My father has always believed that you can lose stuff, but you'll always have memories.
He didn't arrive at this philosophy abstractly. He built a business from nothing in Taiwan so he could give his sons opportunities he never had, and then spent years separated from us while he worked. The times we had together when I was young were few but precious. When he did show up, he made sure something happened worth remembering. Food was especially important to him; he grew up eating bland rice and vegetables. Taking us somewhere extraordinary meant something to him that went beyond food.
What he was really doing, I understand now, was curating stories. Not for an audience, for us. For our future selves that would someday look back and know we'd been loved, and that our time together had mattered.
I absorbed that philosophy growing up without quite naming it. Experiences over things. Memories are the only currency that compounds without risk.
When the Extraordinary Becomes Routine
Some years ago, inspired by my father's example, I decided to dine at every Michelin-starred restaurant in the Bay Area, combining two things I loved, food and shared experience, into something intentional. For the first year it worked. Each dinner felt like an event. Then something shifted. The dinners started blurring together. The project that had started as a way of creating memories had quietly become a routine. And routine, I was learning, is what happens to anything that loses contrast.
The lesson I took at the time: make sure your experiences are meaningful, not just numerous. That felt true enough. But I've since come to think it was only half the insight.
The Blank Look
A few years ago, I started noticing something in my meetings with clients who were two or three years into retirement. I'd ask what cool or fun things had happened since we last met. And a surprising number of them would pause. Their eyes would go somewhere else for a moment. Then they'd tell me things were good; they were traveling, working on the house, picking up hobbies they'd set aside for decades. Everything they'd planned for. Everything they'd worked toward.
But something in the pause told me the answer wasn't quite complete.
When I gently asked more, what came out was harder to name. The traveling was good but felt somehow less exciting than trips they'd taken when getting away had meant something: relief from the grind, contrast against the ordinary week. The hobbies had started to feel routine in the way work once had. And underneath all of it, something they were almost embarrassed to admit: they couldn't point to a single story from the past few months that felt worth telling.
What surprised me most was the guilt. These were people who had built real wealth, who had earned the freedom to do exactly what they were doing. And yet they felt guilty for not feeling more excited about it. Some wondered aloud whether they simply needed to learn contentment, whether the restlessness they felt was a character flaw to be managed rather than information worth listening to.
The Conscious Choice
I don't think restlessness is a virtue and I don't think contentment is a problem. Some people genuinely thrive in the quieter rhythms of life: the morning walks, the grandchildren, the garden, the book that finally gets read. Tranquility is its own kind of wealth.
But for many of my clients, people who've spent decades in mentally stimulating, high-stakes environments — long stretches of undifferentiated routine feel genuinely off. And the difference between choosing tranquility and drifting into it matters. One is a life you are choosing; the other is a life happening to you.
What I find myself doing in those conversations is helping clients curate contrast back into their lives, deliberately, the way my father chose each rare experience with his sons. Not more experiences, necessarily. More intentional ones. Trips planned around something specific rather than destinations checked off a list. Projects with a shape and an ending. Ways of spending time that generate stories worth telling.
My father was right that memories outlast stuff. What I've learned is that they don't accumulate on their own. They need contrast, intention, and occasionally the right question at the right moment: what do you want the stories in this chapter to be?
