I Cried in My Partner’s Office
And it was the most honest thing I had done in years.
I think it was a Thursday.
It was early evening - already dark out in Toronto in December - and we were getting ready to leave the office for the winter holiday break.
I shut down my computer, walked into my partner’s office, sat down, and cried.
I’d been waiting for this to happen for years. Well, not really waiting. If anything, I’d been doing everything I could to avoid it. But I always knew it was coming.
And, so, when I sat down, and cried, I also said, “I can’t do this anymore.”
My partner didn’t say much, except, “I know.” I am not sure what else there was to say.
At the time, I was a partner in my own firm, billing solid hours, building something that we expected would last - and I was sitting across from my closest professional colleague completely falling apart. The gap between what my life looked like on paper and what it felt like in that moment was so wide that there was no way I could fake it into another year.
We had our conversation, agreed on next steps, and I drove home. I delivered the news to my wife and a couple of my best friends.
And, in that moment I knew that something that had long been ready to end had just, well, ended. I just didn’t know yet what would replace it.
Rewind four years.
We’d just left our old firm to start our own. When we gave notice, they didn’t take it well - the partners asked us to leave immediately, waiving the (what we thought was generous ) notice we’d offered. I understood why. We were taking clients. We were competition now.
But we were doing it. Our own firm. Our names on the door (eventually once we had actual doors). More control, more money, more prestige. This was the thing you worked toward. This was supposed to be the answer.
It wasn’t.
I spent the next four years trying to figure out why it wasn’t the answer. Why more control felt like more weight. Why the prestige felt hollow. Why I was resenting my clients, my partner, my work - and if I’m being honest, my life.
So I quit.
And you know, I thought leaving law would fix it. That the problem was the profession, and if I removed the profession, I’d get myself back.
Wrong again.
There was a bottom lower than the one I’d already hit. And in the process of extricating myself from a profession that I had dedicated so much time, energy and emotion to, I managed to find it.
It was depression, yes. And loneliness. But, it was also more than that - the feeling of actually not knowing who I was without the title. I knew something like this might happen - but I really didn’t anticipate the level to which I felt completely lost, worthless and, if I’m being completely honest here, unmoored from any real meaning.
Which was strange, because on paper I had everything. Forty-something. Successful career. Amazing wife. A healthy daughter. A home. Enough financial runway to walk away and figure it out. By any external measure, I was fine.
I was not fine.
Here’s what I know now, on the other side of it:
Quitting wasn’t the answer to the problem I actually had. The burnout, the depression, the grinding resentment - those weren’t law’s fault. They were signals I had gotten really good at ignoring, pointing to changes I didn’t have the courage to make (yet).
For me, the answer was drastic change inside the work - not escape from it. That’s my story. It isn’t (and shouldn’t be) everyone’s.
But here’s what I think is universal: this problem doesn’t respond to the tools that made you good at law. It’s not a research problem. It’s not a precedent problem. There’s no case to cite, no argument to construct that gets you out of this.
Lawyers - especially good, busy, “successful” ones - are uniquely ill-equipped for this moment. Because everything in your training says: push through, stay analytical, trust the process. Grind it out and you’ll end up where you’re supposed to be.
But what if where you’re supposed to be isn’t where you’re heading?
What if the exhaustion, the missed dinners, the drinking, the partying, the distance you feel from your kids or your wife - what if that’s not the cost of success?
I’d be lying if I said I don’t think about that evening cry-meeting every now and again. In fact, I think about it regularly.
A grown man crying in his partner’s office.
And it only happened because I was, finally, honest with myself.
That’s usually how it starts.
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Excellent. Loved the honesty of this, Jordan. As you say, that's usually how it starts!