Risk Leads to Reward.

Vol. 42 No. 7

By

Bob Ambrogi is a Massachusetts-based media lawyer, as well as a journalist and media consultant. The former editor in chief of several national and regional legal newspapers, Ambrogi is also known for writing and speaking about the Internet, technology, and social media. He is a 1980 graduate of Boston College Law School.

I wish I’d known in law school that the path of a career is rarely straight and narrow and that detours that seem risky can end up rewarding.

I went to law school hoping to boost my fledgling career in journalism. But by my third year, I’d grown enamored with law—particularly labor law—so when I graduated and was offered a job at a government labor relations agency, I grabbed it.

Then, just two years out of law school, I took a detour. After a fierce Boston winter, my significant other and I decided to move to the US Virgin Islands—sight unseen, no job in line. At the going-away party the agency threw me, my supervising attorney pulled me aside. “You’re making a big mistake,” he said sternly, “throwing away a promising career.” I worried he was right.

Little did I know that I would land in just the right place at just the right time. The Virgin Island’s first labor relations agency was about to launch. The search was on for a chief counsel. I got the job. Later, building on that experience, I launched my own practice. At an age when many of my classmates still labored as lower-level associates, I was the head of my own firm handling an array of legal matters.

Then came another detour. Family issues required my return to Massachusetts. As I was winding down my practice, a lawyer—a frequent opponent whom I highly respected—threw me a going-away party. In a moment of déjà vu, her voice grew serious as she looked at me and said that my leaving was taking a big gamble with my career. To drive home her point, she presented me with a crystal desk ornament in the shape of dice.

Once again, however, my move landed me in just the right place at just the right time. The statewide legal newspaper was looking for its next editor in chief. The description called for a lawyer trained in journalism with hands-on experience practicing law. Once again, I got the job. As much as I regretted leaving the Virgin Islands, I now felt like a kid put in charge of a candy store.

Those moves started me down the path to where I am today, to where my two careers, journalism and law, happily coexist. Had I stuck to the straight and narrow, who knows where I would be? But by taking detours, I somehow made my way to precisely where I wanted to be.

Law students often look ahead at their careers as a series of ordered steps; follow them in progression, and they will lead to success. But many of the happiest lawyers I know risked taking detours off the standard career path. As with me, those detours often led them to where they really wanted to be.

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