BYA Lifetime Achievement winner Bree Jamieson-Holloway on rising above imposter syndrome

October 31, 2025

Lawyer and entrepreneur Bree Jamieson-Holloway is used to being the youngest person in the room.

In 2020, she was an OBJ Forty Under 40 recipient and two years later became the youngest person ever appointed to the Canadian International Trade Tribunal.

Now, she’s been named the 2025 Lifetime Achievement recipient at the Ottawa Businesswoman of the Year Awards — and she just turned 40.

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Lawyer and entrepreneur Bree Jamieson-Holloway is used to being the youngest person in the room. In 2020, she was an OBJ Forty Under 40 recipient and two years later became the youngest person ever appointed to the Canadian International Trade Tribunal. Now, she’s been named the 2025 Lifetime Achievement recipient at the Ottawa Businesswoman of the Year Awards — and she just turned 40. “It feels amazing,” Jamieson-Holloway told OBJ Friday. “It was a real honour to be recognized by my colleagues and peers and the incredible business community that we have here in Ottawa. These are people that I admire and have so much respect for. So I was truly touched.” Jamieson-Holloway admits she never really felt like she fit in. Growing up, her family struggled financially and, as a mixed-race woman, she said she constantly felt boxed-in and doubted. Though she aspired to success, she said she didn’t believe there were many options available to her. “When my mom would ask me, ‘What do you want to do when you grow up?’, my answer was always the same: I want to be a mom and I want to help people,” she said. “I grew up very poor, so the idea of building wealth really came down to becoming a doctor or a lawyer. I didn’t understand that women could be engineers and surgeons and do anything they want. But I wanted to break out of my socio-economic situation and I wanted to help people. That was really it.” At first, she considered joining the RCMP and studied criminology during her undergrad at the University of Ottawa. When she decided she didn’t want to pursue policing as a career, she pivoted toward law and business. Her education took her to England, where she got her first taste of international relations. “I fell in love with business. It was something that excited me and it was always changing. I could innovate and be creative,” she said. “I studied law in London and was very fortunate to secure a training contract with a great international French law firm, where I trained in corporate finance and international arbitration. I had some really incredible early mentors and cheerleaders who really believed in me and encouraged me.” For a time, she worked and lived in Hong Kong with her husband, whom she met in England, before returning to Canada in 2014 to start a family and a firm of her own. She was 31 years old when she launched Jamieson Law, a virtual firm that specialized in corporate and employment law, as well as commercial leasing. It was a model that paid off when everyone else was forced online three years later due to the COVID-19 pandemic. But in 2022, she decided to close up shop and pursue an appointment with the Canadian International Trade Tribunal, an independent quasi-judicial body that adjudicates international trade matters. Her international experience and the many interests she’d picked up along the way propelled her toward taking on the role of vice-chairperson, said Jamieson-Holloway. “I think back to the University of Ottawa, when I was taking classes. I don’t know why I chose the courses I did, but thank God I did, because it has been the catalyst to so many things thereafter,” she said. “International relations, entrepreneurship, corporate law, commercial trade — I did all kinds of work in those contexts. I supported businesses that were distributing abroad or bringing products to Canada. That global interaction, that connection between people across the world, (taught me about) how we can work together and support each other’s economies. Having that experience, it helped everything make sense.” Despite having already received a lifetime achievement award, Jamieson-Holloway knows she still has a lot of career ahead of her. Her age, she said, sometimes makes it difficult to accept recognition for her own success. “I talk about imposter syndrome very openly,” she said. “When I was named a finalist in that category, I was feeling it. It’s something that so many of us struggle with, especially as women. And, quite frankly, it’s taken me a long time to get to this point. When I do feel those feelings, I tell myself that it’s because I’m where I’m supposed to be: breaking barriers and pushing myself out of my comfort zone.” Her ambitions, she added, haven’t changed. “My whole life, I had really clear goals for what I wanted to achieve,” she said. “I might pivot a little but, ultimately, my biggest goal is to leave doors open for those coming up behind me; to make a difference and a positive impact in whatever way I can; and to raise my children to be good people and believe in themselves. It is my greatest honour to serve. I don’t even really know how to express what it means to me to be of service and do the best that I can every day.”