Aspiration Is Awkward

The uncomfortable and sometimes phony process of becoming who you want to be

I am an American expatriate currently living in South Africa, but I used to think of myself as just an aspiringexpatriate. I was, by definition, allowed to remove the “aspiring” tag the moment I stepped off the plane back in August 2017, but at that point in time, I didn’t think much had really changed about me. I was, after all, the same person, just in a new country and without a return flight.

I recently reflected on this idea of aspiring self versus actual self after I met a neurolinguistic programming practitioner who invited me to take several surveys as part of an overall assessment. They felt similar to other personality assessments I have taken in the past, like the Myers-Briggs Type Indicator and the DISC behavioral assessment. But my current phase of life is significantly different from when I did those other assessments, and my experience taking the neurolinguistic programming surveys felt considerably different.

Looking at my expat status now, I think I have fully transitioned from being an aspiring expat, or one just by definition, to being an expat by values. And yet, as I continue to personally develop, my values continue to change. My current self, for example, enjoys reading and learning so much that I read to learn, but yet I see myself only as an aspiringpolymath. There is a natural tension between what I currently am and what I aspire to be. That’s the tension I experienced while taking those surveys: I felt unsure whether I was answering the questions as my current self or my desired self.


There is a field of interdisciplinary science called decision theory—in particular, normative decision theory—that advises how to make the best decisions given a set of uncertain beliefs and a set of values. The idea is that we ask ourselves what we value and then seek to maximize that value.For example, when deciding what to eat for lunch, we could choose a cheeseburger or a salad. If we value taste, we may choose a cheeseburger; if we value health, a salad may be the most valuable choice.

When deliberating my decision to become an expat, I had some vague sense of what it meant and what I aspired to become. It was grounded in prior travel experience to South Africa (though, in hindsight, a vacation is not representative of everyday life) and in anecdotes told by other expats.

We invariably are seeking to maximize not the valuesof the person we are today but the values of the person we seek to become.

While decision theory can be helpful, it fails to provide us with proper guidance in the real world. After all, values are not constant. In fact, my decision to become an expat was partially a decision to transition to a new self with new values. I literally became an expat overnight in that technical moment I stepped off plane without an intention to return to the U.S., but for it to feel official, I had to undergo a transition from old self to new self. Through any transition of this nature, values evolve and naturally come into conflict.

As an aspiring polymath, I feel I have to make a choice: I could spend my leisure time watching Netflix, an activity my old self enjoys, or I could read ferociously, an activity that I believe my new self will value. Which self’s values do I maximize?


When we aspire to be something that’s different from our current selves, we invariably are seeking to maximize not the values of the person we are today but the values of the person we seek to become. That transition can be awkward. As Joshua Rothman wrote in the New Yorker ,“Being a well-meaning phony is the key to our self-transformations.”

Rothman is referencing philosopher Agnes Callard and her book, Aspiration: The Agency of Becomingin which she distinguishes between aspiration and ambition. Callard offered the example of two students: an ambitious one who takes a music class seeking a good grade and another aspiring to become a classical music impresario. In the case of the ambitious student, they know exactly what they value: a good grade. But, as Callard explains, “the aspirants must grow comfortable with a certain quantity of awkward pretense.” In other words, we can’t yet articulate the values of the new person we aspire to become.

In my case, I couldn’t know what it really meant to be an expat until I fully made the transition to an expat with expat values. And now, I don’t really know what it’s like to be a polymath and won’t until I become one.

Further compounding the awkwardness of an aspirant’s transition is that we often can’t completely explain our motivations during the transition, so we tend to understate our aims. We are left to wonder: Is the aspirational student in Callard’s example trying to become an impresario or merely enjoying music? Or, in another a real-world consideration, is an aspiring influencer who posts on social media as if they were an influencer attempting to become an influencer or just demonstrating aesthetic creativity? And as for me, am I reading for casual enjoyment and learning, or am I actually trying to become a polymath?

These questions reflect the uncertainty surrounding the state of aspiration. We are motivated to avoid internal discomfort—the internal discomfort that is inevitable while we’re stuck in the middle between two selves and without a guarantee that we will fully complete the transition. We can feel phony while acting like something we aspire to be, trying to maximize the value of the future self we have not yet become. As Rothman put it:

It might be easier if our biggest transformations were instantaneous, because then we wouldn’t need to live in states of aspiration. Certain of who we were, we’d never get stuck between selves.


Aspiration is awkward because aspiration is hard. Part of adopting a new self also means leaving behind values of the old self that do not align with the values of the new self. We struggle, though, when we get caught in the middle—aspiring to be and valuing that of the new person while simultaneously being unwilling (or unable) to completely relinquish all the values of the old person we seek to transition away from.

Callard writes that to aspire is to judge one’s present-day self by the standards of a future self who doesn’t yet exist. Yet, as we’re maximizing for our future self, what if our future self never comes to be? Both Rothman and Callard argue that this concern is unfounded:

If we couldn’t aspire to changes that we struggle to describe, we’d be trapped within the ideas that we already have. Our inability to explain our reasons is a measure of how far we wish to travel.

So, yes, aspiration is awkward. But with hard work and tough decisions, each day brings us closer to the new self we aspire to be as our new values become further ingrained. A disregard for those who may view our optimizing for our future selves as phony undoubtedly helps as well.

I don’t know when I officially became an expat in terms of values; it just happened. Still, it happened with intention. I had to buy the plane ticket and immerse myself in a foreign culture to catalyze the transition to the new self I aspired to be.

I’ve still got more aspiring to do. It’s awkward, but it’s better than stagnation. And, as Callard writes, “what happens in the meanwhile is also life.”

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