Risk Leads to Reward.

Vol. 42 No. 7


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.

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