Aspiration is a Path Littered with Happiness

“Happiness” is what researchers call a suitcase word. You can stuff it with many different meanings: from hedonic pleasure to eudaimonic well-being; from satisfaction to euphoric bliss. The vagueness is so frustrating that Martin Seligman, the founder of positive psychology, stopped using the word entirely, preferring “Flourishing.” Even Nobel laureate Daniel Kahneman shifted from happiness to life satisfaction, a much narrower concept.

Being much more foolhardy than these men, about 12 years ago I co-founded a technology company with the explicit mission to help people be happier and more successful at work. We grew to become a leader in the space, collecting hundreds of millions of psychometric data points from people around the world.

We used AI and statistical methods to analyze this massive dataset to see what actually makes people happy. If you strip away the noise and look for the drivers that consistently predict long-term well-being, three things rise to the top: Purpose, Growth, and Belonging. Although there are hundreds of factors that influence happiness at work, once other factors (recognition, autonomy, teamwork, and so on) meet a basic threshold, the vast majority of variation in happiness is explained by these three. The findings proved robust: these factors also predicted real-world outcomes like retention and discretionary effort.

If you look closely, this triad of purpose, growth, and belonging maps directly to the psychological concept of Intrinsic Motivation. It turns out the things that motivate us to act from within are the same things that make us happy in the process of acting on them.

Happiness isn’t something you can chase directly. Doing so is a fool’s errand. Rather, if you consider that the many varieties of happiness are felt-concepts our brain generates when we’re moving toward what it predicts as being “good”, then a different approach opens up. The question is: what counts as good? One might argue that “good” is evolutionarily decided, with the intermediation of biology and culture, and through learned experience.

Aristotle argued that happiness comes from virtuous action - from living in accordance with our highest capacities. He had specific virtues in mind. But the core insight holds even if we fill in the content differently: when you act in ways that align with deep human needs - for purpose, growth, connection - your brain rewards you. Happiness follows.

So, if certain kinds of happiness are byproducts of pursuing the “good,” how do we structure our lives to catch it?

There are many tried and tested methods to increase your happiness or reduce unhappiness. Mindfulness, cultivating relationships, practicing gratitude, acts of service, and so on. The list is large.

But today we’ll focus our discussion on something people don’t talk about much when it comes to happiness. And that is Aspiration. I hold that aspiration is a path that can be littered with happiness. Wherein simply the process of Aspiring will expose you to many different types of happiness.

Until I read the philosopher Agnes Callard, I thought Aspiration was just a loftier form of Ambition. But Callard argues they are fundamentally different, and understanding the distinction is the key to unlocking a “thicker,” more resilient form of happiness.

Ambition is the pursuit of a goal that satisfies your existing values. An ambitious person wants a promotion, money, or status because they already fully grasp the value of those things. They are trying to get more of what they already want.

Of course getting what you want can often be surprisingly disappointing. It’s the hedonic treadmill. You get the promotion. You feel a spike of happiness. Then you adapt, and you’re back to baseline, scanning the horizon for the next promotion. The problem isn’t that you failed, it’s that you succeeded. You got exactly what you wanted, and it didn’t change who you are.

This is what I’d call thin happiness. It sits on the surface of your life. It’s real, but it doesn’t stick around.

Aspiration is different1. It is the pursuit of a goal that requires acquiring new values. Aspiration fundamentally changes who you are.

For example, the aspirant may want to become a person who can appreciate and love classical music, or a person who finds joy in running marathons, or a person who is a patient and loving parent, even though they don’t quite “get it” yet. They aren’t trying to satisfy their current self; they are trying to become a new version of themselves. You cannot understand the destination from the starting line; it is the act of doing the work - the miles run, the scales practiced, the diapers changed - that constructs the person capable of valuing it.

While ambition is about getting more of what you already want and value, aspiration is about learning what to want in the first place.

This is the ultimate form of Agency: the ability to not just act on your desires, but to shape your desires.

Consider a student taking a Music Appreciation class. They might currently not “get it” - they find Bach boring and repetitive. But they aspire to be the kind of person who is moved by Bach. If they only acted on their current values, they would drop the class and listen to pop music. But by staying in the class, they are acting on what Callard calls a “proleptic reason”. They are acting for the sake of their future self.

This might seem irrational. How can you justify pursuing something you don’t yet value? Callard’s insight is that aspiration is rational precisely because it’s how we become capable of appreciating goods that are currently beyond our reach. The student cannot yet give a full account of why Bach matters, but they can recognize that such an account exists and is worth growing into.

