Lessons in Resilience: Growing Up with My Entrepreneur Father

A Tribute to My Father’s Entrepreneurial Spirit

Some of my most formative years were spent in the gentle hum and whir of my father’s shoe factory, nestled in the heart of one of Jamaica’s inner cities. My father, a dedicated entrepreneur, specialized in making quality shoes for men and children—a trade he built from the ground up. As a small business owner, he wore every hat: boss, product developer, head of sales, customer service, HR, payroll, and more. With limited resources and even less access to the business wisdom we take for granted today, he persevered, providing for his family and creating employment opportunities for up to 30 people in our community. 

Our afternoons as children weren’t filled with idle play, but with the rhythms of industry. After school, we’d walk to the factory, waiting for our father to finish his work well into the night. There, amidst the scent of leather and the steady tap of hammers, and other tools, we did our homework, absorbing lessons not taught in classrooms—the realities and sacrifices of entrepreneurship. My father, though lacking formal education, became my greatest teacher; his tenacity and work ethic instilled values that have guided me ever since.

Fridays were especially memorable. On those days, my father would head to the local commercial bank, returning with crisp bills and small brown envelopes. With my love for mathematics, I eagerly helped calculate and count wages for each worker, carefully placing cash in envelopes and labeling them by hand. It was a small but meaningful role in the family business, a chance to contribute. Even as a child, I sensed the significance of those moments: the dignity of honest work, the bonds forged within a team, and the pride of building something from nothing.  I realized my involvement wasn’t just about numbers; it was about belonging to something greater, contributing to a legacy of entrepreneurship.

Then there were the times I witnessed envelopes being stuffed with ‘arbitrary’ cash for others from the community or those who arrived from the ‘country’, who were not employed.   My father was extremely generous and would help anyone in need - to a fault some would say.  I couldn’t write about him and not mention this.

Yet, like many entrepreneurs, my father faced challenges beyond his control. When imported shoes began flooding the Jamaican market in the 1980’s/early 90’s, the landscape shifted drastically. He kept downsizing - or maybe I should say - forced to downsize - focusing on the remaining ever-dwindling loyal business customers, and eventually moved what remained of his enterprise to our backyard. Despite the hardships and the eventual closure of the business, his entrepreneurial spirit never faltered. He adapted, repaired shoes, made and sold boxed lunches, ground provision, among other things and served his community up to about a decade prior to his final days, leaving behind a legacy of grit and perseverance.

Today, after decades working with a multinational conglomerate, I am pursuing self-employment, offering services and authentic business coaching to aspiring leaders, managers, and entrepreneurs.  Just like today, I often reflect on my father’s journey. I am deliberate in my approach to stand apart from overly theoretical, lengthy, or expensive consulting and training packages—I draw from real, practical experiences, lessons and a life lived at the crossroads of challenge and opportunity. I carry his lessons with me: the courage to begin, the resilience to adapt, and the importance of a loyal community. I often wonder what online business ideas or encouragement my father might share if he were here today. Would he cheer on my journey in leadership development? Would he lend his wisdom, bolstering me with the same generosity that marked his life? I am sure he would – in his own undeniable way.

To all resilient business owners and dreamers contemplating the leap into entrepreneurship: the path is not always smooth, but you are not alone. There are vast resources for small business growth, digital marketing for entrepreneurs, and online business ideas, as well as experienced voices in authentic business coaching to guide and support you. The spirit of entrepreneurship thrives in every community, in every story of perseverance, and in every lesson passed from one generation to the next.

May we all find the courage to pursue our ambitions, embrace innovation in business, and make a lasting impact—just as my father did, one step at a time.

Paulette Sterling

I've got the experience, adaptability, and authenticity that aspiring men, women, teams, leaders and organizations are looking for. They need someone who can be the answer to their prayers for practical, effective and economically priced interim help, support, guidance, instructions, and coaching, all while making them feel truly supported.

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