It’s the last week in December which means I’m navigating a reflection crisis around work. This year I decided to be less sentimental about my reflection and came to the realization that we’ve overloaded the idea of work to the point where meditations on career are meaningless. My goal here is not to negotiate any of the conflicts and tradeoffs involved in career discourse, merely to provide a map showing all the different ideas represented when we talk about careers. I specifically take issue with the idea of “finding meaningful work” which is at best an obfuscation, at worst a sure path to nihilism.
In order to draw a map, I need to address the starting point. Humans need to work to eat. We have historically traded labor in order to meet basic biological needs. Whether you believe this is an ironclad biological law, an artifact inherited from Catholicism (“He who shall not work shall not eat”) or just the 19th century industrial capitalist ethos (“The first man gets the oyster, the second man gets the shell.”) is irrelevant. For most people today, laboring for their basic needs is the starting point of a career.
For some merely succeeding at sustenance is a constant struggle. For others meeting biological needs is enough. Although it’s a rich topic, I won’t litigate the political aspects of having one’s basic needs held hostage by labor. Thankfully, by making it easier to meet our biological needs technology has enabled us to have these discussions.
Yet, despite the increasing ease of having one’s biological needs met through labor the majority of humans continue to work. This is because, humans in their infinite complexity are also host to a set of abstract psychological needs. Work steps in to meet these needs. As a result, one’s career becomes an indelible part of their identity. We now spend vastly more time chasing the fulfillment of psychological needs through work than we do biological needs. Career is the place where adults derive meaning, connect to the broader world and find areas for personal growth.
As it turns out, abstract psychological needs are really difficult to meet. One can pick an apple from a tree and consume it to meet caloric needs. But, to my knowledge there is no “prestige tree” that allows me to meet the psychological need of significance. Yet, our psychological needs persist. In order to cope with persistent unmet psychological needs, we create a series of short-term games. These games serve as proxies for our psychological needs. We make sure the games are winnable so as to ensure progress and not endure defeat.
Take the pedestrian example of a woman with an entry level job who makes slightly more money than required to meet her basic needs. She decides to save the excess money in case of an unforeseen emergency. She is now certain that should her car break down she has the money to pay for repairs. The savings meets her psychological need of certainty. As time goes on, she realizes there are many potential uncertainties that she would like to mitigate. She realizes if she is better at predicting the future and allocating capital towards those predictions she will be able to buy more certainty. Our hypothetical saver is now an “investor” (i.e. someone who has an expectation about the future). So, the desire shifts from wanting certainty to wanting to allocate capital more efficiently. She quickly realizes that predicting the future is hard especially while working a full-time job. So she hires a professional to manage her money. She has now outsourced investing and her job is to manage the investment manager. She tells her father about her hiring the money manager. Her father, proud, suggests she push the money manager for a long-term plan. Now instead of wanting to manage the money manager, she wants to be seen as someone who manages the money manager. So, she pushes him to deliver a plan. The money manager responds with a model consisting of a single number that shows her when she can be done working. Through deductive reasoning she treats the number as an equivalence for certainty as well as satisfying her relationship with her father. She decides to acquire new skills to increase her compensation so she can funnel more money into her investments and hit the number. She gets a promotion. The promotion meets a short-term need for growth and the cycle continues ad infinitum across the spectrum of human psychological needs.
What we see from the above example is that as games become difficult, new winnable games are spun up to avoid frustration. These new games create levels of indirection from the initial need. As the layers of abstraction grow new needs arise. We create more games and thus more indirection. The psychological need we attempted to meet through work is now fueling an ever growing chain of proxy games designed to meet an ever increasing set of needs. But, these needs are all anchored by our career.
As the number of needs being chased and the levels of indirection grow, we try to make sense of the situation. We try to simplify. Our attempts at organizing the complexity leave us with the idea of the career path. The career path is best exemplified by the parable of the three stonecutters popularized by Peter Drucker:
A man came across three stonecutters and asked them what they were doing. The first replied, “I am making a living.” The second kept on hammering while he said, “I am doing the best job of stonecutting in the entire county.” The third looked up with a visionary gleam in his eye and said, “I am building a cathedral.”
Most interpret this parable as a story with a beginning and end. Our existential angst simply means we haven’t ascended the mountain yet. We simply need to follow “The Career Path.” The parable lays it out for us: increase compensation by doing the job, build to mastery through repetition and apply that mastery to something “bigger than yourself.” Research bears it out: graduate from job to career to calling if you have any hope of finding life and work satisfaction.
