The Hidden Psychology of Career Choices | LSW#61
My notes from a recent conversation
Last week, I spoke with a friend standing at a career crossroads. Currently at a top consulting firm, he was just offered admission into a prestigious grad school program. He has already built what many would consider an enviable career trajectory.
And yet, instead of feeling elated, he found himself grappling with existential questions. Should he take that new role? Or continue in the current one? What about his other “whacky” unconventional ambitions? What if it doesn’t work out?
Many of us grapple with similar themes. Despite having more career freedom than ever before, we've never felt more paralyzed by the fear of choosing wrong.
Our conversation sparked a deeper exploration into how we navigate career decisions. The following notes — part confession, part reflection — examine the hidden, often confusing, terrain of career decisions. Hopefully, they’ll lift the veil and shed some light on your own unique predicament.
The bad news: you can’t “solve” it away. The good news: it’s not a problem to begin with.
Hey! It’s Sheril Mathews from Leading Sapiens. Welcome to my newsletter, where I share strategies for getting savvier at leadership and work. Previous editions of this newsletter and articles from my blog are at the bottom of this post.
The external landscape
Modern careers are defined by constant change and uncertainty. Understanding their fundamental nature helps.
Choices and uncertainty
“Safe” choices may seem less uncertain, but this is mostly an illusion.
Uncertainty is ever present; it’s simply the brand and flavor that changes. In a secure role, you might have financial security but a stagnated career. A more dynamic position might have financial instability but rich in experience.
We mistake temporary stability for predictability. Industries evolve, markets shift, and seemingly secure roles disappear overnight. The real skill isn’t finding a risk-free path but becoming adept at change itself.
Given this inherent uncertainty, how should we approach early career choices?
Exposure vs success
Early in a career, optimize for variety and exposure rather than “success.” Lateral and winding paths can be more fruitful than vertical promotions.
What we actually end up doing is an infinitesimally small subset of all available opportunities out there. The error is to prematurely narrow our options based on assumptions rather than experience.
We think we know what we like and dislike, but the only way to truly find out is by trying different things. This includes dead ends.
This experimental approach hints at a crucial but misunderstood aspect of purpose.
Finding vs manufacturing
“Finding” purpose suggests there’s a perfect role out there waiting to be discovered, like a buried treasure. This can leave us endlessly searching for something that might not exist. Or that once attained we’ll have it all figured out.
I prefer “manufacturing purpose as we go” over “finding or knowing before we go.”
Instead of searching for a pre-existing answer, we actively create purpose through the choices we make and the work we do. It's like a sculptor shaping clay rather than an archaeologist looking for buried artifacts.
This process happens gradually and often the pattern becomes obvious only in hindsight. Once visible, it still remains asymptotic — almost touching perfection but never quite there.
Few people have it all figured out at the outset. And even then, how boring!
The internal landscape
While the external landscape shapes our options, our internal terrain determines how we interpret and act on them. Thereal work of development happens here.
Purpose vs purpose-ing
Many of us distress over not having found our calling just yet. The fact that you’re still looking for it (or the right fit) isn’t a problem in and of itself. It’s natural and a worthy cause.
The error is to treat it as an anomaly and that it “shouldn’t” be.
The pressure to have everything figured out by a certain age is a societal illusion. Everybody’s timelines are unique. Most either don’t have the luxury or simply don’t want to examine the trajectory of their careers.
“Purpose-ing” is perhaps more accurate as it’s an active and iterative process. Some find it through deliberate effort and testing paths, while others stumble upon it by following their curiosities.
The searching and questioning are not a failure but a vital part of the process. There is no need to judge ourselves.
Fuzzy aspirations
Deeper aspirations and ambitions are like whispers in a noisy room. We’re trained to ignore the unique things that fascinate us.
Society’s definition of success is usually loud, in your face, well-defined, and easier to accept. Meanwhile, private ambitions, especially unconventional ones, are squishy and fragile. They are easy to dismiss; even easier to miss entirely.
