For David FitzGerald ’05, the path from high school to career was anything but linear—and that’s exactly the point.

“I’ve been on what I would call an interesting path,” he says. “Almost a balancing act between passion and what I’m supposed to be doing.”

At Collingwood, music was a central part of David’s identity. But like many students approaching graduation, he also felt the pull toward more conventional definitions of success. That tension would shape the early stages of his journey.

After graduating, David initially pursued music in university, then pivoted to business, eventually building a career in private lending and commercial real estate. Over five years, he developed the skills, confidence, and discipline needed to succeed in a highly competitive industry… but something was still missing.

“I had unfinished business in the music world,” he reflects.

That realization led him back to the creative world, where he studied audio engineering and immersed himself in the industry from a new perspective. Working in studios and collaborating with artists, David approached music differently the second time around, applying the strategic mindset and work ethic he had developed in business.

“I was able to approach things in a more objective, strategic way,” he explains. “And having success in real estate gave me the confidence to go into a completely different space and figure it out.”

His journey eventually took him to Australia before returning to Vancouver, where another pivot awaited. This time, David found himself in recruitment, an industry he hadn’t initially set out to enter, but one that ultimately brings his diverse experiences together at the intersection of people, performance, and proactivity.

Today, as the founder of Starboard Recruitment, David works with organizations ranging from early-stage startups to global companies, helping them navigate growth and build strong teams.

“In a lot of ways, I kind of found myself in recruitment almost by accident,” he says. “But when you look back, it all makes a lot more sense.”

That ability to navigate uncertainty—and even lean into it—has been a defining theme throughout his career.

I’ve been thrown into a lot of situations where I’ve had to be uncomfortable and figure things out. It’s almost like training; learning how to navigate uncertainty and find a path forward.

Looking back, David sees each chapter, music, real estate, and entrepreneurship, not as disconnected pathways, but as essential pieces of a larger story that led him to his current position.

“All these experiences do eventually tie together,” he says. “They make a whole lot more sense if you just keep putting one step in front of the other.”

For current students and recent graduates, his advice is simple, but deeply earned:

Trust your gut. You’re going to make mistakes no matter what, but that’s how you learn to trust yourself.

He also emphasizes the importance of environment and community over immediate outcomes.

“I’ve taken jobs with less pay to work in a better environment,” he says. “Surrounding yourself with the right people is more important than financial gain, especially in your 20s.”

At Collingwood, David found a place that encouraged exploration across disciplines. Something that, at its core, would quietly shape his willingness to take risks later on.

There was a platform to experience so many different things, sports, service, arts, music, and there was a lot of support from teachers.

That support proved pivotal. At one point, David hesitated to pursue music, unsure if it was the “right” path, until a teacher encouraged him to take the leap. “That was very influential,” he says.

David’s journey is a reminder that careers aren’t always built in straight lines—and that growth often comes from the moments that feel the most uncertain.

You don’t have to have it all figured out. You just have to keep moving forward, trust your instincts, and embrace life’s pivotal changes as moments of reflection. Your path may diverge, but it never truly disconnects.