Ten years after I thought I failed

I thought I was drifting, but was actually headed in the right direction

I recently reread an article I wrote almost exactly ten years ago, right before I left the practice of law to join my first legal tech startup.¹ It was a pretty blunt reflection. I had just come off a series of professional setbacks, with the most recent one being shutting down a solo practice I had opened the year before.

Although the article is largely optimistic, the underlying tone was that my pivot was essentially a failure, and that I was now switching to a more enjoyable path. My expectations were low—I thought I was choosing lifestyle over meaning.

What’s clearer to me today, ten years later, is that something else was actually happening. Up until that point, I had chosen work based on perceived status and financial stability. In the summer of 2016, I decided to begin a new chapter where I’d focus on finding work I actually enjoyed.²

What I thought I knew in 2016

In the years leading up to that moment, I had already gone through a few different versions of what I thought my career was supposed to look like. I started out clerking for a federal judge, which was an incredible experience. I thought it would translate well to my role as a litigation associate at Sullivan & Cromwell. On paper, it was about as clear and rewarding a path as you could have.

But even early on, something didn’t quite click. I’ve written publicly about this before, but the underlying problem was that I didn’t feel like I was using my superpowers or building toward anything. Instead, I felt like I was paying my dues, waiting to be someday “chosen” for more significant work.

When I left to join a plaintiffs’ firm, I thought I’d fixed the problem by choosing a smaller organization with less bureaucracy. However, for multiple reasons, that job didn’t work out, and I found myself being let go. That’s when I decided to open my own solo practice.

Owning my own business was the first time I had full control over how I worked. And to be fair, parts of it worked. I enjoyed talking to clients. I liked figuring out how to position my services and generate interest. There were moments where things seemed to come together—but they didn’t last.

What I couldn’t figure out was how to turn all that activity into something financially sustainable. From my 10-year-old article:

I knew I was making a financial sacrifice. And know I said I wasn’t in it for the money. But still. IT SUCKS. In the twelve months that I worked as a solo, I would have generated more profit by working a full-time hourly document review job. I could have taken the most lifestyle-focused legal job and had great hours, earn a good living, and enjoy full medical benefits, matching 401k, etc. And if I was still working in Biglaw? I’d be working hard, sure, but I’d also be making over $300,000 this year. Damn that really hurts just to type out.

At the time, I didn’t think of my solo practice and my law firm jobs as connected experiences. Each one had its own explanation, its own set of circumstances. I could sense what wasn’t working, but I couldn’t quite put my finger on what tied them together.

On my bad days, I told myself that maybe I just wasn’t meant to achieve professional success—that I’d be better off focusing on other parts of life that might make me happier.

Looking back now, that was the wrong narrative.

This is a selfie I took in 2016 when I was interviewing for my first post-law job. At the time, remote video interviews was still a novel concept and I didn’t really have a good setup. So I put up a blanket to cover my messy background and placed the laptop on a laundry basket so the angle would look OK. Crazy a decade later, most of my meetings take place remotely.

The reality of the situation

It took me a long time to see what was actually going on.

In Biglaw, success came from executing careful, detail-oriented tasks as a small part of a larger plan designed by someone much more senior. At the plaintiffs’ firm, there were fewer layers, but what was required day-to-day was similar. And in my own practice, where I had the most control, I couldn’t figure out how to make the economics work.

To be clear, at each step I learned a lot and got better at what was being asked of me. The problem was that my day-to-day was painful. I had to put in an extraordinary amount of effort just to get ordinary results.

It was too exhausting to end up being merely average.

Parts of the job felt right, but none of it carried forward. The more I progressed, the harder it got. I was working, learning, and improving—but it didn’t add up to momentum.

However, there was one thing I wrote back then that I think I got right: My problems stemming from choosing career paths based on how easy it is explain to other people:

Let’s say you just met me and I tell you I’m headed to law school. You might say Oh that’s pretty cool, you’ll have a stable job and make some money. You must be Headed In The Right Direction.

Now you really have no idea whether I’m actually headed in the right direction. I might be taking out hundreds of thousands of dollars in student debt with no serious job prospects. But for the purposes of that conversation, I have successfully convinced you that I’m Headed In The Right Direction without having to expend any real effort explaining how or why . . .

What I didn’t fully grasp then was that my instinct, in 2016 on the heels of a series of setbacks, to then move in a highly uncertain direction—was the best possible decision I could’ve made.³

I needed to stop worrying about explaining to people that I was Headed In The Right Direction.

At the time the “right direction” wasn’t obvious. Me joining a tech startup didn’t look like a step forward. It looked like me drifting. I wasn’t a technical person. I had no sales experience. I didn’t look or act like the other people on the sales team. A well-meaning friend even warned me early on to be prepared to get fired.

But for the first time, I found myself in an environment where the things I was naturally drawn to actually mattered. The things I felt naturally good at—winning over clients, coming up with strategic plans, connecting ideas across multiple parts of the business—were part of the job.⁴

And because of that, something started to feel different. The same instincts that had felt peripheral before started to carry weight. Conversations led to opportunities. Small wins built into larger ones.

It felt easier—and far more sustainable. In retrospect, that was the real difference.

Conclusion

Ten years ago, I was working hard to meet the expectations of the system I was in. Then I stopped trying to map out the “right” path. I didn’t have a clear plan—I just moved toward things that felt interesting, even if they didn’t make much sense on paper.

That meant letting go of the need to justify what I was doing. It meant shedding the burden of forcing myself to stay the course. Ultimately, that’s what helped me creat space to explore what actually made sense.

At the time, I thought I was choosing a “lifestyle” path. Pivoting turned out to be the most important step toward figuring out where I belonged. My takeaway, having lived through the decade that followed, is this:

Sometimes moving forward feels like drifting. But stepping into uncertainty can open doors you didn’t even know were there.⁵

1. Here’s my article on how I found that first legal tech job.

2. A few years ago I wrote an article with a somewhat related theme about how I developed “taste” for digital marketing content during my year as a solo practitioner. Given all the discourse these days around AI replacing white collar work, it seems relevant to point out that developing good taste requires you to explore things you enjoy doing with no end in mind.

3. I shared some of this context in my previous article detailing my personal reasons for making my big career pivot.

4. Here are some examples detailing the experiences/career capital I developed over the years:

• Tactical learnings from my first tech startup and how it led me down the path of social selling

• What I learned at the first legal AI startup I joined back in 2019 when I joined as an early employee

• My experience stumbling into social media fame and the good and bad that came from it

5. I expand on the topic of unknown doors and how to find opportunities in Betting On Yourself