The mistake is to view the “fuzziness” of your ambitions as a negative signal and dismiss them.
But the initial fuzziness of your ambitions isn't a flaw; it's a natural starting point. Like a photograph coming into focus, aspirations need time and attention to become clear.
Elation vs frustration
The notion of a "perfect" career path is misleading.
Every choice has its own set of disappointments. Whichever path you pick, expect equal amounts of elation and frustration. There can be no other way.
Reality cannot live up to the perfection of our fantasies. And they are just that — a fantasy. The real question is whether the trade-offs of our chosen reality are ones we want to live with.
Even those who seem to have achieved their dreams face daily setbacks and doubt. What sustains them isn’t the absence of frustration, but conviction and meaning.
Hardship is easier to endure when it’s on your own terms.
The tension of choices and decisions
Making choices is perhaps the most challenging aspect where many of us get stuck.
Choice vs burden
Having options - what investors call "optionality" - is both a blessing and a burden. You could pursue that startup idea, take the promotion, switch industries, or go back to school.
Choices are great, but you also bear the burden of making them. Those with no options carry a different weight altogether.
Unused optionality - paths we can take but don’t - loom larger with time than trying something and failing. Ignored long enough it can become a grind and a drag on performance.
Is optionality “pulling you forward” or “weighing you down”?
Perfect dreams are a comforting trap
There's a peculiar kind of safety in maintaining distance from our deepest ambitions. Untouched, they remain pristine and unblemished by reality. This isn't about fear of failure but preserving possibility.
After all, if we chase them and they don't materialize as we imagined, what then? The prospect of facing a failed project is scarier than the familiarity of living with unrealized plans.
We try to preserve dreams because we want to avoid regret.
The inevitability of regret
“Regret minimization” was popularized by Bezos. But note that it’s minimization, not elimination.
A common misconception is that the right choice will eliminate regret. But no decision is ever entirely clean. Regret is inevitable no matter what you choose.
The finite nature of life means we can only live out one act at a time, and only so many. Choosing one path means leaving behind ten others, which is its own form of regret and uncertainty.
The real work is to fully own our choices, rather than being haunted by the ones we didn’t. And especially the ones we can’t.
Understanding regret's inevitability brings us to the core of effective decision-making.
Owning consequences
Indecision and hesitancy come from wanting the upside of a choice without the potential downside. The moment we own the risks of a decision, it is freeing.
There is no way to completely hedge against uncertainty. The illusion of a perfect decision is paralyzing. Accepting that choices come with trade-offs helps to move forward with clarity.
Fleeting vs permanent landscapes
For most of us, every job we’ve had was a dream job at some point. Yet inevitably, that relationship and our experience deteriorate. The job didn’t change per se, rather our expectations did.
Whatever situation you’re stuck in today, there are five others who’d love to switch places with you. This includes your past self.
It’s very likely you are in fact living your dream life that you imagined in the past. It’s just that the goalposts keepshifting and so do our expectations of ourselves.
There’s a deeper (albeit clichéd) dynamic at play here: no matter how enticing, external circumstances won’t effect permanent change in our internal landscape. While external markers of progress are useful, working on our internal landscape is often more fruitful than constantly seeking fulfillment from the outside.
Our conversation revealed a universal truth: career decisions are complex because they operate at multiple levels simultaneously. Careers resemble complex adaptive systems rather than causal, linear paths. They respond to countless variables - some visible, others hidden - and evolve in ways we can't fully predict.
Our role then isn't to fully control the evolution but to develop the sensitivity to read and respond to these shifts. The goal isn't to make the perfect choice, but to make a choice that's perfectly ours.
Sometimes the problem is that family or society ingrains in people what they should and shouldn’t do and what careers are “good” or “bad.”
I once worked with a student who wanted to be an auto mechanic but felt like getting a psychology degree was a good backup. He likely would’ve made far more money as a certified mechanic than with a bachelor’s in psychology.
A stimulating and valuable piece, as always, by Sheril. It serves by guiding one to find meaning and comfort in the process of becoming. Thank you for the post.