How To Go Off The Beaten Path: A Summary
Three key themes that have emerged from stories of lawyers who took the road less traveled and ended up having a huge impact
I wanted to take a break from my usual posts by sharing three common themes that have emerged from my first few articles. When I took a look back at my posts over the last two months, there were a few patterns in all of these stories (including my own) that I thought would be good to highlight.
#1: If you have a feeling that you’re working at the wrong place, change your job
Even if it feels crazy. If well-meaning friends, family, or colleagues try to discourage you, you have to ignore them. That’s because even though they mean well, they really don’t see the full picture. The world is constantly changing, and it’s likely that whatever you’re considering doing next—you’ve probably spent more time thinking about it than they have.
Just like for Belinda Johnson. When she first went off the beaten path in 1996, she was a highly paid associate at a Biglaw firm looking to join an unproven Internet startup. Her colleagues all thought she was crazy. At the time time, the Internet had not yet become mainstream thing. It looked like a fad. But Johnson followed her hunch because she’d been following it for some time, and likely knew more than they did.
It’s also important to listen to your hunch. It’s very likely that your “rational side” is telling you things that conflicts with your gut. But guess what. Your gut is probably incorporating a lot of other relevant information, like how you truly feel, emotionally and psychologically, about your current role. If you’ve got a feeling that you should leave your job, you’re probably right.
If it feels risky or scary, that’s because it is. Because your next job probably won’t be your final destination.When Joseph Tsai left his Biglaw job, he ended up going to an investment fund that failed within two years. But that was okay. Because that job set him up for his next job, which is where he learned valuable skills and found the opportunity to join Alibaba.
Once you do find the right place, what should you do next?
#2: Run towards the edge of an evolving space
Once you’re in the right environment, you should take stock of where you and your organization fits into the bigger picture. You want to avoid working on things that haven’t changed much, because moving up in that world requires you to wait in line. It’ll take too long. Instead, you should find a frontier and just go for it.
Note that there is no simple way to find a frontier. Because they come in many different forms. You don’t have to go into tech or join a startup, although it can be helpful.
That’s because the tech startup world evolves so quickly. It’s been doing that for decades. Larry Wilson was on to this trend early, when he decided to hyper focus on serving startups in the 1970s and 1980s, instead of the banks that financed them. The latter was more lucrative, but the former helped his firm, Wilson Sonsini, develop unique expertise not found anywhere else.
Another example: Belinda Johnson joined Yahoo in 1999 through the acquisition of the Internet startup she worked at. Yahoo was an established tech company, but Johnson still had the opportunity to work in a frontier. At the time, the legal and regulatory issues Yahoo faced with were unprecedented. Johnson spent 12 years developing expertise in that ambiguous space, which eventually became her superpower.
But you don’t always have to work in tech to find a frontier. Tom Goldstein made his mark in Supreme Court litigation, which had been around for hundreds of years. He used a clever way to get himself involved in groundbreaking cases, even while working at a large, conservative firm. Which led to him later working on Bush v. Gore, one of the most important cases of the 20th century. Those experiences gave him insight into a massive gap in market: Supreme Court reporting.
The key takeaway here is to go to the edge of a frontier and develop expertise. So what happens after you do that? What’s next?
#3: Go where your expertise is needed
Once you’ve developed expertise, it’s time to find a place where it’s valued. Once again you shouldn’t take advice from outsiders who might tell you to go to some prestigious firm or “hot” startup. Instead, you have to use your own judgment about where your unique skills are desperately needed.
One of the best examples is Joseph Tsai. After spending years developing legal and finance skills, he joined a China-based startup where absolutely no one else on the founding team knew how to incorporate an entity or raise venture funding. It’s not clear to me whether he was world-class at these two activities, but it didn’t matter. In the land of the blind, the one eyed man is king.
The same thing happened to Belinda Johnson. After developing expertise in handling ambiguous regulatory issues for tech, she decided to bring her talents to Airbnb. The startup had no lawyers and weren’t even looking for one. And even if they were, it would be very, very hard to find someone who possessed the experience to deal with novel legal issues that were changing every day.
Sometimes the right place isn’t someone else’s company. Tom Goldstein made his mark after opening up his own firm. There, he could laser-focus on Supreme Court cases, and create a blog on the side for marketing. Any Biglaw firm could have launched a blog like that. But none of them could execute as well as Goldstein, because his experiences gave him a deep understanding of what the market needed.
Note that none of these three lawyers took the standard advice for what was “hot” at the time. Usually when an opportunity is known to most people, it’s too late to take advantage of it. All of the lawyers profiled in my Substack saw something in their niche, positioned themselves in the right place, and created a lot of value for the companies or the markets they served.
I think that’s as close to a playbook as you’ll get.
Even though I made my big break in legal tech, I never imagined I’d be in this space. Sometimes I look back and wonder if I could’ve experienced the (modest) success I have if I’d pivoted to another industry. Reflecting upon the past 5-6 years, I’ve come to realize that there is, in fact, something special about the tech industry that gives you an opportunity to have a successful second act.
Tech is very forgiving of failures and setbacks. Things also evolve quickly, which means you don’t have to wait in line. There are a few other patterns I’ve noticed, and I’ve tried to write about it in a recent Twitter thread.
So this is the theme I plan to focus on in the coming weeks. I plan to share more stories from my own career journey, and from a few lawyers who successfully launched a second act. I haven’t figured out exactly what I’ll be writing about, but I hope you’ll find it helpful or at the very least interesting.
Stay tuned, my friends!
I hope you enjoyed reading this as much as I enjoyed writing it. Feel free to forward this email to anyone you think might enjoy it. Comments and thoughts are welcome, as always. Thanks for reading!
When I made the move to a legal tech startup in 2016, I saw a few things that most outsiders didn’t. How did I know to look? Well, as I mentioned in an earlier post about joining legal tech, my brother in law had done something similar years ago. He graduated from art school and found his way to the mobile gaming industry very, very early. It seemed risky at the time, but when we talked about it, he told me that there were things happening in that industry that very few people knew. That story gave me the confidence to do something off the beaten path.
The same thing happened to Tom Goldstein. He joined Jones Day after his clerkship, and learned how to convince lawyers to represent them for their Supreme Court appeal. But didn’t stay at the firm because they wouldn’t let him argue the cases until he had years of experience. So Goldstein had to make a jump to Boies Schiller, before ultimately going solo and creating SCOTUSblog.
This is not an original idea, and comes from Peter Thiel. For further reading, check out Parts IV and V in this excellent summary of his lecture at Stanford.
You can even join a “hot” space late. Joe Tsai co-founded Alibaba in 1999 at the end of the dot-com boom, and just a couple years before everything came crashing down. But Alibaba was different because it was positioned to benefit from another big trend: China opening up commerce to the rest of the world. You could imagine what an outsider would’ve said to him in 2001 or 2002. “Better get out of tech and get a real job, cuz startups can’t succeed any more.”