Until an autumn day in 1998, I was headed along a well-travelled path, but, on that day, I was diverted. Three years out of the University of Toronto’s storied law faculty, I was employed as a junior associate at a downtown law firm—a civil litigation boutique with an odd mixture of specialties ranging from defamation to maritime law, from insurance to aviation. I was in my office, on the 21st floor of a ziggurat-like tower at Yonge and Queen, sending out e-mails to my colleagues soliciting work. I had just finished assisting a partner in a constitutional case at the Ontario Court of Appeal, and for the first time since joining the firm, I didn’t have much on my plate.

The phone rang. Would I come to the interior conference room, the one with the ugly pastels? There, looking sheepish, were two of my favourite partners: a courtly aviation specialist, a Louisiana native who always wore a fedora outside; and one of the firm’s few senior female lawyers, a soft-spoken Scottish-Canadian. At once, I knew what was coming, why I had no work. I was about to be fired.

They sat me down and said that after a strong start at the firm, I’d apparently lost my drive. I was billing too few hours. I didn’t seem happy. I sometimes didn’t give the impression of wanting to learn. The worst of it was that everything they said was true. I had been miserable for at least a year. I hated beginning my day by finding a nasty e-mail in my inbox (sent at 1:28 a.m.) or a vicious phone message from another lawyer (left at 2:25 a.m.). I despised being on my feet in front of rude, overworked judges. I had such bad performance anxiety that quite often, just prior to a court appearance, I’d excuse myself, go to the washroom and vomit.

The summer before my dismissal, I’d taken a three-month unpaid leave of absence to put on a play—what is known in the trade as a CLM, a career-limiting move. On extremely trying days at the office, I’d think of W. B. Yeats’s dictum, “Too long a sacrifice can make a stone of the heart,” and pray not to turn into the listless drone with “Carpe Diem” as his screen saver. In various moments of deep despair, I had drafted but not sent multiple incendiary resignation letters. Though the shame of being fired was almost unbearable, deep down I was relieved.

The partners offered me an adequate severance package, decent, if tepid, references, and the promise to help me in any way they could. But this job, this phase of my life, was over. So this is how it feels, I thought, staring dully at an ugly abstract painting on the wall. So this, at last, is failure. Firing happened to other people, not to people like me. I excused myself politely and went home.

My friends and family thought I should try for another job in the field. And I’m sure I could have found one. I had decent marks, solid experience, good connections. But I couldn’t stand the idea of interviewing at another firm, trying to convince them that I wanted a job. I didn’t. I wanted out.

And so I shifted from the respectable, besuited profession of law into the relatively disreputable, turtlenecked trade of journalism. Some of my friends were bewildered, others filled with pity. But a few seemed envious.