Like many people I speak with every day, I once held what would be referred to as a dream job. I was a lawyer at one of Bay Street’s elite law firms – one of the so-called Seven Sisters. To the outside world, including my mother, it was a prestigious, enviable position. But much to her dismay, I walked away.
People often ask: why would you leave your dream job?
For me, the moment of truth came just before Christmas one year.
At the time, my now-wife was living in Lithuania. We had a weekly ritual: one cherished phone call. Other than the handwritten letters we exchanged almost daily, this call was our one direct link. It meant everything. And it took effort.
In those days, cell phones weren’t an option, and even landlines were rare in Lithuania. So, every week, my wife would wake early, travel across town, and wait at the home of a family friend who had a phone. I would call at 2 a.m. my time—7 a.m. her time—because that was the only time that fit my relentless work schedule.
Until that week before Christmas.
That week, I didn’t call. I couldn’t. And I knew she was waiting by that phone, wondering what had happened.
So why couldn’t I call? Because I was stuck in a meeting. At 2 a.m. On a financing deal that had to close before year-end. I was the most junior lawyer in the room, surrounded by senior lawyers, none of whom were leaving and all of whom expected me to stay.
That was the moment I realized: this isn’t normal or sustainable. And this definitely isn’t healthy.
So, not long after, I left.
It wasn’t an easy decision. Walking away from a prestigious career, from years of hard work, from what so many people saw as “success,” takes more than just frustration with a situation – it takes conviction. But I did it, and my wife, the woman who waited for that call that never came, supported me every step of the way.
That journey eventually led me to CEO Law, where we’re building something better. A place where lawyers can work at a high level but still have a life. Where clients get top-tier legal services without paying for the overhead of a bloated traditional firm.
We’re not perfect. No system is. But I can tell you one thing with certainty: I’m not calling meetings at 2 a.m. and demanding my lawyers put their jobs before their lives.
My job may have been a “dream job” but it was someone else’s dream, not mine. I am grateful for that moment that helped me realize I needed to move on and create my dream career.
Have you ever had a moment that made you realize something had to change? A moment of truth? Maybe that moment is now?
-Steve