In 2024, Castle introduced the Work Away Benefit, which allows employees to spend up to a month working remotely from anywhere in the world, with the caveat that we still work East Coast hours. When I heard about the program, I decided to take it to the limit and chose the farthest destination I could, where the time difference wouldn’t be too impossible: Oahu, Hawaii.
I spent three weeks working in Oahu and then added two additional weeks of vacation, island-hopping around Hawaii. As someone who loves to travel and is always seeking new adventures, the opportunity to live and work in a completely different place was incredibly exciting.
Living & Working in Paradise
Hawaii exceeded every expectation I had. The weather was perfect, and there was always something to do. Although it was still in the U.S. (which made things easier logistically), the local culture felt so unique and distinct that I often forgot I didn’t need a passport to get there. The biggest surprise? The food. Honestly, I don’t think I had a single bad meal the entire time.
Because of the time difference, my workday ran from 2:30 a.m. to 11:30 a.m. Waking up that early wasn’t always easy, but finishing before noon gave me the rare opportunity of having almost an entire second day to myself. After I closed my laptop, I could head straight to the beach, hike lush trails, snorkel with endangered green sea turtles, or spend time with friends and family who came to visit. On weekends, I tackled bigger adventures, such as an 11-mile waterfall hike, cageless shark diving, and even an open-door helicopter ride. Every day felt like two days in one, and it gave me the chance to make the most of my time on the island.
After three weeks, Oahu really began to feel like home. Everyone I met was so kind, which made my experience even better. The island is also filled with so many “transplants,” people who had moved to Hawaii from all over the mainland. Meeting people from San Diego, Cleveland, and Hartford gave me a sense of belonging and made me feel like I fit right in. I also had the chance to island hop on Kauai and Maui, where I spent time with my colleague, Keri McIntosh, from Castle’s Maui office.
My Biggest Takeaway
Going into this, I knew I’d enjoy the travel experience, but I didn’t expect to learn so much about myself along the way. Hawaii showed me that I’m more independent and adventurous than I realized. More importantly, it reminded me of the value of being intentional with my time.
At home, my weeks often blur together: work, dinner, maybe the gym, then relaxing on the couch binging the newest Netflix series. Even with Caste’s “All Season Fridays” (where every employee has alternate Fridays off), I usually spend my extra personal time running errands, grocery shopping, or doing laundry. By the weekend, I’m exhausted and just trying to recover and prepare for the week ahead. In other words, I spend a lot of time doing what I need to do instead of what I want to do.
In Hawaii, the opposite was true. Because my afternoons were wide open, I made a conscious effort to fill them with things that brought me joy. Every second mattered because I knew my time there was limited. That shift in mindset left me feeling more energized and fulfilled than I ever expected. Ironically, despite working the earliest hours of my life, I rarely felt like lying on the couch—I was too excited to experience everything around me.
That was the big realization: the fulfillment and happiness I felt in Hawaii weren’t about the sunny beaches, the thrilling adventures, or the delicious food (although they helped). It was about choosing to spend my time with intention, and that’s something I can bring home with me.
Bringing it Back to Boston
Of course, it’s easier to feel inspired when the beach is a ten-minute walk away and it’s 80 degrees every day. But what Hawaii taught me is that inspiration doesn’t depend on where you are—it comes from how you choose to spend your time.
Back home in Boston, my goal is to bring that same sense of intentionality into my daily routine. That might mean trying something new instead of sticking to old habits, carving out space for hobbies instead of chores, or simply spending more time outdoors.
After five weeks in paradise, I’ve returned with a fresh perspective, more energy, and a renewed commitment to living each day to the fullest. I’m grateful that Castle offers opportunities like the Work Away benefit, which allows us to grow not only in our careers but also in the way we approach our lives outside the office. This was truly the experience of a lifetime—one filled with bucket-list moments, core memories, and lessons I’ll carry with me forever.
It’s said the average person gets about 80 summers in their lifetime. I can confidently say I made the most of this one, and I intend to carry that same happiness and excitement into every summer and season that follows.
