When I was twelve years old during the summer between 6th and 7th grade, I started sneaking out at night. I lived in a small town on the CT shoreline that was even smaller then, and my family lived in an old Colonial house with a big huge barn, both built in the mid 19th century. Two other girls my age lived in the neighborhood and a lot more boys. There was a room in our barn that eventually became my father’s office, but when I was in middle school it was a hang out space. My two neighbor girlfriends and I would sleep out there almost every night during the summer.  It was the turn of the 1990’s, before technology invaded our lives.

My family’s barn, long before my time.

There was another barn a few houses away where all the boys slept. Like our house, it was a Colonial barn that went with a Colonial house. Where ours had once housed a gas station in the era of Model T’s after an era of agricultural use, the other barn was a former carriage house for an old hotel that had burned to the ground decades ago. There was history in those barns.

The boys’ barn was a lot cooler than ours. It had a large loft space with lots of places to lounge, and it had the feeling of being out of bounds from parents. More importantly, they had a stereo system. Our barn by contrast was a quiet place.

My parents were quiet people. I don’t remember ever hearing my dad listen to music when I was a kid. He was gone a lot anyway, commuting to Wall St and traveling frequently when I was very young and eventually moving to NJ when we moved from Greenwich, CT to this house with the barn another hour further from NYC. When he wasn’t in the office he was on airplanes, and when we did see him he wanted discipline and quiet.

My mother would sometimes listen to music in the car, but she could never handle two noises at once, so if my younger sister and I piped up from the back seat she would turn the radio right off. Music to her was a thing you did only when you were being otherwise quiet. I remember Billy Joel and Billy Ocean and sometimes the Beatles or the Beach Boys in the car, but I don’t remember ever hearing music in the house.

People used to listen to music on Walkmans!

When I was nine we went on a trip with some family friends who had two sons considerably older than me. I ended up in a car with them at some point, and they were listening to Bob Marley, which I made a note of. My tenth birthday wasn’t long after, and for my birthday I asked my parents for a Walkman and a copy of Legend, Bob Marley & the Wailer’s greatest hits album. They obliged.

My first tape ever. Still have it!

I’ll never forget that album. I would lie in the cupboard bed my mother had built me and listen to it over and over in my headphones, the world around me disappearing. I could turn it up as loud as I wished and listen until my batteries died. I felt transported.  All I ever wanted for presents after that was music.

Middle School for me was the era of Milli Vanilli, MC Hammer, Vanilla Ice, Mariah Carey, Wilson Phillips and the like. Pop was king, and there weren’t a whole lot of other options. But it was also a time when preppy kids all over New England were discovering Classic Rock, the Grateful Dead, and a little band from Vermont called Phish. Which brings us back to an old Colonial barn on a hill high above Long Island Sound.

That barn was a quick walk down the street from my barn, but even better was the fact that we didn’t have to use the street to get there. We could cut across the field behind my parents’ house, past their pond, up a small grassy hill, through the neighbors’ woods and past their pond and then we’d come out in the grass behind the boy’s barn.

My family’s barn in red on the right, years later after my dad rebuilt it, our house to the left, and the field we’d sneak across at night.

We had paths like that all over the neighborhood, ways of getting around through trees and over the large granite rock outcroppings that shape the local shoreline so we could get from house to house without ever being seen. As kids, we would go home for dinner and then we’d all come back out after dark to play huge games of Manhunt that would sprawl across many backyards. These were the days when kids still rode bikes without helmets and before anyone cared much about staring at screens. We were analog children who played outdoors. We were free to roam, and we rode our bikes everywhere. Our neighborhood, a small point jutting in to Long Island Sound shaped much like a many fingered hand, was the ultimate clubhouse, cut off from the rest of the world and safe from harm.

The summer I remember the most is the one between 7th and 8th grade. Never once did I go to sleep early, all I wanted to do that summer was stay up late and listen to music with the boys. They were listening to Cat Stevens, Van Morrison, Steve Miller, and Jimi Hendrix like their lives depended on it. American Pie on seemingly endless repeat too. I had never heard anything like this music before, and I couldn’t get enough of it.

People used to make mix tapes!  Click here for a Spotify playlist of some of my favorite songs from these tapes.

At the end of that summer my family moved to San Diego. I fancifully imagined a new life for myself filled with beaches and surfers. Instead, my parents had chosen to move us to suburban inland Rancho Santa Fe, essentially a golf course (we weren’t golfers) with a small town attached to it. Our house was set back from a busy road and there was no neighborhood to ride a bike in.

I never felt more isolated in my life. I was miserable. My sister and I went to school in La Jolla, a half hour drive away, and socializing involved coordinating transportation with parents and lots of time in a car. Since that wasn’t very easy to do, I spent a lot of time alone and I wrote countless letters those years to my friends back east, developing a knack for keeping in touch that would later serve me as a business owner. Many of those letters were accompanied by a mix tape, through which my discovery of music continued.

Eighth grade for me was when Grunge hit the American mainstream like a force of nature. Pearl Jam’s Ten and Nirvana’s Nevermind came out, and I was the target audience. One of my friends from CT introduced me to Nine Inch Nail’s Pretty Hate Machine and I fell in love with this new sound. I died my hair purple to match my teenage depression, and I holed up in my room with my ever-growing cassette collection.

