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My Life is Not a Vacation, It Just Looks Like It

In Paje, Zanzibar. Photo Credit: Andre Perry

A few weeks ago, I asked my sister to do something for me. It was a favor that I had previously requested, but now was urgently demanding. She is a single mother with two very rambunctious young boys that are very sweet the first ten minutes when I return home, then turn into little rascals. Sweet, beautiful, crazy, little rascals. She got upset with me for putting demands on her and told me “Jessica, my life isn’t a vacation like yours.” While I was taken aback and really just wanted to know if she would do the favor for me, I really began to think about people’s ideas of what life should be.
Our lives are the consequence of a series of decisions that we have made over time. Some decisions we make may feel forced, but I assure you, every decision we make is voluntary. Even if someone is holding a gun to your head your decision to avoid death is still voluntary, albeit heavily influenced by the threat of violence.

I was raised in a Ugandan household in Detroit, Michigan where educational excellence was stressed. I was high achieving since I was a young child and always imagined myself in a high powered corporate position. I graduated university a semester early and at the age of 21, I started a full-time career in pharmaceutical sales. Coming fresh out of college with a salary and benefits package of six figures allowed me to buy myself a riverfront condo, at the height of the market, vacation in Miami, NYC, London, Paris and Madrid, and to shop until I dropped every payday. My custom-made walk-in closet was filled with items from Neiman Marcus, J. Crew, Gucci, and Marc Jacobs. I ate out most days, spent too many happy hours at the Woodward in Detroit, a restaurant that is long gone. I blew money fast, had a ton of debt, and still was unfulfilled.

Joshua Tree for the Childish Gambino concert. Photo Credit: David Wilson

At that time, a two-year period at the beginning of my 20s, everyone thought that I was living the dream. I had dreams and goals of being the youngest hospital rep in the company and my management supported my ambitions. My doctors loved me and I was certainly one of the favorite reps in my territory. Life on the outside was enviable.

As I went through the motions of my life at the time, I enjoyed it, but never was content or fulfilled. My whole life I engaged in activities that people convinced me should be fulfilling. In high school I was voted class trendy and hosted the first ever fashion show and freestyle battle. In college, I assumed multiple leadership positions, graduated at the top of my class and was a darling (most times) of the administration and my professors. Ambition abound, I had internships that anyone would give their left arm for and was accepted in a very competitive summer program at Harvard Business School my junior year in college. From childhood, I, with the support of my parents, had laid the foundation for me to take the corporate world by storm and have a very successful career, then of course get married, have perfect children and a beautiful home with at least two luxury cars parked outside.

One day, something in me snapped. It was bonus day and despite my efforts, my sales quota and market forces beyond my control resulted in a check that was so low I am embarrassed to write the number here, while people that I know did not work as hard, had checks 20 times what I had. That day I went home and googled teaching jobs in Japan. I applied, was accepted and began preparing for a move to a country and continent that I had never even visited. This was in 2008. This was before Twitter was popping, before Instagram, and before the “Black travel movement”.

Surfing in Peru. Photo Credit: Elton Anderson

Prior to this move I had traveled to ten countries on three continents. I had not done any solo travel, but that did not stop me. In the back of my mind I always knew if things did not work out I could hop on a flight home and reapply for a job on my old team, and go back to the life I was leaving behind. So, I packed my bags, put the contents of my two-bedroom condo into a storage unit, and had an unforgettable going away weekend. As a final preparation, and without a second thought, I shaved my head, a move that many people in my family were not fans of, but my practical mind pushed me to do it because I just knew I wouldn’t find anyone to do my black hair in a small city outside of Kyoto.

