The Power of Mentorship and Paying it Forward

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“Too often we underestimate the power of a touch, a smile, a kind word, a listening ear, an honest compliment, or the smallest act of caring, all of which have the potential to turn a life around.” -Leo Buscaglia

A Little Background

I grew up in Orlando, Florida in a single parent home. My biological father was a man of little moral character who often drank, gambled, and raged. After I was born, he stayed for two chaotic years until my mother had finally had enough. At the age of two, he permanently disappeared from my life.

For much of my childhood, my mom took on multiple jobs to support our humble lifestyle. Things were rarely easy. Together we endured a series of obstacles, including rent problems, violent boyfriends, and constantly moving around. Luckily, after one of the boyfriends was arrested, I was sent to live with my grandparents. My grandfather acted as my first paternal mentor. He inspired me through his work ethic, integrity, and commitment to family.

In many ways, my childhood circumstances were not unique. However, they did teach me how to operate independently in the world and to value every opportunity I am presented with. Most importantly, my deep frustration with and desire to escape the constant social and economic uncertainty of my childhood served as my primary source of motivation throughout my adolescent years.

For me, gaining admission to a top university was the first logical step towards improving my circumstances. Going into my junior year of high school, I had an above-average resume and a lot of potential. With my natural intellect and work ethic, I always did really well in school and excelled at the game of golf. But sometimes it takes someone special to help you unlock your full potential.

It is within this context that I first met Howard Sherman. Without Howard, I would not have been able to evolve from an economically disadvantaged Floridian who had never seen snow to a graduate of Princeton University who has lived in 8 different countries and learned the transformative power of paying it forward.

The Initial Encounter

I stumbled into Howard’s office for the first time during my junior year of high school. A few months prior to our first meeting, a relative had given me his phone number at a Thanksgiving gathering. She told me he was an interviewer for Harvard. Hoping to gain some insight into the Harvard admissions process, I called the number. When Howard answered, he informed me that he was a psychologist, not a Harvard interviewer. Nonetheless, he told me to “come to his office to talk.”

Our initial encounter felt a lot like a college admissions interview. During the two-hour session, I revealed to Howard my life story, academic history, and athletic achievements. After listening patiently, he told me that he believed I had a shot at getting into one of the nation’s top schools. Most importantly, he said that he was excited to help make that happen.

The Pursuit of the Top

After my first encounter with Howard, we began meeting on a weekly basis. It was then that we established the ambitious goal of getting me into an Ivy League institution. At first, I was both scared and excited. I had solid grades, test scores, and athletics, but I constantly asked myself how I was going to make it to one of these universities. I was coming from an average high school in Florida and didn’t have any connections. Yet for some reason, Howard believed in me. This pursuit for the Ivy League became my burning desire over the next year and a half.

In our initial sessions, Howard taught me the fundamentals of the college admissions process. He helped me understand everything from the importance of writing compelling essays to the nuances of applying for financial aid. Through all of the anxiety, uncertainty, and excitement, he constantly encouraged me, remained positive, and drove me to work harder.

That spring of my junior year, he flew me to Boston to visit his son Jason, who was a senior at Harvard. It was the first college I visited, and it was incredible. I participated in the golf team’s annual Masters pool, went to a student-professor dinner, and met someone from Zimbabwe. The visit further opened my eyes to the personal growth and opportunities that would be available to me if I could somehow hack my way into one of these universities. I was hooked.

Perhaps more important than helping me package my accomplishments and craft my personal narrative, Howard challenged my narrow world views. He constantly encouraged me to think on a global level. He frequently recounted stories of his travels, sent me interesting articles from the New York Times, and candidly discussed his views on politics, religion, and economics. At the time, I had left Florida on fewer than five occasions, and I had never heard of the New York Times. For me, these sessions were deeply valuable. Hearing his perspective on ethical issues, his experience with the Peace Corps, and his adventures living in Greece sparked my curiosity about the world outside of Orlando.

For all of his time, knowledge, and effort, Howard simply asked that I help him change out a few light bulbs in his office. In fact, he would even pay me generously for small tasks like changing light bulbs, and this helped alleviate the burden of my financial situation. The additional $20 per week was a big deal at the time.

When admissions day rolled around in the spring of 2011, I was accepted at Princeton and Wharton on full financial aid. That was a special day, and it was one that Howard and I cherished together. 18 years of hard work had finally manifested into the tremendous opportunity I had been seeking. Accepting Princeton’s offer was just the beginning. I still had a long way to go.

Around that time, I started to wonder how my relationship with Howard would change moving forward. His mentorship, generosity, and support allowed me to realize my potential and gain admittance to one of the nation’s top schools, but how would our relationship evolve from there?

