Reflections on a Less-Than-Linear Path in Law


Reflections on a Less-Than-Linear Path in Law

"A career path is rarely a path at all. A more interesting life is usually a more crooked, winding path of missteps, luck and vigorous work. It is almost always a clumsy balance between the things you try to make happen and the things that happen to you."

                     — Tom Freston


I was one of those atypical teenagers who knew exactly what I wanted to do when I grew up. Somewhere in my Law 12 class, I figured it out. I wanted to be a lawyer.

In law school, the trial moot and clinical Law Students’ Legal Advice Program were my favourite parts. I wanted to do, not just read.

I knew a big firm wasn’t for me. While the beautiful shiny offices were enticing, I wanted a small firm where I could dig in, do meaningful and interesting work, and wear jeans and cool shoes to work.

I knew exactly what I wanted. Or at least I thought I did.

I got my summer articling job in an unconventional way: an offer on the spot while I was waiting tables. It was at the cool little firm I had dreamed about. I summered, articled, and became an associate. I was on my way to the career I’d always hoped for.

A few months after I was called to the Bar, my mom was diagnosed with terminal cancer. Seven months after that, so was my dad. My world turned upside down. My firm fired me. My parents died, seven months apart.

I joined another firm and tried to get back on track. There are a lot of reasons why that didn’t work out. After a certain point, I knew it would never work and so did the firm.

I applied for an in-house job, and after months of interviews I was their second choice. When I asked why I didn’t get the job, I was told it was because I had “taken some time off” after I lost my parents, and because I had never been properly mentored. I’m not sure which answer surprised me more.

The same week, I got a call from a law school classmate, offering me a spare office in a space he was going to share with two other sole practitioners. I never wanted to be a sole practitioner. It sounded terrifying. I had no clients, no clue how to run a practice, and no inclination to be my own boss. I also had no alternatives, so I figured I would give it a year and see what happened.

The transition was hard, but the good days were great, and the freedom was even better. It was a lot of learning, and I was grateful to have colleagues around the office to bounce things off.

I eventually got my own space, with the hope of having a few other like-minded lawyers join me. I ended up falling in love with a space far too big, but took the leap and signed the lease.

A funny thing happened. Every person who has taken an office here, with a single exception, has been in the first year of starting their own solo practice or new partnership. At last count, about ten new practices have started here. Friends joked that I was running an accidental lawyer incubator.

With the pandemic came more change. I found myself with four empty offices and needing a plan.  

Out of the pandemic The Lawyer Incubator was born. It is the first of its kind in Canada, though they do exist elsewhere. It gives new solos support, resources, and structured mentorship. It is exciting to be able to take some of what I have learned over the last eight years to help new sole practitioners set up a practice that they are proud of, with the hope that they will all become so successful they will eventually outgrow the space too.

The role of mentor is becoming one of my favourite of all the many hats I wear. As I transition my own practice away from litigation and into a mediation focus, I find myself more comfortable traveling this winding and sometimes unpredictable road.

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