What a roller coaster weekend. While I don’t have any commentary on Silicon Valley Bank, the whole thing did remind me to finish up an article that’s been sitting in my drafts for weeks now. Today I’ll be sharing some of my thoughts on the value of catastrophe and how going through failure and major setbacks gave me the freedom to do what I needed to do. But first:

Quick Promo

Some of you may know that I’m part of Angel Squad, a community dedicated to angel investing. On March 28th, they’re going to be hosting a webinar showing how to make angel investing your side hustle, and how to get started. They will be bringing on three people who are at various stages on their investment journey: just beginning with no prior experience, someone who has made angel investing into a real side hustle, and the general partner from Hustle Fund. You can learn more details and sign up at the link here.

There are a lot of crazy things happening in the world right now that makes me think about the value of catastrophe. Let me clarify a bit, first. I’m talking specifically about business or professional catastrophes. Not personal ones. Not things that affect your health or loved ones. I’m talking about catastrophes that affect your job, career, or money.

I’ve experienced a catastrophe twice in my career

The first time was when I failed the New York bar exam.

When I failed, I realized that it could all be taken away from me in an instant. It didn’t matter what accolades I had on my resume - if I couldn’t pass the bar, I couldn’t practice law. Although I did end up passing on my second attempt, the experience of being blindsided by the bar exam potentially destroying my career shook my world. I began to realize that relying on credentials and “golden tickets” was too risky.

The second time I experienced catastrophe was when, six years out of law school, I was denied admission by the California bar. I’ll share the details of that story someday, but it was a more extreme version of my bar failure. Basically I was told that I lacked "sufficient good moral character" to practice law.

This bar denial was the worst thing to ever happen to me professionally. I was 33 years old, six years out of law school, and everything I had ever worked hard for felt like it went down the drain. What do you do when they say you’re not allowed to practice law? My choices were to either leave California, or engage in purely federal practice, like immigration law.

I chose a third option: leaving the practice of law

Pivoting from law to sales ended up being the best decision I ever made. It was something that I’d always thought about but never had the courage to do. My identity was too tied up in being a lawyer, and there was too much opportunity cost to pursue something else. That’s where the catastrophe came in.

When you lose everything, it hurts. But at the same time, it frees you from the burden of having to live up to some imaginary ideal. So many lawyers, because of where they went to school or how well they did there, end up tying themselves to career paths that make no sense. “I went to a top school and worked at a top firm, there’s no way I’m gonna take a pay cut for this job.”

Having that freedom let me explore a new world, of sales and legal technology. I worked alongside smooth talking hustlers, and idealistic technologists. I did not see myself as “better” than them, because my catastrophes took my healthy sized ego down several notches. I learned the art of sales, and found that I had some natural talents that were hidden by the hyper conservative legal profession.

I found my voice on social media and developed a small but loyal following.

When the pandemic hit in 2020

It could have been a third catastrophe. My sales pipeline dried up overnight and I was almost certainly going to be fired. Instead, I was prepared. My experience with catastrophes prepared me. I acted quickly and decisively, leaning hard into social media, posting constantly, hosting meetups, and making silly videos. I had nothing to lose, and everything to gain.

And gain, I did. Shortly after we found out it wasn’t quite the end of the world, sales bounced back and I was swimming in opportunities and deals. Most importantly, I developed a unique set of skills and a personal brand. Guess that’s what happens when you try a million things and experiment methodically.

Today I have a unicorn job and an online audience that ensures that I will always be able to find work, no matter what happens in the world. My work is meaningful, I have a ton of autonomy, and I get paid generously for doing things I truly enjoy. None of this would have been possible without those catastrophes earlier on in my career.

So my hope for all of you, odd as it may sound, is to have the same experience. I hope you lose the burden of being trapped or feeling like you’re Headed In The Right Direction. Even if it means you have to experience catastrophe. Because brilliant moves don’t come from researching your way to a solution. Sometimes it comes from having your back against the wall.

And then improvising your way forward.

Newsletter Update

Thanks to all of you who checked out my article Selling To Lawyers: Generating Pipeline. My plan is to update it with in depth deep dives for each subsection based on reader interest. Based on the poll, it seems like most of you are interested in hearing more about outbound techniques. Stay tuned! I will work on a deep dive article and release it in the coming weeks.

Latest News

• Robot lawyer startup Do Not Pay is in the news once again, this time being hit with a class action lawsuit from Jay Edelson, a plaintiffs’ lawyer once called “the most hated person in Silicon Valley” by the New York Times. While I have no comments on the actual case, it’s gonna be a lot of fun to see the sniping back and forth on Twitter, which has already begun (see here and here).

• Notorious recruiter known for perpetuating outdated career advice for lawyers dropped another article, this time including some incredibly bad advice that leads you to breach your ethical duties to your clients. I posted a screenshot of the advice on Twitter, which generated a lot of buzz, and interestingly half of the reactions were “there’s no way this is true” and the other half was “this is totally true, and why I hate Biglaw.” Fascinating stuff.

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