Is Honesty an Expensive Hobby?
When does cunning becomes a strategic choice? Or, why are shitty people so wealthy?
Society claims to reward honesty. But when telling the truth can cost you your job, your housing, or your health coverage, morality stops functioning as a compass. It becomes a luxury. An expensive hobby. Feasible only for those who can absorb the fallout.
Everyone else learns—often quickly—that sincerity is a liability. And cunning, far from being a vice, becomes the safest available form of self-preservation.
If morality is to be anything more than a branding exercise, it has to be a structurally supported option—not a gamble that only the lucky can win.
When is Honesty a Liability?
The systems that regulate access to survival—employment, healthcare, housing, public benefits—routinely punish those who tell the truth too plainly.
A tenant who reports a landlord’s negligence risks a non-renewal.
A patient who shares too much during intake may be flagged as “unstable” or “non-compliant.”
An employee who raises ethical concerns becomes a performance risk.
A job applicant who answers literally instead of strategically gets screened out by automated filters.
In each case, truth-telling doesn’t earn trust. It triggers scrutiny. People learn to answer just enough, to frame themselves carefully, to choose omission over vulnerability. Not because they want to deceive, but because they cannot afford to be punished for being legible.
This echoes what I described in No Unprofitable People: how entire populations are rendered invisible not because they are dishonest, but because they cannot perform the version of honesty institutions demand.
Why Cunning Behavior Emerges
No one needs to say it aloud. The lesson is structural. Gatekeeping logic doesn’t forbid honesty, but it makes it risky. Disclosing too much can slow an application. Saying something the wrong way can get you flagged, ghosted, or denied. The stakes are highest for those who already live close to collapse: people without financial buffers, people unfamiliar with institutional language, people who can’t afford to get it wrong even once.
Those most often accused of being evasive are often the ones most deeply aware that full disclosure will be used against them. Cunning, then, isn’t a betrayal of moral values—it’s what moral commitment looks like when survival is uncertain. What institutions read as “manipulative” behavior is frequently just the exhausted fluency of people who’ve been taught that truth is dangerous unless it’s perfectly packaged.
This is friction not just as inconvenience, but as a filtration tactic.
In The Spectacle of Fraud, we explored fraud prevention theater—targeting those who struggle with bureaucracy while the truly strategic slip through untouched.
Nowhere in recent history has this dynamic been more publicly legible than in the election—and reelection—of Donald Trump. The first campaign revealed that sincerity, consistency, and humility were not prerequisites for power. The second confirmed that they may in fact be disqualifying. Performative certainty, shamelessness, and refusal to answer plainly were not liabilities. They were assets. Trump didn’t invent this logic. He exposed it.
The entire structure rewarded him not in spite of his cunning, but because of it. Power, it turns out, requires neither consistency nor integrity. It requires fluency in the system’s demand for performance. Who better than a TV star to do it?
This dynamic plays out every day at lower levels, with less visibility and higher stakes.
The disabled applicant who forgets to mention part-time gig income may be accused of fraud.
The immigrant who answers honestly at a border crossing risks detention.
The neurodivergent worker who discloses their mental health history gets quietly passed over.
Meanwhile, corporate actors exploit legal gray zones and get celebrated for innovation. Developers displace entire communities and speak on economic panels. Lobbyists help rewrite eligibility rules, then praise efficiency.
In this system, performance is rewarded and vulnerability is penalized. And the dividing line between “strategic thinking” and “disqualifying dishonesty” is defined entirely by where one sits in the hierarchy.
As I outlined in Actuarial Medicine & Hidden Exclusion, predictive analytics and risk-based triage don’t make systems more fair—they make them harder for anyone who can’t pre-emptively self-sanitize.
There is nothing noble about a society where honesty is an act of heroism. If truth-telling gets you evicted, dropped, or disqualified, then does moral clarity have any place in daily life, except as spectacle?
Until the consequences of candor are absorbed structurally—until telling the truth is survivable for everyone—it will remain something that only the protected can afford.
Making honesty viable isn’t about urging people to be more forthcoming. It’s about dismantling the conditions that punish them when they are. That means
fewer traps
Shorter forms.
Clearer processes.
Systems that don’t require you to guess which version of yourself will be accepted.
Refusability that isn’t symbolic but real: the right to say no, to exit, and to disclose complexity without it becoming a liability.
Refusability Is the Future of Design explores this principle in depth: until people can leave a system or say no without triggering harm, they are not participants—they are hostages.
Who gets to be honest in your workplace, your clinic, your city? And who gets punished for it?