A few months ago, I watched a semiconductor company's stock price triple in just six months.
I left the chip industry over a decade ago. My colleagues who stayed (some of whom remained at the same company and watched the stock climb, others who joined businesses that were later acquired or went public) have, by any dollar measure, done far better than I have.
I know this because that familiar pang showed up again. It always does. Sometimes it's sparked by a LinkedIn announcement, a dinner with an old colleague, or just a moment when my wife wants something and I find myself doing math our account doesn't justify.
This time, it was looking at a soaring stock chart, even though I'm genuinely happy with the life I chose.
The pang is difficult to describe. It's not regret; I'm clearer on the decisions I've made over the past decade than any I made before them. It's more like a phantom limb. The arm is gone, but the nerve still fires. I made the right choices for me but, for a split second, the old measuring stick activates anyway.
I've contended with this feeling for years. A friend I'll call Terry finally helped me see it differently, though not in the way I expected, and not until after he died.
The friend who coded for the love of it
Terry was my college roommate. For the first few weeks of university, I barely saw him; he was always in the computer lab, coding late into the night. Within six months, we became close friends, the kind of bond that forms quickly and holds for decades.
He was brilliant, but not in a conventional, credentialed kind of way. While the rest of us studied for exams, Terry just coded. He didn't care about his grades; the degree was just a piece of paper, and he was there for the work. He didn't even get into the Computer Science department, but it didn't matter; he just joined the student CS club instead.
Over time, his reputation spread the way it does when someone is genuinely passionate about what they do, even if they stayed below the radar. He eventually accomplished more in the field than most people with the degree.
In the early 1990s, before most people had even heard of the internet, Terry became obsessed with the World Wide Web. Before Mosaic existed, he was building his own graphical web browser, writing code for something most people couldn't yet imagine. When he graduated, he joined a tech company that promised to support his browser project, but they didn't follow through. So, Terry simply released his code into the wild as a free resource for others.
That browser ended up contributing to the development of the major commercial browsers we use today. People who built the early web recognized his work, even if the broader world never knew his name.
Billions of dollars in value, simply given away
Over the years, his ideas kept leading him to interesting places. He worked for companies that AOL acquired, then Amazon.
Later, he became an expert witness in a major patent lawsuit in which the largest internet companies in the world were sued over a fundamental browser capability. Because Terry could prove that his freeware browser had implemented that capability years earlier, the patent was invalidated. His work, given away for free decades prior, protected billions of dollars of value for tech giants.
Yet Terry never made a lot of money. His ideas were worth billions. He was not.
For years, I carried a quiet regret for him. Back in college, I had suggested we start a tech company together-my family's business was doing well at the time, and my father might have invested. Terry wasn't interested.
Later, watching what his ideas went on to enable, I kept thinking: He could have been famous. He could have been wealthy. He was too brilliant for what he received.
I thought this was concern for my friend. It took me a long time to see it was actually about me.
Measuring a life by the wrong ruler
Terry didn't measure his life in money or recognition. He coded because he loved it. He lived simply, by choice, because a simple life gave him the freedom to do what he actually wanted.
By the time his career wound down, work had become optional, not because he had accumulated a vast fortune, but because he knew what his "enough" looked like. He had solved a core personal challenge most people spend their entire lives chasing, and he had solved it on his own terms.
This became even clearer to me when I eventually left the chip industry to become a financial life planner. Suddenly, I was the one making choices that didn't optimize for wealth accumulation. By then, I thought I had done the inner work to figure out what I wanted. I understood, intellectually, that money isn't the total measure of a life. I believed it, and I could say it to my clients with genuine conviction.
I see the same challenge in my clients. They set a target for "enough", a number that will finally mean they can stop grinding, stop worrying, stop measuring themselves against people who have more. Then, when they get close to that number, the number moves. It's rarely about the math. Something in them still doesn't believe they've “arrived”, so the goalpost shifts to protect their identity instead. I recognize it because I was doing my own version of it with Terry: not moving a number, but viewing a friend's outcome through lenses I couldn't set down, even as I started making my own decisions that incorporated life, not just numbers.
So, I continue to feel regret for Terry, the sense that he had been under-rewarded, that he should have had more. It took me a long time to realize that this "regret" was actually my ruler, not his. He had built the life he wanted. I was the one measuring it wrong.
When life intervenes
Then, life intervened.
It wasn't poverty or a bad business decision. A family member became seriously ill, and Terry became their primary caregiver, a choice made from love, which consumed over a decade of his life.
Terry had always loved to travel and learn. He used to talk constantly about the places he intended to go and the subjects he planned to master. He assumed, reasonably, that the time would come.
But after that family member passed, the pandemic arrived. And just as the world finally began to open back up, the cancer came.
He was diagnosed four years ago. I visited him to catch up over dinner, and he complained about some pain he was feeling. For the first time, he turned down food that I knew he liked. He found out a few days later after going to his doctor.
I couldn't bring myself to believe it would end the way it did. His odds weren't good, but I kept expecting him to beat them. I was already planning what we'd do when he recovered, how I was going to take him out to a fancy restaurant to celebrate. Meanwhile, he was telling me about the grand world tour he was planning.
He died with those plans unlived.
It wasn't because he measured wrong, made a financial mistake, or chose the wrong career. He had gotten all of that right for himself. He died with unlived plans simply because he had assumed the time would be there, and it wasn't.
I was one of the last people to speak with him. He even left something for me in his will. Yet, I still routinely reach for my phone to call him during my commutes. He was one of the few people I could think out loud with, and that reflex doesn't care that he's gone.
Knowing in your head vs. feeling in your bones
What changed for me after Terry died was where my understanding of life lived. Before, I knew these things in my head. Afterwards, I felt them in my body. There is a profound difference between an idea you hold intellectually and the same idea landing heavily in your bones.
The pang of financial envy still comes. I don't expect it to stop. But what's changed is what happens in the moment right after it hits.
Terry lived life on his own terms. He figured out "enough" earlier than most, and yet, it still didn't guarantee him the future he expected. That's the part that clients don't usually see, especially when their number keeps sliding out of reach. Terry set his target and left it alone; whatever he built his "enough" on didn't depend on outrunning anyone else's. On some days, mine still does, and I know the pattern well enough to catch it when a client is doing it.
None of us get to relive our lives with different choices, so I will never know for certain if I've made all the right decisions. If I knew the exact date of my death, planning would be easy. Without that answer, I have to live in the tension: spend now or save for later, act today or wait for the right moment.
What I've settled on is simply doing the best I can with what I know right now. I try to be honest about why I'm making a choice, consciously checking in with my heart and body so that I am not deciding from a place of scarcity or just drifting along with the current.
The ruler I inherited - the one that believes net worth is the best way to compare - is still in my hands. I just try to remember to set it down when it isn't serving me.
Terry knew how to do that. He lived it more completely than I probably ever will, and I am still learning what it means to truly feel that truth, rather than just think it.
