There was a time in Greenwich when people kept a car for more than a year and could look at their house and say, “Maybe this is enough.” When my grandparents, Jean and Dean Barker, moved to Greenwich in 1968, it was actually a pretty ordinary town. They bought a house with half an acre of land and a barn for $60,000 in the Riverside neighborhood. They raised two children in this house, worked full time jobs, and made ends meet. All of this, though, is a grainy history of a time I know little about but have pieced together from recollections of my family. My story begins years later when I was six years old living in a much different version of this town, a place that rapidly became a settlement for investment bankers, celebrities, and other social elites who commuted to Manhattan. With the price of living in Greenwich skyrocketing, families like my own were being pushed out of this community by the high cost of living and the perceived social stigma of being lower class.

A neighborhood that was once made up of unique, old-fashioned two- or three-bedroom houses quickly became a mega-suburb of mansions that seemed to pop up overnight without warning. As these mansions invaded Riverside, it made the old houses seem like remnants of something forgotten, waiting to be crushed and rebuilt bigger and better. I saw it happen with my own eyes. Construction was accepted background noise. As a kid, the contrast between these old and new houses meant something to me. I felt like, as a family living in an old house, maybe we were remnants also waiting to be displaced by a wealthier family.

I lived in the barn next to my grandparents. Except, it was no longer a barn. My grandparents, along with the help of my mom and dad, turned it into a house, and by 1996, the three-bedroom house was full, and I shared a room with my younger brother, Jon.

As a six year old, most of my memories are of roaming around the neighborhood on my bike with my friends. But it was also around this time that I began to understand that my friends’ families were wealthier than my own. I spent so much time at their homes and so little time at my own simply because there was more to do there. They had endless stocks of toys, games, big TVs, video games, pools, country club memberships. I had a TV, with a service that seemed to be behind on payments whenever I brought friends over to watch it. One of my friends, Mark Figgy, lived in a house that was a game in itself; it was so large that wandering through it felt like finding my way through a maze. I never thought of my friends as being spoiled back then though; I only thought they were lucky. I got used to their lifestyle and the contrast to my own became stark. Things at my home were much different.

Our house was set back from the main road with a long, L-shaped driveway that was also connected to our grandparents’ house. Facing out from the house on the left was a fence with houses on the other side. On the right, was the small yard connecting to my grandparents’ house, and in front was a small patch of woods. When I was eight, we started to feel the pressure of construction. I literally got a front-row seat, and was amazed how quickly the mansions grew. The patch of woods was completely cleared out, and in its place came a house, twice the size of ours, completed in half a year. On the fenced side of our yard, some monstrosity was built that looked more like an oil tanker with a slab of yellow paint than a house. It was so tall that it blocked out the sunlight in our yard.

I didn’t know why people had to keep getting bigger and better homes or why they needed to fill in every square inch of land with a house until there was no nature left anywhere, but this growth kept happening, and it was creeping right up to us. I didn’t know it at the time, but this epidemic of construction and expansion was the housing bubble. Banks were lending money for new houses freely to people who couldn’t actually afford them, and greed got the better of many people.

Of course, having a luxurious house was not enough for most folks. They needed luxurious cars to go along with the house. My parents seemed to like trying out lots of different cars, but they were definitely not luxurious. I got used to the routine of my parents bringing home something from one of the used car dealerships a few towns over (the only car dealerships in Greenwich were BMW, Mercedes, and Lexus, though if you were extra special you went to Miller Motorcars, filled with Ferraris, Bentleys, Aston Martins, and the like) and then having it towed away a few months later by someone who came over curiously early in the morning. At first I thought maybe this guy was paid by my parents to return a car they didn’t like, but when I asked my mom about it, she gently informed me of what was actually going on. “That’s the repo man son. He comes to take the car away if we can’t pay for it.” Ah, and I thought my parents were just discerning customers. If any of my friends asked me why we kept getting different cars, I would tell them that my parents just liked to try out cars. I actually didn’t mind seeing the repo man after a while because it meant we would probably be trying out something new, which I thought was fun. And anyway, most kids never asked about our cars because their parents changed cars almost as frequently, albeit, at their own will, and with much nicer cars.