I recall the day that I boarded the plane, sweaty and drained from unpacking and repacking my two 100-pound suitcases – I had never lived abroad so I packed EVERYTHING that I might possibly need, including a year’s worth of deodorant, toothpaste and books. Most of the books stayed behind. As I walked to seat 34A, I glanced around the plane. NO ONE looked like me. The plane was full of Asian people and as I sat in my seat a sinking feeling came over me as I realized this would be life for the next year. In America, we take diversity for granted, for I was heading to a country that was very homogenous, to the tune of 98.5% of the population being ethnic Japanese.

Birthday in Cuba. Photo Credit: Elton Anderson

When I landed in Osaka and looked out of the window, I could not read ANYTHING. You see, this isn’t like most European countries, where even if you do not speak the language you can make out the words, this was the land of Kanji, Katakana and Hiragana, the three Japanese writing systems. After overcoming culture shock, learning some Japanese and falling in love with the food, people and culture, Japan quickly became one of my favorite countries and subsequently one of the best years of my life.

At some point during my stay in Japan I told myself, I would not go back to live in the US for three years. By the end of it all, I lived abroad for nearly seven years. I lived in London, Benin, and Rome and I traveled to a lot of countries, 70 and counting. I obtained a Master’s degree and worked for the UN, too.

In 2014, having a serious case of FOMO – I missed births, weddings, funerals, birthdays, and the drama of dating in the US in your 20s – I decided to move back at the age of 30. I found a “great” job working at a consulting firm just outside of DC, shared a dope Capitol Hill apartment with one of my closest friends from childhood, and I was categorically UNHAPPY. Again, here I was living a life that people thought was enviable, but I was disinterested. During that year, after crafting the perfect honeymoon for a very famous friend, I started my company Jet Black, a boutique travel firm that works with individuals, governments and brands to encourage tourism to countries in Africa, Central and South America, and the Caribbean.

After a full year in DC, armed with a logo, a few ideas and a URL, I quit my job, moved my things into storage (are you seeing a pattern?), and I began traveling, again. In the beginning, I didn’t have a clear idea for the business. I hosted a group trip to Haiti in November 2015 then stopped working on the business. After coercing myself to climb out of depression and put effort into my business, in April 2016, things went into full swing. Subsequently, nearly a year later, business is booming, I am traveling more than ever, working more than ever and happier than ever.


Morocco for Elton’s birthday. Photo Credit: Elton Anderson

Many people look at my Instagram and because I am always traveling to swoon worthy locales, assume that I am on vacation (I work more now than I ever have in my life). People assume that I am independently wealthy (not just yet). People assume that what I am doing is not a “real life.” I assure you it is.
To bring it back to the beginning, we all make choices. We have been socialized to believe that a successful life is finding a high-powered and high-paying career, buying a huge house and fancy car, having a beautiful family and that cute little dog. But, the thing is ordinary life never interested me.

Life for me is experiencing new foods and new cultures. Life for me is learning new languages and arguing in foreign languages. Life for me is experiencing the world with my closest friends. Life for me is taking calls in Bali with clients in New York. Life for me is setting goals of reaching Diamond Medallion on Delta Airlines. Life for me is about dreaming and achieving the impossible, off-the-beaten path. Life for me is convincing and inspiring people to live alternative lifestyles. Life for me is releasing my attachment to material things.

Exploring Bali. Photo Credit: Elton Anderson

I do not have a car, nor an apartment. My only fixed overhead is my cell phone bill. Beyond student loans, I do not have debt. I live within my means, and while to some my life looks fancy, it is actually quite simple, at least in my eyes it is. I never know what day of the week it is. My body is now incapable of getting jet lag. I very very rarely do things that I do not want to do. I am not focused on becoming rich, but rather having enough to do the things that I want to do.
My life is not a vacation. It just looks like it.

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This Post Has 27 Comments
  1. I lived reading this! It spoke to my soul! I’m so so proud of you, being a fellower Detroiter and just living in your purpose and following your own path!

    I dream of leaving this mundane life behind and would love to travel like you do. I’ve traveled quit a bit, but have never lived abroad or solo traveled. The fear of money creeps in and I wonder how I will afford life abroad if I can barely afford it here in Detroit? Do you have any tips? Where to start?

