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Dilia Caballero

Committed to Balancing Work and Family

Between working as an attorney in the Brokerage Legal Department for E*TRADE Financial and raising four kids all under the age of 14, I’ve learned a thing or two about what it takes to balance professional and personal life. Here are my pointers for succeeding professionally.

Have an open mind with your career. You may be surprised at what ends up becoming your passion. Factors beyond your control, such as the economy, may take you down an unexpected path. I entered law school intent on practicing international law. Unexpectedly, I loved my third-year bankruptcy law class so, after graduating law school, I began my legal career as a corporate/bankruptcy attorney. At the time, there was plenty of bankruptcy work and no prospects in international law. Yet a combination of coincidence, economic reality, and the influence of mentors and bosses has led me to become a securities law attorney.

Life will throw various demands at you. Keeping an open mind about the direction of your career will enable you to find opportunities—even with the limitations that family responsibilities may necessitate.

Dilia CaballeroValue ALL people and make connections. My father gave me his copy of Dale Carnegie’s How to Win Friends and Influence People when I was in middle school. Some may find the book self-serving and opportunistic, but its premise is simple: Treat people as you would want to be treated. Take an interest in your colleagues, whether or not you work with them. You never know when they may do you a good turn.

A few months in a new job in Washington DC, I overheard one of the litigation attorneys talking about his vacation. We realized we had family in the same town in Florida. After that, we got to know each other more, and he later asked me to join him on the firm’s hiring committee. Several years later, after he had left the firm, he called me twice to interview for a position as an in-house counsel at a company. He is now my boss.  It’s a small world and, as the Beatles song says, “In the end, the love you take is equal to the love you make.”

Be flexible and versatile. When I moved from Boston to Washington DC in the late 1990s, I could not find a position in bankruptcy or corporate law, so I joined a firm looking for an attorney to work in investment management and its Latin American practice. In retrospect, it turned out to be an inadvertent but great career choice—not to mention much more family-friendly than life as a bankruptcy or mergers-and-acquisitions/transactional attorney.

But less than three years after I joined E*TRADE—and months after I returned from maternity leave following the birth of my fourth child—the E*TRADE mutual funds and a stable of independent investment advisers that were the bulk of my job responsibilities were liquidated or sold. I found myself at a crossroads. To retain my job, I had to be willing to take on new responsibilities and learn a new area of law—in other words, I had to step out of my “comfort zone.”  Rather than resisting or running away, I embraced the opportunity. Now I have a greater breadth of experience and I am a more nimble professional as a result.

Dilia Caballero's ChildrenWork hard—and go out of your way to fill emotional “tanks.” So, working hard … that’s obvious, right? We would not be Coca-Cola Scholars if we had not worked hard. You have to have a strong work ethic to earn goodwill (which is often necessary because of the unexpected—yet inevitable—events, such as when you have to be home for almost a week with a child who has swine flu), move forward professionally, and generally balance professional and family life.

As for “emotional” tanks, my 3-year old daughter has a book, How Full is Your Bucket?,  about a child and an imaginary bucket of water. The same imaginary buckets appear with the people with whom he interacts. When he does not let his sister play with him, you see water spill from her bucket, and she angrily knocks down his castle. His bucket fills when he gets an A on his test, and the lonely student catches several drops when the boy plays with him.

The message here is be kind, build people up, and do not be afraid to give praise and positive feedback. Too often, people assume that nothing need be said if someone is doing a good job. Yet that means the only feedback folks ever receive is critical or negative. Saying “thank you and job well done!” to someone takes very little time or effort—but it can have a big impact.


Dilia Caballero, a 1989 Coca-Cola Scholar, is Director and Associate General Counsel at E*TRADE Financial. Prior to joining E*TRADE, she was an associate at Dechert LLP in Washington DC in its Investment Management and Latin America practice groups and an associate at Choate Hall & Stewart LLP in Boston in its Corporate and Bankruptcy groups. She is married to Tom, an attorney with the U.S. Senate, and mom to Alex, 13; Thomas, 10; David, 7; and Sophia, almost 4.