What I Learned Switching from Law to Business

A few years ago, I switched from being a lawyer to a technology salesperson.

How did that happen?

I became a lawyer because I loved the thrill of public speaking. Trying cases seemed like a way to do this for a living. But when I started practicing, I realized that this isn’t what lawyers do.

So enough of being an adrenaline junkie, it was time to be practical. Why not focus on doing something I’d be proud of? Helping to build a great company struck me as a good goal.

I suppose I could have done that as a lawyer. Great companies need great lawyers, after all. But my reasons for making a change went beyond being disappointed at not being able to go to court.

Lawyers are technical specialists; I am not cut out to be a technical specialist. How did I know? My other great passion in life is history.

What is history? It is, in principle, anything. Economics? Yes. Politics? Yes. International relations? Yes. Philosophy? Yes. History is whatever it needs to be to understand the process of change.

For me, that’s exciting. It feels like constantly learning new ways of thinking to understand whatever is most important.

Being a technical specialist is very different. Specialists master a complex but defined body of knowledge. They apply their skills to solving the toughest problems in their area of expertise. As their skills expand, their careers grow.

But they operate within the boundaries of their expertise. Lawyers, for example, use the same tools of research, drafting, and analysis for their entire careers. They focus on evaluating and minimizing risk.

This is a critical part of any challenge. But it’s just one part of the challenge, it’s not the big picture. Minimizing risk isn’t the ultimate objective.

The ultimate objective is defined by generalists who think about the whole problem and draw on specialists to help them solve it. I wanted to work on the ultimate objective, and that meant that I had to leave the law.

I wanted to leave the law … but not leave behind everything I’d accomplished. I’d put a lot of sleepless nights into becoming a lawyer and I hoped that all that effort would help me in my new career. I wanted to start a new life but not start over from the beginning.

Fat chance. I started from the beginning. And now I know why.

Doing something new involves a terrifying amount of uncertainty. The problems are novel, the evidence is unclear; so what do you do? Most people, including me, fall back on their instincts.

My instincts as an ex-lawyer were often wrong in business. Being a lawyer taught me to avoid mistakes. I checked citations, confirmed case law, and tried to predict pitfalls. But I wasn’t balancing risk and reward; I was working until I dropped in an effort to eliminate risk.

When I switched to business, my inclination was to outwork every challenge. Every good idea seemed like an opportunity. A missed opportunity is a mistake. Mistakes are unacceptable. So I tried to do everything.

This was the opposite of right. In business, you’re responsible for setting rational priorities, including deciding not to do things that could be useful. If you try to cover all the bases, you’ll waste your resources. If you do the wrong thing, at least you will have learned something.

And, of course, I didn’t have any of the right skills. Businesspeople aim to produce measurable results. They design processes, gauge outcomes, and adjust as needed.

I had never done this.

But surely, I could learn! I had talent after all.

It turns out that relying on talent in a new context can be pretty humbling. What was I good at? Arguing. What happened when I switched to business? I lost arguments about business strategy; lots of them; even when I was sure I was right.

I was used to winning arguments even when I was obviously wrong!

Why was this happening? I didn’t understand the context. This shouldn’t have been so surprising. The same thing happened to me in law school. My first few attempts at legal writing were pretty rough even though I’d always been a good writer.

To write well about law, I had to learn to think about law. I had to understand the components of a legal argument, practice crafting each of them, and repeatedly employ them against opposing arguments. Only then did my talent for writing matter.

Law, at least, gave me a defined time to learn. I had three years of law school and two years of clerking to practice. When I switched to business, I parachuted in with minimal preparation. My “practice” was doing things in the real world.

In the early days after I switched, I discovered how attached I was to law. Not to the work, but to the identity.

I had been an attorney at a well-known firm. I’ll confess, I liked it when people nodded with respect when I told them what I did for a living. Now, I was a rookie salesperson. Most of my friends in my new industry were much further along in their careers. And I’ll confess, that was hard.

My life went from being a linear progression of greater seniority and expertise to a series of experiments, the results of which were partly out of my control. Even if I liked my new role and did everything right, my company could fail. And by the way, it was unlikely that I’d do everything right.

I was used to worrying about doing well. Now, I had to focus on always doing better. This was difficult. In my old life, failing an exam wasn’t a great learning experience. It was an F. I had gotten to where I was not just by being excellent but also by very consciously avoiding screwups.

My identity was that I was someone who was good at what I did. Now, I was someone who would become good at what I did. I had to cultivate the tenacity and objectivity to get there. I was lucky to be around people who invested in me, even when I was frustrated and, no doubt, frustrating.

There was plenty of frustration. But every once in awhile, I’d catch myself doing something really well. And then I’d remember that this was something new, an ability I’d recently gained. This was something that the old me could not have done and would not have wanted to try.

And I’d smile.