20 Years of You Can’t Win If You Don’t Enter

Over two decades ago, one article changed everything. Here’s how You Can’t Win If You Don’t Enter was born—and why its message is still true today.

Book Excerpt:

One night, I was lying in bed, reading the August 2001 copy of Reader’s Digest, when I came across an article called “Get in the Winner’s Circle! Tips from a contest junkie who’s proven that the best things in life are free” by Barb Taylor. I read and reread that article, and as I did, I made a decision—from then on, I would win all the things I wanted in life, like a new car!

Get in the Winner’s Circle!

Tips from a contest junkie who’s proven that the best things in life are free
by Barb Taylor
From Calgary Herald

Vacations in Italy. Hawaii and Mexico. Doing rolls in a stunt plane or being whisked off in a limousine for a night of wining, dining, and theatre. Hardly the lifestyle you’d expect for an average-income family of four living in a duplex and driving a rusty old Volvo. Certainly, not the lifestyle we envisioned when I left my teaching job 12 years ago to become a stay-at-home mom.

Our magical life began in 1988 after a sleepless night spent attending to our newborn son. The following day, I entered a contest sponsored by a local radio station, inviting listeners to send letters to Santa. I pleaded with Santa for one night of uninterrupted sleep. My entry was selected for a one-week trip to Lake Tahoe from radio station CJAY 92. I was hooked.

Now, I enter lots of contests, anywhere from 200 to 300 a year. I find out about them while shopping for groceries, listening to the radio, browsing through magazines and regularly perusing a contest newsletter to which I subscribe. Over the years, I’ve spent three to four hours a week researching new contests and filling out forms.

But the hard work has paid off. I averaged $10,000 in annual winnings; I’ve won two Dirt Devils through the Safeway Score & Win; and I’ve gone on a total of 14 major trips thanks to this winning hobby. My writing talents have won me a fair share of prizes as well, everything from a pair of $1,000 earrings for a local magazine’s limerick contest to a pair of lift tickets for a Calgary Herald-sponsored Ski Memories contest.

Our winnings have also included clothing, appliances, a backyard barbecue, and a patio set. We rarely pay to go to a movie or theatrical production. We frequently dine on gift certificates we have won. The luxuries our income doesn’t provide for, my contesting does. Even our children get in on the act and have won a bike, a skateboard, and passes to local attractions.

We’ve watched beautiful sunsets in Maui (courtesy of the Lite 96 jet) and Oahu (thanks to KissFM), walked the Freedom Trail in Boston (Calgary Co-op supermarket and Kraft foods), and even sent my in-laws to Scotland (a cross-Canada random draw from United Distillers). Will it ever end? Not as long as I can fill out an entry for or clip a Universal Product Code, or UPC as it’s known (the bar code on products you buy).

Most of the trips I have won fall into the middle “good-and besides it’s free” category. While not all-inclusive, your major costs of airfare and accommodation are covered. You stay in above average accommodation, usually a three-star hotel. You are generally responsible for your own meals, spending money, and, occasionally, airport taxes. Trips we’ve won in this category included a one-week trip to San José del Cabo at the tip of Mexico’s Baja peninsula. We enjoyed beautiful, uncrowded beaches, drinkable water, and simple but clean accommodations.

My husband and I experienced our “dream come true” trip courtesy of a local real-estate developer. By dropping off three entry forms at a tour of show homes, we won a one-week trip to Florence, which included stopovers in Paris and London. In Florence, we stayed at the Hotel Brunelleschi in a $650-a-night room that had floor-to-ceiling louvered windows opening onto a tiny flowered courtyard. We had a breathtaking view of the Duomo and the Campanile.

Nowadays, friends often rub my arm for luck before they head off to buy their lottery tickets. I can only shake my head in wonder – I’ve never won anything in a lottery.

So, you must be wondering, how do I do it? In the world of contesting, luck really has nothing to do with it: It all comes down to effort and persistence. For every contest I win, there are 100 I’ve lost. Here are some suggestions to put the odds in your favour:

DO

    • Pick free contests. These are usually drawbox contests and can be found in grocery stores and other businesses. Radio and television phone-in contests also cost nothing to enter.
    • Also, pick the “better odds” contest: Look for contests that have a limited contesting area, offer lots of prizes, require you to “do something” (write a story, solve a puzzle), or that run for a short time span.
    • Enter often. If it’s a “better odds” contest, I’ll enter five to 20 times. Try to space your entry mailings throughout the length of the contest’s running.
    • Collect UPCs. Remember that hand-drawn facsimiles are usually accepted in mail-in contests, and believe me, they really work. I’ve won many contests using hand-drawn facsimiles.
    • Subscribe to a newsletter detailing currently running contests. A good one is the Canadian Contest Newsletter, P.O. Box 776, Stn. U, Etobicoke, Ont. M8Z 5P9. On the web, you can find them at: www.canadian.contests.com.

DON’T

    • Swipe the entry pads and then stuff the draw box. Getting greedy may get you disqualified for taking unfair advantage.
    • Don’t try to win more than once a month on a given radio station. If you make a nuisance of yourself by trying to win every prize offered, you lower your chances of winning something you really want.
    • Don’t waste money sending in dozens, or hundreds, of entries to a contest that gives away only one prize. This is a quick road to contest burnout.
    • Don’t get scammed! If you’ve won a contest you haven’t entered—beware! If you have to be earning $40,000 a year and are required to attend a sales presentation—think twice!
    • Don’t send money to receive a prize—ever.

Reprinted with permission from the August 2001 Reader’s Digest.

NOTE: The Canadian Contest Newsletter has since closed. To find new contest sites and sweepstakes aggregates, visit ContestQueen.com and click on FIND.

I am so passionate about contesting and excited about winning, I decided to write this book after the 100th person asked me what my secret was to winning so much. I knew I was onto something with the system I had developed over the past few years, and I wanted to share my discoveries, ideas, thoughts, and enthusiasm with others.

Twenty years later, the message behind You Can’t Win If You Don’t Enter still holds true. Contests may look different today, but the heart of winning has not changed. Showing up, believing it is possible, and taking action are what turn opportunities into prizes. Thank you for being part of this journey with me. Whether you have been reading since the beginning or you are just discovering The Winning Edge, I am grateful you are here and excited for what we will win together next.