Reflections from a Recovering Attorney

Part II: It's Not You; It's Me

I used to joke about being a job whore.

It didn’t seem to be in my DNA to stay in any one job too long. In fact, over my 18-year career as an attorney, I was a partner in a law firm and the owner of a small, boutique real estate firm. I worked in-house for large corporations and I filled an Of Counsel role later in my career. I chased those titles because I thought that was how I was supposed to define success. I mean, I’d gone to law school. Naturally, then, my life’s aspiration should be to become a partner in a law firm; right?

The truth is that I declared in 5th grade that I wanted to be an attorney. I was assigned to deliver the closing argument for the defense of Brutus, who was on trial for the murder of Julius Caesar. It was important to me to look “lawyerly”. I spent so much time picking out what I was going to wear the night before the mock trial that I wasn’t particularly focused on my message to the jury. With my Dad’s coaching, I penned a suitable defense littered with big, impressive words and – if delivered with the appropriate theatrical effect – was sure to lead to an acquittal.

Except that I was more focused on how the bow-tie blouse looked with my faux-tweed herringbone jacket. (Yes, I had a faux-tweed herringbone jacket in the 5th grade. Be nice! It was the 80’s, and shoulder pads were all the rage. Even for 5th graders.) I hadn’t memorized my argument, so when the note card with my closing argument fell out of my Pee-Chee on the way to the dais, I was literally at a loss for words. I looked the part, but there was no substance. Brutus was convicted and hanged for murder.

Rather than rethink my career choice in the wake of my first professional defeat, I was undeterred. I had declared that I was going to law school and would become an attorney. I am a first-born, a people pleaser, a goal achiever. If I said I was going to do something – by God – I was going to do it.

And I did. After a very successful law school experience, I practiced law for nearly 20 years. Not as a Perry Mason-type, courtroom litigator. Rather, as a commercial real estate attorney. I strategized with clients, and drafted purchase and sale agreements, and leases, and development agreements. I routinely went to hearings, but hearings in front of city and county officials and not at the courthouse. I was good at it. All of it.

Still, despite an amazing law school experience and significant professional success, I am not sure that I was ever particularly well suited to spend my entire working life as an attorney. Sure, I was successful and made a good living, but I didn’t like going to work. For many years, I suffered from an incurable case of the “Sundays,” wasting an entire weekend day by dreading another start to the workweek.

Instead of taking a hard look at the practice of law to figure out if it aligned with my skillset and core values, I would just move to another job in the legal field. From private practice to corporate America, then back to private practice, and on to sole practitioner, and back to private practice. With every move, the newness always wore off. Sometimes, it was quickly apparent that I wouldn’t last long. With other moves, I worked harder at making the situation work. But after a while, I couldn’t work any harder at making it work, and I found myself looking for the next spot to land, the next big thing, the next job that would fill the dissatisfaction I felt with the practice of law.

All of this hit home for me when, three years ago, I was sitting in a large conference room in a large building in a large city at my partnership admission meeting. For an hour, I was peppered with questions about my legal career, my aspirations, why I wanted to become a partner, how I contributed to the firm, and many others.

There was one question that struck me: how did I see my job changing if I was lucky enough to be invited to join the partnership? I thought for a minute, and answered that, truthfully, my job wouldn’t change much. I was helping to lead the Real Estate group in the Boise office, mentoring new associates, speaking at CLE’s on behalf of the firm, co-chairing several office committees, and leading business development efforts. The only thing that would change was my compensation structure.

I listened to myself answering the question and I thought about my response the entire flight back to Boise that night and for weeks afterwards. If I wasn’t finding the practice of law terribly fulfilling, why did I think a higher paycheck was a good trade-off for attending more meetings, dealing with partnership politics, and handling more administrative responsibilities that would take my focus off of my clients?

And since when did I make a decision that was based solely on making more money?

Less than two weeks later, I was moving my father back to Boise from Phoenix. He retired from his second career on his 66th birthday. He deliberately worked until 66 to maximize his retirement and Social Security benefits. That was important to him because he’d been diagnosed with Parkinson’s Disease in his mid-40’s, and was concerned about mounting medical bills during retirement.

Dad lived with us in Boise for 5 months until he found a home to buy. He was a hobbyist wood worker, and wanted a large garage to continue his hobby into retirement. He closed on the purchase of a patio home on a corner lot with a 3-car garage on December 12. We started moving him into his home on December 14. He had a heart attack and died unexpectedly on December 26. Most of the boxes were never unpacked. And those Social Security checks he was so worried about maximizing? He received 4 of them after working 44 years of his life and putting off travel and other things until retirement.

Talk about a wake-up call.

I was done with suffering through the “Sundays.” I had to quit thinking or talking about a career change. It was time to make a move…not to another firm or to another corporate legal job. I knew I had to leave the law. But why brokerage? I’ll talk more about that next week.