Five years. In the digital age, that’s a geological epoch. It’s long enough to see trends born, celebrated as gospel, and then quietly buried in the potter’s field of bad ideas. Five years of building Jobicy—what began as a simple thesis about the future of remote work—has been less a heroic entrepreneurial journey and more a prolonged, often painful, anthropological study. I have been a reluctant ethnographer in the strange, ritual-filled land of modern careers, and I can report that the natives are restless, their maps are outdated, and many of their gods are false.
The prevailing narrative, the one peddled by keynote speakers and LinkedIn gurus, is one of progress, of data-driven enlightenment, of a meritocratic utopia just around the corner. We are told that hiring is a science, that careers are “journeys” to be “curated,” and that company culture is a magical elixir that turns disengaged employees into passionate evangelists. It is a comforting, marketable, and almost entirely fraudulent story. My experience has taught me something far less tidy: that the world of work is governed not by elegant algorithms but by a messy, contradictory, and deeply human set of anxieties, ambitions, and absurdities. This is not a success story. It is a collection of field notes from the front lines.
The Alchemy of Hiring: Turning Paper into People (and Failing Miserably)
The single greatest delusion in the professional world is that we know how to hire. We don’t. The entire apparatus of modern recruitment—from the keyword-scouring Applicant Tracking Systems (ATS) to the brain-teaser interview questions once beloved by Silicon Valley—is a monumental exercise in missing the point. It’s an attempt to apply the sterile logic of the assembly line to the maddeningly unpredictable business of human potential.
Resumes as Creative Fiction
Let us first dispense with the foundational myth: the resume. A resume is not a factual document; it is a piece of marketing collateral, a work of speculative fiction co-authored by the candidate and a host of online “optimization” guides. We, as employers, demand this fiction. We punish honesty and reward strategic embellishment. Then we act surprised when the person who shows up on Monday is a slightly more disappointing version of the demigod described on paper.
The ATS, our technological gatekeeper, only compounds this folly. It’s a machine designed to find the perfect key for a pre-defined lock, scanning for acronyms and buzzwords with the intellectual depth of a vending machine. It filters for conformity, for candidates who have walked the most predictable paths. It mechanically rejects the artist who became a coder, the philosopher who became a project manager, the military veteran who has leadership skills that can’t be distilled into a tidy bullet point. We have built a system that actively selects for the least interesting candidates.
In our quest to de-risk hiring, we have successfully de-humanized it. We’ve become so obsessed with predicting the future that we’ve forgotten how to recognize present potential.
The antidote, one might assume, is the interview process. But what is that, really? It’s a highly artificial social performance where one party pretends to have all the answers and the other pretends to believe them. We ask canned questions—”What’s your greatest weakness?”—and receive canned answers. It is a ritual of mutual deception.
What five years of hiring for my own company has taught me is this: hire for trajectory, not for a static snapshot of past accomplishments. The most valuable question is not “What have you done?” but “What are you capable of figuring out?” Look for the people who are intellectually restless, the ones who light up when they talk about a difficult problem they solved, the ones who have a history of messy, non-linear curiosity. These traits don’t fit neatly into an ATS profile, but they are the very engines of innovation and resilience.
The Great Reassessment, or Why Your Employees Secretly Despise You
The term “The Great Resignation” was a masterpiece of corporate misdirection. It framed a fundamental shift in the employer-employee power dynamic as a mysterious, spontaneous exodus, like a flock of birds suddenly deciding to fly south. It was anything but. It was not a resignation; it was a rebellion. A quiet, decentralized, and long-overdue mutiny against decades of accumulated indignities.
The pandemic did not create dissatisfaction. It merely provided the catalyst—a moment of existential reflection combined with newfound logistical freedom—for people to act on a discontent that was already simmering. For years, companies had been demanding more for less, eroding the boundaries between work and life, and replacing job security with the empty rhetoric of “being a family.” The family, it turned out, was profoundly dysfunctional, and the children were finally old enough to move out.
The Illusion of Corporate Loyalty
Loyalty is a human virtue; in the corporate context, it is a strategic tool. Companies demand it from their employees but rarely offer it in return. The moment market conditions shift or a new strategic imperative is handed down from the board, the loyal employee becomes a line item on a spreadsheet, an unfortunate but necessary casualty of shareholder value.
This isn’t necessarily evil; it is the logical outcome of a system that prioritizes capital over labor. But the cognitive dissonance required to preach loyalty while practicing disposability is staggering. And employees, contrary to the belief of many a CEO, are not stupid. They see this. They understand the game.
We are told to bring our “whole selves” to work. The unspoken corollary is that the company reserves the right to discard that whole self the moment it becomes inconvenient.