Princeton and Beyond

In the months prior to my departure to Princeton, I continued to meet with Howard regularly. A week before heading to campus, he bought me my first suit and taught me how to use chopsticks at a local Japanese restaurant. As it turns out, these were two of the most valuable things anyone has ever done for me. During my first two weeks on Princeton’s campus, I went to a sushi restaurant with classmates and attended a JP Morgan networking session.

During my first semester at Princeton, I struggled to adapt to the university’s rigorous academic standards. Howard encouraged me to continue pushing forward, assuring me that I would soon feel as comfortable as my peers that had attended elite prep schools. Before taking my first semester exams, he told me it was time that I experience the world first-hand.

Over the next week, he helped me plan a 10-day trip to London and Amsterdam. Howard funded the entire endeavor. Immediately after finishing my exams and experiencing my first snow, I jumped on a plane to Heathrow Airport – alone. It was scary, exhilarating, and my first time outside of the United States.

The trip resulted in a burning desire to continue traveling and opened my eyes to the vastness of the world, which I had previously had very little exposure to. Those days, I thought a lot about what I had missed by staying only in Florida for the first 18 years of my life. However, with only a small amount of capital in my checking account, I’d have to be creative if I wanted to keep exploring.

That summer, Howard encouraged me to keep traveling despite my financial struggles. He helped me reach out to the United States Ambassador to Luxembourg, who agreed for me to stay in the Embassy and shadow him for a few days. In a last minute attempt to fund the trip, I took a flight to Norway and earned a living by painting houses for 8 weeks.

Eager to see more, I spent the following summer learning Portuguese in Rio de Janeiro and my next semester studying youth unemployment in Barcelona. In many ways, Howard lived vicariously through my experiences. When I was unable to afford something that would broaden my perspective, he always helped out.

The Fragility of Life

After returning abroad from Spain, I pursued a highly coveted, well-paying internship in investment banking. After dozens of resume reviews, months of technical preparation, and a lot of coffee, I landed an internship with Barclays in New York City. Much like my admission to Princeton, this was a particularly special moment for me and Howard. In large part, it was the realization of my pursuit to escape my social and economic instability.

That spring, I returned home for a few days. I met with Howard, and we discussed what it would mean to begin a career on Wall Street. The next day, he went in for hip replacement surgery. Less than 48 hours after the surgery, I received notice that Howard had had a stroke. He was in a coma, and his chances of recovering were slim.

Within a week, it was clear that he would not recover. His family made the decision to remove him from life support. As many people do in these situations, I said my final goodbyes and wept deeply.

This was my first encounter with death. I was fortunate enough to have a loving family and girlfriend to support me through that time. Ironically, I found myself wanting to talk to Howard about the experience. It was another “first” in my life, and I knew he would have something valuable to contribute to the discussion.

Paying it Forward

In a relatively short amount of time, Howard had a tremendous impact on my life. The most important lesson that he taught me through both his words and his actions was the value of paying it forward. During each encounter, he always reminded me that it was my responsibility to remember my humble origins and to help others. At the time, I didn’t fully appreciate the value of this simple, but powerful principle.

To understand the nature and power of paying it forward, consider the full effect of Howard’s actions in my life. Through simple, highly personal gestures – sharing life experiences, providing light financial comfort, and challenging me to think on a global level – Howard allowed me to tap into my potential. For me, that meant attending a top university, developing a more open and global perspective through traveling, and getting on my feet financially.

In fostering the realization of my own pursuits, Howard instilled in me the value of mentorship and helping others in whatever way possible. At this point, I have only practiced this principle on a small scale. Whether it’s advising friends and strangers on the college admissions process,  helping family members procure scholarships and jobs, or sharing my story and experiences with people from all over the world, I try to find small ways each day to enhance the lives of others.

To the extent that I have positively influenced the life of even one other person, the impact of my efforts may extend to that person’s friends, family, and any strangers they meet. Further, it might even reach their future families and generations of others that will come after their time.  

In short, paying it forward has a powerful butterfly effect. In helping one person, you often indirectly helping dozens and perhaps generations of others. You don’t have to donate millions of dollars or start a non-profit organization to pay it forward and have it mean something.

In fact, paying it forward often takes on a simple, personal character. Whether that means taking 20 minutes out of your day to edit a friend’s resume or helping a coworker be accountable for their yearly goals, you can have a tremendous impact with relatively little effort. Through approaching every day of life with paying it forward in mind, we can foster a more collaborative, understanding, and productive society.

It has been nearly three years since my good friend and mentor Howard Sherman passed away. My story is only one of many in which he actively chose to take part in. I think about him nearly every day, and about how in his mind, paying it forward never involved expecting anything in return. For all that he did for my life, Howard only asked for a ticket to my graduation at Princeton. He passed away a year before I could give him that ticket.

Below is a picture of Howard and me at my high school graduation party. It is the only photo we ever took together.


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