Your Reset Guide

After three amazing weeks on the road – visiting fellow sweepers, attending the national sweepstakes convention, and doing some Words for Winning research – let me tell you, I came home to a completely neglected sweepstakes system.

If you’re like me and had a busy summer, or if you’re just getting ramped up as the kids head back to school and work picks up again, you might be wondering how to get back into your sweepstakes groove. Here’s exactly what I’m doing to catch up, and what you should do too.

First Things First: Clean House

The very first step is to go through whatever organizational system you use – whether it’s RoboForm like me, a spreadsheet, or your browser bookmarks – and remove everything that’s expired. I was honestly embarrassed when I taught my monthly sweepstakes masterclass last week, and my RoboForm lists were mighty thin because I’d been so busy!

Once you’ve cleared out the expired entries, you’ll have a clean slate of what’s actually current. This is crucial because you always want to enter what you already have in your system before adding anything new. Trust me on this – I might have a good memory, but the whole point of organizing is so I don’t have to remember every single entry.

The Golden Rule: Dailies First

Here’s something that can’t be stressed enough: always do your daily entries first before adding new giveaways to your system. If you get overly excited and start entering a bunch of new contests, then come back to your dailies later, how will you remember what you’ve already entered? You might accidentally disqualify yourself by entering twice.

Your Comeback Strategy

Now for the actual catch-up process. Here’s my step-by-step approach:

1. Start with your locals. Check all your local media for giveaways first. Your odds tend to be better with local contests, and many radio stations are ramping up their fall promotions right now. I’ve already seen announcements for contests starting in September, plus there’s usually a huge fall lineup of concerts and sporting events if you live near a major city.

2. Hit your favorite sweepstakes aggregate. Start with what’s been recently posted and work your way back. This helps you fill your funnel with giveaways that have the most potential since they’re fresh.

3. Dedicate time to single entries. These “one and done” contests are perfect for catching up because they don’t require daily maintenance. You can knock out a bunch of these and feel like you’re making real progress.

Don’t Forget About Instant Wins

While you’re getting back into the swing of things, search for contests with instant win components. You could literally win something right now! I demonstrated this during my livestream by entering a couple of instant win games on my phone. Didn’t win that time, but the point is – you never know when you might hit it.

PRO TIP: Search your favorite aggregate for the word “instant” to find all the contests where you can win immediately and still be entered for the grand prize.

Managing Your Expectations

Here’s something that trips up a lot of people, especially newcomers: You could win tomorrow, or it might take months. The old rule of thumb was 3-6 months from when you started to when you won your first prize. That was back in the mail-in days when Patience, Persistence, and Postage were the three P’s of sweepstakes.

Now it’s different. You can win instantly, but you also need to remember that contest timelines vary wildly. Something ending August 31st might not draw winners until mid-September, and you might not hear about it for another few weeks after that. Some contests I’m entering now don’t end until December – I wouldn’t hear about those until January!

This is why reading the rules is my number one tip. Always know when a contest ends and when winners will be announced.

The Reality Check

Let’s be honest about something: there are so many giveaways running at any given time that it’s physically impossible to enter them all. Sweepstakes have been around since the early 1900s, and this hobby is just getting bigger. There will always be another contest you miss, and that’s okay. You weren’t meant to win everything.

The average sweeper enters about 100 giveaways per hour – and that’s exactly why organization is key. Whether you use RoboForm, spreadsheets, or browser tools, find a system that works for you and stick with it.

Getting Your Family On Board

One thing I love about this hobby is how it can bring families together. Craig, my wasband, was skeptical at first when he saw me PIN Code Hunting, but after I won him gold grandstand passes and a lap around the track in a pace car (he’s a huge race fan), suddenly it was “Are we entering that one?” and “Have you seen this giveaway?”

The same thing happened with my boyfriend George. Once the prizes started showing up – especially that big family trip to Universal Studios – he became my biggest supporter and giveaway cheerleader.

A Few Practical Reminders

Check your notifications daily. Some sponsors only give you 24-48 hours to respond when you win. Miss that window, and they move on to the next potential winner.

Budget for “free” wins. I always say it’s a cheap night out, not a free night out. Even when you win concert tickets, you still need to get there, maybe grab dinner, and possibly buy a t-shirt. Same with trips – airfare and hotels might be covered, but you’ll need money for tips, meals, and souvenirs.

Track your wins. I use a spreadsheet to track who won what, when they won it, what sponsor it was from, and how I entered. This helps me see patterns in what’s working and what isn’t. You can download your own copy of my tracking spreadsheet from my website.

The Bottom Line

Don’t overwhelm yourself trying to catch up all at once. Spread it over a week or two. Remember, this hobby is supposed to be fun! Start with cleaning out your expired entries, focus on your locals and dailies, then work your way through those single-entry contests.

And hey, if you missed some giveaways while you were busy living your life, that’s perfectly fine. There’s always another contest, another chance to win something amazing.
Now get out there and start entering! Plus, I have a feeling that some big prizes are coming our way. Until next time, keep those entries coming!

P.S. Remember to check out the giveaway in the description of my YouTube video – you could win one of my books!