On Father Figures, Legacy, and Mentorship

The ability to find a solid mentor who encourages the confidence to step into the person you aspire to be is hard—for many it will be impossible.

Published: Jun 17, 2023  |  

CEO and founder of Hugo Mentors


Many of my most formative memories feature my father: The exhilarating freedom of first riding a bicycle is forever paired with memories of his patient guidance—him holding me steady as I found my bearings. Much later, the heady thrill of gaining acceptance to business school and the early years of forging my career were similarly launched by years of his steadfast advice.

For better or worse, we are all shaped by our father figures, by their presence or absence, what they do or do not. Our first teachers, parents show us how to communicate, interact with the world, and, ideally, how to stand on our own two feet.

As we mature, we seek the same training wheels of support from other adults that can teach us how to step into our future selves. Paternal guidance is pivotal in personal development—even if it doesn’t necessarily (or even frequently) come from a father.

My father taught me the significance of mentorship, both personally and professionally. A New York real estate legend—and loving dad and grandfather—Robert I. Shapiro freely shared his expertise with those seeking guidance.

Founder of City Center Real Estate and dubbed “the King of Air” by the New York Post, my father had an expansive career spanning over six decades. While professionally driven, he was generous with his time and expertise, shepherding countless young brokers into the world of real estate. All he asked was that they “pay it forward.”

Big-hearted and brilliant, the legacy of my father’s teachings persists in the many lives he touched—including mine and my children’s. He took my son under his wing at the tender age of 13, inviting him to shadow him during a two-week summer internship. Two weeks turned into years of mentorship, which ultimately inspired my son to pursue an Urban Planning degree.

While my father is gone, echoes of him resound in my son’s adult life, in his budding real estate career and his apartment, where vestiges from Dad’s office decorate the walls and his conference table has gained a second life as a dinner table. 

It was only over the past few years that I have come to realize how significantly my father’s mentorship shaped my path too. Ironically, in his own early career, my father never had the mentor figure he so readily played for others. I think this is partly why he was so willing to take on that role: he understood how important it was and how hard it was to find. 

In my professional life, I encountered the same vacuum of workplace guidance. As a woman in tech in the internet’s early days, there was a profound dearth of others like me who could shepherd me forward—an issue that, sadly, persists to this day. Yet back at home, there was always Dad, encouraging me to trust my abilities, and offering up ideas and connections wherever he could. While I lacked a formal mentor within my profession, looking back, I realize I had one all along.

But finding a good mentor shouldn’t be a matter of genetic luck. Few of us are born into the lives we dream of, or have family members working in the profession we aspire to pursue. Seeking to support my children as they were entering high school, I read The Path to Purpose by William Damon of Stanford’s Center on Adolescence.

His research reinforced what my father knew intuitively: With the guidance of a mentor, young people are more able to “to successfully discover, define and pursue purposeful missions on their own.” 

Finding that mentor to guide you is the hard part. During one interview about his career, my father emphasized that the most important first step for someone entering the business is “to get a good mentor”—although he admitted this can be intimidatingly difficult to realize.

His best advice was to “find out who you want as a mentor and run after them.” Yet this is easier said than done. For young people, asking for help from a seasoned mentor can feel intimidating or overwhelming. For those from underprivileged or marginalized communities, it can feel virtually impossible—something ample scholarship and anecdotal evidence alike support. 

Reflecting on the gifts my father gave to our family, I realized I could do my part to remove barriers to such guidance. It was my turn to—as he’d so often encouraged—“pay it forward.” Over the past five years, I’ve taken on a number of projects to bring the benefits of mentorship to a broader audience. I created Hugo Mentors, a mentorship network that connects high schoolers to academic experts, to help curious students find their way. 

Over the past few years, we’ve seen hundreds of mentees discover their agency as independent thinkers, budding innovators, and future leaders. With Hugo Scholars, our scholarship arm, we’ve been able to extend this experience to an even broader group. We are currently planning a pilot mentorship program in partnership with a top research university to support underrepresented groups and grow the STEM pipeline.

And, in honor of my father, I’ve been working on developing a real estate mentorship program. We all need some advice and help in finding our way—mentorship should be more accessible and available at earlier ages.  

I feel my father’s presence all around me every day: in the skyscrapers shaping the city skyline, as I ride my bike, and most importantly, in my work. Like good father figures, effective mentors do more than support: they empower us to step into the person we aspire to become. In dedicating myself to fostering mentorships that help others discover their purpose, I know I’m carrying his legacy on. 

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