The Trip

“I Wonder If We Could?” – The Silva Family Gap Year

“Daddy please get a new job”. Over the past nine years I have heard these words over and over again from my two daughters. In 2009, after six years of Arizona land investing to leverage our way into early retirement, we paid our fair share of “stupid tax”. With the RE crash of 2008, we lost our house, our savings, our land investments and I was laid off from my job. Like many people, we were starting over. We did the only thing we could do…worked insanely hard to pull us out of bankruptcy.


I started a small consulting company. One client, turned into two, and three ETC.. Forty-hour work weeks, became fifty, sixty, eighty and often over a hundred. I was traveling more and more and found myself away from my family the vast majority of time. Shelby and the girls continued to ask me to slow down my work. Every year I promised I would, and every year it just got more intense. Shelby was left to raise our girls and run a household solo.


In November 2016, while on a return flight home from Houston, staring out the window, I had a vision that was both painful and saddening. A vision ten years in the future, my kids were in college, I was finally ready to have the family time I always wanted, but it was too late. There was no second chance, no matter how hard I begged. With Makena turning 13 this past summer, I realized my years to “slow down” and spend time with my family and girls was becoming minimal. In 2016 I was home less than 30 days and rarely home this year, I had missed a significant portion of my girls lives and had become disconnected from my wife. I have no regrets as I love what I do, and we needed to pull out of the Real Estate crash that we were very much a part of.


On my flight I asked the same question that seems to start all my adventures…”I wonder if”…I wonder if we could spend some time on our boat sailing? I wonder if I could put work on pause long enough to reconnect and actually be a father to our girls? I wonder if we could have an epic family adventure?


While the idea of taking a “family Gap Year” sounds cliché, quaint and sweet, to be honest, “putting family first” was incredibly difficult for me. My life has become consumed with work, with clients, with four hours of sleep and traveling non-stop. Putting on hold the addiction of work, the non-stop pace, of feeling important and needed by my clients has been one of the most challenging choices I have had to make. A close friend has called this year an “intervention” for me.


After presenting the idea to Shelby and the girls, they were on board from the beginning. We set out planning the Silva Family sailing adventure…a final opportunity to capture the innocent years of young adulthood with our kids before they become “too cool” to call me Daddy and Shelby Mommy.


We are sailing our 1982 38′ Ericsson from Anacortes Washington, down the West coast of the United States to Mexico and will spend the winter in Mexico sailing, exploring, but mostly connecting as a family. We’ll home school our girls and thank God Shelby is not only a veteran teacher, but has spent the last 5 years working directly with other home school families.

Life is too short and I felt the grip of a major regret forming. As challenging as putting business on pause for a year has been, I could not reconcile the knowing that 10 years from now, when our girls are out of the house and I had seen them very little being consumed by work, that I would regret not slowing down earlier. There remains a significant source of guilt and anxiety I have around the choice, but I always come back to knowing deep down, that it’s time to focus less on work and more on my children, my wife and my family.

Like my buddy Karl Kruger says while paddling….breath…stroke…breath…stroke.


I have come to realize that saying “family first” sounds nice, but I’m not sure I have followed it much in my life. I’ve given myself permission to capture the next year focused on Family and to give our girls an experience that I hope will shape and mold them for a lifetime. Fair winds and following seas and may The Answer (our boat) carry us safely to Mexico.