Around this time my father started his own business. He is an actuary, which means he designs pension plans. This is an endeavor that used to require a considerable amount of data entry. He would receive pages and pages of data via mail or fax, and he began employing me to enter that data. Faxes were new at the time and the paper they printed on came in rolls. It was shiny paper and it faded fast and you’d have to pin down the corners in order to work from it.  My dad taught me how to build databases using an early version of Microsoft Access.  I had always been good with numbers, and I quickly learned how to catch errors when the data didn’t add up correctly.  This is not what your typical teenager was doing in 1992.

My dad and I in the same Alfa last spring, 25 years later in Montana where my parents live now.

I would put in a few hours every week, enough to make money for more tapes. My dad had moved to San Diego a year ahead of us, while I was in 7th grade back in CT. He bought himself an Alfa Romeo Spider Veloce that year, which was fortuitous because he’d always wanted one and it turned out to be the last year they ever made them. When I moved to San Diego with my mother and sister the following year, rides in the Alfa became my first memory of spending one on one time with my dad. It was a two seater, so by default it could only be the two of us in it. I’ve insisted since then that he maintain it.  It is the the only family item I care about inheriting one day.

People used to buy music in stores!

On the weekends my dad would drive me to the Sam Goody in Escondido around the Lake Hodges Reservoir, teaching me about down shifting to round the many turns in the windy road. With the top down and our hair in the wind and the southern California sunshine in our faces, I was a long way from home. When we got to Sam Goody my dad would stay in the car to read while I went in to spend my data entry earnings on new music. I don’t remember ever spending any money on anything else at that time, except perhaps a new tape rack when I filled one up or blank tapes to make more mix tapes for my friends back east.

At the end of 8th grade, I kinda hated everyone.  A year of isolation in San Diego had taken a toll on me.  We returned to CT that summer, and since our house was rented out while we were gone, we stayed in a 400 square foot cottage we had spent our early childhood summers before moving to the house with the barn. My sister and I had slept on the screened in front porch as kids, but at 13 and 14 years old that got weird. And it was impossible to sneak out of. I remained miserable.

My first Grateful Dead tape

A few weeks after I returned to San Diego for 9th grade a boy I’d gone out with over the summer in CT sent me a tape. There was a note that went with it that said something along the lines of “you should check out the Grateful Dead.”

That tape was a portal. Like the Bob Marley tape 4 and a half years prior, it took over my ears. I was hooked. As much as I’d gotten in to Grunge in 8th grade, I now got in to the Grateful Dead in 9th grade. I kept entering that data for my dad, but now I was spending all my money on Grateful Dead albums.  I didn’t know yet that albums weren’t the way to go when it comes to the Grateful Dead, and I bought them all.

At some point later in 9th grade we had an assignment in English class to present a poem. We were allowed to choose a song, and so I chose Ripple, doing my best to transcribe the lyrics like many a confounded Deadhead before the internet era made lyrics readily available. To say I was laughed at by my classmates would be putting it mildly. Very mildly.  They thought it was Country, and they did not understand.

9th Grade Taylor and her taper friend

However, my teacher was cooler than my classmates and he passed the word on to the head custodian at the school who was well known for being a huge Deadhead. He had long long hair that he wore in a multi-banded ponytail and he was a friend to all students. When he learned about my interest in the Grateful Dead, he started making me tapes. Soundboards even. It was the first random act of Deadhead generosity and synchronicity that would eventually come to dominate my life.  I cherished those tapes, and I got to know the different eras of Grateful Dead music (and keyboard players) through them and the notes he’d included on the cases.  For my 15th birthday that spring I asked my parents for tickets to go see Jerry Garcia Band at the San Diego Sports Arena.   Lucky for me they granted my request, and I did get to see Jerry once before he died a couple years later.

By the time my family left San Diego at the end of my 9th grade year and moved back to CT to the house with the barn, I was a Deadhead for life.  It would forever be the music that rescued me in the depths of teenage loneliness.  I think we all have an attachment to whatever music sneaks in to our consciousness right before the end of innocence.  The lyrics are the words you first use to self define, it becomes the music you can rely on to be there for you when you need it, and when it’s a band as monumental as the Grateful Dead, it quickly becomes something so much deeper than just music.

Although I certainly had no idea when discovering the Grateful Dead that I would end up working with them, nor the level to which their surrounding community would create my world, I was never surprised when it happened.  Music always meant everything to me, and it was always my reward for work.  I ended up there through a natural enough of series of events, having been drawn to the Jamband scene and the festival circuit that was emerging when I entered the professional world in the early aughts, and you can click here to read the story of  how I came to be a Grateful Dead licensee.

As for the barns, my family’s still stands (under different ownership), and the other one was dismantled and rebuilt.  When we moved back from San Diego and I went to high school in CT my dad took over our play room and turned it in to his office until they eventually sold the place 12 years later.  He spent much of that decade restoring the barn, and for a few years when I first started Little Hippie, he built me my first “warehouse” in it.  The other barn changed ownership a few years ago along with the house that went with it when the parents of my friend who grew up there moved out.  I still spend as much time as possible in that neighborhood every summer, and I’m still friends with, or at least in touch with, most of the people I grew up with there.  I was around when that barn was taken down, and I had a little private memorial in my head for all the adolescence that happened there.  Even though it wouldn’t be until 10th grade that I discovered Lou Reed and the Velvet Underground, I had already been “Saved by Rock ‘N Roll” thanks to those young summer nights sneaking out listening to music with the neighborhood boys.