Intern to Evangelist: 6 Tips to Create the Fairy Tale Career of Your Dreams

Kaishon Holloway, UConn 2015, shares his story and advice for current students looking to create their dream careers.

I was born in Fairfield County, Connecticut which is aptly named the Gold Coast — it’s home to countless hedge funds, billionaires, and sprawling estates. However, it’s also home to one of the largest wealth gaps in the country — that’s where I come in. I was raised in Bridgeport, Connecticut which is located in the northern part of the county and on the southern part of its socioeconomic spectrum. We don’t have many silver spoons in that part of the Gold Coast. This unique dichotomy of extreme wealth and extreme poverty was the backdrop of my life. Being Black, gay, and at the lower end of this ever-present wealth gap motivated me early on. I quickly learned that a formal education and a successful career was going to be my pathway to a storybook ending.

My career journey started in 2011. I had just graduated high school and landed my first job as a cashier at a local family-owned grocery store. A month later, I started my first semester at UConn Stamford, and a month after that my father passed away unexpectedly. Shortly after my father’s untimely death, my mom spent a month in the hospital dealing with her own health issues and I finally turned 18. This was a huge turning point in my life — facing my parents’ mortality while juggling the new responsibilities of young adulthood.

This series of unfortunate events gave me a life-altering jolt and much needed wake up call. Besides burying my father, the most vivid memory of that time was visiting my mom in the hospital on my 18th birthday. We spent hours talking about my future and mulling over existential questions about life and who I wanted to be in this world. All while facing the very real possibility that I may be doing it alone.

By the end of the conversation, I decided that I was going to pursue a career in luxury real estate. My interest in the field was heavily influenced by the beautiful homes in neighboring towns and the palatial mansions I saw featured on shows like Million Dollar Listing. That evening I started to design the life that I wanted; I looked up every luxury real estate brokerage in the area and emailed hundreds of agents about potential mentorship opportunities. Two weeks later I landed my first internship working for a top, high-end real estate agent in Greenwich, Connecticut and the rest is history.

Over the next four years, I worked various jobs and internships across multiple industries. This journey wasn’t always a yellow brick road and definitely presented its challenges. Some of those challenges included: working multiple jobs at once, commuting long hours on public transportation, getting rejected from my school’s business program three times, and being forced to drop out of college for a year due to financial strain. Even so, I was still able to stay employed, get back into school, and finally graduate. Ultimately, I leapt over all of the hurdles in my way to build the career of my dreams.

Here’s what I learned along the way:

  1. Grit + Glamour = Success: The way I landed my first job at the grocery store was by showing up to a job fair and showing out in the interview. It’s also important to mention that it was 105℉ and there was a 2-hour wait outside while I was dressed in my Sunday best wearing shoes two sizes too small. Luckily, I had carved out the inside of those shoes the night before, so I had a little more wiggle room for my toes. By the time I got to my interview and told them that I “dress for the job I want,” I had my first job offer. Being able to present a polished package and nail the interview despite all of the obstacles taught me an important lesson — enduring temporary discomfort and powering through with a smile can end in a sweet reward.
  2. Shoot your shot: Always apply for that job or email that person you idolize — you never know what response you might get and you only need one. When seeking my first real estate internship, I emailed over 300 agents. Only one responded and two weeks later that person was my new boss paying me double what I was making at my other part-time job.
  3. Say yes and figure out the rest: If you have a once in a lifetime opportunity on the table, say yes and take it. I’m a big fan of taking safe, calculated, and well-researched risks but with an emphasis on the risk. I’ve had many instances in my career where opportunities came up that required skills that I didn’t possess at the time or required me to move across the country. Was I going to pass up a great growth opportunity because I didn’t know InDesign or had to live in a new state for 3 months? The answer is no.
  4. Authenticity is key: On paper, being gay, Black, and poor doesn’t exactly work in your favor in the place where they filmed The Stepford Wives. Though it was intimidating to compete for jobs against peers with more connections, access, and money, I used what made me different to stand out amongst the crowd. It can be exhausting being the only person who looks like you in the room, but I also learned that what made me different often put me under the spotlight. This extra level of attention led the Center for Career Development to notice me and connect me to an incredible summer internship program. I was able to secure the internship, move to another state, and gain hands-on experience at a great company. Over time, I gained confidence and felt comfortable openly talking about Black issues and being out in a work setting. Being authentically me allowed me to create real connections with my colleagues and gain lifelong friends.
  5. Make genuine connections with people: When I landed my first corporate internship at a tech company, I made a concerted effort to build relationships with my teammates. I decided to start a lunch series called “Lunch with Kaishon” where I would have lunch with teammates, fellow interns, and senior leaders across the business. This allowed me to show people who I was and what I could do. I was able to learn my colleagues’ fascinating backgrounds beyond their job titles. By the end of one semester of lunches, I had formed many relationships that would have otherwise taken months to build if I hadn’t been so direct and proactive.
  6. Pay it forward: The reason I got my first internship (at the tech company) was that a former classmate referred me. That internship turned into a glorious 7-year career with the organization that culminated with me being an evangelist, the face of the company. As an evangelist, I had the opportunity to travel the world as a keynote speaker educating HR executives on how to build a diverse talent pipeline for their organizations. This unique position also gave me the chance to interact with job seekers and show them how to use a plethora of free resources to land their dream job. I’m grateful every day for that opportunity and being plucked out of obscurity to do what I believe is my life’s mission — to motivate others and use my platform to effect positive change. Small acts of kindness like recommending someone for a job, making yourself available for a 15-minute call, or sharing your wisdom on a panel can go a long way. I take as many opportunities as I can to participate in two-way mentorships with my peers, as well as people younger and older than me. You can learn a lot and get a well-rounded perspective on the world that way.

Learning and staying true to these principles has served me well throughout my experience. I hope these tips help you navigate your career journey and fully live your own personal mission.

By Tara Malone
Tara Malone Associate Director, Regional Campuses Tara Malone