How I Found My First Legal Tech Job
I'll also talk about the startups that rejected me, and why I left a $200k/year job on the table
If you recall from my previous posts, I had just spent the last year getting fired from my job and closing down my solo practice. I knew I needed a win to get back on track. Any win, really. So in 2016, I decided to go back on the job market. In this post, I’ll be sharing the ups and downs of that process. I ended up having to choose between two jobs, one of which paid more than double the other. Crazy, I know. But let me give you some background first.
How I ended up here
Before I begin, I want emphasize that there were three things that were super important to me as I entered the job market in 2016. First, whatever job I ended up with had to involve working with people as a core responsibility. Which would make it different than all my previous jobs. In the past I’d always optimized for money, and all of my jobs involved trivial amounts of person-to-person interaction.
Which made me miserable, and reduced the odds that I’d thrive. I always felt like I had to pretend to be someone else at work. As I wrote in 2016:
Looking back at my own job history, for all my big talk on following your passion, I’ve usually chosen the job that pays the most . . . I think the main reason why people are unhappy with their jobs is that people are forced to recreate themselves into this “ideal” employee personality. (source)
Second, I wanted to make sure I stayed in the legal industry. Not because it would be a “waste” of my J.D. to do something unrelated to law necessarily. But because I thought staying in the same field would give me competitive advantages by leveraging my resume, contacts, and experience.1 I did rule out practicing law though, because I just felt like it wasn’t right for me.2
Third, no job was too small for me. I knew I was making a pivot, so I’d have to take a step back in pay and title. Given that I’d spent the previous year on a solo practice that lost money, psychologically, it was easier than ever for me to accept making a low salary.
Ultimately, I knew I had to broaden my search. I’d have to look at roles and opportunities I’d never considered before. I didn’t want to squeeze myself into this next job—I wanted to find the job that fit most closely with who I was authentically:
I think we could all benefit from taking stock of our unique traits instead of trying to change ourselves to fit into some predetermined role set by our employer, peers, or society. It’s tempting to see changing yourself as “self improvement” and that when you improve your weakness, you’re becoming a better person. But really it’s just trying to turn yourself into someone you’re not. (source)
With that in mind, I began to send out resumes.