A Funny Thing Happened On My Way To A Law Career

I never expected to be TikTok famous. But life works in funny ways. I mean, my original plan was to become a successful trial lawyer. Which is why I became a litigation associate at the most prestigious Biglaw firm that would hire me. For some inexplicable reason, I thought being in litigation meant that I’d be cross examining witnesses or delivering closing statements.

But that’s not what happened. Instead of going to court, I found myself spending all of my time managing e-discovery, building privilege logs, and dealing with “pls fix” emails from the partners. I mean, I wanted to persuade juries! This wasn’t the kind of work I wanted to do.

So at 33, six years out of law school, I decided to start over by doing something different. I decided to join a legal tech startup as an entry level sales rep.

Friends were concerned when they first heard. “You’re going to use your law degree to sell technology to lawyers?” they asked. “Like fax machines and dictaphones?” I mean, they weren’t trying to be mean about it. They tried their hardest to be supportive. Even though what they said didn’t exactly inspire a lot of confidence.

“I think it’s so great that you’ve decided to switch to a lifestyle job,” they said, apparently not knowing what it’s like to work for a startup or carry a sales quota.

I never could have imagined it then, but pivoting to legal tech sales changed the entire trajectory of my career. I joined the space right around the time the digital transformation wave hit the legal industry. Over the next few years, things really took off. And I got to ride the wave.

That’s how I ended up doing exactly the kind of work I’d been looking for. Instead of trying to persuade juries as a trial lawyer, I found my place persuading other lawyers — as a salesman. I made a small reputation for myself, which led me to be recruited for a unicorn job that was designed specifically for me and my personality.

Which brings me to this column.

I believe we’re experiencing a career epidemic in the legal profession, where more lawyers are unhappy at work than ever. Much of it is driven by student debt or golden handcuffs. But there’s more to it than just that. I’ve spoken to so many lawyers over the years who feel trapped at their jobs. What should you do if you hate what you do? How do you find out what else is out there?

That’s how I’d like to help. Over the years, I’ve discovered that there are plenty of lawyers out there, doing incredibly interesting things. Not all of them are in tech like me. Some are still at firms or legal departments, doing cool stuff on the side. But others work in uncharted territory. They’ve founded companies, worked in highly specialized roles, or created massive audiences on the internet.

And the craziest part? Most of them work at jobs that didn’t even exist just a few years ago.

That’s what happened to me. After starting over in legal tech sales, I had this newfound sense of freedom. I lost the burden of having to follow a prescribed path to reassure myself that I was Headed In The Right Direction. That freedom empowered me to experiment and try things that I never would have if I had a traditional job.

Like TikTok. I’d heard of the app but never thought much of it. At least until a few lawyers encouraged me to try it out. One of my earliest TikToks went massively viral and I quickly learned that I was pretty decent at making silly short-form videos. It dawned upon me that these videos gave me a uniquely powerful way to engage with the legal community.

Which has business value.

My social media platform has also opened my eyes to what else is out there. By engaging with the community, I’ve learned that there’s this larger, vibrant ecosystem of lawyers and legal professionals doing really cool stuff. And in the coming weeks, I’d love to share with you more about what I’ve seen and heard. There are a lot of exciting things happening in our industry.

But if there’s one thing I hope you take away from this article, it’s this: If you want something more from your career, don’t be afraid to go off the beaten path. There’s just as much opportunity out there. Hopefully my stories will help you find something better.

Stay tuned, my friends.


Alex Su is currently the Head of Community Development at Ironclad, a leading legal technology company that helps accelerate the contracting process. Earlier in his career, he was an associate at Sullivan & Cromwell and clerked for a federal district judge. Alex graduated from Northwestern Pritzker School of Law, where he was an editor on the law review and the student commencement speaker. In his free time, he writes about his career journey and legal tech in his newsletter Off The Record. You can find Alex on Twitter or connect with him on LinkedIn.