoid disqualification.
14. Use all entry methods. If a sweepstakes allows multiple entry methods, use each one at least once. For example, if you can mail either a postcard or a 3×5 card, use both.
15. Organize your entries. Write the due date in the upper right corner of prepared envelopes so it’s covered by the stamp when you mail them.
16. Use return addresses. This allows the post office to return any undeliverable entries and allows you to correct errors before resubmitting.
17. Mail entries early. Avoid mailing entries close to the deadline to ensure timely delivery and avoid disqualification.
18. Hand-print addresses for restricted sweepstakes. For sweepstakes limited to one entry per person or household, hand-print addresses to avoid accidentally submitting multiple entries.
19. Spread out your entries. Instead of sending all your entries right before the deadline, stagger them to increase your chances.
20. Mail on different days. Many people mail entries on weekends or Mondays. Mailing yours midweek might reduce competition.
21. Use permanent ink. Ensure addresses on envelopes don’t smudge and become unreadable by the post office.
22. Source extra envelopes from card stores. Stores that sell greeting cards often have extra envelopes they don’t need. These can be purchased cheaply or even obtained for free.
23. Mail from different locations. Mail entries during errands or travels to get them into various mailbags for better chances.
24. Send thank you notes. Whether you win online or through mail, thank the sponsors for the prize. Sponsors appreciate hearing from winners and it shows your gratitude.
25. Leave space for barcodes. When decorating envelopes, leave about 1.5 inches at the bottom for the post office to apply barcodes legibly.
26. Indicate unlisted phone numbers. If your phone number is unlisted, mention this on your entry to avoid disqualification.
27. Purchase decorated envelopes. If you like the look of hand-decorated envelopes but aren’t artistic, buy them from people who sell them online.
28. Check with Customer Service for entry forms. Save time by asking at the customer service desk for all available promotions and sweepstakes forms.
29. Use greeting cards as postcards. Cut greeting cards to postcard size, using the blank side for addressing.
30. Vary your envelopes and labels. For contests limited to one entry per person, use different kinds of envelopes and return labels to avoid suspicion of multiple entries from one person.
31. Enter local contests. Local contests often have fewer entries and better odds. Look for them in various local stores and radio stations.
32. Prioritize budget-friendly sweepstakes. If you’re on a budget, enter contests wisely. Sometimes, entering for smaller prizes can increase your overall chances of winning.
33. Use varied envelope sizes. Unless specified, mix up the sizes of your envelopes for different sweepstakes to catch judges’ eyes.
34. Use computer-generated labels. These are fine unless hand-addressing is required. Labels save time and ensure clarity.
35. Smaller wins make great gifts. If a contest has many smaller prizes, enter for a chance to win them, as they make great Christmas or birthday presents.