I was twenty-one years old, sitting at a dinner my father had brought me to.
His banker was hosting the evening for a small room of entrepreneurs. My father was one of them. At one point, having had too much to drink, the banker stood up to toast the room. He said that building a business from nothing was like a divine act of creation. Then he added: it was a shame these companies would eventually go to the children, who hadn't accomplished anything themselves.
My father tried to brush it off and change the conversation, but the words were already out.
What he said out loud
Sitting at the dinner table, what went through me wasn't shock; it was recognition. I had already heard this sentiment in the background noise of my life - in the hushed tones of the company's executives, distant relatives, and family friends. Sitting at that table, my immediate internal reactions were shame and frustration: Yes, I know. Of course I know. What made you think I didn't know this?
Beneath the shame was an exhausted feeling of resignation. It didn't matter what I did or where I went. This was the yardstick I was given; I was born with it and there was no way to change it.
My father and I never spoke about that toast. Not that night, not in the days following, and not in the decades since. There didn't seem to be a point; the moment had already happened, and the words were already said.
When the thing I owed disappeared
Eight years later, the business collapsed.
Severe economic and political turmoil in Taiwan swept through the market, taking my father's company with it. Although he was semi-retired by that time, he had reinvested almost everything he owned back into the firm, wiping out most of our family's wealth overnight.
The immediate aftermath was pure survival: a terrifying feeling of scarcity that drove me to work myself into the ground for the next decade just to feel safe again. But a subtler, more insidious shift happened alongside the financial loss - one I only recognized recently.
The thing I was supposedly unworthy of no longer existed.
I never got the chance to earn my way into deserving it. I couldn't grow it, run it, or become the successor who justified the inheritance. The company was gone, yet the verdict handed down by that banker outlived the thing it was about. I was left measuring myself against an achievement that, from that point on, only existed in memory.
A target that never moved
If I step back and look at what I have done, I've built a life that’s pretty cool. I graduated from Berkeley and Yale, served as a finance executive at a well-known chip company, and sat on the boards of three non-profit organizations for years. I started my own firm in 2019 and that decision played a major role in where I am today.
Yet, I rarely talk about these milestones. Not out of modesty, but because none of them felt like a big deal.
The banker hadn't just called my father successful; he viewed the founding of a business as an act of creation. My father built something from nothing and took it public. To my twenty-one-year-old self, that set an impossible bar: Founder and Heir belonged to two completely different categories, and you could not cross from one to the other.
No point in trying
Because I believed I could never recreate his "divine act," I subconsciously stopped myself from ever trying to build something of equal scale. For a long time, I thought I never tried because I didn't need to - that what I had was already enough, and I wasn't the type to chase more. The schools, the career, the boards — I did all of it because I believed I was supposed to, or because something in me felt called to it. None of it was me reaching for something bigger. Now I realized that, since I was young, some part of me had already decided that it isn't possible for me to do what my father did. If I already believe I can't reach it, why try?
I am not sure what happens from here. I'm not going to pretend that I've made peace with these feelings. I'm not even sure what making peace looks like in practice.
What has changed is clarity. I can finally start to see my own achievements without immediately discounting them. I can trace the voice that whispers "not enough" back to its origin.
I still don't often feel pride when I look back on my life. But I know now that the issue isn't what I have or haven't done. It's that I spent thirty years measuring my life against someone else's miracle.
