Embracing My Squiggly Path: The Strengths of a Non-Traditional Career Journey

My career path has never been a straight line, and that's exactly its power. From the hustle of a hospitality takeout window to the strategic boardrooms of tech startups, each turn has taught me the resilience and adaptability that only a non-traditional path can teach. This journey hasn't just shaped my professional life; it's forged who I am, armed with an eclectic toolkit of skills and experiences that I bring to every challenge and opportunity.

Starting in hospitality, I mastered the art of customer service, learning to anticipate needs and forge connections that last. Climbing from an entry-level position to managing top restaurant groups in Boston, I developed a keen sense for business operations and human dynamics. These early years weren't just about serving food; they were my first lessons in the intricate dance of customer relationships—a foundation I would rely on throughout my career.

But in 2016, life threw me a curveball. Diagnosed with fibromyalgia and stepping up as a medical proxy for my godmother after her stroke, I faced a stark choice: continue in a physically demanding role or pivot to preserve my health and provide the care my family needed. I chose the latter, turning to online consulting, where I could sustainably leverage my deep understanding of service and operations.

This pivot was not a step back but a broad leap into a rich landscape of opportunities. I embraced everything from business planning to customer success frameworks. The breadth of my work expanded exponentially—supporting not just restaurants but construction firms, healthcare providers, artists, and more. Each client and project added layers to my expertise, painting a vibrant tableau of industries and challenges.

It's important to recognize that expecting a linear career path often reflects privilege. For someone like me— an African American, female, gay, differently-abled individual, and a former ward of the state—access to the traditional networks that typically create a straight line from internships to C-suite roles is not just limited; it's often entirely out of reach. This reality makes my squiggly path not just a personal journey but a testament to the strength and creativity needed to navigate systems not built for people like me.

In reflecting on this, I am profoundly grateful for the incredible network that has buoyed me through every high and low. More chosen than biological, this extended family has been a constant source of strength and support. I was also blessed to attend incredible institutions; my education at Phillips Academy of Andover and George Washington University opened doors to networks of remarkable individuals who have played a crucial role in my career. This combination of a loving support network and strong foundations has been instrumental in helping me navigate my non-linear path and in reaching the place I am today.

In 2017 my journey led me to the heart of a fintech startup empowering the LGBTQ+ community. As CEO and Director of Content for PridePocket, I wasn't just managing a business; I was nurturing a community, advocating for privacy, and crafting a platform that stood at the intersection of technology and social good. This role underscored the impact of my work, transforming abstract strategies into tangible support and inclusion.

As the pandemic reshaped the economic landscape in 2020, I found many clients squeezed by the downturn. Transitioning into an Account Executive role at a MedTech company to offset the squeeze, I quickly realized how a sales pitch could undermine the genuine relationships I aimed to build with every client. This experience deepened my commitment to operations—where I could focus solely on enhancing customer experiences without the dual motives sales professionals must navigate with such grace.

Returning to my roots, I joined TIO International in 2023, where I scaled customer success operations to an enterprise level. Here, I redesigned the company's customer success frameworks, boosting engagement by 40% and standardizing onboarding processes for the first time, leveraging my diverse experience and strategic vision.

Now, as I serve private clients in the nonprofit and small business sectors, I continue to apply my extensive background while I search for the next opportunity in customer success. I bring a wealth of experience, skills, and adaptability—qualities that some companies may overlook because of my nonlinear path, but the right leader will recognize as a jackpot.

This 'squiggly' career has been more than just a series of jobs; it's been a journey of meaningful transformations, unexpected lessons, and profound connections. It's taught me that the most unconventional paths often lead to the richest destinations and that every twist and turn enriches not just my professional expertise but my personal resilience.

I share my story to celebrate the non-traditional path and to inspire those who walk their own winding roads. We are not defined by the straightness of our paths but by the breadth of our journeys and the depth of our growth.

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Let's connect and share our unique paths as we forge ahead, proud of the roads we've traveled and excited for the ones we'll discover.