Boyd Benjamin comes from a long line of Gwich'in fiddlers in the North and is widely known for his musical talent, but when he was growing up he had loftier dreams.

"One of the things that I wanted was to become a pilot, that was first and foremost," said Benjamin, who grew up in Old Crow, Yukon, where planes had a major role.

 "Yeah we can be First Nations people and we can live and work amongst the rest of the people." - Boyd Benjamin

"It's a fly-in only community, which means the runway runs parallel to the town," he said. "I can hear planes taking off and landing."

That's when his obsession with flying began.

"I never let that pass me by."

From medevac pilot to Air Canada

On top of performing and mentoring youth, Benjamin has been flying for over 10 years now, most recently with Whitehorse based Alkan Air where he spent several years as an on-call air ambulance pilot.

But recently, he landed a pilot gig with one of Canada's largest airlines — Air Canada.

Boyd Benjamin

Benjamin on an Alkan Air plane where he's worked since 2009, mostly as a medevac pilot. (Submitted by Boyd Benjamin)

"One of the reasons why I chose a company like Air Canada … was because it would make a bigger statement for me… to work for a company that bears the national flag," said Benjamin.

"This is a good way for me to say to people in our country, that yeah, we can be First Nations people and we can live and work amongst the rest of the people."

He says he hopes that this new adventure can help show northern youth that "we can work together successfully, in a positive way and still hanging on to who you are — realizing it, and embracing it."

Off to Toronto

On Monday, Benjamin starts training with Air Canada Jazz, a fleet that provides services to smaller communities across the country.

"Mostly excited," said Benjamin about how he feels. "And also, I'm a little nervous."

Boyd Benjamin

Benjamin is a performer, an inspirational speaker and a mentor for Northern youth. Now he's a pilot for a national airline, which he says was a childhood dream coming true. (Gary Bremner)

But he recalled a statement he made during his TED Talk a few years back: "It's OK to step out of your comfort zone and make yourself feel uncomfortable."

"If I'm going to stand on a stage and say that to people, I better do that myself."

Benjamin said he'll be sure to take his fiddle with him to Toronto for training, where he'll find out where he'll be stationed for work.

"I can jam somewhere, whatever city I end up in," he said.

"I'm sure there's a little pub somewhere with local musicians and live music. I can get involved again and do what I do here, but only there."

With files from Leonard Linklater