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Big Dream

Midlife Career Transitions

Advice for the restless from lawyers who have reimagined and retooled their careers.

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October/November 2007 Issue | Volume 33 Number 7 | Page 44

Midlife Career Transistions

No More Default Judgments: Recapturing the Dream

After 30 years in practice, this corporate counsel launched a new seafaring life and a new career. Here are the DIY steps that led her to living the best of her life in the law—on her own terms. Plus: Resources for Reinventing.

I practiced law for almost 30 years, doing the right thing at the right time for me. But times change, and today the right thing is running a coaching and consulting business for lawyers from my floating office aboard our official cruising home, along with writing, speaking and enjoying time with my family. I didn’t have a plan but somehow I got here in ways that are available to each of us—if we are open to our dreams and avoid defaulting to the safe and expected. This is my story and my personal do-it-yourself guide for recapturing the dream.

Taking Inventory and Realizing Options

It all started at an ABA meeting in San Francisco. The topic was hot and I had a neat list of action items, insights and strategies to accompany it. I was 50, at the top of my game. Or was I? Was it my game or was I defaulting to someone else’s playbook?

My notes from that day held a clue: While the meeting proceeded, I jotted down a summary of my savings, pension, social security, a 401(k), vesting dates, and a comic hint at a budget that assumed I could live aboard some derelict cabin cruiser in the near future … if I never bought another book, saw the inside of another restaurant or even ordered in!

It was the start of a tug-of-war between defaulting to success on the attractive terms offered by others and a life in the law on my terms. It was 50 years down, 50 to go. And although I didn’t see it then, I was on the move.

Five years later, I found myself, retirement papers in hand, on my way to a new cruising life. To be sure, the work during those five years was great. The clients kept getting better; their plans for the business more daring; their challenges more satisfying. At the same time, I was becoming acutely aware of the contrast between where I was and where I might be … someday.

And someday came soon enough. The organization where I worked as corporate counsel announced a huge merger that upended the company. There were good options for me but it was not my first merger and I recognized the feeling: It was as if someone had bought my house, expecting me to stay there as an obedient servant while they threw out my friends and my furniture. Enough!

Since San Francisco, I had inventoried my resources and revisited my dreams. I had started to experiment with the boating life. At least part of me was ready to see that merger as an opportunity for a graceful exit from one great life to another. It would be a lie to suggest that I was without doubts, but I took the dive anyhow. Tonight, looking out at the sea grass, the sunset and a symbolic rising tide, I understand better how this dream triumphed over default. As I see it now, here are the ways my mind opened up to turn my “someday” into my life today.

Following the Magnet’s Pull: DIY Steps

I started listening to my subcommittee. If we each have a committee in our heads telling us with impeccable logic what everyone else thinks we should do, my committee now had a well-staffed subcommittee reminding me that I was a bit bored, rocking around in my personal doldrums. Even as a child I had wanted to be a writer, a painter, an entrepreneur, and, of course, I had wanted to live on a boat! I began to think about the subcommittee’s dream. Gradually the outline of that imagined life took on the details that made it possible.

I inventoried my resources, including my dreams.  I got my arms around my finances. But only when I set my dream free did the analysis begin to make sense. Through the lens of the dream, expensive needs were falling by the wayside: A boater doesn’t need a 10-room house, three cars or a cappuccino maker—well, maybe that last thing. But I was rapidly learning what I didn’t need and how much I was paying others to do things I might actually enjoy doing myself.

I experimented. My husband and I were boat show groupies, but with “someday” edging in, fantasy boats lost their appeal. We bought a 27-feet “practice boat” to test my determination. We attended boat shows with a practical eye. I began to picture myself biking to market in different ports, cooking aboard and taking my turn at the wheel. The more I imagined, the more I obsessed. The dream had become a magnet.

I committed. We bought our live-aboard boat and, a year later, the expected merger came and I decamped from my counsel position. I had my new life. Then a few months later, I was on the brink of defaulting again, nearly taking a job that was a carbon copy of the one I had left! In the end, I resisted, in part because I could feel the lightness of my new life and the weight of the old, but mostly because I had made such a public declaration that the freedom of cruising was my new life.

I called for backup. That close call made me realize that this was not going to be the last challenge. Fortunately, I had already planned to attend a program in Santa Barbara designed to help people launching new lives recognize their options and ability to reinvent themselves. The program worked its magic. I had the boat, but my dream now had backup dreams as well! Soon I was on my way to a new career of being a speaker and a writer, a coach and consultant to lawyers, living the best of my professional life on my own terms, terms that included plenty of time for family, friends and self.

Even so, I’m working hard at leaving room for new dreams. Maybe I’ll get my captain’s license, build an inn, walk across the country or paint again. Who knows? Maybe I’ll even go back to the law. But if I do, you can be sure that it won’t be a default judgment.

About the Author

Barbara D'Amico is the former General Counsel of J.P. Morgan Chase’s Retail Financial Services Businesses, a certified coach and the founder of Esquire Crossroads, a coaching and consulting firm dedicated to supporting lawyers in law firms and law departments in achieving professional success and personal satisfaction, including successful career transitions.