Today I’ll be describing a methodical way to experiment and iterate your way to success. I’ll use my own career journey as an example to describe my framework, which can also be used for sales and marketing, to identify what channel works best for you. I’ll also share some news from the legal world this week. But first, a quick word from our “sponsors.”

Quick Promo

If you’re tired of all the tech bros talking about how AI will replace lawyers, and want to see how it can actually help solve problems in the real world, come join us for a webinar on Feb. 23 demonstrating how Ironclad leverages ChatGPT to help with the contracting process. You can register for the webinar here.

Experiment your way to success

Experimentation is incredibly powerful. It can be used to solve a wide range of problems involving uncertainty. Today I’ll share how to experiment methodically, using examples from my own career. I’ll then touch upon how this framework can be used in other contexts.

Before I get into it, I want to share some context about why it’s so relevant to the legal industry. Most lawyers believe that it’s better to research and prepare before acting, i.e. “measure twice, cut once.” This makes sense for law work because often the answers are knowable. It also might be a product of formal schooling, where there’s always a right answer, and over-preparing pays off.

In uncertain environments, it’s far less effective. You could spend a ton of time and energy preparing for an initiative that ends up being a huge mistake. Often it’s because the environment is constantly shifting, and your “solution” relies on mistaken assumptions.

The cleanest example is a common career problem. Let’s say you spent your entire life preparing to be a lawyer but realize it’s not the right career path for you. How do you choose what to do next? Most lawyers approach this problem by doing what feels natural. Like researching career paths, looking up job openings, and having coffee chats with people. It pains me to say it, but this is the wrong approach.

So what should you do instead?

Step 1: Try lots of new things

When I first had a hunch that practicing law wasn’t for me, I didn’t immediately try to find a new career path. Instead I did a bunch of different things. Some were law related, like clerking for a judge or doing supervised trials at the prosecutor’s office. Others weren’t, like volunteering for political campaigns or doing academic research. I did a TON of experiments.

So should you. Don’t quit your day job just yet. Take volunteer opportunities, or side projects. Try lots of different hobbies. This will give you real-time feedback on how it actually feels to work on that new thing. No amount of Internet research or chatting with experts will give you that kind of authentic feedback.

How do you choose what to experiment with? There’s no right answer. Basically you want to try things that are very different. Think breadth instead of depth. It helps to have the mentality of: Let me find out what definitely doesn’t work, so I can cross it off my list. It also helps to try things that feel weird and unusual, and not something that you can easily imagine working out.

Step 2: See how the world responds

While I was doing all these experiments, the outside world thought I was completely lost. A few years in, I quit my Biglaw job to go to a plaintiffs’ firm, and then I opened up a solo practice. Which led me to mess around with content creation. From a traditional lawyer’s perspective, I was unfocused and spreading myself too thin. How could I build a successful career if I didn’t just pick one thing and do it for decades?

It’s a fair point. When you take on a bunch of different projects, it’ll feel overwhelming. It’s a natural reaction, because you’re used to being a perfectionist. Which pays off well in structured environments, so this new series of experiments will feel very sloppy. That’s ok. It’s not time to focus yet, so keep doing things and feel free to flake out on projects that you don’t enjoy.

Having said that, you should pay very close attention to how the projects are going. How does it feel to be actually doing the work? How do the people you’re working with respond to you? What do your results look like? This part is more art than science, but you want to identify projects where it feels like results come easily. You don’t have to understand what’s happening exactly—just that something special is happening.

Step 3: Invest more into what’s working

My experimentation stage lasted years. During that time, most of the things I tried didn’t work out. But there was one thing that jumped out. As a political campaign volunteer, I was a standout cold caller. There was no one else that came close to my performance. Maybe because my peers were just volunteers. But still—this was evidence that something was working.

This is the type of feedback you’re looking for. Something that works that you can’t explain. In startups they call it “traction” which may mean an initial spike of revenue. Whatever you want to call it—once you find it, lean into it. For me, that meant jumping into a startup as an entry level salesperson. Because I knew success at that job depended on how well you did cold calls.

How exactly to “invest more” into what’s working depends on your specific scenario. Mine involved a pretty major pivot into a new career path. By then I had paid off loans, saved up some money, and had a lot of support from my wife. I had also run into lots of setbacks within my traditional lawyer career path. So it made sense for me.

Making a pivot, or “big” bet once you have a hunch something is working doesn’t feel as risky as it sounds. You already have evidence that the new thing might work really well. This is very different than someone who just researched a job opportunity or career path on the Internet.

Marketing applications

Interestingly, the framework above is the exact approach I took to marketing as well. As an entry level salesperson, I couldn’t figure out how to scale my outreach. Once again, I followed the same approach as I took to my career. I tried a million different things, one of which was posting on LinkedIn. I gained traction relatively quickly, and invested more of my time and energy into it.

It didn’t take long before the LinkedIn posting started leading to inbound sales conversations. Having the ability to generate new conversations with buyers is the holy grail of sales. Eventually, I was recruited to Ironclad to focus on this full-time. Which would have been an extremely risky pivot to make back when I was a practicing lawyer. But now I had so much evidence that it worked, and was valuable. It became as close to a sure thing as it got.

If you’re a startup or law firm trying to find the right marketing channel for you, don’t just copy me. The lesson isn’t to jump onto LinkedIn and start posting (although it may—it really depends!) The lesson is to start experimenting with channels, and find out what shows immediate traction. It might be social, but it might be something else.

Happy experimenting!

Latest News

• Last week, The American Lawyer published an article about how risky posting on social media is, if you’re an associate at a large firm. Personally I believe smaller organizations, like startups and small firms, are more open to you posting online. That’s because social media can help with marketing and recruiting, which large firms often don’t need help with.

• Speaking of social media, my interview with Tik Tok influencer & soon-to-be author Cece Xie went live on Above The Law! She spoke with me about how she went from being an associate to a Tik Tok sensation with over 400k followers. She also has a Substack, which you can find here.

• Facebook and Gibson Dunn got absolutely smacked down in an opinion by Judge Chhabria. You can find the relevant excerpt here from my Twitter, and the full opinion here. Part of me thinks this is incredibly embarrassing for GDC, the other part of me thinks this is incredible marketing for GDC’s litigation department. Who wouldn’t want their outside lawyers to engage in shenanigans to help win a case?

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