With so many competing demands each day, sometimes my life seems like a circus. Often, I ask myself—

Am I a spectator, a performer or a ringmaster? And then it comes to me. I am the bear on the ball in the tutu and high heels, dancing faster and faster as the ball rolls along. Like other working mothers, I’m always juggling three balls: career, family and self. Sometimes I teeter, but I do not fall. On the contrary, I’ve learned some valuable strategies and lessons to help me thrive.

I’m the single mother of two tween boys and a 13 lb. male dachshund, the CEO of a women-owned firm in a classically male-dominated industry, and I still wear four-inch heels and little black dresses. I earned my MBA at Yale and cut my teeth on Wall Street as a young woman – (one of only three in a 50-person sales & trading training program). Liar’s Poker didn’t lie—it was a rough and tumble boys club where political correctness had yet to be invented, never mind the concept of equal pay.

Fast-forward twenty years. Progress for women in finance remained painstakingly slow. So, I decided to run my own show and sweat for my own equity. People suggested I was choosing a less secure path. Maybe. But to me, establishing a workplace where the team collaborates to make a bigger pie is far more reliable than continuously defending your own small slice. After all, the best way to predict your future is to create it.

Being CEO has given me the platform to empower women across their many roles and walks in life – as mothers, wives, partners, daughters, employees, etc. At O’Brien, we are constantly striving to increase our clients’ financial confidence and help them break the ‘money taboo’ – the idea that it’s impolite or improper for women to talk about money. Amazingly, women will talk about almost anything except money! Only when the subject of money is not taboo will women have real power.

As the decision maker, I can also follow the dictates of my own conscience. That means prioritizing honesty, authenticity and approachability to motivate employees and guide clients. It means creating a business environment that prizes integrity and nurtures ability so that everyone thrives. Every morning now, I can look myself in the mirror and feel good about the work we a re doing. I am an accidental entrepreneur. My goal was to create opportunities for my clients, my team and myself that weren’t available at existing financial firms. I never realized the joy that would bring.

While challenges continue, I have also been very lucky. My education, training, background and early career opportunities positioned me well to go out on my own. It is my personal mission to promote women’s financial wellness and to help empower women who may not be comfortable with finances or advocating for themselves. After all, how can you be a true partner, or teach your children a healthy relationship with money unless you are comfortable with it yourself? How can you be truly well if you don’t have confidence in your financial future? With the right information and tools, I believe all women can gain that confidence.

Back to the juggling. The balls of career, family and self are never equally weighted; they demand different levels of time and attention unpredictably. As long as you keep juggling, it doesn’t really matter. Juggling and dancing, dancing and juggling. To stay balanced over time you divert energy to one or another ball based on what’s most pressing in the moment. My two bear cubs, Alex and Gabe, sure keep the family ball spinning. Who knew I could be such an effective third base coach in my high-heeled, high top sneakers? I’m proud to report that Alex, going into high school, knows more than I do about both the Reformation and the Renaissance and that Gabe, the starting pitcher for his baseball team, can throw a 55 mile per hour fast ball. (I only know this because one of his pitches hit me in the thigh, leaving a bruise the size of a grapefruit).

Every so often a scary clown races in, bound and determined to knock you off the ball. Last winter the big ball got out from under me when I fell and tore my ACL while skiing on an icy, mogul-filled trail. I felt humbled and lucky. I’m not an hourly worker and as the CEO, I gave myself a bit of time off to heal, although being bedridden didn’t sit so well with my Type A personality! Bottom line: I still got paid. Family and friends pitched in at home, and my team kept the office running. It really does take a village. Now I’m doing PT and almost back to dancing on that ball in my tutu and heels, although I’m modulating the speed—and keeping my distance from clowns.

Balancing on and juggling the balls isn’t easy. One of the main reasons I thrive is because I don’t expect a smooth ride. I’ve been divorced, and just last year I experienced an almost unbearable personal loss with the sudden death of my partner. I don’t always know the right answer, and I accept that. I have come to understand that time and health are finite and that rarely do time, health and money intersect. You need to relish those moments and the important people in your life—including yourself. So that when you fall off the ball, as we all do, hopefully you’ll find a net.

My top five “secrets” for balancing career, family and self:

1.) When you feel like quitting – don’t. That’s exactly the time to run harder. If you slow down, you’ll only end up farther from where you need to be.

2.) Sometimes it will seem like your world has fallen apart. It’s no shame to drop to all fours and acknowledge the setback; it can even be cathartic–as long as you keep going. Do whatever it takes to maintain forward momentum/keep moving on/forward.

3.) Don’t expect a balance of work, family and self on any given day– aspire to achieve this over weeks, months or even years.

4.) On your worst or hardest days, wear your best tutu. In all seriousness, don’t look like a victim and you’re less apt to feel like one.

5.) Making gains requires taking risks. People tend to regret the things they haven’t done more than those they have. Take the leap and trust that you’ll find a net.

Jill Fopiano


O’Brien Wealth Partners