Why Attorneys Often Fail as Businesspeople and Entrepreneurs

Once an attorney leaves the law to start a business or join an existing business, the attorney has pretty much kissed goodbye his or her career working in the law. In most cases, once an attorney leaves the law firm world and does something that does not involve practicing law, the legal world will not welcome that attorney back. The legal profession is like a “guild,” and guilds punish people severely for leaving them. If you leave a guild, you better be certain you are doing the right thing.
A. Harrison Barnes
Harrison Barnes

When I was at my first law firm job, I had an office next to a guy who would buy all sorts of used pinball equipment and sell it on eBay. At that point in his career, he was about ten years out of law school and quite miserable. He commuted at least an hour to work each day, constantly told me his suspicions that his wife was having an affair, and often slept in his car in the parking garage when he needed to go to court early in the morning—which was at least a few days a week. One of the highlights of his year was when he had to take a trip to Orlando to depose a witness. After the deposition, he decided to spend a few hours at Disney World. His cell phone had died and he could not retrieve messages.

When he returned to his room at about 8:00 pm that evening, there were a bunch of messages on his hotel phone as well as a fax. A partner in Los Angeles was very upset with him because he wanted to hear how the deposition went. The final message was quite dire: “A lawyer always needs to be reachable. I’m taking you off this case and putting an attorney I can trust on it.”