POST #9: An Unconventional Path: Reflections on Career Planning Missteps

During high school, I was firmly against the idea of college. By 18, I was juggling multiple jobs, generating several income streams, and opened my own restaurant soon after graduation. College seemed irrelevant.

The journey from aspiring chef to a finance and accounting professional with multiple degrees wasn’t straightforward. My passion for business and operations has driven my success. While I never envisioned working in corporate accounting, I found it aligned perfectly with my entrepreneurial spirit.

At 17, I believed college was a waste of time, but by 21, I kept a promise to my mother and earned a Bachelor’s degree in Public Policy and American Government. Despite graduating with a 3.47 GPA, I felt unfulfilled, having rushed through college while running my restaurant. Soon after, I sold the business and impulsively enrolled in law school—an experience I ultimately regretted.

After three semesters of law, I pivoted to pursue an MBA, which transformed my professional outlook. Concepts from my MBA classes continue to shape my career today, and a recommendation from my professor led to my first role as a junior analyst at Full Sail University. This marked the beginning of a diverse career, spanning roles from VP of Sales to Interim-CFO, and leading me to live and work in places like Rio de Janeiro, Denver, Singapore, and Orlando.

Unlike my wife’s structured career path with Ernst & Young, mine was unconventional and filled with twists. Looking back, I’ve made mistakes—rushing through college, pursuing law without understanding the profession, and not fully immersing myself in the college experience.

The key lesson I’ve learned is to be intentional. Whether you're studying or working, seize opportunities to gain real-world experience, set clear goals, and approach your career with a thoughtful plan. It’s never too late to make the right decisions, but being intentional from the start can save time, money, and stress.

Deepak Kumar