The Estate Sale From My Nightmares

Sometimes you win, sometimes you lose... out on thousands of dollars.

There are few things that will get me up and out of bed earlier than 8:00 AM. I have never been and likely will never be someone who enjoys waking up before I hear birds outside my window. However, there is one thing that will jolt me out of bed faster than someone screaming “fire!” - the promise of an estate sale.

I’ll spend the entire night before a sale tossing and turning, usually in a puddle of my own sweat. The little dreaming I get is manic… I’m the only person in a closet brimming with untouched dead stock from the 1930s. I calmly take the clothing off their hangers admiring their pristine condition, thanking my lucky stars that I’m the only vintage hound in a 100 mile radius. It’s soon accompanied by a terrifying vision of vintage dealers streaming out of a house, men in an array of 90s band tees carry Ikea bags stuffed with thousands of dollars in vintage as I watch helplessly in horror. Last year, one of those nightmares came true.

One evening I was on my phone flipping through two hundred or so photos for a less than desirable looking estate sale when I came across an image that stopped me in my tracks. A WWII era hand drawn shirt with a $7 price tag boldly gracing its lapel. At this point my hands started to sweat. Although it looked to be a child sized shirt, I knew that it’s one of a kind nature and cultural significance could command a hefty price tag - one that my bank account desperately needed.

As I consulted my partner Jake about attending the sale, which was starting the following morning, several questions swirled in our heads. Would the shirt be covered in offensive drawings? Was this piece just the tip of the iceberg? How early did we need to wake up to be first in line and shoot our shot?

We decided to wake up at 3:00 AM, making a 1.5 hour trek down the mountain to see what this shirt was all about. We spent the duration of the pitch black drive making bets on if we would be the first to arrive. Surely if another vintage clothing dealer had also seen the listing, they would be simultaneously speeding to our shared destination.

We were instructed to wait at a century old Baptist church down the road from the home. An hour before the sale we would all be shuttled to the house in groups based on arrival time. As we rounded the bend and approached the parking lot of the church, my knuckles whitened around the steering wheel in anticipation…. Jake and I were instantly met with dread when we saw the lights of another car illuminating the foggy parking lot. We slowly pulled beside the vehicle, which seemed to have multiple shadowy figures inside, side eyeing its passengers and hoping to get a subtle glimpse of their identities.

For several hours, under the cover of darkness, we sat as a parallel pair - the only two crazy enough to wait 6 hours in the frigid December temperatures. Jake and I spent most of the time spiraling and over analyzing the situation, trying to convince ourselves that perhaps it was just an enthusiastic old man who wanted to be first to the garage tools (if you’ve been to enough sales you know the sentiment is not that far fetched).

We periodically got out our nervous jitters by walking around the church and its adjoining cemetery, shining our phone flashlights on the grave stones and trying to find the oldest in the lot - it was some year in the 1800s. I squatted down to nervously pee by the side of the church about seven times, hoping I wouldn’t dribble on my heavy 1960s shearling coat! *gasps*

As dawn approached a few other cars began to trickle in, and eventually someone working the sale showed up to hand out numbers. We all emerged from our cars, and as I put one wobbly leg in front of the other I caught my first daylight sight of the group - three early 20-somethings, with the ring leader of the lot dressed head to toe in vintage workwear. The knots in my stomach clenched harder than Arthur’s fist as I put on my best face and accepted number 4 and 5 in line.

It was t-minus around an hour until go time and we had enough sitting in the car, so we stood in a circle nervously chatting with the other sale goers. As we were standing there numbers 1, 2, and 3 rolled past us in their car and drove out of the parking lot. Although I knew it was unlikely, I crossed my fingers, hoping that they had called it quits.

The man handing out the numbers for the sale had joined the group, and various members of the circle began brandishing their phones and showing him pictures of what they wanted in the house, asking for the treasure map on how to get there. He was receptive to their requests, and since our competition was still missing, I took my golden opportunity to show him the image I had been obsessively checking for the last 6 hours.

When you enter the front door go left, you’ll meet a hallway turn right - the shirt will be hanging on the bedroom door.

