A little glad to be known

Back in the 1990s, there was a café in Burlingame where I frequently went for lunch. I always ordered the same sandwich and the same drink.

One day, as I sat down, the server smiled and asked if I’d be having the usual.

I was surprised they remembered me. For a split second, I felt a flash of warmth; someone had paid enough attention to know what I liked. But almost immediately after, a strange wave of awkwardness set in. I had noticed.

I never went back.

I didn't consciously decide to avoid it. There just always seemed to be a convenient reason to go somewhere else – it was slightly out of the way today, or I wasn't quite in the mood for that sandwich. Looking back, this had happened at other places, too. The moment that people there began recognizing me, I somehow stopped enjoying the food as much.

It took me decades to realize that this wasn't about a sandwich, or even about customer service.

Quiet near the car

I have faint, fragmented memories of living in an apartment with my parents when I was very small. Around the time I finished kindergarten, my father’s business took off, and our family’s financial life changed dramatically.

That’s when the warnings began.

For years, my parents continued to drive an older Oldsmobile. They only bought a Mercedes once other executives at the company had nicer cars, and staying in the old car would have made them stand out. My father made sure that we didn’t make noise whenever we were near it, so others wouldn't connect the vehicle to our family.

When my parents bought jewelry, we went to the store after business hours. The owner would lock the doors behind us and bring out collections from the back room while we were the only customers inside. My mother kept most of her pieces in safe deposit boxes, wearing them only to formal events where other women wore high-end jewelry, too.

My father explained that it was about safety. In Taiwan during the 1970s, people with signs of wealth could easily become targets of crime. But as I grew older, I realized the fear ran much deeper than property crime. When my father was a child in the mid-1940s, my grandfather had become well known in his community and was subsequently targeted by the government. To my father, being noticed wasn't just uncomfortable; it was potentially life-threatening.

As Taiwan modernized and luxury cars became common, my father didn’t get quite as stressed out. But by then, the lesson was already stuck in me. At five years old, I learned about money and the importance of hiding at the same time. For most of my life, the two remained inseparable.

A different kind of target

When I started fifth grade, I came to the United States while my father stayed in Taiwan to run the business. On the surface, America felt very different. Wealth here wasn't as obvious, partly because it was so easy to get credit. I drove a BMW in high school, and my friends often gathered at our house because we had space for everyone. I didn't stick out the way I would have back home.

Yet the instinct to stay hidden followed me.

I avoided talking about money with my friends or downplayed it if it came up. A part of me questioned whether they would stay true friends if they knew. With girls, I wondered whether they were interested in me or the money. Underneath it all was a persistent layer of uncertainty, maybe shame: How would people judge me for having money I hadn't earned?

Supposed to forget me

When I was around thirty, my father’s business collapsed, and most of our family’s wealth went with it.

That was decades ago, but habits embedded in our bodies die hard.

And yet, I am finding that hiding isn’t who I actually am. Because standing out feels uncomfortable, I rarely seek out leadership roles. But when I get deeply excited about an organization or its mission, I get involved. Over time, people notice. Most of the leadership positions I’ve held over the years came because someone asked me to step up.

In those moments, the internal tug-of-war begins. When someone speaks well of me, I feel surprised, uncomfortable, and want to make myself smaller. When I find out people were discussing me when I wasn't in the room, whether good or bad, I feel odd. People are supposed to forget me when they don't see me.

That is what happened at the café table. Being remembered felt good for a second. Then my childhood lesson took over, translating recognition into danger.

When the money arrives

I see something similar in many people who come into wealth.

A few years ago, I worked with a client* in his late twenties whose family came into significant wealth almost overnight, and a trust fund was set up for him. As the money became available, he moved into a nicer apartment, but he was afraid of showing any other sign that his circumstances had changed.

What scared him most was exposure. He worried about his friends – would they treat him differently if they found out? Would he lose them? At the same time, he was seeing someone he really cared about, but he was terrified to tell her about his finances. He worried that, once she knew the full picture of his family's assets, he would lose control of his own life and choices.

I recognized those fears because I had asked myself the same questions while growing up.

Over six months, he and I worked together to figure out how the money might fit into his life. We explored what he wanted his life and relationships to look like. By the end, he was far more at ease. He began buying nicer things for himself, mostly subtle, understated items that brought him joy without signaling to the outside world.

His decisions were thoughtful, and there are plenty of good reasons to be discreet. But sometimes I ask clients a simple question: whose values are you living?

My family’s rule of invisibility came to me at age five, attached to the money itself, and it took me decades to separate the two. When someone comes into wealth, whether at age thirty or sixty, it arrives with a set of implicit rules. Most people never pause to consider which rules came with the money that entered their lives.

Hitting publish

I feel that old instinct every time I publish one of these articles.

Through my own personal work and years in a men's organization, I've gotten much better at being vulnerable and expressing my feelings. But publishing is different. When someone I know mentions an article, I wonder what they think of me now. It isn't as sharp as what I felt at that table in Burlingame, but it’s an uneasy sense that this isn't the way I am supposed to be.

Even while working on this draft, I caught it happening. An early version said my friends gathered at our house because it was the biggest. I flinched at that line and immediately wanted to soften it to sound less showy. Decades after my family lost that wealth, I still don't want to be seen as someone who shows off.

I always intend to stay one article ahead of my publishing schedule, but I keep finishing them just days before they're due. The part I put off most is the short LinkedIn post that points people to each article. I never consciously decide to delay it; there just always seems to be a reason to write it later.

Each time an article goes out, I re-experience a version of what happened at that table years ago: a moment of warmth at being known, followed by the urge to retreat into the background.

I don't know if or when I will feel something different. Nonetheless, I have decided to persist and keep publishing anyway.

*Client stories in this article are composites, with identifying details changed to protect client privacy.