We spend a lot of time chasing happiness—trying to become more joyful, more fulfilled, more content. We believe we know what stands in the way of our happiness: too much work, too little time, not enough money, family stress. The obstacles feel tangible. But a big obstacle is not actually these identified barriers, but something else– our ability to tolerate contentment. We are so conditioned to work to improve problems that a lack of problems actually becomes an unsettling place. Once we learn more about this place, a new path emerges.
We often resemble the proverbial dog chasing a car. The chase is clear, energizing, and instinctive. What happens when the dog catches the car? When our family is healthy, when our finances are stable, when our health is intact, it can be surprisingly difficult to dwell in that satisfaction. Spending our time solving problems conditions us to feel at ease when we are solving problems. This creates a paradox: in order to feel at ease, we need a problem, a project, something to fix.
This need arises from the culture we live in. We’re bombarded with conflicting messages about self-improvement and happiness. First, we are told to be better, reach higher, grind, never settle. This message tells us that satisfaction is dangerous—that we should always be pushing. It is in the struggle that we find joy. This teaches us to build an identity around chasing—but when the chase ends, we don’t know what to do next. It is difficult to enjoy where we are because we’ve been trained to always be striving, equating the striving itself with joy and contentment.
The other main message suggests that fulfillment is out there, waiting, we just have to find it. We’re told to “find what makes us happy,” as if happiness will naturally sustain us once discovered. Superficially there is similarity, but this second message equates happiness more with something that happens at the end of the search, a destination at which we arrive. It is curiously silent once we reach the end of the rainbow.
Both messages share something in common: the need to keep moving. If happiness is found in the obstacle, in the struggle itself, what happens when we do not really have problems? If happiness is in the friction, it's nearly impossible to have enough. If joy is found in trying to make things better, what happens if we are accepted and loved for who we are, without reservation? Conversely, It is incredibly hard to turn off the searching function when we’ve lived our life searching. We have no practice dwelling in contentment, so stopping the search feels foreign. After all, we’ve spent our life searching for happiness, not considering what to do once we’ve found it.
This creates a reality where many of us are much more comfortable in pursuit than in arrival. Discontent becomes a default mode. We’ve trained ourselves to be productive when things are broken, to be focused when there’s a problem to solve. Contentment feels unfamiliar, even threatening. In its presence we grow restless, create new goals, or manufacture new problems—not because we want to suffer, but because we’ve developed skills for searching, not for dwelling in joy.
This is not to say that the pursuit, the obstacle, should be joyless. Instead, it's learning to love both the journey and the destination. For many of us, we have figured out (to some degree) how to enjoy the journey, but we have no idea how to enjoy the destination. This means that we are never able to really arrive, to find contentment in what we have. We have spent little time thinking about what happens once we’ve crossed the finish line. We are at a loss when we look around and realize we don’t know how to inhabit the stillness. The problem isn’t the journey or the destination. It’s learning how to stay at the destination without immediately packing our bags again for the next journey
The characteristics that equip us well to achieve, to enjoy the journey and embrace the challenge equip us poorly to be content. Seeing the potential of what things could be, figuring out how to turn that potential into reality– that is the excitement and the process of creating. Contentment is a different skill, and is more about taking satisfaction in the way things are, rather than in the potential of what they could be. The skills we develop and refine for the journey may be the inverse of the skills we need to be content in the way things are.
There’s nothing wrong with enjoying the pursuit. There’s deep wisdom in striving, in stretching, in overcoming. But if that’s all we know, we’re left with an underdeveloped capacity to experience what we’ve been working for. We are skilled at discontent and practiced in wanting more, but need practice loving the people we’re with, enjoying the things we’ve accomplished, and belonging to the communities we care about. The challenge becomes this: how do we embrace that moment with as much skill as we embrace the journey, the edge, the pursuit? How do we accept that contentment isn’t a trap or a delusion, but something worth inhabiting?
Perhaps we should consider contentment as a skill– akin to the skills we force ourselves to learn for the chase. Most unfamiliar things become more comfortable with practice. If we want to get better at being content and joyful, we need to sit with joy and contentment. If we want to be more present in good moments, we have to practice being present in those moments, rather than listening to the urge to move on.
Superficially, this seems silly: practicing how to feel good? But it’s no stranger than practicing how to tolerate grief or pain. In fact, many of us are more practiced at sitting with suffering than with joy. We’ve developed tools for discomfort—coping skills, therapy frameworks, resilience strategies. How much time do we devote to developing joy or contentment frameworks? When joy arrives, we often push it away, deflect it, minimize it, distract ourselves, or turn it into the next project.
Most of us have spent a lot of time training in discontent: chasing goals, solving problems, overcoming obstacles. As a result, our ability to recognize and remain in moments of ease is underdeveloped. Contentment feels unfamiliar, even suspicious. However, learning how to sit in contentment actually expands the path. When we intentionally practice it, something shifts. We start to notice that contentment isn’t rare, it just doesn’t demand our attention the way struggle does. The more we tune into it, the more we realize that its everywhere. Far from being elusive, it is infinitely available.
The more we attune to it, the more it begins to show up. Perhaps as a result of what we achieve, but also in the ordinary. It’s not that the circumstances of life suddenly improve—it’s that we start noticing the parts that were already good. We can train ourselves to live more fully in this contented space of enough, rather than skipping over them and immediately scanning for the next problem, or chasing the next win. Just as we train ourselves to chase and to grind, we can also train ourselves to receive what is already here.
Cheers,
Doc
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