How My Failed Solo Practice Set Me Up For Success Years Later

The upside of having free time to try side projects with no end goals

I really never expected to have this much success on social media. But I was lucky and have been able to ride the right tailwinds. Like when the pandemic hit, I was in the right place at the right time, with all the necessary skills in place. I knew exactly how to create compelling content that could quickly build a community through social media. I was incredibly lucky to be positioned the way I was right as the world shut down and everyone moved online.

But here’s the thing that I’ll always remember: None of it would’ve been possible if I hadn’t gone through my Year In The Wilderness. Which happened right around the time I opened my solo law practice after getting fired from my law firm job in the summer of 2015.

There were a few factors that led me to hang a shingle. As I’ve mentioned before, I’d spent years reading obsessively about prominent lawyers and how they made it big. They all took risks, or went off the beaten path. I knew going solo would be a big risk, and feel different and scary. But armed with the knowledge that it worked for others,¹ I plunged right in.

Well. I tried to at least. Being a solo is hard enough as it is. It’s not just about making a website and setting up bank accounts. There are more existential questions you’ve got to answer. Like what should you be working on? Where do you find clients? Should you specialize?

I felt like I had an even tougher job. Because I hadn’t been admitted to the California Bar yet. I was five years out of law school, with big time litigation experience under my belt, and already passed two bar exams, including California, where I lived. So I got started by doing some work, remotely (before it was cool) for friends & family in New York.

As you can imagine, it was hard to find paying clients. Everyone had problems, but few were able to afford to pay me. I went from making six figures as a law firm employee to making absolutely nothing in just a few weeks.² Some part of me felt like I’d made a huge mistake.

But there was some good news. Because I had no clients, no commute, and no busy work to do, I had a lot of free time. Which let me work on side projects with no concrete goals.