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Driving While Indigenous – Motivational Event & Gala

Purple graphic with bokeh pattern and headline Driving While Indigenous Motivational Event and Gala

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November 20, 2026 at 9:00 am - 4:00 pm

Venue

Presented by

Jill Featherstone – Host
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Jill Featherstone is the author of the Amazon #1 bestselling book, The Tale of Tiger Lily. She is a retired university professor, the founder of the Featherstone Group, and the host of Driving While Indigenous the Podcast, which airs Mondays on all podcast platforms.

“Empowering our Indigenous young people is always on the forefront of whatever I am doing, and whether it’s through workshops, speaking, events, or social media, I am always in search of ways to reach people on a larger scale.”

Jessica Dumas – Host
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Jessica is a professional speaker coach and the host of The Confidence and Communication Podcast. She has been recognized for her professional expertise as a recipient of the Manitoba 150 Women Trailblazer Award from the Nellie McClung Foundation for 2021, Ace Burpees Most Fascinating Manitobans for 2019, the 2017 Future Leaders of Manitoba and the CBC’s Top 40 Manitobans under 40 for 2015. She has a 2017 TEDx talk called The Journey to a Woman’s Identity.

In Partnership With

Featherstone Group logo

Featherstone Group and Support Services recognizes the ever-evolving and ever-resilient Indigenous ways of life and is committed to providing relevant, innovative and experiential services centered on empowering the self to become stronger as a whole.

Our mission is to create powerful spaces where Indigenous people can see themselves represented, hear stories that inspire them, celebrate Indigenous excellence, and leave believing more deeply in what is possible for their own lives.

GET READY, WINNIPEG! Creative Manitoba is a proud partner with Driving While Indigenous!

Driving While Indigenous is celebrating 5 incredible years! Join us for a powerful, high-energy experience featuring a fierce lineup of Indigenous changemakers, leaders, and voices who are ready to ignite the room. With hosts and Emcees- Jill Featherstone, Jessica Dumas, Ted Williams and Greg Personius!

November 20, 2026

9 am – 4 pm – Driving While Indigenous Motivational Event

6 pm – 12 am – Driving While Indigenous Gala

Driving While Indigenous began with the desire to be inspired.

Founder Jill Featherstone loved the idea of attending motivational events— being in a room filled with energy, powerful speakers, big ideas, and people who made you want to dream bigger. But when she started looking for those experiences, she realized there simply weren’t many happening close to home. She wondered, “Why are we travelling across North America looking for inspiration when we have our own Indigenous powerhouses right here?​ We have the storytellers. We have the entrepreneurs. We have the artists, leaders, comedians, musicians, professionals, dreamers and changemakers. We can create our own stage.”

And that is how Driving While Indigenous was born.

Jill and her team of volunteers have created a space for Indigenous people to come together, laugh, connect, dream bigger and leave feeling motivated about what is possible. Created with community service providers in mind— the people who spend their days pouring into others, supporting families, helping our youth, strengthening communities and carrying so much responsibility. 

“We cannot tell our youth to chase their dreams if we are not chasing ours.”

Creative Manitoba is thrilled to partner with the Featherstone Group, bringing speaker Dawn Marie Chartrand to the stage!

Dawn Marie Chartrand is an Anishinaabe artist, entrepreneur, wellness facilitator, singer/songwriter, and speaker from Rolling River First Nation, based in Winnipeg, Manitoba. Her work is rooted in creativity, culture, connection, and the belief that art, movement, music, and laughter can be powerful pathways to wellness and healing. Dawn began painting in 2017 as a way to express her visions, dreams, and life experiences. Since then, her artwork has reached audiences throughout Turtle Island and beyond, with original paintings and murals featured in Indigenous businesses, schools, organizations, and communities.

Through OM-Digenous Yoga & Wellness (est. 2022), Dawn facilitates culturally grounded experiences that bring together art, gentle movement, breathwork, laughter, music, and Indigenous teachings. She has worked with children, youth, families, adults, and Elders in communities and organizations across Manitoba and beyond.

As a speaker and facilitator, Dawn shares from lived experience with warmth, humour, and authenticity. Her presentations explore themes of
identity, resilience, healing, creativity, and reconnecting with culture and community. Whether she is speaking, painting, singing, or facilitating a wellness experience, Dawn’s goal is to create spaces where people feel welcomed, connected, and inspired.​

Early Bird ticket sales end Oct. 20th and we are 65% sold out! For more information and to purchase tickets please visit:

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