Living the Good Life: How I Managed to Work and Play While Kitesurfing in the Dominican Republic

For the past three weeks, I have been living a dream life while still managing to work and be productive. I have been writing blog posts, managing social media accounts, drafting case studies, and executing email marketing campaigns while staying in a three-bedroom penthouse apartment overlooking the beach and kitesurfing in the afternoons when it gets windy. And the best part? I have not taken a single vacation day from my job, all while spending no more than a few hundred dollars.

But my charmed life is not limited to the last few weeks. In fact, it started with a layoff from a job I hated. This article tells the story of how I went from being laid off to living a life of freedom, becoming my boss, and enjoying the finer things in life without breaking the bank.

Step 1: Get Laid Off

Two years ago, I was laid off from my job as Communications Director at an internationally renowned and venerated DC think tank. While it had a good reputation, it was not a good place of employment. Organizational goals were disconnected from daily activities, and the people were ensconced in various fiefdoms. The think tank practiced death-by-meeting like an art form, and management once even held a staff meeting to inform us that they did not have the money to meet payroll that month.

I began looking for work wherever I could find it, which led me to an old colleague who had started a marketing consultancy. He had a re-branding launching that very week and needed someone to set up and manage new social media accounts. Work grew from there, and by the time I was finally laid off from the think tank several months later, I had more than replaced my salary with consulting work.

Step 2: Find One, Amazing Client

Among all my clients, I found one that I gelled particularly well with because they were doing innovative work in healthcare. Their leadership was forward-thinking, and they gave me largely free reign to beef up their social media marketing activities in support of clear overall business goals.

Step 3: Go Work For Them, If You Want

My work with this client grew over time, until they raised the possibility of bringing me in-house. They comprised roughly 50 percent of all my consulting work, and culturally it was a good fit. My condition was that I would continue to work on my own schedule, coming in to the office as needed for meetings, check-ins, or events. They were more concerned with getting results than having a lot of butts in their office chairs all day long, which was perfect for me.

Step 4: Learn How to Kitesurf

Kitesurfing is the perfect activity to do in-between work, especially if you can only do it for a few hours a day. In the Dominican Republic, kitesurfing only gets windy for a few hours each afternoon, so I could work in the morning and kitesurf in the afternoon. I spent my time with my laptop out on my porch overlooking the ocean or at the bar restaurant on the beach next to the kitesurfing school. Both places had excellent Wi-Fi.

Step 5: Combine Other Lifehack Strategies and Execute on Grand Plan

To bring my dream to life, I used several lifehack strategies such as renting out my place on Airbnb, forwarding my cell phone to my Google Voice number, and using web-based software like Dropbox, WordPress, Salesforce, and Google Docs. These tools enabled me to work remotely as easily from the Dominican Republic as I could from home or the office.

One non-technology-related bonus was that shortly after getting to the hotel, I and another couple struck up a conversation with the hotel manager about the three-bedroom penthouse that overlooked the ocean on the top floor. She offered to put us up there at no extra cost, since the place wasn’t booked. This development was mostly luck, but it goes to show what being social and willing to take a risk with some people you don’t know can get you.

In conclusion, I have managed to live a dream life of working and playing while kitesurfing in the Dominican Republic, and the experience has taught me that freedom is worth more than money. While it may seem daunting to take control of your life and become your boss, with the right mindset, lifehacks, and support, anyone can do it.