    Thank you so much for your inspiration! I wish you continued success and happiness!

    1. Hi Enjoli, thank you for your kind words. The most important starting place is ensuring that you can use your skills to earn enough money to do the things that you want to do in life, that may also mean reducing other costs in your life to make room for new interests. Wishing you all the best!

  2. I can relate to a lot of this. I am taking a leap of faith in 2021 and doing something I have always dreamt of doing but felt the pressure of being “normal”. I find fulfilment exploring the path less travelled even if it means I may get lost every now & then. Travel blogging has been the most exciting because it combines two things I love the most, writing and storytelling. Next year I am taking a leap of faith and doing something that has been on my mind for the longest of time. A road-trip from Cape-To-Cairo!!! This has been so encouraging. Thank you.

  3. I can totally relate Jessica. My idea of true freedom and happiness is the ability to explore and go at my own pace. Not living the same day twice, if you would. I currently work at a top tier tech company in Seattle (yup, that one…) with a generous salary and stock compensation that will position me well into the future, allows me to travel internationally 4 times a year and I have never been more miserable in my life. I dread going to work every single day. Like you, I landed in the third realm of corporate America hell because of societal norms. The whole 9-5 repetitive routine is draining for me. I’m more of a random, seat of the pants kind of gal. Truth is, I will take happiness over money any day because happiness last longer. I have decided that I will sell all of my stock next year, quit my job and use the proceeds to travel. I already have my list. I hope to meet you somewhere in the friendly skies. All the best to you on your travel endeavors.

    1. Hi Michelle! Thanks for your comments. Haha. I chuckled out loud at the “third realm of corporate America hell,” hilarious! Good lucj with your journey, maybe don’t sell all of the stock at once. Hahaha. And yes, hopefully we will bump into each other, somewhere!

  4. If I knew then, what I know now, I would be doing the same thing. My hope is that in my retirement years–3 more years, I can live abroad. Loved the article!

  5. Wow – great article. I can totally relate to the “throwing everything in storage and getting out of dodge” part! I move to New Zealand four years ago and haven’t looked back. I experience FOMO as well but in order to overcome it, I have the goal of being able to travel home whenever I want. I appreciate all the hard work you do- it is so important for our world to see a beautiful black traveler, living well and working hard. If you are ever in New Zealand some time visit me and my tiny house! It needs to be on your travel list!

    1. Thank you so much for sharing!! I am planning to visit New Zealand towards the end of the year hopefully!! Wishing you all the best.

  6. I am totally inspired and just like me, the ordinary life never interested me. Still doesn’t . Keep up the outstanding work

  7. Great read, appreciate the transparancy and realness. You continue to inspire with your life and courage, much respect. Keep doing your thing, we’re all in your corner.

  8. I loved reading this! I graduated from university this May and decided to move to Thailand for a year because I was so tired of defining success/happiness strictly in terms achieving my professional and academic goals. Traveling challenges me, teaches me, and makes me happy. There’s nothing like planning a trip with friends or deciding to explore somewhere on your own. Tbh, it was seeing black women like you on insta and on blogs that encouraged me to make this decision. It’s been very difficult but I have ZERO regrets. So thank you!

    Also I did SVMP too. Great program 🙂

    1. Hi Temi! That is really great to hear. Congrats on making the move and creating the life that you want to live that is not based on what other people think success is!

  9. What a beautiful article. I have recently started following on instagram your travel stories, I find them amazing. Hope to visit some of your travel destinations following your recommendations.

  10. Oh wow … this read for me was wonderful made me think about me and my life ….I’m from Detroit ,Michigan. .. and wish I could do this type of traveling. … Tha k u for the hope …. one day I’ll be booking a trip … what’s crazy is I stumble on your I.G. page ! “BLACK JET ” I’ll see u soon !!!! God Bless U !

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