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,

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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.

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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.

There really was no plan. I guess if I had to articulate some strategy that was in the back of my mind, it probably went something like this: If I can work on a million projects, maybe one of them will take off, and make up for all the busts. Worst case scenario, I could cross them off the list, one by one, and never try them again.

So I dove headfirst into my projects. I got active on social media & created a Facebook Page for my firm; started regularly contributing to online forums; opened accounts with Vine and Youtube and started posting videos; launched a personal website/blog; created affiliate links and Google ads; and added an email capture pop-up and began building a list on Mailchimp. There’s probably more that I can’t even remember now. It was a prolific year for me.

But now, looking back, every little thing I did ended up mattering. A lot.

All I needed to do first was get started. In those early days, I spent a lot of time looking things up before launching anything. Most of the articles I researched had to do with how to set up your website and build traffic, so that’s what I focused on. It was almost as if the content itself was an afterthought.

But really, getting website traffic has very little to do with whether you use Wordpress or Medium or Blogger, or whatever. It has nothing to do with the cleverly named page names and keywords that I once thought were super important. Instead, it was pretty straightforward.

The best content drives the most traffic.

Looking back it made sense. You can spend a lot of time spinning your wheels to game the Google algorithm (which was responsible for most of website traffic) which may or may not work. But if you make great content people want to read, the “finders” (search engines, aggregators, and links) will take notice. I mean, Google invests a lot of money and resources into finding high quality webpages on the Internet, so they will find you.

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But only if your content is good.

What makes content good? I wasn’t sure, exactly, but I had a hunch it was nothing like the user generated content I’d usually see on Facebook or Instagram. It was all highly curated posts from people showing off. I remember very clearly thinking “this ain’t it.” My favorite posts were those where people shared stories about setbacks or challenges, or exhibited some type of vulnerability. They just seemed more real to me.

Instead, what I saw on social media was completely different. It was all highlight reels. Personally, I felt like it was really having a negative impact on the audience:

One of my major beefs with social media is that no one ever talks about their setbacks … This selective news-sharing is the reason why so many people are depressed. Facebook is full of everyone’s highlight reels. It’s easy to feel like you’re alone in the struggle. (source)

Back then I really only used Facebook, but I imagine it was the same on Instagram and other platforms too. It was something I privately complained about to friends, for years. Deep down inside, I hoped that someday, I’d have the courage to do it differently:

I’m not bold enough to write about my specific problems/issues–perhaps someday I’ll have the courage to write about them and share it on my mailing list. (source)

After my blog started receiving decent traffic, I noticed that most of the traffic was coming to just a handful of posts. The most high quality stuff. There was a common theme among the posts, which was law school admissions for students with bad college grades. Following the advice I’d read online, I decided to start collecting email addresses by putting up a pop-up form on those specific pages.

What people want might surprise you. By building an email list, I started to communicate directly with my audience, and there were a few things that surprised me. For example, I didn’t expect so many of them to be international, from all over the world. But the bigger surprise were the parents.

I’d originally created my content for people like myself—those of us with bad college grades who wanted to go to law school. But instead, parents of teenagers and college-aged students were signing up for my email list. They were worried about their own children, who weren’t doing so well in school, and wanted a blueprint (or maybe just reassurance) that it was still possible for their kids to become lawyers.

I wasn’t sure what to do with this information, or with this audience. But it taught me the importance of having direct conversations with people who love your content because they might be responding to your posts for reasons you didn’t expect. That realization eventually led me to focus on social media—where I could engage directly with my audience—instead of my own website, where I’d have to wait for them to come.

The Practice By mid-2016, my online platform was buzzing. I was receiving a few hundred daily visits to my website and had built up an email list with 1,000+ subscribers. I had added some Google ads and affiliate links, which more than covered my hosting costs and other expenses. The website was profitable.

But my law practice wasn’t doing so hot. I really struggled being a solo, and soon came to a realization: This was not working. Not only because I wasn’t earning very much money. As I later recounted:

[T]here were a lot of downsides. Working as a solo meant I was no longer part of a team. There were long stretches when I didn’t have any prospective clients because it’s REALLY hard to balance sales/marketing with doing the underlying legal work all by yourself. I worried about where revenue would come from next month. I spent an inordinate amount of time researching their problem only to have prospective clients say never mind, I actually realized that I don’t need a lawyer. I was glad that they figured it out, but wish that I hadn’t spent all that time doing so much work. (source)

So I learned that I didn’t want to be a solo practitioner. But I couldn’t continue practicing law. I had to close the practice. Which meant that I needed to once again Figure Out What To Do With My Life.

