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Bree Jamieson Holloway: What Will You Choose to Embody?

Feb 28, 2023

This featured story is brought to you by the Power of Why Podcast in collaboration with Invest Ottawa, with critical support from BDC Capital’s Thrive Venture Fund and Title Sponsor of International Women’s Week. We teamed up to produce this special series to celebrate women leading in Ottawa for International Women’s Week (IWW 2023) and shine the spotlight on our IWW 2023 featured leaders to unpack their passion and purpose.

Each year, five inspirational leaders are selected to represent International Women’s Week. They are role models achieving a significant impact on our economy, community and society, and embody the spirit, goals and values of IWW.  

Bullied, mixed-race, and living in poverty, many told a young Bree Jamieson-Holloway that hers was an uphill battle too formidable to overcome. 

So she turned inward.

Heartened by her grandmother’s motto to “push on, regardless,” she crafted a vision that would anchor her life’s work: travelling the world, starting a family, and helping people.

Now a published author, mother, equity champion, international corporate lawyer and founder of her own firm, Bree has realised her dreams — and then some. 

Last year, Canada’s Deputy Prime Minister announced her appointment as the new Vice Chair of the Canadian International Trade Tribunal.

Here’s how she made it.

This episode is for you if:

  • You’re struggling to feel hopeful about your future
  • You don’t see yourself represented in the leadership roles you want to achieve
  • You’re passionate about diversity, equity and inclusion 
  • You enjoy business but aren’t sure how to pursue it with a social conscience

Looking for a specific gem?

[3:00] Yes, you can overcome adversity

[3:30] Intergenerational knowledge transformed Bree’s life

[4:15] “Push on regardless”

[8:00] Visualization; or the art of realizing your dreams

[12:15] Here’s how Bree broke free of her limiting beliefs 

[14:48] Bad at math? Become a lawyer. 

[17:00] Building a business that (actually) helps people

[21:00] Introducing the new Vice Chairperson of the Canadian International Trade Tribunal 

[26:43] On changing your career (not your values)

[27:49] Who gets access to justice?

[34:04] Your foundation is everything — keep it strong

[37:35] Moving the needle takes big leaps and baby steps

[44:17] Staying fiercely committed to DEI + access to justice

Listen to the episode on Spotify / iTunes / Google Podcasts 

Tune in to the podcast or take the time to digest each article found below. Regardless of the format, there’s great content in store for you!

Naomi Haile: Share a bit about your origin story.

Bree Jamieson-Holloway: I grew up in southwestern Ontario, in a city called Brantford, surrounded by intergenerational trauma and living in poverty. I was bullied in school. Being mixed race, I was always searching for a community but could never find one. I was either too much of one thing or not enough of another. It’s complicated for a child to manage all that chaos. 

But anybody can overcome adversity, if they have willpower, focus, determination and resilience. 

I was fortunate in that I had two strong women guiding me: my mother and my grandmother. They surrounded me with love. It gave me a strong foundation and moral compass. My grandmother always used to say, “push on regardless,” a motto for my life. No matter how bad it gets, I won’t give up. 

Naomi: With that motto, are you tapping into something? Is there a purpose that pushes you to keep going? 

Bree: I’ve never thought about it beyond the moment. There were times where I didn’t know how I’d get through the day, or the hour, but I’d always say to myself that it’s going to be okay. I don’t know if I understood what it meant as a child but it was the thing you did, that my grandmother had done, that my mother had always done. They were wonderful people so it made sense to me that things were going to be ok. 

As a child, my end goal was to help people and be a mother. Simple. But you can imagine this poor girl, living in a world totally different from the one I’m in now, just knowing that that was what I was put on this earth to do, and I was going to achieve them. 

As you get older your goals become clearer. I’d picture myself walking through the streets of London or Paris — dreaming of a different life, what that felt or sounded or looked like, and what it meant to me. Over time those dreams crystallized. 

To push on and keep going means getting out of my limiting environment to see the world, experience new people, cultures and life from a different perspective.  

Naomi: My mentor says that you have to see beyond the circumstances of your current situation. Visualization activates your senses so you can navigate your dreams as though they’re your reality. I encourage people to do this, because I did the same thing. 

Before moving to New York, I would lie down and think about walking through the streets of Harlem, being on campus, going to coffee shops. You mentioned London, but you’ve also spent time in Hong Kong. What drew you to go abroad?  

