INSPIRED BY A SHOESHINE BUDDY
Author rises from Dorchester to the White House
Different people have different definitions of “Success.”
For me, neither money nor title nor privilege has anything to do with it. A “success story” to me will always be anyone who continually tries to be the best person they can; works hard; and looks out for others.
After a childhood of abject poverty which saw me and my family evicted from 34 homes by the time I was 17 years of age as well as living in multiple cars along the way, I somehow ended up in the White House working for two presidents; as an official at the Pentagon; as a principal at the two largest law firms in the world; and as a bestselling author.
During and after those careers, I often spoke at schools. Most especially, schools which housed poor and disenfranchised students. A common question was: what inspired you to escape that poverty and dysfunction?
When asked, I tended to give the usual answers: I avoided the “bad” kids; I never succumbed to peer pressure; I stayed away from alcohol and drugs; and I refused to let those with more money or “station in life” define me or belittle my dreams.
All true. But I was still missing a key factor.
Then, when my best friend from my Dorchester childhood — Gerry Donovan — paid me a visit a few months ago, that missing ingredient flashed before my eyes. When I was but 12 years of age, it was 10-year-old Gerry and his incredible work ethic, which inspired me at precisely the most needed time of my life.
I first met Gerry when he was a precocious 5-year-old who walked into my grandparents’ home — uninvited — on Hamilton Street in Dorchester, found 7-yearold me sitting in the living room and promptly announced: “Hi, I’m Gerry. What’s your name? Want to come out and play?”
The friendship has endured ever since.
While it is not my place to go into the details, Gerry also overcame a truly dysfunctional childhood. More than that, he was a little force of nature who was never going to wait for life to come to him. By the time he was 10 years of age, he had established his own business.
During that time, my family had lived and been evicted from three different apartments on Hamilton Street. One of them being the very triple-decker where Gerry and his family lived.
Just down the street from us on Columbia Road was a Ford Dealership. On his own, 10-year-old Gerry established himself at the resident “Shoeshine boy” at that dealership where he would shine the shoes of the salesmen — and occasional customers — after school on weekdays and during the mornings on weekends.
Soon thereafter, he was kind enough to bring me into the “business.” Entirely because of Gerry, something truly remarkable happened. Thanks to the generosity and tremendous work ethic of my 10-yearold best friend, I became inspired with the realization that perseverance, hard work, and belief in oneself will always pay dividends no matter the circumstances.
But more than inspire me, Gerry also always had my back. During the short time we lived in the same triple-decker, I had agreed — against my better judgment but in support of my brother — to transfer from the public Grover Cleveland middle school in Dorchester (which I loved), to Gate of Heaven high school (a parochial school) in South Boston (which I hated).
While the kids at Gate of Heaven were at best middle class, the ones in my freshman class were especially cruel to me because of my poverty, dirty clothes, and hole-filled shoes. To be sure, they did not know better and were just mostly being kids, but it did hurt. Especially as I had my first crush on a very kind girl named Ann in the class at the time.
That cruelty did affect me. But not for long. It was Gerry who continually lifted my spirits when I got home. Because he lived the life, he also knew just what to say and when.
One more invaluable lesson I was able to pass along to other children and adults struggling in life.
As Gerry got older, the force of nature that was him only created more energy. By the time he was 13, he somehow got a job in a grocery store. Then, against all odds, by the time he was just 24 years of age, he had bought a home in the suburbs of Boston. Simply amazing. From there, he carved out a remarkable 30-year career as an IT professional and manager. Today, he is still happily married to his high sweetheart Carol; the father of two boys; and the proud grandfather of two girls and one boy. By any definition, the true measure of “success story.”
In many ways, life today for those less fortunate, disenfranchised, or discriminated against can be much tougher than the obstacles Gerry and I fought every day to overcome. But, inspiration can still often be found in those closest to us.
I found mine in a 10-year-old who started his own business and never looked back. No matter our age or station in life, we all need illumination and support from time to time.
It is out there. It’s just up to us to recognize it and implement the lesson.
Douglas MacKinnon is a former White House and Pentagon official and author of the book: “The 56 — Liberty Lessons from those who risked all to sign The Declaration of Independence.”