Shakespeare had a way of pinning down the human condition with just a few syllables. When he wrote "some by virtue fall" in Measure for Measure, he wasn't just being poetic. He was diagnosing a specific, painful type of failure that we still see every single day in our careers, our relationships, and our public institutions. It's the idea that you can do everything "right"—you can be honest, diligent, and morally upright—and those very traits are what lead to your undoing.
It's a bitter pill.
We’re taught from childhood that virtue is a shield. If you're good, you'll be rewarded. But the reality is often the opposite. Sometimes, your best qualities are exactly what make you vulnerable to people who don't play by the rules, or they make you too rigid to adapt when the world shifts under your feet.
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The Psychology of the "Virtue Trap"
Why does this happen? Most people assume that when someone fails, it’s because of a "fatal flaw" or a secret vice. That’s the easy narrative. It’s much harder to process the fact that someone like Angelo in Shakespeare's play, or a modern-day CEO known for radical transparency, might fail precisely because they took their virtues to an extreme.
Psychologists often talk about "overused strengths." Think about it. Honesty is a virtue. But radical honesty without empathy is just cruelty. Loyalty is a virtue. But blind loyalty to a failing company or a toxic partner is a recipe for disaster. When we talk about how some by virtue fall, we are talking about the tipping point where a positive trait becomes a liability.
In the professional world, this often looks like the "Expert's Blindness." You’re so good at what you do, and so committed to the high standards of your craft, that you miss the broader political or economic shifts happening around you. You're so focused on the "virtuous" way to complete a task that you become inefficient.
Take the example of a meticulous editor. Their virtue is their eye for detail. They catch every typo. They ensure every comma is in its place. But if that editor holds up a multi-million dollar launch for three days because of a single hyphen in a footnote, their virtue has caused a systemic fall. They were "too good" for the context they were in.
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Real-World Examples: When Being Good Goes Wrong
History is littered with figures who exemplify this. Look at Jimmy Carter’s presidency. Regardless of your politics, historians like Kai Bird have noted that Carter’s rigid adherence to what he felt was "right" often made him an ineffective legislator. He refused to play the "dirty" game of Washington politics—horse-trading, backroom deals, and ego-stroking. Because he was so committed to the virtue of political purity, he struggled to pass key parts of his agenda. His virtue was his downfall in a system built on compromise.
Then there’s the tech world. Remember the early days of "Do No Evil"? Google’s founding mantra was a virtuous stake in the ground. But as the company grew into a global behemoth, that very slogan became a stick to beat them with. Every business decision—necessary for survival in a capitalist market—was viewed through the lens of that original virtue. When you publicly claim the moral high ground, the fall is much farther, and the landing is much harder.
The Problem with High Expectations
People who live by a strict moral code often expect others to do the same. This is a massive tactical error.
When you operate from a place of high integrity, you often have a "blind spot" for deception. You don't see the knife coming because you would never carry one yourself. This isn't just a literary trope; it’s a lived experience for many whistleblowers. They see something wrong, and their virtue—their sense of justice—compels them to speak up. They expect the system to reward their honesty. Instead, the system often protects itself by crushing the individual. They fall by their virtue of truth-telling.
Why We Love to Watch a Virtuous Fall
There is something deeply human—and honestly, a bit dark—about our fascination with this. We find it relatable. Most of us aren't villains. We're people trying to be "good," and we’ve all felt the sting of a good deed being punished.
When a public figure who has built their brand on being "the moral one" makes a mistake, the public reaction is visceral. It's not just "Schadenfreude." It’s a collective sigh of relief that perfection is impossible. But it also serves as a warning: if you're going to stand on a pedestal of virtue, you'd better make sure it's bolted to the floor.
Navigating the Grey Areas
So, should we just stop being virtuous? Of course not. That’s the wrong lesson.
The goal isn't to abandon your morals; it's to develop "situational awareness." Virtue without wisdom is dangerous. In the Stoic tradition, Marcus Aurelius and Seneca often wrote about the need for Prudentia (Prudence). It’s the ability to govern and discipline oneself by the use of reason.
Basically, it means knowing when to apply which virtue.
- Courage is a virtue, but charging into a hopeless battle is just foolishness.
- Generosity is a virtue, but giving away your last cent leaves you unable to help anyone tomorrow.
- Trust is a virtue, but trusting a known liar is a choice to be a victim.
The phrase some by virtue fall serves as a reminder that morality isn't a checklist. It's a balance. It's about knowing that your greatest strength is also the most likely place for a crack to form.
Moving Toward a More Resilient Virtue
If you’ve recently experienced a setback despite having the best intentions, you’re in good company. It’s a rite of passage for anyone trying to lead an impactful life. The key is to analyze the failure without becoming cynical.
Don't tell yourself "I’ll never be that honest again." Instead, ask: "How did my honesty prevent me from seeing the full picture?"
Actionable Steps for the "Virtuous" Professional
If you find yourself constantly being "too good for your own good," try these shifts:
- Audit your strengths. Identify your top three virtues. Now, imagine a scenario where those qualities would be a disadvantage. If you're "loyal," imagine a scenario where that loyalty protects a harasser. If you're "efficient," imagine where that efficiency kills creativity.
- Seek a "Devil's Advocate." If you’re making a decision based on a moral principle, find someone who focuses on pragmatism. Listen to them. You don't have to agree, but you need to see the "non-virtuous" angle of the situation.
- Practice "Bounded Trust." Instead of giving 100% trust to everyone you meet because "that's the right thing to do," offer trust in increments. Let people earn the right to your highest virtues.
- Accept the "Grey." Most life-altering decisions aren't between Good and Evil. They are between two different "Goods" or two "Lesser Evils." Accepting this complexity prevents the rigidity that leads to a fall.
The reality is that some by virtue fall because the world is a chaotic, non-linear place. It doesn't always reward the best person in the room. But by understanding the mechanics of this phenomenon, you can protect yourself from the sharp edges of your own integrity. You can remain a person of character without becoming a martyr to your own high standards.
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Focus on developing a "flexible" integrity. This doesn't mean compromising your soul; it means hardening your skin. Recognize that your virtues are tools, not suicide pacts. When you use them with intention and a healthy dose of skepticism toward the world around you, you’re far less likely to find yourself wondering how being so "right" went so wrong.