Bree: It comes back to the dreams I had as a child, of taking myself out of the confines of my socioeconomic status. I can’t tell you how many times people said that, statistically speaking, I’m not going to be successful. On the other side were people who said I can do anything I put my mind to, and that’s what I chose to listen to. 

It’s all about what you choose to hear, and what you choose to embody.

Experiencing the world was a powerful opportunity. It gave me a stronger toolkit when I came back home, to empower myself and grow. I had to break through a lot of fear to go on that adventure. The dreams were done. I had to make them real. 

Naomi: How have your experiences informed how you run your business?

Bree: Growing up, I knew I wanted to help people, to be a mom. To avoid living in poverty, being a doctor or a lawyer were the only two options that I knew were available to me. I was terrible at math. I didn’t see myself becoming a doctor, so I became a lawyer instead — and somehow became a corporate finance lawyer.

I ended up in the UK through a scholarship from the University of Ottawa, and that’s where I experienced business and entrepreneurship. Originally I wanted to be a human rights lawyer. Coming from a very poor background I had huge student debt to pay off. Law was an opportunity to help people, use my voice and stabilize myself financially. 

I studied business and entrepreneurship and found it incredibly interesting, but I felt ashamed for switching to corporate law to pay my loans off. But then I got into corporate law and realized there were few people who looked or sounded or identified like me. All of a sudden I’m forging a path for more representation. 

I can also help people build their lives from a business standpoint, so entrepreneurs can support their families and achieve their dreams. No path is a straight line, and I will always find ways to help people. 

I came back to Canada after my first daughter was born with my husband, who’s British. I was trying to find a law firm that spoke to my values and I couldn’t. At the forefront for me was diversity, equity and inclusion. 

I was pregnant with my second child and needed flexibility. So I just went for it and created Jamieson Law. It became something really special. We’re a firm of all women — not by design, it just happened that way. We’re diverse. We champion DEI and help our clients develop policies and strategies that support it. 

Diversity benefits businesses. It positively impacts their bottom line. 

Our approach adds a lot more value than just legal advice. 

Naomi: How have you transitioned from heading your own firm in the private sector to your new role as Vice Chairperson of the Canadian International Trade Tribunal? 

Bree: It was the hardest decision I’ve ever had to make in my career, but also the easiest. It’s hard to give up something where your team is so in sync with complete honesty, trust and transparency. That only exists with a lot of effort, compassion, empathy and understanding. It’s a huge achievement in and of itself. Saying goodbye was difficult, not just for me.

I talked to my team openly about this opportunity, and we shared what it meant for all of us. This choice will help me make a positive impact on a bigger scale for Canadians, but what does it mean for my team, for my clients? I worked hard to make sure they gained something to further their journey in a positive way, too. We have a really great plan for our clients. 

The Canadian International Trade tribunal is committed to providing fair access to justice. It’s in line with what matters to me and the team is incredible. 

In a leadership role my diverse perspective can foster an environment where, hopefully, people can see themselves in me, and know that that is an opportunity they can achieve.

Naomi: What does that look like? 

Bree: Access to justice isn’t a new issue. What are the gaps, the blind spots? From a procedural equity standpoint, it’s about things like plain language. Are we taking out the legal jargon so it’s clear what a person’s rights are? Are we adequately guiding them? Are we considering cultural nuances? Are we accessible to people with disabilities? Equity looks different for everybody. 

If we can create a justice system, and a quasi-judicial one as well — administrative tribunals, the courts — where all people understand their rights, know how to access it, and can be guided through the process in a way that is equitable to them, we will move that dial forward. 

This is an issue we need to constantly work on and bring awareness to. To improve this system is what drives me every single day. 

Naomi: To have someone in leadership think about equity at a systemic level is powerful. When did you realize that diversity, equity and inclusion can be part of your life’s work? 

Bree: It’s always been a part of my life. From the moment I was born I lived in the middle of an intersection. From a young age, I knew I had to advocate for it because I didn’t feel like I fit anywhere. That’s a powerful realization for a child. I want to be the representation I wish I had as a young person. 

Naomi: You’re also a mentor to young women entrepreneurs. Do you have any advice for our listeners?  

Bree: With women mentees limiting beliefs like imposter syndrome often come up. I’ve had that and empathize completely. Maybe they don’t see themselves in leadership, or are missing certain experience criteria because that equity didn’t exist when they were younger to give them those opportunities. 