This process inevitably creates an “Awkward Phase.” Because you don’t yet possess the value you are chasing, your behavior feels like imitation. You are faking it until you make it.

You might feel like a fraud. An imposter. You will certainly experience conflict where you are torn between your old, strong values and your new, weak values. For instance, the aspiring home cook labors over a braise for three hours and wonders why they didn’t just order takeout. They are torn between their old, strong values (convenience, instant gratification) and their new, weak values (the slow satisfaction of feeding others something made with care). The conflict is real, but it’s also the work.

But this awkwardness is not to be shied away from. It is the scaffolding required to build a new self. You should feel free to embrace the faking just as a child embraces imitation without understanding until one day it all clicks and eventually becomes second nature.

How do you know you’re genuinely aspiring rather than merely conforming to external expectations? The test is whether the new value, as it develops, feels like an expansion of who you are rather than a suppression. Authentic aspiration enlarges your sense of self; mere conformity shrinks it.

So, if aspiration involves feeling like a fraud and battling your own desires, why do I claim the path is “littered with happiness”?

Because aspiration forces you to engage with the deep drivers of well-being: Purpose, Growth, and Belonging.

It Creates Deep Meaning: Aspiration is, by definition, a search for meaning. You are engaging in the work of identifying and formulating new values for yourself. It is self-creation. Purpose comes built-in. This replaces the “thin” happiness of a reward with the “thick” happiness of identity. The joy of being a parent or an artist is woven into who you are, making it resilient to the ups and downs of life.

It Forces Growth: You cannot aspire without growing. Ambition can allow you to stagnate in your character while advancing in your career. Aspiration forces you to expand your internal machinery. Aspirants often start because they feel a sense of lack: they see a dedicated doctor or a passionate artist and feel that those people are in touch with something “real” that they are missing. Aspiration bridges the gap between who you are and who you feel you ought to be. It forces you to grow internal machinery you didn’t have before.

It Creates True Community (Belonging): This is often overlooked. When you successfully aspire, you don’t just gain a hobby, you gain a tribe. You gain entry into a community not just through proximity, but via shared values. When you finally “get” classical music, you share a specific, deep psychological reality with every other classical music lover. When you become a runner, you join the running community. You belong in a way you couldn’t before you did the work.

Crucially, community isn’t just the reward of aspiration, it’s often the vehicle. The Music Appreciation student is trusting their teacher to hold the value for them until they can hold it themselves. Mentors, guides, and fellow aspirants carry us through the awkward phase when our own motivation falters. The communities we aspire to join are the same ones that make our aspiration possible.

It Unlocks Inaccessible Joys: Aspiration expands the surface area of the world that can bring you happiness. Once the student finally “gets” the symphony, or the runner finally hits that runner’s high, they unlock a source of joy that was previously invisible to them. More crucially, these joys are available throughout the journey, as most pursuits are not binary events but rather true paths of progress.

Finally, we must remember that aspiration is not just about the destination. The title of this essay is that the path is littered with happiness. If you focus too much on the destination, aspiration becomes obsession. When you reach the destination you will be disappointed.

On the other hand if you dwell too much on the present moment, you can stagnate. You may lose track of true north. The trick is to balance a healthy focus on the destination with the wisdom to appreciate the messy process of becoming.

While the “awkward phase” is hard, there is a profound joy available to us in the Progress Principle. As you aspire, you begin to change, and to hit milestones. You start to understand the music a little better; the run gets a little easier. You see glimpses of the view on the other side of the mountain.

Because your brain loves to predict “good,” these moments of progress trigger deep satisfaction.

And even when aspiration doesn’t deliver what you expected - when you take the class and Bach still doesn’t move you, or you become a parent and find it harder than the books promised, demanding a patience and selflessness that you do not naturally possess and must painfully manufacture day by day - the journey itself will have expanded you. You will have developed capacities, encountered others on the same path, and learned something real about what you value. That growth doesn’t disappear.

Aspiration does not make you “happy” like a warm bath makes you happy. It makes you happy like climbing a mountain makes you happy. It involves struggle, uncertainty, and effort. But if you take care to pay attention to the journey itself and keep yourself open to the pleasures that crop up like wildflowers on the mountainside, then the rewards can be deep, profound, and cumulative.

So as you think about your intentions for the new year, don’t just be ambitious. Go Aspire, acquire new values, and become happier in the process.