Even though there were times when I felt out of place in Riverside, it wasn’t that bad. Even if we were poor, there were lots of good things about living in this community.

The Stavroses were our closest family friends. Alexander was my age, and Fiona was my sister’s age. During the summer, we would go with them to Roxbury Swim and Tennis club. We would go with them because we were not actually members, but members could bring guests with them. I never found out how much membership cost, but it was obvious that it was high from the look on Mrs. Stavros’s face when I innocently asked her. It wasn’t even the most exclusive club in the area. It was in Stamford, Connecticut, while the really nice clubs were all in Greenwich. The club had giant hedges around the property as if to conceal itself from the lesser quality of Stamford, and once inside, the hedges provided the illusion of being safe in some home away from home: Greenwich away from Greenwich; wealth away from the main mother ship of wealth. I just liked it because I could practice my front flips into the pool. I knew that we couldn’t go there unless we were invited by the Stavros family, and at times it bothered me, but I mainly learned to appreciate any privilege that was in front of me.

Accepting privilege was a big part of how I came to terms with our situation. We might not have been able to keep up with the Joneses – or even run the same race – but the Joneses were very generous. There were times, though, that that generosity felt like something else entirely: pity.

By second grade, I was a full-fledged Lego enthusiast. I lived and breathed Legos. Most of my friends were just as passionate about the art of the brick. One of my friends, Patrick Fitzgerald, had a room full of Lego sets that were decorated like trophies. I went out shopping with Patrick and his mom once, and, out of the blue, she offered to buy me one of the nicest sets. As a seven year old, my first reaction was to say yes. She knew my family, and she knew my parents probably couldn’t afford to buy stuff like that. It was such a small cost to her. I really did want her to buy it for me, but I was hesitant. I knew it wouldn’t feel good getting something as expensive as this for no good reason. But the willpower and judgment of the seven-year-old self is a fickle thing, and I caved. I told her I would ask my parents.

My mom was embarrassed when I told her. She gave me the disappointing news that I would have to wait until Christmas – story of my childhood. Our moms obviously had different ideas about the value of a hundred dollars. To Mrs. Fitzgerald, it was the type of money you go out and spend on your kid and his friend on the weekend. To my mom, it was the type of money you spend on your kid for a Christmas present.

If I were a parent and my kid asked me if his friend’s mom could buy him a hundred dollar toy, I would probably be offended. It seems like a ridiculous amount of money to spend on someone else’s kid. I can’t say for sure if Mrs. Fitzgerald felt compelled to buy the toy out of pity, but it sure felt like it. What I can say for sure though, is that her wealth desensitized her to what something is actually worth. I didn’t have all the words for it back then, but I began to see how spoiled my friends were. Maybe this is why people’s houses kept getting bigger and better. The adults who had them built were probably just grown up versions of my spoiled friends. If they had the money to spend on something, they felt they might as well spend it on things they didn’t need.

When I was ten, my parents and grandparents decided that they had had enough. The price of existence in Greenwich was too high for my family. My grandparents owned some land in the middle of nowhere, which was a location that increasingly appealed to them. We moved to Conway, Massachusetts, sold the houses in Greenwich, and sure enough, our old remnant of a house got eaten up by the housing bubble. The house was literally torn down and replaced with something that was suitable for the updated Greenwich lifestyle. When we moved to Conway, everything was different: life felt slower, people seemed more down-to-earth, but most of all, it felt like we fit in. I felt like I came from a similar background as my new friends, I no longer thought about people’s wealth, and I didn’t need to make excuses for not being rich.

Personally, I’m so grateful that we moved out of Greenwich. I went to a private high school on scholarship where many students were from Greenwich. A lot of them seemed to turn out exactly as one would expect – still spoiled and obsessed with status. I remember hearing debates about who was more “old money.” I don’t know if I would have turned out the same way if we stayed in Greenwich, but I’m glad I didn’t stay to find out. Eventually, as we settled into Conway, my parents worked to get decent jobs, and we can now enjoy living a more comfortable life. It’s not that we’re wealthy now, but at least I don’t see the repo man anymore.