Stand Tall: Jim Waddington

Meet one of the driving forces behind Orangeville’s annual Celebrate Your Awesome event, a salute to pride and diversity in Dufferin County.

November 29, 2021 | | Local Heroes

Don’t be surprised if Jim Waddington can’t fit you into his Day-Timer.

A tireless community advocate and one of the driving forces behind Orangeville’s annual Celebrate Your Awesome event, a salute to pride and diversity in Dufferin County, Jim is also a working photographer. For years, his mission has been to turn up at all sorts of community events to take photos, which he shares on social media. From festivals to fashion shows and hundreds of other things in-between, Jim is on it.

Jim Waddington. Photo by Pete Paterson.

Jim Waddington. Photo by Pete Paterson.

Born in Montreal in 1960, Jim’s early life was challenging. His mother died when he was eight and his father when he was 18. Still, he earned a diploma in social sciences from Dawson College and later graduated with honours from the recreation leadership program at Humber College. For the next decade or so, he worked with at-risk youth at Charlestown school in Caledon.

In 1994, life threw Jim another curveball when he suffered a brain hemorrhage. “I had to learn to do everything over again,” he says. “That experience changed my direction and made me re-evaluate things.” No longer able to carry out his duties at Charlestown, he eventually started a photography business, work he enjoys immensely.

Outside of work and his involvement in Celebrate Your Awesome, Jim is a member of MENtors, a group of local men who help with the work of Family Transition Place. He has also served on various boards and committees, including the Dufferin County Diversity, Equity and Inclusion Committee. And before Covid, he and Teena Avery cohosted a Rogers Cable show called Dufferin Life.

About five years ago, the seed of Celebrate Your Awesome took root in Jim’s mind, and he approached a few people about creating an event to celebrate 2SLGBTQ+, an initialism that refers to people who identify as two-spirited, lesbian, gay, bisexual, transgender and queer. The plus sign is intended to include those who prefer other identity terms, such as intersex. Regular meetings at various Orangeville restaurants ensued.

Jim credits that group, which currently includes Wayne Townsend, Lisa Post, Ricky Schaede, Shannon Leighton, Greg Glasman and Julie Elsdon-Height, with turning the vision into a popular reality. “The team members are brilliant,” he says. “They all bring something to the table.”

Of the event they created, Jim says, “We looked at demographics and asked, ‘How do we introduce pride and diversity to our changing population?’” The result is an all-day, family-friendly celebration of everything that makes everyone unique, regardless of what that is. Though the pandemic forced the festivities to take place virtually for the past two years, plans are afoot for another live gathering on Mill Street in Orangeville next June.

  • Story Continues Below Advertisements
  • Jim’s contributions to the community were recognized when he was awarded the 125th Anniversary of Confederation Medal. And this year, he won the Orangeville Arts and Culture Award for Community Arts Volunteer. In addition, Celebrate Your Awesome won the Creative Cultural Event Award.

    Whether it’s a misunderstood minority or the community as a whole, Jim says, “David or Goliath, everyone needs to be recognized, because everyone plays an important part in our society. And we all have a need to be treated equally – and to stand tall.”

    About the Author More by Jeff Rollings

    Jeff Rollings is a freelance writer living in Caledon.

    Related Stories

    Local Heroes 2021

    Nov 29, 2021 | In The Hills | Local Heroes

    Our 14th annual salute to local people who make a difference – we’re grateful to each of them for making 2021 a whole lot brighter for so many.

    Nature Booster: Janice McClelland. Photo by Pete Paterson.

    Nature Booster: Janice McClelland

    Nov 29, 2021 | Alison McGill | Local Heroes

    How the Erin resident transformed a passion for the outdoors into many fruitful years of volunteering for the Bruce Trail Conservancy.

    Ken Hunt. Photo by Pete Paterson.

    Ice Angel: Ken Hunt

    Nov 29, 2021 | Nicola Ross | Local Heroes

    Thanks to this community builder, the Palgrave Mill Pond is a place where the village meets in winter to skate, play shinny and connect.

    Yes, She Can: Ashley Lawrence and Kadeisha Buchanan

    Nov 29, 2021 | Nicola Ross | Local Heroes

    Two pivotal players in Canada’s first Olympic gold in women’s soccer in Tokyo call Caledon East and Shelburne home.

    Valerie (left) and Shannon McGrady. Photo by Pete Paterson.

    Inspired by Matthew: Valerie and Shannon McGrady

    Nov 29, 2021 | Jeff Rollings | Local Heroes

    The mother-daughter duo advocated for Orangeville’s new Bravery Park – which honours all military personnel, including their late son and brother.

    Phone Friends: TeleCheck Volunteers. Photo by Pete Paterson.

    Phone Friends: TeleCheck Volunteers

    Nov 29, 2021 | Jeff Rollings | Local Heroes

    We salute three longtime volunteers with TeleCheck, a free telephone check-in service for people older than 55 who are living in their own homes.

    Leave a Comment

    Your email address will not be published. Required fields are marked *

    By posting a comment you agree that IN THE HILLS magazine has the legal right to publish, edit or delete all comments for use both online or in print. You also agree that you bear sole legal responsibility for your comments, and that you will hold IN THE HILLS harmless from the legal consequences of your comment, including libel, copyright infringement and any other legal claims. Any comments posted on this site are NOT the opinion of IN THE HILLS magazine. Personal attacks, offensive language and unsubstantiated allegations are not allowed. Please report inappropriate comments to