# Moving goalposts Canonical page: https://www.gabrielvaldivia.com/notes/moving-goalposts - Author: Gabriel Valdivia - Published: 2026-09-22T12:15:00.000Z - Updated: 2026-09-22T12:15:12.296Z The problem with success is that you might actually achieve it. I'm nearly 40, and I've been in design since my late teens. The peers I had when I was starting out are now vice presidents and heads of design at some of the world's top tech companies. Serial startup founders are cashing in on their exits. Long-term employees are getting promoted and using their bonuses to buy second homes. After twenty years of working toward something, people around me are starting to collect the rewards. There's a certain inertia to a career. It rewards consistency. Simply by staying on track, you tend to get better, make more money, gain more influence, and slowly move further along whatever path you started on. Eventually, the distant future you spent years working toward starts becoming the present. It's natural, then, to stare in the mirror and wonder what you have to collect. I suppose this is part of what fuels a midlife crisis. The energy you invested in your twenties and thirties is supposed to start paying off around now. Of course, life doesn't guarantee a return on that investment. Plenty of people work just as hard and never get the payoff they imagined. But for many, if it hasn't arrived yet, it's at least close enough that you can imagine it. You begin thinking of your stamina as a finite resource — "how long can I actually do this for?!" Retirement is no longer some abstract idea reserved for old people. It gets rebranded away from AARP magazines and bingo tournaments into a "work optional" lifestyle where you can occupy your time with what you *actually* want to do. It becomes a lustful light at the end of the tunnel. And all of this forces a question that was much easier to ignore when the finish line was still far away: what exactly were you trying to win? --- I spent a large chunk of my professional life chasing goals. I've been fortunate enough to achieve many of them, only to realize that the euphoria you're promised is quickly replaced by another mountain to climb. Some say that's the point, but that only works if you enjoy climbing mountains. The last time I found myself seriously questioning which mountain to climb next, I came across [a letter Hunter S. Thompson wrote to his friend Hume Logan](https://news.lettersofnote.com/p/beware-of-looking-for-goals-look), who had asked him what to do with his life. Thompson's argument is that you and your environment are constantly changing, so it's risky to organize your life around goals. > Every man is the sum total of his reactions to experience. As your experiences differ and multiply, you become a different man, and hence your perspective changes. This goes on and on. Every reaction is a learning process; every significant experience alters your perspective. > > So it would seem foolish, would it not, to adjust our lives to the demands of a goal we see from a different angle every day? How could we ever hope to accomplish anything other than galloping neurosis? His solution is to reverse the relationship. Instead of shaping your life around a predetermined destination, let the destination emerge from the kind of life you want to live: > As I see it then, the formula runs something like this: a man must choose a path which will let his ABILITIES function at maximum efficiency toward the gratification of his DESIRES. In doing this, he is fulfilling a need (giving himself identity by functioning in a set pattern toward a set goal) he avoids frustrating his potential (choosing a path which puts no limit on his self-development), and he avoids the terror of seeing his goal wilt or lose its charm as he draws closer to it. That idea resonated deeply. It became the tipping point that pushed me to quit my job and start an independent practice. When I stopped asking what I wanted to achieve and started asking how I wanted to live, I realized it's actually simpler than I thought: I enjoy making things, more than many of the outcomes that work is supposed to buy me. Take away the making, and those outcomes become a lot less appealing. The goal is to spend my days making things. The rest is just a byproduct of it. For years, I had treated the work I enjoyed as something I was supposed to eventually graduate from. More success and money meant getting closer to a future where I wouldn't have to work at all. But if I actually enjoyed the work, what exactly was I trying to escape from? --- The problem with choosing a way of life instead of a destination is that it's much harder to keep score. Goals are wonderfully legible. You either got the promotion or you didn't. You made a million dollars or you didn't. You sold the company or you didn't. There's comfort in having a number that tells you whether you're moving forward. When I started my own practice, I found myself drifting without a system to tell me if I was on the right path. I no longer had a peers to do a 360 review or a manager that could promote me. I turned to money as a metric to tell me if I was heading in the right path. It's reasonable, I think! There's so much anxiety surrounding the decision to venture on your own (Will I find enough clients? Can I charge enough? Can I maintain the life I had built without the security of a salary?) so making money became the de facto antidote for it. When I finally got to my number, I remember looking at how much I had made that year and feeling incredibly proud of myself. Then, not even two seconds later, I thought: how do I make more? There I was, back at the rat race. That's the trouble with using money as a measure of success. There is no natural point at which the scoreboard turns off. Whatever number you reach simply becomes the baseline for the next one. I've since set out to define alternate metrics that could signal whether I'm heading in the right direction. I've started asking myself questions like: am I spending the majority of my day doing what gives me energy? Is the output of my work aligned with my values? Am I exploring new experiences and learning new things? Am I offering opportunities to people in need? These metrics don't fit neatly into a spreadsheet. But increasingly, they feel like much better evidence of the path I want to walk. Of course, that's my scoreboard. Yours might look completely different. Maybe it's raising a family, becoming exceptionally good at something, traveling the world, or retiring at 40. The important question is whether you arrived at that definition yourself or simply inherited it. When I feel lost, which happens often, it's tempting to reach back for "more money" as the answer. I tell myself I can spend a few years grinding, make enough to retire, and then finally live the life I want. But following that logic often leaves me questioning why I would spend my life doing something I want to escape from, just to return to the kind of life I could have been living all along. That's when I have to remind myself why I chose this path in the first place. I get to make things, follow my curiosity, spend time with my family, and decide what deserves my attention. I suspect this is an easy thing to miss. We spend so much time working toward a better life that we rarely stop to ask how much of it is already available to us. There will always be another milestone that promises a little more freedom, security, or possibility. The light at the end of the tunnel is just a brighter tunnel. I doubt I’ll ever stop wanting more. There will always be another number that feels close enough to chase. But lately, when I catch myself calculating how many more years it will take before I can finally stop, I try to remind myself to look around. It’s easy to spend your life earning the freedom you already have.