At this year’s Board Governance BootCamp, attendees had the rare opportunity to hear from Canadian business icon Arlene Dickinson during a keynote fireside chat focused on leading with courage. Drawing from nearly four decades of experience in business and entrepreneurship, Dickinson offered a candid and inspiring reflection on what it truly means to act with courage in leadership.
“Courage,” she shared, “is really about understanding that our fears aren’t going anywhere. By addressing them, we put ourselves in a position to overcome them. If we just let ourselves be afraid, we never really get anywhere.”
Dickinson spoke about her personal approach to tackling challenges head-on. “I’ve always believed that if you go right at the thing that’s giving you the most grief, you’ll be far better off than if you put it on a list and let it slip down. I don’t make lists for this reason. I do what’s right in front of me, one step at a time. That’s how I’ve found my courage: by confronting each challenge as it comes, not postponing it because it feels too hard.”
She reflected on the evolution of courage in her own life. “I didn’t lack courage, but I sometimes lacked belief in myself. That belief has grown with age. We get one life and one chance to say the things that matter to us. Now, I realize it’s in the little moments of vulnerability that we find courage. Vulnerability, self-belief, and understanding that it doesn’t matter what others think – what matters is what you think of yourself.”
Dickinson also shared her experiences making unpopular decisions, particularly as a leader and board member. “An unpopular decision can simply be going against the grain. It doesn’t mean your decision is wrong. It just means you’re ready to stand for what you believe, even if everyone else disagrees. I trust my sense of what’s right and wrong, and that has guided me in business and on boards alike.”
She recalled the lessons from her time on *Dragon’s Den*, where she was the only female investor: “I would make choices that everyone else thought
were crazy. But I never listened to them. That experience taught me how to make unpopular decisions and stand by them. In life and on boards, you have to voice your opinion, even if it’s against the majority. Voting with your convictions and not with what others expect is what good leadership means.”
Her advice resonated with the BootCamp audience, many of whom are non-profit leaders navigating complex organizational and societal challenges. Dickinson emphasized that courage is critical not only in business but also in the non-profit sector: “Standing up for what you believe, even when it’s unpopular, is essential. It’s about making decisions in the best interest of your team, organization, or community, even if it’s difficult.”
Her insights reinforced a core theme of the 2025 BootCamp that courageous leadership requires fortitude, self-belief, and the willingness to act, even in the face of fear and uncertainty.