The lesson here for anyone building a company is to abandon the sentimental nonsense of loyalty. Aim for something more honest and more durable: mutual respect and a transparently transactional relationship. Be clear about what you offer—interesting problems, fair compensation, respect for people’s time—and what you expect in return. The best people don’t want a corporate family; they want a professional alliance. They want to do good work with other smart people and then go home to their real families. Anything else is an intellectually lazy fantasy.
Culture as a Cudgel: The Hollow Gospel of Ping-Pong Tables and Pizza Parties
If there is a more abused word in the corporate lexicon than “culture,” I have yet to encounter it. It has become a catch-all term for everything and nothing—a vague, aspirational fog that is used to justify hiring decisions, enforce conformity, and provide a convenient excuse when things go wrong. “He just wasn’t a culture fit” is the modern-day equivalent of a medieval witch trial; it’s an unfalsifiable charge against the non-conformist.
We are sold an ersatz version of culture, one that can be purchased and installed like new software. It’s a culture of perks: the free lunch, the beanbag chairs, the obligatory happy hour. These are not culture. These are amenities. They are the shiny objects used to distract from what culture actually is.
The Difference Between Stated Values and Lived Reality
Real culture is not what’s written on the motivational posters in the hallway. It’s not in the all-hands slide deck. Real culture is the set of behaviors that are rewarded and punished within an organization. It is a product of incentives. Who gets promoted? Who gets listened to in meetings? What happens when someone makes a costly mistake? What is tolerated from high-performers who are also, for lack of a better term, jerks? The answers to these questions define your culture. Everything else is just marketing.
As a founder, I fell into this trap myself. I wrote down values—”transparency,” “ownership,” “intellectual honesty”—because that’s what you’re supposed to do. But the real work wasn’t in writing them down; it was in the excruciating, day-to-day effort of living up to them, especially when it was unprofitable or inconvenient to do so. It meant admitting when I was wrong. It meant firing a brilliant but toxic employee. It meant sharing bad news with the same candor as good news. This is the unglamorous, grinding work of building a genuine culture. It is infinitely harder than ordering a ping-pong table.
Navigating the Labyrinth: The Absurdity of the Career Ladder
The concept of the career ladder is a pernicious relic of a bygone industrial era. It suggests a clear, linear, upward path, a predictable sequence of steps leading to a corner office and a comfortable retirement. This model is not just outdated; it’s a form of psychological cruelty in an age defined by volatility and disruption. For most people today, a career is not a ladder; it’s a jungle gym, a labyrinth, or, for the less fortunate, a hamster wheel.
The Fallacy of the Five-Year Plan
We encourage young people to create five-year plans, a practice that assumes a level of predictability that simply does not exist. The skills that are valuable today may be obsolete tomorrow. Industries are transformed overnight. Entire job categories vanish. To cling to a rigid, long-term plan in such an environment is not a sign of discipline; it’s a sign of denial.
The most successful and, more importantly, the most resilient professionals I’ve encountered are not planners; they are opportunists in the best sense of the word. They are masters of the strategic pivot. They cultivate a portfolio of skills, not a single specialty. They build networks based on genuine curiosity, not sycophantic calculation. They view their career not as a single, monolithic entity, but as a series of interesting projects and experiments.
The obsession with job titles and hierarchical progression is a trap. It encourages people to optimize for external validation rather than intrinsic growth. It leads them to take the “safe” promotion at the big, soul-crushing company rather than the lateral move to the small, exciting startup where they might actually learn something. It teaches them to climb, but not necessarily to grow.
So, Where Does That Leave Us?
After five years of observing this strange world, I am left with more questions than answers, a position I find far more intellectually honest than the confident certainties of the thought leaders. The neat, predictable models of hiring and career development have crumbled under the weight of their own inadequacy. We are in a messy, transitional period, and the old maps are useless.
Perhaps the single most important lesson is the necessity of a profound and unrelenting skepticism. Question the platitudes. Interrogate the assumptions. Be wary of anyone offering a simple, seven-step solution to a complex human problem. The systems of work, as they are currently constructed, are not necessarily designed for your benefit. They are designed for efficiency, for predictability, and for the perpetuation of existing power structures.
The only rational response is to cultivate a fierce intellectual and professional sovereignty. To build a career based not on a pre-ordained path but on a set of guiding principles: curiosity, adaptability, and an allergy to corporate dogma. To recognize that the most valuable asset you possess is not your resume, but your ability to think critically and learn continuously.
The world of work is not a meritocracy. It is a chaotic, often irrational, and sometimes deeply unfair system. But within that chaos, there is room for agency. There is space for those who are willing to reject the comforting illusions and forge their own way. The ultimate question, then, is not how to win a game with rigged rules. It is this: how do you build a game worth playing?