This is the story of my remote work transition—how a trip to Jamaica for my 30th birthday changed everything.
I couldn’t get out of bed.
Not because I was sick. Not because I was tired. But because the thought of walking into that office—navigating the cliques, the stuffy office, being the outsider on an established team, the two-hour round-trip commute from Decatur to Marietta—made my stomach turn.
I was 29 years old, freshly laid off, newly relocated, and drowning in a contractor role at Home Depot that was supposed to be my ‘fresh start.’ Instead, it was my breaking point.
Then I went to Jamaica for my 30th birthday.
And everything changed.
The Job That Broke Me
I was working as a UI developer in Angular with a design background. Everything felt too cliquish. There were so many office politics that didn’t make sense to me. I believe that two heads were better than one and that “team” meant we had each other’s backs. It felt like I was in high school all over again. The daily commutes, the gossip, the stuffiness, and more. Unfortunately, it got harder for me because I was asked to provide another option.
The manager of another department, with whom I had worked closely, saw me designing a user experience wireframe for another project and asked if I could redesign the internal document management dashboard he was working on. The options he was originally given didn’t align with his vision.
Unfortunately, the original designer wasn’t happy with that ask and refused to work with me. I approached him beforehand, explained the situation, and asked if he’d be open to collaboration. However, he shut me out of access to files. Refused to work with me and complained to my manager as if I made the decision.
My team decided to stand with him, as I was the new member, and they had been working with him for quite a while. It made the office unbearable for me.
I had longed to go on a trip, and as my 30th birthday was in a couple of months, I realized I needed a break. I started researching places to go.
A friend of mine suggested I go to Jamaica. She had just been there and was telling me about the fabulous time she had. I decided right then and there that I would try it out for myself and see what I could get into. Not to mention that I wanted to be near the beach and I wanted to go by myself.
Jamaica: Where Everything Changed
The day before my 30th birthday, I boarded a plane to Montego Bay. I will admit that I was scared but excited at the same time. I stayed at the Decameron Hotels and Resorts for 4 days and 3 nights. Although there were moments of loneliness, I wouldn’t change that trip for anything in the world. The people in Jamaica were very nice, and the resort had great amenities and provided me with an amazing birthday breakfast.
The days that followed, I decided to go on a few tours, including a day tour to Negril. Stopped at a couple beaches along the route towards Negril, and saw some of the bluest waters. Rick’s Cafe was the final stop. Watching people go cliff jumping including some in our group was awesome.
For late lunch, early dinner, I had festival bread, rice and peas, and jerk chicken. The tour guide was excellent, funny, and personable. The tour was filled with history, jokes, and a deeper understanding of Jamaica.
For a night trip, I went and swam in The Luminous Lagoon, which was so pretty. If you haven’t been before, I would say it’s not one to miss. The reason that the waters turn blue is due to the presence of millions of dinoflagellates. They are a type of algae or marine plankton. At nighttime, these microscopic organisms start to glow when they are disturbed. They give you a lifejacket, and you can swim in the water for about thirty minutes. I felt so free there. I remember those colors as if I were just there yesterday.
During my stay in Jamaica, I decided I was done with traditional office life. I was ready to start my remote work transition. I didn’t want to be stuck in the office where I couldn’t experience all that life had to offer. I didn’t want to have to take off work and not get paid because I wanted to take a trip. I wanted to have my autonomy in this world.
As I stood on the sand looking out at the water, I realized how amazing life is and how I want to experience more of it. I told myself that when I return to Atlanta, I will start the journey of a remote job to achieve a more location-independent career.
I returned to Home Depot with a newfound sense of hope, determination, and encouragement. I knew that the life that I wanted was close by. I needed to make a couple of shifts to escape the dread I was feeling.
The Reality of My Remote Work Transition
Shift + Escape is a passion of mine. I can explore the world while working in the tech industry. I started mapping out my remote work transition strategy. I could either find a company to work remotely with or build my business. The goal is to do both.
I was afraid, but I wanted to travel more. I didn’t know what would happen or how I would exactly make it happen. I knew that I needed this shift to make my dream come true. In 2019, the year started with the Home Depot contract ending and starting a new contract role as a UI developer for IHG. In the last quarter of 2019, I worked briefly for a tech startup as a remote UI developer.
In January 2020, I was unemployed. I used that time to improve my resume and to take a couple of trips. I went to a cabin outside of Atlanta and to Vancouver. I had a great time and even thought about relocating to Canada. I started researching the process. I didn’t pull the plug because the borders closed.
During my job search, there were more remote roles than in-person roles as COVID was at its peak. I was applying to different roles.
I received a LinkedIn connection from a recruiter for a React Developer role at U.S. Bank. I went through two rounds of interviews before I was hired. I started in April 2020. This was just what I needed. After having worked in a remote setting a few times in my career, this was different than before. This meant that I could really have a remote work transition and log in from anywhere.
What I’d Tell My Past Self
A couple of years into working remotely, I took the next step in my escape and officially formed my own company, La Prince Studios, where I began working with my own clients as a design strategist.
I met virtually with different clients who needed everything from graphic design to websites. Some of the clients stayed, and some didn’t. I had made so many mistakes, mistakes that I won’t make again.
One client I still think about sometimes had a cleaning business and needed a redesigned website. It was a word-of-mouth situation as to how we met. Their current website wasn’t converting new clients. They wanted new business from internet traffic.
Everything started great, we were vibing and creating good work. However, due to the client not wanting to pay for assets such as photography, the constant revisions and double work, the client stopped communicating and ghosted.
That experience refocused me. It allowed me to sharpen my skills, improve my contracts, time, and judgment. When working with clients, put everything in writing up front before doing any work. In your contracts, discuss everything from cost to deliverables, as well as getting paid a deposit before you start the work. Remember, you don’t have to say “yes” to every client that comes your way.
This journey has pushed me to the limits. Making the remote work transition requires resilience, but it’s absolutely worth it. I have been rejected more times than I thought I would. Rejection has been repurposed to me as redirection, and it continues to be so. To be honest, this remote work world can be lonely at times.
It can feel like trying to stay afloat in the middle of the ocean without a life raft. I have to find time to get out of the house when I do feel lonely because cabin fever is not only a movie, but it’s real. I find coffee shops or coworking spaces to fill that void.
Since being remote, I have been able to enjoy life a little bit more. I have been able to travel and work without having to deal with office politics and long commutes. My next goal is to relocate completely out of the country.
This remote work transition hasn’t been easy. I’ve made plenty of mistakes. I have encountered wins and losses. It has pushed me to great heights. It’s not a permanent vacation, but a redesigned life. That’s why I created this Shift + Escape tell-all. This blog is the roadmap I wish I’d had: a chronicle of the ups and downs, and a realistic plan for anyone else who is ready to trade the hamster wheel for the world. I’ve shared my map of rejection and redirection. Now, it’s time to start drawing yours.
If you’re feeling that same dread I felt—that sinking feeling every Sunday night, that sense that there has to be more than this—you’re not alone.
Every Tuesday, I send one email with real strategies for building a remote career without quitting your job tomorrow. No laptop-on-the-beach BS. Just honest guidance from someone who’s been where you are.
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