Winning for a Living - Documentary about Canadian Contesters

Carolyn Wilman, the
Carolyn Wilman on the Harry Potter movie set, part of a contest she won. Image © Carolyn Wilman

The Bottom Line

An interesting documentary that follows four Canadian sweepstakes fans and shows a little bit about their lives, methods, triumphs, and disappointments.


  • Interesting overview of contests and sweepstakes.
  • Gives a look at both sides - contesters and marketers
  • Offers winning tips and advice
  • Good program for beginner contesters.


  • Makes sweepstakes entry seem 'weird.'
  • Most of the sweepstakes advice is basic.


    • A look at the sweepstakes hobby, mostly from an outsider's perspective.
    • Covers basic tips on winning methods as well as the triumph of winning and the disappointment of losing.
    • Describes the sweeping experience as it relates to four fans including experienced and new contesters.
    • Focuses on Canadian contests and sweepstakes.
    • My favorite quote: "Once they start winning, they can't believe it's just that easy," Carolyn Wilman.

    Guide Review - Winning for a Living - Documentary about Canadian Contesters

    Winning for a Living is a television documentary created by the Emmy-nominated Canadian production company, "Handel Productions, Inc." The 45 minute documentary follows four contesters as they talk about their favorite hobby, reveal some of their methods, and share their triumphs and disappointments.

    The contesters offered a wide range of expertise, including:

    • Carolyn Wilman, the Contest Queen and organizer of the Annual National Contestors Convention, a sweepstakes convention for Canadians.
    • Mike Smith, a long-time contester who has won a quarter of a million dollars worth of prizes in his 30-year sweepstakes career.
    • Rosemary Chiu, who used contests to help raise her three sons after a separation left them destitute.
    • Fern Corraini, a new contester who recently won her first large prize - a $1,000 check.

      This is an interesting documentary for anyone who is thinking about starting the contests and sweepstakes hobby. It covers some good basic information, including using Roboform for online entry, the importance of reading the fine print before entering, and how to save time when filling out mail-in ballots.

      It also does a good job of showing the absolute thrill of victory, while reminding us that winning is anything but a sure thing, even for the "professionals" who dedicate so much time to it.

      I also enjoyed the (sadly too short) clips from marketers, who presented their side of the sweepstakes hobby.

      What disappointed me a bit was that the documentary seemed to have a bias that sweepstakes entry is somehow a "weird" or embarrassing thing to do. Clips of people afraid to tell their families about their hobby, or whose obsession damaged their marriage, outweighed Carolyn Wilman's more positive message that the sweepstakes hobby promotes positive thinking, hope, and the feeling that anything is possible.