Never Enough
The funny thing about achieving your goals is that the goalposts always move
I’ve finally gotten to the age where I’ve seen the lifecycles of multiple goals play out. It usually looks something like this: goal setting → work → success/failure. In my personal life, two iterations of this stand out.
The first one, I’ve actually written about. I dedicated most of my sophomore year of college chasing a prestigious investment banking internship. A combination of studying and networking got me there, and the celebration after was glorious.
The second was Ironman Texas, which took up a big chunk of my senior year of college. Athletic goals are very straightforward. A set amount of swimming, biking, and running can get anyone past the finish line of an Ironman. Achieving this goal gave me the same euphoric feeling.
I’m now writing this three years after receiving the offer letter and a year after ringing the first-time Ironman finisher bell. While I think back to those memories fondly, my feelings now are a fraction of the intoxicating happiness that I had once felt. Almost immediately after each experience, thoughts of recruiting for the next job or signing up for the next race crept into my mind.
The bubble of success floats around, just out of arm’s length, popping when you finally reach it. In all facets, achievement and the feelings tied to it are fleeting. What was exciting at one point becomes normal. The funny thing about achieving your goals is that the goalposts always move. There’s this infinite desire inside of us that can’t be satisfied by the finite nature of success.
The problem with chasing the shiny things of this world is that it wears you down. David Foster Wallace frames this well:
“If you worship money and things — if they are where you tap real meaning in life — then you will never have enough. Never feel you have enough. It’s the truth. Worship your own body and beauty and sexual allure and you will always feel ugly, and when time and age start showing, you will die a million deaths before they finally plant you…Worship power — you will feel weak and afraid, and you will need ever more power over others to keep the fear at bay. Worship your intellect, being seen as smart — you will end up feeling stupid, a fraud, always on the verge of being found out. And so on”
Hiding behind the façade of self-improvement this message is echoed by the culture of optimization. We’re fed consumer products and social media content on “maxxing” different parts of our lives. This culture prospers by maintaining a gap between who we are and who we could be. In addition to chasing goals, we’re taught to chase this constantly moving, better version of yourself.
The difficult part of criticizing these societal pillars is that they aren’t innately bad things. Goal setting and self-improvement are virtuous things to focus on. The issue comes from positioning your life around them. The idolization of doing so contributes to the widespread dissatisfaction and unhappiness in our generation.
To deal with the fleeting sense of satisfaction and difficulty with finding meaning in life, I’ve seen people respond in each of the following ways:
1. Maybe the real treasure was the journey
For many, the journey of achieving something is more meaningful than the achievement itself. If meaning is derived from the process rather than the outcome, an endless cycle of goal chasing could sustain that sense of meaning. If the destination doesn’t satisfy, maybe the point was never the destination.
There’s truth in this. Part of living life to the fullest involves finding joy within the journey. Studying banking technicals and training for the Ironman were meaningful during those periods of my life. But meaningful and meaning are two different things.
Just because something is important doesn’t mean it deserves to anchor your life or can bear the weight of your life’s purpose. Some things matter but aren’t what ultimately matters.
The journey falls short of fulfilling more existential desires because it’s conditional. What happens if you stop making progress? What happens if you fail? If you tie your sense of meaning to the journey, meaning becomes something you maintain, not something you have.
2. Live for something bigger than yourself
Another common response is a repositioning of purpose towards noble causes such as philanthropy or caring for friends and family. Again, these are good pursuits and deeply valuable in their own right. The issue arises when identity and meaning become fully dependent on them.
If your sense of meaning is grounded in being a good friend, a provider, or someone who serves others, it becomes tied to your ability to fulfill that role. What happens when you’re unable to show up in the same way, or when circumstances change? Even the most meaningful relationships and responsibilities are not fully within your control.
Living for things bigger than yourself can feel more fulfilling than purely self-centered pursuits, but it can still leave meaning contingent on performance or circumstance. It becomes something you sustain rather than something that is fundamentally secure.
3. Contentment
Others deal with the hard questions in life by leaning into contentment or choosing not to think too deeply about them. In many ways, this the easy route. I tend to fall into this camp. I’ve lived an extremely fortunate life thus far, free from severe hardship or trauma. I’m grateful and content. If you asked me why, the answer would likely be something like good job, friends, family, or life trajectory – nothing to complain about.
Each of those things, however, are still circumstantial. I could get fired from my job, lose a loved one, or my life trajectory could change. In that case, would life still feel the same? If contentment is built on things going well, it raises the question of whether it holds when they don’t.
Answering The Hard Questions
These are the more existential questions that sum up my feelings:
Why do things never feel like enough?
Why are we always searching for something more?
What gives my life meaning?
Tying personal value and meaning to something earned, built, or sustained is inherently unstable and ultimately unfulfilling. This pattern, however, shows up in many belief systems as well.
In Buddhism, Nirvana is achieved through following the Noble Eightfold Path. In Hinduism, outcomes are reliant on one’s karma. In Islam, actions such as following the Five Pillars contribute to ultimate salvation. The underlying structure stays the same: your meaning and value is in some way attached to what you do.
If both meaning and value are meant to be stable, they must come from something outside of ourselves. The Christian faith addresses this, proposing a different idea: you aren’t enough, and no amount of good works will ever make you enough. Despite this, you are loved anyway. Your value is not something you achieve or maintain, but something given to you. You have worth because you were created in the image of God, not merely because of what you accomplish.
The meaning of life changes fundamentally under this view. It is no longer about proving your value, sustaining it, or searching for it, but about receiving it. To love and glorify God, and to live in response to that relationship.
The feeling of never being enough and always wanting more is not a problem to solve through effort. The answer was never meant to be found within yourself in the first place.



great read!
Great blog as always :)