For a long time, I thought building a better life meant building a bigger business. I was pushing toward a multimillion-dollar roofing company, putting my energy into a goal that looked like success. Eventually, I stepped back and asked myself a more basic question: What do I actually want my days to look like?
The answer kept coming back to time with my family, travel, new cultures, and enough freedom to enjoy the life I was working so hard to build. That’s what started our plan to move to the Dominican Republic.
Making room for life outside work
Life in the United States has often felt like a grind to me. Work, bills, and the pressure to keep moving can take up so much space that enjoying life becomes something you fit in afterward.
I’ve also grown tired of the political atmosphere and the tension I feel around me. Those feelings are part of the decision, but the bigger question is personal: How much of my life do I want to spend chasing more, and what do I want that effort to give my family?
I’m ready to work toward a more flexible, semi-retired way of living. I still want to create things and build businesses. I want more say in how that work fits into our lives.
The appeal of moving abroad is the possibility of a slower rhythm: more family time, more shared meals, more exploring, and fewer days spent feeling like everything revolves around the next bill. Those are hopes we’ll have to test in real life.
Why the Dominican Republic makes sense for us
Mexico was another possibility. At this stage, the Dominican Republic feels like the more practical choice for our financial situation and the stability we’re trying to build.
There’s a family connection, too. Jessica was born in Puerto Rico, and both of her parents are originally from the Dominican Republic. She has family there and has visited the country several times. The food and culture are already familiar to her.
I want our children to have a deeper connection to their family’s roots. Living somewhere gives them an opportunity to experience everyday life, language, and traditions in a way that an occasional vacation can’t fully offer.
I haven’t been to the Dominican Republic myself yet. That matters. I’m making this decision with a lot of enthusiasm, but I still have plenty to learn. This journal will follow that learning as it happens.
Why we’re looking at Santiago
Santiago stood out because of the kind of life I want to build around it. I’m drawn to the mountain adventures around Jarabacoa and the beach activities around Cabarete—especially whitewater kayaking and kite surfing.
Having those possibilities within reach is a big part of the appeal. So is being able to return to the United States by air when we need to. We still have to work through the actual routes, travel times, and costs.
When I picture this next chapter, I picture ordinary days with more room for things we enjoy. Outdoor adventures are part of that, alongside family routines and the work of getting settled.
The comfort of what we already know
When I ask myself what will be hardest to leave, I keep coming back to familiarity. I know how things work here. That can feel like security, even when work and income are unpredictable.
I’ve lived in other countries and felt safe there. Those experiences have made me question how much of my comfort comes from actual certainty and how much comes from simply knowing a place.
There will be practical adjustments. Reliable electricity is one concern we’ll need to investigate when choosing housing, including what backup power is available. We’ll also need to understand our options for healthcare, schools, transportation, and daily expenses.
I’m willing to make those adjustments. I also want to be honest about them as we learn.
The lunch that made the idea feel real
The turning point was surprisingly simple. I emailed Jessica about going to the Dominican Republic, and she was open to doing it. Then we went to lunch and talked about the possibility together.
That was the moment it started to feel real. A thought I had been carrying became something we could actually plan as a family.
We’re still early in the process. Most of our passports are ready, but one of the kids still needs theirs. We haven’t booked flights yet. There are decisions to make and work to do before we leave.
Even so, the commitment is there. I’m preparing to leave my apartment, and we’re moving forward with the plan.
What Wild at Last will follow
Wild at Last starts here, while we’re still figuring things out. I want to document the preparation, the decisions, the adjustments, and eventually the everyday experience of living in a new place.
We’re hoping to build a new chapter for our family, our work, and our personal lives. Along the way, I’ll share what we learn—including where our expectations need to change.
I spent a lot of time thinking about how big a business I could build. Now I’m giving just as much thought to the life that business is supposed to support.
A life we don’t need a vacation from. That’s what we’re working toward.
Be wild at last.
—Michael
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