After toiling in unsatisfying writing jobs after college, Judith Messina WG76 applied to Wharton in search of stability and a sense of accomplishment. What she found in her time on campus would lay the foundation for two of the great loves of her life. Luckily, the marketing course she wanted was full, and in the class she took instead, she met her future husband, the late David Fleischer C70 WG76. Much later, after more than a decade in operations at Citibank, Messina parlayed her business acumen into a return to writing as a journalist, reporting for Crain’s New York Business and then for other publications as a freelancer. Still at the keyboard today, Messina found time between deadlines to reflect on her career pivot, an award-winning story, and success both in and away from work.

I had wanted to be a journalist since my teens, but life takes unexpected turns. I was working at an organization where I was writing, but I didn’t feel I was achieving anything. A friend went to business school, and that seemed like a good way to build a stable career — and hopefully find other ways to continue writing.

I met my husband in an insurance class. I walked in late — there were only a few seats left, and, not wanting to be conspicuous, I took the first one I saw. It was next to him. We introduced ourselves, then later ran into each other in the student lounge and started talking. Eventually we had a date, and that was it.

Throughout my career, in banking and journalism, I saw the importance of how you manage people and processes. It’s difficult, it takes know-how, and you have to learn it over time. You make mistakes, and so it takes humility — and also, courage. But management is what makes things work. Departments that run well have strong managers.

I never lost my love for writing and storytelling. Eventually I decided to go for it. I left Citibank and went to journalism school, and my husband was enormously supportive — encouraging me even when I wondered if I could do it after all those years.

For a business journalist, my background was unusual. Having an MBA and having worked in a bank gave me insights that hopefully made me better at what I did. It certainly didn’t hurt that I could read a balance sheet.

One story that stands out was about Silicon Alley in the late ’90s, when it began to falter. We called the piece “Up in Smoke.” It captured a major moment when New York’s tech scene collapsed before eventually rebounding. You have to talk to dozens of people and tell a big story in a way that’s coherent from beginning to end and keeps people glued to the tale.

Success in life is having a loving family and friends, and striving to live well. It’s about happiness and about giving of yourself. In work, success is loving what you do, doing it well, being creative, and going beyond expectations — not just for yourself, but for your audience or clients.

I’ve stubbed my toe as a reporter a couple of times. You learn how to ask questions, how to be direct without being off-putting. That’s something that comes with experience.

I’m not sure if I’ll ever completely retire. But deadline life can be demanding. I do have a book idea in mind, so that might be my next endeavor.

What matters most to me is my children, my friends, and continuing to do something meaningful in this life. I also work with several nonprofits, giving back and hopefully helping to make the world a better place.

I’m still striving — finding the next story, reporting it. There’s always another story to tell.

 

Published as “Judith Messina WG76” in the Spring/Summer 2026 issue of Wharton Magazine.