This was a very strange time for me. I spent the next few months with nothing on my plate. I wanted to make sure to avoid the mistake I made a year ago, right after I got fired. In retrospect, I shouldn’t have rushed to my next thing. Opening a solo practice wasn’t the right move for me, and maybe I could have avoided it by taking a break.

So this time I vowed not to make the same mistake again. So I ended up spending a lot of time with friends and family. Since I had some extra time, I also spent a lot of time doing something completely new. I started playing around with making videos.

There is something uniquely compelling about video content. I’ve always been a text-first person—I enjoy reading/writing and consume information through books rather than TV. But for some reason, I decided to dabble in video-making.

I can’t remember what my first video was, exactly, but I remember trying a bunch of different concepts. Months ago, I had signed up for Vine, the now-defunct video platform that predated Tik Tok. I recorded videos of random moments, with no real plot behind them. You could only make really short videos which was pretty limiting. That led me to try out Youtube. Here’s an example of one of my first videos:

Over the next few weeks I made more of these. I had no idea what I was doing, but they were fun to make. I also would bring a camera with me whenever I spent time with my family, and turn the footage into a little story.

I barely got any views but I really enjoyed the process of making them. And people (at least those who watched them) thought they were funny.

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I noticed that there seemed to be a much stronger reaction to my videos, these 25-second long pointless sketches. Especially when you compared them to the lengthy blog posts that I loved writing but no one seemed to care about.

I never imagined how important that lesson was, and how it would impact my decision to start trying video content on Tik Tok during the pandemic, many years later.

By the end of the summer 2016, I was getting restless. Not just because I hadn’t worked in the weeks after I shut down my practice. I mean, I really felt like I needed to rebuild my confidence. I thought it would be nice to get a steady paycheck again too. But the real priority, what I really needed—was momentum.

Years ago, I learned that after encountering failure, it was super important for me to do *something* to regain my confidence. There was some precedent for this: Years ago after I failed the bar exam, I won back my confidence by running the Chicago Marathon.

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I’ve found that when you come off failures or setbacks, it affects how you think about future goals, and not in a good way. I needed to get back on track because this was my self perception:

I now feel like I’m currently on a losing streak. This latest move to become a solo practitioner failed. It is tempting to become more careful. More risk averse. More timid. I used to be proud that I took more risks than most lawyers with my background. Usually my risks worked out, and I saw myself as a successful person. Since then, my self-perception has changed. I sometimes see myself as a failure. That’s the worst part. (source)

So I needed to find work. Something. Somewhere, where I could have some modest success and get my head back in the game.

Modest success. That’s all I needed. I mean, when I graduated from law school in 2010, things were so different. The world was my oyster. I had a great firm job lined up, a great legal resume, and a lot of promise. I remember my friends telling me that they had high hopes for my future, and predicted that I would be the most successful out of all of them—all because of what I was able to accomplish in law school. Now I was just searching for some small, modest success. During a moment of self awareness, I wrote:

Looking at my peers’ LinkedIn updates in the next few years will be challenging. (source)

No matter. I just needed to put one foot in front of the other. So at the age of thirty three, six years after getting my J.D. from a “Top 14” school, where I was a law review editor and its graduation speaker, I started interviewing for entry level jobs.

Little did I know, that next job would change everything.

Thanks for reading! Stay tuned for Part 3 where I’ll share what that next job was, how I found it, and what it was really like to go back on the job market. Subscribe if you’d like to follow along!

1. There’s another story I’ll write about someday, about John Quinn, the founder of Quinn Emanuel, leaving Cravath to go solo after spending a few years as an associate. He later built his early client base by cold calling in-house counsel. It’s a pretty inspiring story.

2. I later ran the numbers and here’s how unprofitable that year as a solo was: I could have spent that time doing low paying contract document review work and taking lots of time off. That would have earned me a lot more money than what I ended up doing.

3. Qualifier: I’m not sure how true this is anymore given what I’ve read about Google prioritizing ads instead of quality organic content. But that’s the lesson, right? Algorithms change, but they will always prioritize quality. The success of Tik Tok really comes from its algorithm and how good it is at finding & surfacing great content to its users. Quality content is timeless.

4. I especially enjoyed making this minute long video comparing my jump shot to Ray Allen and Steph Curry’s. I still share this one with people.

5. I’m not a runner, and hate long distance running. Chicago was the first and only marathon I’ve ever run.