The parable and associated quest for meaningful work is so insidious because it completely obfuscates what’s happening. There are three interesting obfuscations at play: (1) obfuscation of goals (ends) (2) obfuscation of style (means) (3) obfuscation of attainment.
First, the obfuscation of goals. Where many interpretations of the parable fall short is treating the path as a progression. So career discourse centers around “finding your calling” since that’s the goal. But, the truth is there is no graduation from “making a living” to “building a cathedral.” Each of the stonecutters answers represents a need humans routinely and consistently meet through work. We desire all three of compensation, mastery and contribution.
Second, the obfuscation of style. This is the most difficult to explain as it’s generally very personal. But, I believe obfuscation of style (means) is the most damaging because it replaces elements that are deeply personal with the universal goal of finding meaningful work. One can build a cathedral through massive acquisition of capital, assembling a team of experts or by becoming the CEO of Cathedral Builders, Inc. Humans want those things and it’s OK for them to attain them. Cathedral building can merely be a side effect.
Third, the obfuscation of attainment. Meaningful work is largely an unattainable goal. Chiding humans for wanting simple, attainable things causes them to doubt their intuitions and emotions. It’s cruel. It puts them on a path of indirection and a path of indirection is ultimately a path which leads to nihilism.
In keeping with my initial goal of drawing a map. I will attempt to illuminate what’s happening in the parable of the stonecutters. First, we accept that compensation, mastery and contribution are living human goals. Second, we acknowledge that humans have different means for meeting these needs. For simplicity’s sake I will reduce the style discussion to whether or not one uses intrinsic or extrinsic motivation for validation.
The combination of goal and orientation gives us six base level psychological needs (Certainty, Variety, Growth, Status, Connection, Contribution) that we are meeting through “work” outlined below:
Making a living → Certainty (via Money)
Doing the best job → Variety (via experimentation)
Building a cathedral → Growth
Making a living → Status
Doing the best job → Connection (via Scene)
Building a cathedral → Contribution
Finally, with our abstract set of psychological needs outlined, we reject indirection. We accept that there are winnable games which must be played in order to build skills, maintain momentum and learn in pursuit of deeper psychological needs.
In creating my map and illuminating the quest for meaningful work, I’ve created an infinite loop with one of two not exciting choices: (1) you can see the path you’re on (2) you can’t see the path you’re on. This sort of begs the question: why have career goals? If work is just something we do to meet abstract psychological needs, why optimize for career at all?
As far as I can tell there are three ways to avoid the career path: (1) Never enter the path (r/frugal, Mr. Money Mustache) (2) Only play winnable games, take your ball and go home (Sovereign Individual, Fuck You Money, Artists) (3) Create new living realities (Infinite games, dent in the universe)
Option (1) is to never enter the park. There is no beginning, so there is no end. One can work to meet basic biological needs and refuse to partake in any work-related activities beyond sustenance. They can meet their psychological needs elsewhere. This is the realm of people who live extremely frugal lives and follow people like Mr. Money Mustache.
Option (2) is to only enter the park exactly on your terms. There is some level of extraction involved. One works, but only to avoid playing a larger game. This usually takes the form of fuck you money or art. A note on fuck you money: it’s generally rare. Usually fuck you money is the realm of faux-sovereign individuals LARPing as Tim Ferriss style hackers or Bitcoin millionaires who’ve “won the game.” The other option (2) camp is artists. Artists attempt to build a work that is frozen in time. There is no required interaction with the world, merely individual expression frozen as a snapshot in time.
Option (3) is to change the terrain entirely. Begin or alter indelibly the infinite games of civilization. Work is not really a consideration in the means-ends sense. This is history making freedom in the truest sense. There is no concern for ends. Put yourself out there and move the world forward. I don’t have a clear answer on how to approach this one. It’s the frontier for a reason and “be more like Elon Musk” tends not to be salient advice for anyone.
That leaves six terrains across four areas for me to continue exploring the world of work:
(1) Never have a career, work to meet basic biological needs
The Standard Career Path:
(2) Take on the quest for meaningful work which ends in nihilism
(3) Follow the career path, but play shorter and shorter iterated games while being aware of the bigger game being played
Sovereign Individual Path:
(4) Treat work as a flip, exit as quickly as possible
(5) Freeze time through the creation of art
(6) Figure out how to act with pure freedom in a publicly enduring way.