The Temptation of Doing Wrong / Why Playing by the Rules Fails

The Temptation of Doing Wrong / Why Playing by the Rules Fails

(This article & podcast are a part of our ongoing Getting What You Want series.  Links to the rest of the blogs at the bottom.)

There's a very specific type of rage—neighbor to resentment—that explodes in our face, chest, and gut when you see people rewarded for breaking rules you diligently followed. The winner lifting their trophy high in the air with the smug look of satisfaction that says, "only losers follow rules." And, I hate to tell you this, but on some level, it's true.

Do you think Beyoncé would have made the world stop if she followed the rules with a traditional rollout for her eponymous aka self-titled 5th studio album? Hell naw. And, if I've learned anything in my 37 years on this planet it's two things: 1: Charcoal over propane and propane accessories; 2: If you want a successful long career, follow the rules of those who've done it before you, then add your own amendments.

That’s the real cheat code. Because rules, as we’re taught them, aren’t sacred. They’re flexible, bendable, and often designed to keep you in your place. What separates icons from invisible men is the willingness to notice when the rulebook stops serving you and toss it in the trash.

Resentment comes from playing a rigged game too long. The temptation to “do wrong” is often just the realization that the old way was never meant for you to win.

Why Resentment Shows Up

Resentment isn’t proof you’re weak or bitter. It’s proof you’re awake.

  • You see the system is rigged.

  • You notice effort isn’t equally rewarded.

  • You recognize that morality, in practice, is often a stage play something we’re told to perform, not something the world actually runs on.

That realization hurts. And it tempts you toward rebellion.

As James Baldwin put it: “To be a Negro in this country and to be relatively conscious is to be in a rage almost all the time.” (James Baldwin)

Truthfully, to be conscious (woke/aware/considerate) in this country is to be in a rage almost all the time. Baldwin’s phrasing captures the particularity of Black American life, but the insight stretches wider: awareness itself makes rage nearly inevitable. If you’re paying attention, you can’t help but notice the endless contradictions the sweet lies whispered by culture, the promises broken by power. The more awake you are, the more the dissonance grates; what was once polite discomfort hardens into steady anger. 

The Lie to Me Sweetly Rule

American culture thrives on polite dishonesty. The lie to me sweetly rule is our national bedtime story: smile, be nice, believe in fairness. Don’t ask questions about why your landlord owns five houses or why your boss makes 400x your salary. Don’t point out the fact that the “self-made” millionaire had family money, connections, and a cushion for every risk.

Those who break the lie-to-me-sweetly pact are branded as bitter, cynical, or “not a team player.” But all you did was say what you saw.

Here’s Machiavelli, whispering across centuries: “It is better to be feared than loved, if you cannot be both.” (Niccolò Machiavelli) He knew that power is rarely polite, and the world doesn’t run on sweet lies—it runs on leverage.

The Itch to Go Wrong

Once resentment hits, it’s natural to ask: why not me? Why not cheat? Why not lie? Why not stop caring?

That itch isn’t shameful, it’s the moment you realize that being “good” has been weaponized against you. You’ve been following rules designed to keep you polite, quiet, and broke, while others cash in on shortcuts and shamelessness.

As Friedrich Nietzsche wrote: “Nothing on earth consumes a man more quickly than the passion of resentment.” (Ressentiment)

He saw ressentiment as more than a passing emotion; it was a corrosive force, a spiritual poison that twists frustration into obsession and turns suppressed weakness into imagined morality. In his view, entire value systems can be built on resentment, what he called the morality of the slave, where envy and powerlessness disguise themselves as virtue. When you feel resentment rising, Nietzsche would argue, you’re at a crossroads: either transmute that poison into strength or let it eat you from the inside out.

Two Paths of Rebellion

Resentment gives you two options:

  1. Destructive rebellion – self-sabotage, revenge for its own sake, lashing out at anyone nearby. It feels good for a minute, but it burns your future right alongside your enemies.

  2. Liberating rebellion – breaking the right rules, the fake rules, the rules that were never meant to protect you in the first place. This is quitting the job that drains your soul, calling out bullshit in your community, dating the person you weren’t “supposed” to, or building something that scares polite society.

The difference is whether your rebellion is aimed at freedom or at your own knees.

As Audre Lorde warned: “The master’s tools will never dismantle the master’s house.” (Audre Lorde) Resentment only becomes fuel when you stop using it to play the same rigged game.

Your Takeaway

Resentment is not the problem; it’s the alarm. The problem is the lie you were told—that life is fair, that good things come to those who wait, that “doing right” guarantees reward.

So here’s the point: The temptation of doing wrong comes when you realize playing by the rules fails. Sometimes the “wrong” thing is the only way to make life right.

Stop letting people lie to you sweetly. Start choosing your own rules.

Missed the previous blogs in this Getting What You Want series?

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