I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Saturday Reflections, I take time out to reflect.
In her book Aspiration: The Agency of Becoming, philosopher Agnes Callard defines aspiration as “the rational process by which we work to care about (or love, or value, or desire …) something new.” It is “the distinctive form of agency directed at the acquisition of values.”
This is worthy of an entire book because it’s not clear how we can choose to develop new values since our existing values would seem to be the driver of our choices. We can’t easily decide to rearchitect our values (although taking medication might do it for us).
Callard writes:
Grasping new values is hard for us because, to paraphrase Augustine, our hands are already full…. Gaining a value often means devoting to it some of the time and effort one was previously devoting elsewhere. Sometimes one’s new value requires complete divestment from an old value, for instance when a former pleasure-seeker turns herself toward asceticism. Even in cases where our old value-outlook does not specifically contradict our new one, we often experience the effort of coming to apprehend value as a struggle with ourselves. Leisurely self-containment is ruled out for someone who sees herself as being in a defective valuational condition. Grasping new values is work.
I had forgotten about Callard’s work until I began reviewing my old reinvention blog when I received a hosting renewal notice last week. Now that I’ve refreshed my memory I’m starting to wonder if this entire process of reinvention at midlife has a fundamentally aspirational quality. I want to have different values than those I had before.
Bored by the endless striving of burnout culture, I have considered how I might set down my ambitions. I have questioned my participation in consumer culture and my use of social media because I thought I needed to for whatever my future career might be. I’ve directed myself towards contemplation and boredom. I’ve begun working based on inspiration, rather than succumbing to my inner slave master’s demands that I achieve more and more with the remainder of my life.
How aspiration provides a way out
Callard’s idea of aspiration provides a way to escape the achievement society. I was immersed in it as a child, teen, and young adult, and continued to participate in it until I left my technology career in April of 2024. I sought ever larger salaries, an ever growing investment portfolio, and ever nicer houses.
And yet I was never entirely attached to the achievement society that says that external, conventional success and money is what matters. I stopped out of my career numerous times to do things I was inspired to do. I slacked off at work.
But I never entirely changed myself or my values. The values of the achievement society — burnout culture — ruled me. Even when I did something different they were in my mind whispering I needed to get back to earning societal accolades, money, and a better job title.
Callard contrasts aspiration and ambition:
We can… contrast aspiration with the kind of pursuit that is large in scale but is not directed at producing a change in the self—these are the pursuits I cann “ambitious.” An ambitious agent aims, usually over many years, to achieve something difficult and perhaps important. Nonetheless, the pursuit is not, with respect to value, a learning experience: she is not, as she proceeds, coming to a better and better grasp of why she is doing what she is doing. An ambitious agent’s behavior is directed at a form of success whose value she is fully capable grasping in advance of achieving it. Hence ambition is often directed at those goods—wealth, power, fame— that can be well appreciated even by those who do not have them. [emphasis mine]
Am I aspiring?
I think I sense an aspiration growing in me, the aspiration to become a more effective, autonomous, risk-taking, emotionally peaceful person. And how am I doing that? By finally giving up on buy-and-hold investing, which never worked for me, and exploring more active trading.
You might think, “that sounds like the achievement society!” And yes I would agree with that if my primary goals with this effort aligned with my earlier burnout culture goals — wealth, power, fame.
But those are not my goals. I don’t seek much more wealth than I already have. I seek only to conservatively use it to provide the lifestyle I want. I don’t seek power, except over my own emotional state which has confounded my investing decision-making again and again. I don’t seek fame. I’m not planning to start a content creation business in which I sell trading advice and stock picks.
I want to become a different person — one with different values, preferences, and emotional states. I seek to cultivate the values of frugality, risk-taking with cautionary guardrails, and minimalism (I don’t want to keep buying more stuff!) I seek to prefer the quiet of trading in my own house vs going out to try to promote a career of some sort (as I did when I took professional photography courses or showed my art in juried shows or interviewed for a job at an animal shelter). Most importantly, and an aspect that Callard doesn’t talk about in her book, I want to rearchitect my emotional makeup. This perhaps is only a side effect of Callard-style aspiration, but to me, it’s one of the most important goals I hold right now.
The tortured disorientation of personal transformation
Callard says that aspirational work has a “characteristically tortured and disoriented presentation.”
She writes:
Roughly speaking, the problem is that being practically rational involves acting for the sake of some envisioned end…. Having an end in view is, of course, merely a prerequisite for the characteristic activities that we usually think of as the mark of the practically rational agent: she reflects on whether this end is, in fact, likely to be achieved by her; she compares it with other ends and decides that it is to be pursued over them; she figures out the best means to achieve it.
The aspirant has trouble engaging fully in any of these activities, and that is because she fails the basic prerequisite of acting for the sake of some envisioned end. Her thought about what she is doing cannot be completely clear, both for the negative reason that she has insufficient contact with the value to understand how or why it is to be achieved and because her mind is positively clouded by the presence of distorting values.
In other words, becoming a new person with new values is messy.
You might say, “Anne, you have an end in mind. You want to become an emotionally equanimous trader who generates enough income and financial security that she need not pursue any other financial, business, or employment schemes. So you are not aspiring; you are merely ambitious.”
There is some truth to that and it might point to a weakness in Callard’s formulation. However, I find the character of this wish to turn into an emotionally equanimous trader to be hazy and at the same time compelling in a way that other goals I’ve had were not. Furthermore I seem to have sort of happened upon this path accidentally. I didn’t consciously choose it.
A sense of disorientation
I feel disoriented. What mattered to me before doesn’t matter so much now. What will matter to me in six months, or a year, or two years when I finish this reinvention blogging project — I don’t really know yet.
In his book Transitions: Making Sense of Life’s Changes, William Bridges suggests that disorientation is a key characteristic of the middle stage of big personal transitions:
The “reality” that is left behind in all endings is not just a picture on the wall. It is a sense of which way is up and which way is down; it is a sense of which way is forward and which way is back. It is, in short, a way of orienting oneself and of moving forward into the future….
The old sense of life as “going somewhere” breaks down, and we feel like shipwrecked sailors on some existential atoll.
I do feel that right now. I feel strange that I gave up on showing and selling my art. I feel strange that I left my technology career that I worked so hard to achieve behind. I feel strange that maybe I’m not going to do much different everyday than what I’m already doing. It feels like not enough… and at the same time, everything I want, and the path that is going to bring the next version of me into being.