It was a time in my late 20s when I was enjoying some newfound career success. My income had taken a big step up, and I was fortunate enough to have the luxury of making some frivolous purchases.

I was living in Boston, but I still considered Manhattan to be my true home. On a whim, I went to the airport and took the next shuttle plane to New York City. I had no plan, other than an adventure. In those days, pre-terrorism concerns, you could show up at the airport for a same-day flight between nearby cities, and the price was not exorbitant.

As the day drifted toward evening, I wished I had flashier clothes for a nightclub. Walking down the street, I saw a store much fancier than any I had ever been in before. I had heard of the designer’s name, but never seen his works up close. Since the whole point of the day was “adventure without bounds”, I dared to enter.

Such colors! Textures! Designs so garish and outrageous! I felt shy, almost embarrassed to even be in the store at all. Shrinking away from the displays, I thought to myself, “There is no way I could ever wear anything in this whole place.” I looked at a few price tags, and everything cost fully 10x the most I had ever paid for that type of garment. Shirts, shoes, suits… everything 10x.

“May I help you?” a sales woman came by, looking more like a fashion model than a clerk.

The store was quiet and empty, an airy space, with everything very far apart. Only one other customer was shopping, silently in the back.

Perhaps I wanted to test my courage. Expand my notion of who I am. Maybe I was influenced by the pretty woman suggesting “you would look great in that.” I knew she was just doing her job as a salesperson, and not flirting with me… but looking in the mirror I did gain confidence. I felt like maybe, just maybe, I could be the kind of person who wears this kind of clothes.

A silk shirt with the design of bamboo in blue and green, in an Asian-inspired style, had captured my imagination. I studied Japanese sumi-e painting during High School, and I felt like this shirt was not only beautiful — but also a special projection of my true inner self. I loved it. It was $1000, and I couldn’t believe I was seriously considering buying it.

My reverie in the dressing mirror was interrupted by the one other customer. He was a heavy-set middle-aged man who sat contemplating a mountain of clothes that would cost more than a nice car. His face was twisted and tired.

“That’s not for you!” he called out, in an accent I couldn’t place.

“Excuse me?” I asked back? I thought he was implying I didn’t deserve my purchase. I looked younger than my age at that time, and I often felt hurt or insulted when people didn’t take me seriously as a buyer.

“I said you don’t need that! What do you want to waste your money for, buying expensive clothes? You’re young and beautiful! You would look great in anything, like the t-shirt you have right now! These clothes are for ugly old men like me. I have to buy this nonsense so people will look at me. But you were just fine the way you came in.” And the harsh man with the permanent scowl briefly managed a weak and gentle smile.

I bought the shirt anyway. That night, walking the streets of Manhattan with my silk shirt and long hair flowing, I felt like a rock star. I did get noticed, and a few times I saw heads turn as I heard people on the sidewalk wondering whether maybe I was a celebrity. It felt intoxicating. Growing up, I was always the nerd in the back who nobody wanted to look at or or speak to. I had become important, a success, if only for the evening. It was the first time I felt as if people were looking at me.

In the coming years, a few more times I bought from that same brand. Not many. I knew in my heart that my income was not enough to support such extravagance… but sometimes I would consider one to be a special treat or celebration. I always remembered the old man. Was he trying to undermine me? Was he admiring me in a way that was unwelcome? Depressed and cynical? Maybe just wise? Or all of the above.

I treasured my collection of those pricey shirts, not just for their cost but for what they symbolized to me. I didn’t know it at the time, but that day was a moment of ultimate freedom. I traveled with no luggage or plan, spent too much on an outfit, had a night out on the town, then strolled into a fancy hotel to rest and return home the next day. For twenty-four hours, the world felt limitless. I could go where I wanted, do what I wanted, make myself great, and get attention. In my late 20s, I had achieved what I craved in my teens: the lonely boy finally got noticed.

This past summer, I finally said goodbye to that designer collection. And threw them out.

In my 50s I may now be the age of the “old man” in the store, and I’m glad I no longer need to scream “look at me”.

I also realized, with some shame, a deeper truth about that good feeling. I had “touched the sky” by splurging on “rich people stuff”. I couldn’t afford a private jet. Or a $10M home. No exotic million-dollar car, or even a basic Ferrari. My teenage financial goals were never achieved. But a few moments of high-end impulse shopping gave a momentary sense of having “made it”.

After a few more years of growing up, and a stack of case studies during my MBA, I’ve learned that most luxury brands are built on this feeling. “Aspirational” purchases, they call it. Things that make people feel like the person they wish they were. Tiffany makes over 90% of its revenue on purchases under $100. Think about that. The money doesn’t come from selling $50,000 vases; it comes from $40 key rings people buy because they come from the same store. Sure, the key ring is nice, but honestly it’s just $2 of metal in a colored box imbued with symbolic meaning.

(And don’t get me started about the desire to own a chunk of one metal over another, or polished lumps of coal… or the irony that people literally wear chains of gold in public, as if to confess the imprisoning role in their lives played by money. If you need people to know you have it, then you’re sadly insecure.)

Everyone wants to feel special, and I’m not pretending I don’t still have my eye on some fancy things. I’m not pure from the urges of materialism and showing off. And I’m certainly still an insecure young man on the inside. Just trying to keep it under control.

Looking back, my most lasting pride has always come from deeds, not peacock feathers.

I brought out the Anemone Shirt one last time, for a “Vintage TED” gathering in 2018.
A famous marine biologist recognized the shirt and remembered me from TED fifteen years earlier.
Do I think she remembered the shirt more than me? Probably. It still felt good to be seen.