I was working five jobs. Driving all across Calgary. 50, 60, 70 hours a week. Falling behind on mortgage payments. Falling behind on utilities.

And I still couldn’t make ends meet.

2011 started with my investment portfolio completely dried up. I knew I had to make an income—so I started taking on work I would normally never touch. I worked in retail for six months. The working conditions in all five jobs? They sucked.

In some cases, I had to fight for safer, more wholesome working conditions. In other cases, I had to fight for the money I was owed—because employers made promises they wouldn’t keep without prompting.

I’d have a good week here and there when unexpected money came in. Then another stretch of really bad weeks.

I tried reasoning with my bosses: “If you just gave me more hours here, I could let go of this contract over there.” None of them would listen. They were worried about me burning out. But I was already working five jobs, driving all over the city, 50, 60, 70 hours a week. And they were unwilling to budge.

If that wasn’t bad enough, I was living with the worst roommate I’d ever had. He had this weird all-or-nothing thinking about his career—apparently, he had an engineering degree, but his solution to making an income was either “I’ve got to become a male stripper, or I’ve got to go work on the oil rigs.” He did end up in jail, by the way.

I hated having him around. I didn’t even want to go home most of the time. It was supposed to be my sanctuary. Instead, I refused to go home. I’d go to open mics, play gigs, rehearsals—anything to spend less time at home.

And that was just the first half of 2011.

In this post (and video), I share what happened during one of the hardest seasons of my life—and what came next.