Ambition often gets framed as a relentless climb, fuelled by sacrifice and measured by constant progress.
But women doing cool shit are not just grinding toward the next milestone. They are finding ways to hold ambition and joy at the same time, all while showing up as their authentic selves.
As Dragons’ Den producer Paula Sanderson said, “break up with imposter syndrome. It’s not doing you anything good.”
Throughout their candid 2025 Toast Summit ‘Women Doing Cool Shit’ conversation, Sanderson, Swati Matta, Head of Women’s Health at Dialogue; and Michelle Bourgeois, partner at PwC, returned to a simple but often overlooked idea. In the midst of pursuing hard goals, taking risks, and managing burnout, there has to be space for personal fulfillment.
Joy does not cancel out ambition. It sustains it.
The panel, moderated by Chris McMartin of the Scotiabank Women Initiative, explored the realities of building careers, navigating leadership, and pushing for greater equity. But beneath the strategies and stories was a deeper call: to stop defining success solely by external milestones and to recognize the value of enjoying the work and the people you do it with.
Hosted for the first time in Toronto by Toast, a membership-based collective focused on getting more women hired, supported, and promoted in tech, the Toast Summit brought together women in tech, allies, and leaders for a full day of candid conversations.
Reclaiming space by rewriting the narrative
While confidence was a recurring theme, none of the panellists offered hollow encouragement. Instead, they shared concrete moments of growth.
Matta recalled pitching her first company and delivering a bare-bones introduction, only to be told by an investor that she was underselling herself. When the same investor reintroduced her using the full scope of her experience and skills, Matta said she barely recognized the version of herself he described, but it helped her see what she had been leaving out.
The habit of downplaying impact isn’t just individual, the panel agreed. It’s systemic and cultural. “Institutionalized imposter syndrome” is how Sanderson described it, pointing to the way Canadian politeness can keep women from claiming the spotlight. Bourgeois noted that over-indexing on kindness and waiting your turn can prevent even the most talented women from being seen.
“You might not think you’re doing something cool, but other people do,” said Sanderson. “So just own it,”
One antidote, the panelists agreed, is storytelling. At Dragons’ Den, Sanderson said the difference between a forgettable pitch and a winning one often comes down to how well the person behind the product can tell their story.
“You just know when you feel that spark,” she said. “It’s not the horse, it’s the jockey.” Being able to share the full picture of who you are and what drives you matters, and often, women leave out some of their most defining qualities for fear they’ll be perceived as less committed, especially when those qualities are personal.
As Matta put it, “It’s hard to show up with that confidence that if I share that I am a mom, that I’m also 100 percent here and putting everything I got to this project.” But now? She leads with it. She’s found that embracing the full picture of her life has made her more effective, not less.
Amplifying others as a leadership strategy
Throughout the conversation, the speakers emphasized the value of amplification: advocating for other women in rooms where they aren’t present and nominating each other for awards, opportunities, and platforms. Sanderson described a group of friends who gather over wine and laptops to submit each other for awards en masse. “
“It’s a game, and you just have to play it like the boys do it,” she said. “Why aren’t we?”
It’s also about being honest about ambition. Sanderson noted that women often hesitate to apply for Dragons’ Den even when invited. “I’m not ready” is a refrain she hears more often from women than men. It’s why she and her team frame outreach as a conversation, not a commitment. Just applying, she said, can be a game-changer.
Bourgeois added that amplification isn’t only about visibility. It’s also about correcting assumptions. She’s seen women passed over for opportunities because of unspoken expectations about their availability or desire. Bourgeois explains, as an example, saying “[she] has a child, but you know what? She’s amazing at running big projects.”
“That is the kind of amplification to make sure it’s not just the story, but what the people really want for their careers.”
Each of the speakers linked the act of amplifying others to a larger belief in community. Matta reminded the room that the job isn’t just to do cool things: it’s to ensure others are invited in too.
“How do we work together as a community, to help each other be that hype woman for each other…and ensure that when we are out there, we speak for one another, we support each other.”
Failure, joy, and redefining success
On the classic topic of failure, all three women remained candid.
Matta spoke about a consulting job early in her career where she was chastised for speaking up in a meeting, by (of all people) another woman leader. It was “a failure of not speaking for myself,” she said. That moment became a defining one in her journey toward building health tech solutions for women, shaped by both the barriers she faced and the kind of leadership she wanted to model.
Bourgeois shared how early career embarrassments taught her what she would and wouldn’t accept from those in positions of power. And Sanderson offered examples of rejection from Dragons’ Den leading to wildly successful pivots by entrepreneurs who used the “no” as motivation.
Even when speaking about burnout, the panelists framed it as part of the cost of doing meaningful work. “A lot of burnout is when you feel like you’re not in control,” said Bourgeois. Taking small steps to reclaim control — whether that means taking the day off, scheduling a massage, or even reframing how you see the work — can help recalibrate perspective.
“If it was easy, anybody would do it,” she said.
Throughout the session, it was clear that joy doesn’t arrive fully formed. It gets built through small moments, supportive communities, and the ability to keep showing up, even on hard days. As Matta summed up, “You could be doing really cool shit, but with jerks, it’s not fun.”
The work matters, but so do the people who make it possible to laugh, reset, and keep going.
Digital Journal is the official media partner for the Toast Summit.
