In 2018, I found myself at a crossroads in my career. I was a partner at a litigation boutique and had also been a partner at a fairly large firm, but neither was quite right for me. I hesitated to move to another shop and simply hope that it would turn out better. Then a mentor suggested that I start my own firm. At first, I thought it would be impossible. I didn’t have my own book of business and, if I failed, I didn’t have another way to pay my mortgage.
Then I ran the numbers and I realized that, as a sole practitioner, I could generate far less revenue than I had been and still run a profitable business. I also decided that, with at least another couple decades of practice ahead of me, I was too young to be governed by fear. Even if starting my own firm didn’t work out, I was confident that I would bounce back.
I launched my firm, Book Law, in November 2018. I did bring some files with me, and I soon realized that I had previously underappreciated the work done by support staff—I spent much of the first week preparing, serving and filing notices of change of lawyer. I quickly hired a part-time clerk to help with administrative work. Early on, I also had to retain other lawyers to help me on certain files that were too large or too urgent for me to do alone. It became clear that I had two choices: restrict the complexity and volume of my caseload or hire more people. I love complex litigation, so I chose the latter.
My initial concern—that I’d struggle to bring in enough business—never materialized. I actually ended up liking the business development side of having the firm almost as much as I like litigating. To paraphrase one of my mentors: I eat lunch every day, and I’m happy to eat it with someone interesting who might have a file for me. There was also something special about helping clients who had specifically chosen me to represent them. Somehow, files kept turning up when I needed them.
Best of all, I felt liberated. I made all the decisions. I worked as many or as few hours as I wanted, without guilt or judgment. I took on certain clients because I wanted to help them, even if the files were modest in size. I worked where I wanted, when I wanted, with whom I wanted.
Over time, though, I encountered challenges that caught me by surprise. I wasted dozens of hours, plus many thousands of dollars, attempting to adopt software programs that were supposed to deliver magical time-saving features. Those efforts frequently ended in disappointment. Meanwhile, the countless hours I spent with my bookkeeper trying to figure out why my trust account was off by $0.10—an amount that the Law Society insisted I couldn’t write off—gave me a new appreciation for sole practitioners and small-firm owners who sometimes complain about over-regulation.
Another major challenge was the HR side of the operation. A law firm’s greatest asset is its people. When I started my firm, I wanted it to be a great place to work, where everyone was treated with respect and could develop into their full potential. It’s far more difficult than you might expect, however, to build and manage a positive workplace. First, you have to hire terrific people, but a lot of lawyers and clerks are reluctant to join a startup that lacks a proven history of success. Then you have to retain those people, who will rightly demand clear workplace policies, thoughtful on-the-job training, mentorship and ample vacation time. Even if you offer all that, turnover is still inevitable. People end up leaving for a variety of reasons—to move to another city, to pursue another area of practice—and I often found myself having to pick up the extra work until I could find and train replacements.
A few years after I launched my firm, I spoke to the same mentor who had nudged me down that path. After I described my various problems, she proposed a new idea: that I join an established firm. I protested. Wouldn’t I lose my independence? To which she replied: “Are you really independent now?” I wasn’t. I could barely take time off. And even though I (usually) made more money while billing fewer hours than I had at my prior firms, my days were full of non-billable tasks that I rarely enjoyed. Overall, I was working more than ever.
I was reluctant to join another firm, but in 2025, I made the decision to join a litigation boutique that I liked a lot: Affleck Greene McMurtry LLP. I’d known the managing partner, Michael Binetti, for years, and we got along well. I had sublet space from AGM for a while when I had my own firm, so I also knew most of the other lawyers and staff, and I felt that the firm had a good vibe. We went through a thorough due diligence process on both sides and decided we would be a good fit for each other. I’ve now been at AGM for about a year. Without a doubt, it was the correct decision. It’s lifted a huge weight off my shoulders—in particular, a lot of firm management. At the same time, I haven’t had to compromise on the core values that my partners and I share, including genuinely caring about each other, our colleagues and our clients.
None of this means that I regret having struck out on my own. On the contrary, I’m glad that I did. I learned an incredible amount and gained a lot of confidence. But it’s never too late to change course. I remind myself that everyone has different strengths and weaknesses, different assignments that they prefer and different circumstances, all of which may shift over time. Some lawyers stay at the same firm for their whole careers. Others move around, jumping from private practice to in-house counsel and back again. There is no right or wrong road to follow. What really matters is enjoying the journey.
Hilary Book is a partner at Affleck Greene McMurtry LLP. She specializes in corporate and commercial litigation.