In recognition of Mental Health Month, we sat down with Jackie Dinsmore, Managing Partner of Caravel Law, to talk about her career arc, burnout, balance, and what it really takes to build a legal career you can sustain. 

Section 1: Background in Law

Jackie’s interest in law took root long before law school. It was growing up with a deaf aunt and uncle that made her keenly aware of the inaccessibility the community faced. Law became an avenue through which Jackie imagined herself challenging and dismantling these barriers. Her original goal was to become a lawyer who could sign and advocate for a community that was too often overlooked.

But, as Jackie explained, “life happens” and when a summer offer from Bay Street rolled in her father explained to Jackie why she’d be crazy to turn it down. He wasn’t wrong — it reshaped her path entirely. But the original spark never faded: 

“That opportunity changed the trajectory of my career and exposed me to a world of law I hadn’t fully imagined—but the original motivation, the desire to help and to make the system fairer, never really left me.” 

As you built your practice, how did your picture of a legal career change — for better and worse? 

When asked this, Jackie explained she entered law school with what she called a “save the world” mentality, drawn to underserved communities and the people who most needed an advocate. What she hadn’t anticipated was the emotional toll of that work — or the scarcity of sustainable jobs in those areas. She was soon pulled into corporate law on Bay Street, where the mood was lighter: deals closed, corks popped, and the heavy emotional weight of family or child-protection work simply wasn’t there in the same way. 

“The trade-off, of course, was meaning versus sustainability. Corporate law offered structure, compensation, and predictability—but it also required letting go of some of that early idealism.”  

That trade-off was not a singular, career shaping moment. Jackie revisited and redefined this “give and take” several times across her career, and continues to.

Were there early moments where the profession weighed on your well-being? 

Jackie’s answer came without question.  

“When I was on Bay Street, my mother had been diagnosed with Stage 3 breast cancer, and there was real uncertainty about whether she would survive. My mom is my best friend, my confidante, my everything. The idea of working until 3 a.m. night after night while she was fighting for her life was unbearable.” 

Around the same time, a rare four-day-a-week role opened at a large media company— almost unheard of in 2002 — and she landed it against stiff competition. That fifth day became sacred: doctor’s appointments with her mom, presence, and a quiet hope that the flexibility might matter again one day when she had children of her own.  

The reality was less ideal. Jackie soon realized she was still working five or six days a week and only getting paid for four. The pace of the work remained the same, and flexibility seemed to be a false hope.  

“What I wish I had known then was that flexibility without structural support is not true flexibility—it’s just a different kind of pressure.”  

Section 2: Building Caravel with Intention 

Why come back to law through Caravel (then Cognition)?

At the time, Cognition was the talk of the industry — the original pioneer of the flexible legal model, and everyone was watching. Jackie had already left the media company and built a successful handbag business that grew into a children’s clothing line, she felt a pull back to law but her relationship with the profession was complicated.  

“I had one foot in the entrepreneurial world and one foot still firmly planted in legal reality, and it became impossible to ignore how broken the profession was.”  

Caravel was for Jackie exactly what it promises to be for the lawyers she now leads with the firm, a place where law could be done better. The founders invited Jackie in as a third owner to help grow something revolutionary and offered her an opportunity to apply entrepreneurial thinking to a profession that needed it, badly.  

What exactly did Caravel offer that drew you back? 

“Caravel was reimagining law long before “legal tech” became a buzzword. It stripped away unnecessary overhead and bureaucracy, delivering exceptional legal talent at a cost that actually made sense for entrepreneurs and in-house teams. 

From the client side, law had become expensive, impractical and disconnected from real business needs. From the lawyer side, the picture was just as bleak—no flexibility, little autonomy, and a profession that routinely shut the door on its people. Brilliant lawyers were being pushed out, not because they lacked talent, but because the system couldn’t accommodate real life. 

Caravel felt like a solution for both sides of that broken equation.”  

What did you set out to build here for other lawyers? 

Jackie’s answer was groundbreakingly simple: 

“I wanted to create a place where lawyers could do excellent, meaningful work and have some control over their lives. That meant flexibility in the type of work they took on, the volume of work, and the stage of life they were in—without sacrificing quality or ambition.” 

Just as important was a culture people wanted to come back to, paired with best-in-class training in legal technology. 

“When lawyers are energized and supported, clients feel it immediately.” 

What were you adamant about doing differently as a firm leader? 

True balance, as Jackie explains, is key here.  

“Client service and hard work are non-negotiable. That said, I fundamentally rejected the idea that every client needs a lawyer five days a week, forever. Some need three days. Some need coverage for a maternity leave. Some need a year—and then the lawyer can complete that engagement and take a dream trip to Australia. 

Why couldn’t we design a system that met client needs and respected the humanity of the lawyer delivering the work? I never believed this was a pipe dream and Caravel proves it isn’t.”  

What does a sustainable legal practice look like to you?

Jackie’s answer is all about the tools at a lawyers’ disposal. Tech, team, and structure that matches how you want to practice.

“Law will always demand hard work—it attracts people who give 120%. But technology and AI are finally allowing us to remove the mundane, repetitive work that contributes so heavily to burnout. That frees lawyers to focus on complex, interesting, judgment-driven work—the reason most of us went to law school in the first place.

At Caravel, autonomy is key. Lawyers choose their engagements. They are never forced into files that don’t fit. And once an engagement ends, they’re not immediately thrown into the next one. They can take a break, a secondment, or simply reset.

That breathing room is everything—and it’s why our attrition rate is under 5%.”

The proof is in the pudding. Caravel offers a structure that allows lawyers to fall back in love with their careers.

Where do you find balance in your own life? 

“I believe deeply in working hard and playing hard—there’s room for both. It took me years to learn this, but now I live by one rule: book the trip. As Managing Partner, there will always be something urgent. But if you don’t take the trip, one day you may not physically be able to. 

Interestingly, I often look outside the legal profession for inspiration. Other industries have figured this out—so why can’t we? At Caravel, we believe lawyers can.” 

Can you tell us about Caravel’s informal returnship program? 

“Too many lawyers—especially women—step away to raise families and find the door slammed shut when they try to return. The assumption is that time away equals irrelevance. It’s heartbreaking and completely wrong.”  

These are exceptional people who took on one of the hardest, most meaningful roles there is — parenthood. Caravel doesn’t treat that as a liability. 

“Watching lawyers return, rebuild confidence, and thrive again—on terms that work for their families—is one of the most rewarding parts of what we do.” 

Section 3: The Future of Practice 

How has mental health culture shifted in law? 

For decades, she says, mental health in law was simply ignored. 

“The message was simple: suck it up… Thankfully, that mindset is changing.  

The shift away from pure billable-hour thinking toward value-based models is a huge step forward. When worth isn’t measured solely by time, lawyers can become healthier humans. 

We still have a long way to go—but progressive firms are showing what’s possible.” 

What would you say to a lawyer feeling burnt out right now? 

“There is light at the end of the tunnel. You can take the maternity leave. You can work three days a week. You can choose your clients. You can take the vacation. You can show up for your life and still have a meaningful, ambitious career. 

Working hard and living fully are not opposites. Just make sure you do both. 

And yes—join Caravel.” 

While Jackie’s pursuit of advocacy within legal may not have taken the shape the anticipated, she landed there nonetheless. As a leader, mentor, and innovator in the industry, Jackie continues to champion a better way to practice law.  

Interested in learning more about the Caravel model? Connect with us today.