Transitions: Don’t Be Afraid to Roll the Dice

Transitions. I have had a lot of them in my career. Some planned. Some not.

Just a couple years out of law school, my significant other, Kathy, and I decided to chuck Boston winters and move to the U.S. Virgin Islands. At the time, I was a staff attorney for the state labor relations board. I still remember the going-away party they gave me. A senior attorney pulled me aside and told me I was making a big mistake, throwing away a promising career.

I did not know then that I would arrive in the V.I. just as the territory’s first labor board was getting underway and searching for an experienced labor relations lawyer to be its first chief counsel. Right place, right time. With the experience and visibility that job gave me, I later launched my own practice focusing on labor and employment law. Soon, I represented most of the V.I.’s major labor unions. Still a fairly young lawyer, I was regularly conducting trials and handling appeals, including to the 3rd Circuit in Philadelphia.

Eventually, family issues compelled me to leave paradise and return to Massachusetts. As I arranged to close my law practice, I began to search for gainful employment in Boston. Near the end of my time in the V.I., a lawyer who I often went up against threw me a going-away party. Unlike that senior attorney who pulled me aside several years earlier, this lawyer didn’t tell me that I was making a mistake by leaving. She did, however, tell me I was taking a big gamble with my career. To prove her point, she gave me a crystal desk ornament in the shape of dice.

As it happened, the state’s legal newspaper, Massachusetts Lawyers Weekly, was looking for an editor – a lawyer trained in journalism and with hands-on experience practicing law. Right place, right time. Becoming editor-in-chief of MLW, I was a kid put in charge of the candy store. That job started me down a path that I continue on today, with stops along the way as head of an editorial division at ALM and as editor-in-chief of the National Law Journal.

By no means was that the last transition in my career. Later, the need to care for my ailing father led me to leave ALM and find work I could do from home. That transition led me in more new directions, and to more transitions, bringing me to where I am today.

I write all of this not to bore you with my stories, but to offer you a bit of courage to pursue and embrace transitions in your own career. Early on, as I made one transition, I was told I was throwing away my career. A bit later, as I made another, I was warned I could be gambling it away. Instead, each time, I found new and rewarding opportunities, ones I would never have encountered otherwise.

Had I not changed course so many times, my bank account would no doubt be richer. But the variety of paths I’ve traveled has enriched me in ways money never could. My career has been nothing if not eclectic. In hindsight, I would have it no other way.

Do you spend your days in the office secretly craving a change? Whatever it is, go ahead and roll the dice. Odds are, you won’t regret it.

8 Responses to “Transitions: Don’t Be Afraid to Roll the Dice”

  1. Hi Robert, Anne here, community manager intern at Livefyre. I’m a college student, and I’ve enjoyed a couple of transitions in school — one of them being to decide not to follow a predetermined major and design my own instead. I tell everyone who asks me about it that it’s such a joy to tailor my studies to what I want to learn — why waste my time (and money!) doing anything else? I had the same experience when my plans unexpectedly changed for studying abroad. I went from planning, being accepted, and nearly signing all the forms to send me to England for a semester, to staying on campus, getting a job, and taking over as captain for the equestrian team at my school instead. I wasn’t expecting it, but I was happier when I followed my heart in both situations. I don’t regret either change!

  2. @annedreshfield Sounds oh so familiar! I started out undergrad as a J-major, doubled briefly in journalism and economics before dropping both to major in English. To this day, I am still happy with that decision. Like bobambrogi , I heard the “throwing away” mantra. There’s always someone who has to say it whenever you find yourself in a phase of transition, it seems. It can be good to have such people; they can offer a viewpoint you may not consider or be able to see yourself. Sometimes, though, you just have to roll the dice and see what happens. Your life is what you make it, no?

  3. @econwriter5 Very true, I think. While I always grumble inwardly when people are skeptical to my face, but in hindsight their skepticism always makes me think. Usually, I still know that I made the right decision. They always make me think, though, and that can never be a bad thing. 🙂

  4. Adrian_Dayton

    I loved this article Bob. i’ve also had many career changes, but change is something I really enjoy.

    I remember in a job interview once hearing the CFO tell me, after seeing on my resume that I had stared my own import company, then left to start a real estate management company, “you need to be concerned with your resume at this point in your life.” I didn’t heed his advice and instead I have looked for opportunities to learn and grow whenever I had the chance. It has made for an amazing adventure.

  5. @Adrian_Dayton One downside to jumping jobs and industries, it makes it challenging to compile an orderly resume.

  6. @bobambrogi @Adrian_Dayton Pre-recession, you bet. It looks like you can’t hold a job. I wonder though, post-recession, if that perception will change. There were articles about how changing jobs 3-5 times was considered “normal” for younger generations, with predictions of 7-10 job changes for future generations. Makes one thing “change is the only constant” might actually be taken literally, no?

  7. […] from firm life to solo life, changing mentality towards hourly billing, some sound advice on rolling the dice and a thoughtful piece on transitioning from job to vocation. Sprinkled in there was the first in […]

  8. Very inspiring article. I’ve been interested in so many different areas of the law, teaching, writing, but the only changes I’ve made in my 22 year career are to leave the District Attorney’s office and go into private practice, and to leave the partnership I was in and go solo. However, throughout all these years, incredible amount of jury trials, death penalty cases, first degree murder cases (state and federal), and further, despite the local Federal District Judge, a friend of my family, not so subtly :advising” me to pursue my other aspirations, hopes, career choices, etc. (I also own a Ninjutsu dojo, or martial arts school, of which brings me great pleasure, but not any money – that’s not the “way of the ninja”!), I have not made any other changes, despite knowing that I will most likely be very glad I chose to do so. Perhaps this article will finally push me…..I have a triple major in English, Philosophy and Political Science, and my father has been a professor at a college in my town until his retirement last year. I know I am strongly attracted to teaching,as well as writing, particularly fiction or journalism, and I believe I would be quite good at it if I made the “leap of faith”…..reminds me of an old Indian story, as related in a Joseph Campbell book, about a young warrior who went out on his own to prove his worth, and had an older “guru” who was guiding him along the way, (sorry, too much Joseph Campbell), tell him, when the warrior reached a chasm that was very dark, and appeared extremely deep, and wide, “go ahead and jump….it’s not that far”