Soon after he divulged the secret location, the group showed back up and the shuttles to the house began. When we finally arrived my feet had become thoroughly numb from the cold. I stamped them as I stared at the front of the house, a large but unassuming two story likely built in the first half of the 20th century. I squinted and tried my best to make a mental map from clues on facade, picturing the object of my desire hanging on the bedroom door.

Ten minutes before they let the shivering lot of us descend on the house, the baby faced dealer who had been appointed number one approached the same man who we had chatted with earlier, phone in hand, asking if he knew where this was in the house. And just when I had abandoned all hope, the man paused, and while chuckling said “You’re not the first person to ask me that… it’s in one of the bedrooms.” My mouth dropped as I thought to myself - this is our fighting chance, only we know where the shirt is!

Like soldiers, we lined up facing the front door. Someone working the sale began calling out numbers… one, two, three…four, five! Time moved slowly and quickly simultaneously as I followed the directions I had been given. When you enter the front door go left - the group of three, who had also chosen left, were paces ahead of me. You’ll meet a hallway turn right - they were all at the hallway, 1 and 2 were nearly past it - I was inches away from turning right and assuming victory when number 3 looked to her right side… X marks the spot! Her face lit up as she ran down the hallway, victoriously grabbing the shirt right before my very eyes!

Filled with anguish, I quickly pivoted and scanned the room. The three of them were ransacking the closet so I decided to try my luck on the second floor. I ran up the stairs, carpeted in thick piled orange shag, taking two at a time. I found myself in an upstairs bedroom and began to wildly grab anything that looked decent - taking around a half second to make each decision. I bounced over to another closet in an adjoining bedroom, and by that time the trio had also reached the upstairs, quickly sifting through the closets after me.

Hauling my overflowing bag filled with a web of clothing - mostly still on its hangers, I reached the lawn to look over my spoils. Although I had missed out on what I came for, I told myself if I walked away with anything of value, it was still a win. I brought various items I wasn’t interested in to the trio and congratulated them on the score, being careful not to linger long enough to see what else they might have grabbed. They told me they had arrived only 10 minutes before us that morning, having traveled the same 1.5 hour distance to get to the house.

As I was folding what I planned on purchasing and getting ready to check out, Jake approached me with a solemn look on his face. “They found a pair of senior cords”. My heart dropped. These hand drawn corduroy pants can easily fetch $1,000 in the current marketplace, and they had found a pristine pair from the 1950s! This coupled with missing out on the WWII shirt sent my ego into a devastating spiral, and an overall bratty mood.

Although I have countless experiences where another dealer has gotten to pieces before me, times where the pangs of jealously were hardly felt and I was genuinely happy for the person, something about this especially stung. In all honesty, it took me awhile to get over the loss of potential income. I pouted and felt sorry for myself, I played the morning back over and over again. I wished we had woken up just a little bit earlier, surely then we would have been able to secure the goods!

In some ways the vintage business in the past four years has become more dog eats dog, with increasing competition due to an influx of new dealers entering the marketplace during the pandemic, coupled with decreased spending habits from buyers. The health of our business and its finances have hit their lowest point in 2023 and 2024, and the pressure Jake and I were putting on ourselves was extreme. This sale felt like the straw that broke the camels back.

Despite missing out on those two heavy hitters, we did turn a decent profit on the items we got from the sale. One highlight was finding a distressed 1920s shop coat that ended up with a charming old painter in Boston.

As I’ve had time to reflect on the estate sale from my nightmares, I came to a few reflections:

1. Community > competition. You can’t win them all, and I am genuinely happy to commune with others about vintage, celebrating each others successes along the way.

2. Boundaries. Competitive fast paced environments are not the place for me when I am running on little sleep and feel rigid with my expectations.

3. “Failure” is a teacher. In all our perceived failures, there are lessons to be learned about ourselves and how we interact/react to the world. As a small business owner I have had many lessons through failure, and I now accept it as part of getting closer to what feels aligned with my spirit.

At the end of the day I acknowledge this is just a side effect of the business, and there is not a single dealer in the world who scores 100% of the time - in fact I often come home with nothing! And truthfully, I’ve had my fair share of big wins and unbelievable opportunities that I am so grateful for - some I’ll be sharing soon!

If you relate to this story, find any part of the experience humorous, or have a reaction you would like to share - I would love to hear from you!

xoxo,

Kari

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Vintage that didn’t get away…