Five years ago, Keegan Matheson stood up, shredded the papers on his desk and walked away from his banking job in the middle of the day.

He didn't know where he was going.

But, as he talked to his father on the phone, his feet took him down to the Halifax waterfront where he spent the next couple of hours nursing a few Keith's and listening to a busker pull Bob Dylan out of his guitar.

"I sat there and calmed down and kept convincing myself that it would be OK," he says. "There's always the worry that you've made the wrong decision, but at the same time it was exciting because that was the moment where things really shifted for me. And I knew that, for better or for worse, it was the start of something."

By the time his last pint glass went dry, Matheson had decided to become a baseball writer.

A throwback to his younger days, when Matheson and his grandfather went to see the Blue Jays play in Toronto. (Submitted by Keegan Matheson)

Covering the Jays

At 28, he's on the Blue Jays beat. When his team's playing, Matheson can expect to wake up to at least one request for a radio or TV hit. And later you'll likely find him in the press box reporting for Baseball Toronto, the independent online publication he created after finishing up a contract with MLB.com.

Hard work, talent, education and a degree of luck and privilege have seen him through the time since his Office Space moment.

But there's something about Matheson's path that resonates for so many; the risk taker who succeeds against the odds. It makes us dust off our own dreams and wonder, could we make this happen?

Matheson has been fielding that question often in the last few weeks, thanks to a visit home to Nova Scotia this fall that took him back to the same place he'd contemplated his future at 23.

Five year ago today, I stood up from my desk in the middle of the day at my bank job and walked out.<br><br>I walked to the water, sat in this exact spot, drank two Alexander Keith's, and decided to become a baseball writer. <a href="https://t.co/LA7WbctyMc">pic.twitter.com/LA7WbctyMc</a> —@KeeganMatheson

The tweet he shared of that moment has been liked 1,900 times, with dozens of people responding to his courage with stories of their own.

"It's been amazing to see the response," he says. "I've had a lot of direct messages and people asking for advice, for advice about their own job. And my first reaction is: don't ask me for advice. Mine is not the life to model one's own after."

Keegan Matheson did what people who hate their jobs everywhere want to do: he walked out in the middle of the day and decided to pursue his passion. (Submitted by Keegan Matheson)

Being young and kid- and mortgage-free made it easier to take the risk, he says. And he took a second job while he established himself, blogging about baseball at dusk and at dawn while paying his bills through a landscaping gig.

At home in New Glasgow, he found plenty of support for his decision but few role models. By the time he moved to Toronto to pursue a sportswriting diploma, he could support himself though his writing.

'Things have changed'

Matheson doesn't often let himself think about the fact that he's done what he wanted. So much so that he's able to work for himself, one year into an online publication whose subscribers are "in the high hundreds."

It only really hits him when he's in place and can see it from a new vantage point — walking onto the field in Fenway Park for the first time.

"You're up in the press box or you're down on the field and you have a different view. It's moments like that where I look around and say, 'OK, things have changed,'" he says. "But I try not to, because I feel like if I do that too much, it will slip away."