Passion Projects: From Corporate Attorney to Curated Travel Consultant

What was your previous business/career?

I am an attorney. My first job after undergraduate school in 2000 was as a business consultant with a fancy pants US accounting/consulting firm. Then, after graduating from Howard Law School in 2007, my first job as an attorney was in the New York office of a large fancy pants US international law firm. I was a corporate attorney in the Private Equity/Mergers & Acquisitions Group. In between and after these two high-profile corporate America gigs I worked for a congresswoman, a non-profit, as a contract attorney, and founded, ran, and closed three businesses focusing on client experience and project management for startups, small businesses, and entrepreneurs.

Why did you want to leave and do something else?

Either I was restless working in an office for someone else or, although I loved each of my businesses, they did not speak to my heart. It was hard articulate to this idea during those moments in my life; I just knew that I was uncomfortable and ultimately unhappy or at least not as happy as I knew that I could be. So, I had to keep moving. In 2010, I left a very comfortable job that could have resulted in a financially stable and prestigious career because it was clear that it was time to move on – I needed more, I needed different. I had absolutely no idea where I was moving to or toward, but I was certain that I would know it when I found it.

Also, I noticed that each time I entered large firm life, my experiences were right in the middle of a financial crisis. First in 2001 as a business consultant with Arthur Andersen, I had to come to terms with the Enron Scandal. And then in the aught years as a corporate attorney at a well-respected firm, my career straddled both sides of the Great Recession and included work on notable PE/MA deals and bankruptcy matters. I decided to pay attention, listen to my heart, and accept that perhaps large firm life was not my life’s goal.

What was your final “jumping point” into pursuing your passion as your business?

My “jumping point” was the 2014 Best Friend Road Trip – four whole years after I left the firm.

I was fortunate to have grown up traveling the world, and since I was born and raised in New York City, I felt like I had access to every part of the world – all foods, music, cultures, people. But, at some point I realized that, although I had traveled the world and lived with representatives of the world in my city, I had not traveled the United States.

I had always wanted to drive cross country in an effort to see more of the US, but I was frightened. I was afraid of what I would find as I drove across my country, my ancestors land – land that was stolen from my ancestors, land that my ancestors were stolen away to, land that my ancestors fled to looking for a new start, land that my ancestors stole. I was frightened of what might find me.

In each state, each city, each town, each community I let go of some fear, pain, worry, anxiety, depression, and trauma, and I simultaneously expanded and got lighter. This country is absolutely beautiful and filled with absolutely beautiful people. I was greeted with smiles and encouragement and excitement and wonder. I got to see and touch parts of the US that I may never ever see or touch again. I have traveled all my life and in that wrinkle in time, travel saved my life.

In December of that same year, Presidents Barack Obama and Fidel Castro made an announcement that our governments were going to begin to play nice, build toward a new normal, do better by their citizens, and rebuild our relationship. Subsequent changes to U.S. legislation made it possible for me to start a consulting business with a focus on travel to and trade with Cuba as the starting point. I am clear that the 2014 Best Friend Road Trip was the detox, the cleanse that opened up space in me to be willing and able to fully participate in my life and take advantage of this opportunity.

What is your current business, your “passion” business?

My current business, Diaspora Travel & Trade, is a full-service consulting company. We provide curated travel experiences, commercial opportunities, relationships & networks, and related content for those travelers and traders interested in the “Americas.” We specialize in sustainable travel, social enterprise, and the commercial and cultural activities of Black and Indigenous communities of this region.

Diaspora is defined as: (1) people settled far from their ancestral homelands; (2) the place where these people live; (3) the movement, migration, or scattering of a people away from an established or ancestral homeland.  In this context, Black refers to folks whose ancestors come from Africa and Indigenous refers to those folks whose ancestors are indigenous to the “Americas.”  

I started Diaspora in 2015 with a focus on Cuba, because at that point I had been traveling there for almost a decade, I had a network of family, friends, and colleagues to work with, I had stories from my paternal grandmother about our Cuban ancestry, and US people were excited to learn about this island nation so close, yet so far away.  In 2019 we are expanding our promoted projects and programs into Jamaica and in 2020 into Brazil.

How long have you had this passion?

I have had a passion for travel and for trade my entire life. My love of travel comes from my parents. Not only did we travel throughout the year, but my childhood home in the Hell’s Kitchen neighborhood of New York City was also a cultural center. There I learned to love the world. They had parties and performances and presentations and dinners with people seemingly from every corner of this planet. I grew up with the world in my backyard – as far back as I can remember I knew that we are all more alike than we are different.  

My love of trade/commercial activity/business also comes from my family. I was born into a family of entrepreneurs, successful business owners in every generation. I grew up watching the adults run their own businesses, and I saw the power, pride, joy, struggles, failures, and obstacles that come with this path. It is possible that there has never been a time when I believed that I would work for someone else as my ultimate career. I have always known that I would be my own boss.

What is a typical day like for you in your business?

I have two different schedules, one for the U.S. and one for Cuba. And in both I am NOT a morning person!

I take a really long time to get focused and motivated, and I take multiple breaks throughout the day.  One of which is working out in the evening.

In Havana, the difference is that my trainer starts harassing me at 5:45 a.m. so I work out in the morning and not at night, I have many more face-to-face meetings and interactions, email and social media is usually done in the evening when the WiFi zones have less people.

Is there anything you wish you would have known about taking the step to turning your passion into your business that you would like to share with our readers?

I wish that I had known how much more productive I would have been if I had just accepted my personal work/creation habits and processes. I wish that I had allowed myself to learn and develop these habits and processes without the anxiety, worry, and shame that I wrapped myself in. It takes me a very long time to get focused on a task – all tasks, any tasks, even small tasks, but certainly those larger tasks where I am generating ideas and words for programs, projects, proposals, papers, and presentations. My mind is always racing with so many thoughts, and this causes me to just not want to do anything so that I can get some peace. I just want to listen to music or read a book or watch a show and zone out.

I have always been the person who waited until the absolute last minute to complete a project and I was that person who said “I work best under pressure” because the final product was always great. But I was painfully and shamefully aware that it was not MY best. If only I had given myself more time, if only I didn’t procrastinate and could focus, or did not have so much on my plate. But how do I get more time if I won’t start earlier.  So even though I had success, I did not celebrate it … and I was constantly mentally and physically exhausted from this struggle process.

Everything changed when I accepted that my “procrastination time” is part of my process. That it is NOT time wasted or spent improperly, it is part and parcel of my genius, my greatness, my success. I decided to accept and embrace that part of me and not criticize – no matter how strange or seemingly time consuming. The result is that I enter into the production part of the process in a space of excitement and peace and joy and with a willingness to participate. It’s not such a struggle, it’s not so painful. But, it is still very much a work in progress.

What are three pieces of advice you would give a reader who wants to turn their passion into their business?

“Do well for yourself and good for others, they are not mutually exclusive.” – Dr. Ronald W. Davidson

—We can make the world a better place AND have personal joy, health, and wealth. We don’t have to choose.

“Whether you believe you can do a thing or not, you are right.” – Attributed to Henry Ford

—Thoughts are things and worry is a form of prayer, so stay intentional and positive.

“Life is both too long and too short to do ish that does not bring you joy.” – Kasara E. Davidson

—Live your best life because you gotta be there until the end.