What I always say, and this is something a male mentor taught me when I was younger, is to build a strong foundation. It doesn’t matter what age you are, where you come from, what language you speak, what your beliefs are, what color your skin is. Believe in yourself, be resilient and you’ll build a foundation so solid that nothing can shake it. 

You must understand who you are and what you are setting out to achieve. Then you can take those steps forward, big and small. These steps aren’t clear cut. Sometimes you’ll take a massive leap and other times you’ll wake up and say “I need to stay in bed today.” That’s still you stepping into your power. 

With an unshakeable foundation you will inevitably achieve your goals. You know who you are, where you come from, what matters to you, who your support system is, and what your priorities are — and you won’t sweat the small stuff. 

It’s not about other people knowing you. It’s about you knowing yourself. Anything is possible, you just have to push on regardless.

Naomi: How have small steps moved the needle in your life? 

Bree: Some days I’m taking baby steps, or no steps, and other days I’m taking huge leaps and big risks. It depends on how I’m feeling and what my capacity is. Challenges push me to find my power, even if it means taking a step backwards: because that doesn’t mean you’ve failed. Sometimes you need to regroup, to pause. 

I am not going to feel guilty. I am going to rest because that’s what my body needs. You’ve got to take care of yourself. Recognizing that is huge. To push on regardless doesn’t mean not feeling your feelings or not being connected to your humaneness. It just means not giving up. 

Naomi: What are some of the best investments you’ve ever made? It doesn’t have to be financial, it can be something you’ve done for yourself. 

Bree: Believing in myself from a young age, despite everything. In 2004, spending $632 on a flight to England even though I was in university, on OSAP and working two jobs. It was a lot of money but I was ready to turn my dream into a reality, to actualize the person I knew I could be. 

I saw my worth. It was the greatest financial investment I’ve ever made. It brought me my career, my wonderful husband and my four beautiful children. I am grateful for that every single day.

Naomi: What are some things that you’re curious about? 

Bree: My biggest curiosity has always been people. I’m curious about their identity, to the extent that they’re willing to share with me. I’m curious about what drives them. It’s the key to finding out what changes people want and what changes need to be made as a collective to move that dial.

Naomi: Is there anything happening in the world that you’re keeping an eye out for? 

Bree: Diversity, equity and inclusion and access to justice are in the back of my mind in everything that I do. I’m always listening, trying to keep my pulse on how people are feeling, what people are talking about. I have my perspective and my lived experience, but there’s so much out there. 

When you really tune in and listen, you get to hear things that open your mind. That knowledge is powerful. 

Naomi: For folks interested in these things, what are your trusted sources? 

Bree: I don’t follow specific sources. It’s about looking broader. I’ll read tiny articles in obscure publications because this person’s perspective is so unique. I love podcasts. Friends and people in my network will often suggest publications or writers or audio books. 

That’s another great way to educate yourself, because the people around you understand who you are and what’s important to you. So if they’re willing to share that information I take it seriously. 

Connect with Bree

LinkedIn – Bree Jamieson-Holloway

About the Power of Why Host, Naomi Haile

headshot of Naomi Haile, wearing a white sweater

An intrapreneur, consultant, and interviewer.

Naomi Haile is curious about people, their paths and what drives them. In 2017, she launched the Power of Why Podcast. Her guests have taken the non-linear path in business, venture capital and other creative professions to share their story. Each episode explores people’s philosophy on life and work.

As we all navigate our lives and careers, Naomi hopes that everyone she connects with – guests and listeners – can shape products, companies, and communities of impact.

Naomi is a consultant at QuakeLab. She recently graduated from Columbia University, studying Human Capital Management.

In support of its Women Founders and Owners strategy, Invest Ottawa offers programs and services that enable and accelerate the growth and success of women entrepreneurs from every walk of life. Visit www.investottawa.ca/women to learn more!

Invest Ottawa
Invest Ottawa, is Ottawa’s leading economic development agency for fostering the advancement of the region's globally competitive knowledge-based institutions and industries. Invest Ottawa delivers its economic development services through a unique partnership with the City of Ottawa, where the City and Invest Ottawa, through its members set the strategy and manage the programs that move Ottawa’s economy forward. Invest Ottawa is a non-profit, partnership organization that operates on an annual budget that comes from a variety of sources including: municipal, federal and provincial government; membership fees; professional development programs; and private sector contributions.

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