Letting Serendipity In

noun: serendipity; plural noun: serendipities

  1. the occurrence and development of events by chance in a happy or beneficial way.


I was driving alone on Highway 7 outside of Albany, New York a few weeks back. I was on my way to Bartlett, New Hampshire to pick up my boyfriend, Roy who had decided two days before to end his Appalachian Trail thru-hike. I had stayed at a hotel near Newburgh, New York the night before and was about 3 hours into my 7-hour drive to pick up Roy at a motel in Bartlett, New Hampshire. I was driving on a city street in Albany when my GPS labeled the road I was on as Hoosick Road. To practically anyone else in the world, Hoosick Road would be meaningless. But for me? I burst into tears. My father had passed away just two months earlier and Hoosick Falls, NY was the location of his beloved prep school, Hoosac School.


I was in a quandary. I had promised Roy that I would be in Bartlett by 1 PM but here I was presumably within driving distance of Hoosac School. I was driving in the middle of upstate New York and had no idea how close or how far I was from Hoosac and had no co-pilot to Google the location. I kept going forward on my current trajectory and hoped for the best. I know that in the South at least, a road named for a destination usually leads to that destination; as in Goldsboro Road has Goldsboro at the end of said road. I figured that if Hoosick Road would lead to Hoosick Falls, NY. I asked Siri, “How far is Hoosac School” and she answered: “30 minutes.” I decided to drive another 15 minutes on my current course and if Hoosac School was any closer, I would take a detour. After 15 minutes, Siri answered that it was 15 minutes away. I pulled off to the side of the road. Hoosac School was just .2 miles off Highway 7 (my current route) right before the Vermont border! Before I knew it, I was driving on the school campus and imagining my father as a fifteen-year-old with his fourteen-year-old brother, Jim. This was serendipity. Of all the places in the world, my GPS took me past my father’s alma mater just weeks after his death. It was meant to be.

Here are my thoughts on letting serendipity in:


I completed the StrengthsFinder assessment when I become a Strengths Coach. Connectedness is one of my top 5 Strengths. People with the Connectedness Strength believe that there are no coincidences. I believe that everything is interconnected. I believe that my father wanted me to see where some of his happiest memories occurred. I believe that the Universe was drawing me to Hoosick, New York and that my path would be less than a mile from Hoosac School. As Cara Thomas wrote for Thrive Global, “One of the first steps to attracting more serendipity is to actually believe that you are surrounded by it.” I can’t say I was expecting my GPS to take me past Hoosac School but I believe that serendipity made it happen that day.


When I punched in Bartlett, NH on my GPS that morning, there were three routes, two of which went through Hartford and/or Boston. I didn’t want to go through a big city on a work day and I wanted to go through unfamiliar territory. I saw that it took me around the outskirts of Albany but I had no idea that was close to Hoosac School. Highway 7 is a rural highway with very few services. I didn’t know if I was crossing into Vermont, Connecticut or Massachusetts. I was open to the unknown. The unknown is uncomfortable. I could have stayed on the interstate or the Massachusetts Turnpike, where there would have been restrooms and Starbucks along the way. Thomas wrote, “Say yes to what’s in front of you, especially that uncomfortable invitation. It’s there for a reason. The less you want to go, the more magic is bound to happen.” Serendipity isn’t likely to happen unless you open up to the unknown and uncomfortable.


I’ve been writing a gratitude journal for over 8 years. I feel like if I’m grateful for what shows up in my life, there will be more from where that came from. I think of my ex leaving and how that, in part, led to my sobriety. I’m so grateful he left so that I could be fully present every day and every moment. On that day as I was driving to pick my boyfriend and his injured knee in the rural New Hampshire, I was grateful that nothing more catastrophic had happened; that I was able make the fourteen hour drive and that I was brought within reaching distance of a place that was so important to my dad and who he was, one that I had never visited before. As Thomas wrote, “The ‘thank yous’ seem to build resilience to get out of a negative mindset, which only clouds me in my worries and prevents me from seeing the bigger picture — or what great things are in front of me.” I could have dwelled on Roy’s injury or taking off time from work, but instead, I was grateful that it took me past Hoosac School. Being grateful opens you up to serendipity.


There is a “knowing” to serendipity. It’s the expectation that something good is always coming. Instead of foreboding failure or evil, look for and expect serendipity. I’m writing this piece largely to share with you my experience so that you, too, will expect serendipity in your life. Perhaps it’s always looking for the silver lining instead of the other shoe to drop that brings it about. As Thomas espoused, “We multiply our magic by sharing it with others — whether it’s sharing what we’re looking for, or helping others fulfill what they’re looking for. And sometimes serendipity comes from something as simple as a status update and discovering that you’re in the same country as an old friend.” Go forth and expect serendipity in your life.

Probably the most serendipitous for me was that I had some of my father’s ashes with me as I drove along Highway 7. I had left home in a rush to get to Roy as quickly as possible. I knew I was headed to New Hampshire and thought I might travel to Lake Winnipesaukee where, if I had the opportunity, I would leave some of my father’s ashes. So there, at the base of what was an old church and now an admission building, I left some of my father’s ashes. His memories are there and now a small piece of him.

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