A Cautionary Tale For Stupid Idiots Who Think They Can Lead With Integrity
It's a terrible career move, but hey—at least you can sleep at night.
So You Want To Lead With Integrity?
Stranger In a Strange Land
So you’ve decided you want to lead with integrity. You’ve decided you want to be one of the good ones. You’ve decided your values and your principles will drive you.
That’s cute.
Welcome to the worst career-building strategy ever.
Integrity is expensive. It will cost you promotions. It will cost you popularity. It will often disturb the peace. It will put you in awkward conversations with folks in the C-suite who’ll wonder why on earth you voiced your opinion in that public Slack thread. Hell, you’ll probably leave bad jobs over it rather than—heaven forbid!—sticking around, nodding your head, and playing the game of climbing the ladder with the rest of those schmucks1.
If you’re lucky? It might buy you self-respect. You might attract a few like-minded folks, like moths to the flame. Maybe you’ll make some friends. But you will end up on a lot of shit-lists too.
Worse, you’ll start to notice how so many of the people around you don’t operate the way you do. You’ll begin to feel like the only one who didn’t get the memo. Like you’re speaking a language no one else around you ever learned.
The Career Tug-of-War
Here’s the brutal truth: you are constantly at war with yourself.
Part of you wants to grow. To learn. To hone your craft. To do meaningful work with people you respect and admire. To lead with integrity. To actually give a shit.
And part of you wants to climb. To get the title. The comp. The skip-level praise. To be seen—promoted, even! In the room. At the table. Winning the game, not just playing it.
The Price of Ambition
You can feel both of these things at once. Most of us do. The friction is constant. Often, it wears you down.
At some point, the rope starts to fray.
For some, it’s when they realize they can’t always be “one of the good ones” and keep their sanity. Climbing the ladder often tithes your values. Winning sometimes means becoming the villain in someone else’s story.
A friend of mine—seasoned leader, multiple time Director and EM—told me about the moment the cost became clear to her. She walked into a room of women leaders—VPs, Directors, accomplished folks—seeking solidarity. What she got instead was: “Play the game. Give the men what they want. Nod your head. Play along.”
That’s when the realization hit her: she’d have to become someone she couldn’t live with to get what she thought she’d always wanted.
That’s the tug-of-war. And nobody wins cleanly.
Aimlessly Aimless
You optimize for one side too long and you start to lose touch with the other. If you play the game too long, you stop recognizing yourself. If you stubbornly stand by your principles in the wrong environment, you get chewed up, labeled as “difficult”, and ultimately left behind.
The only sustainable move is to be honest about what you’re optimizing for right now. This month. This job. This season of your career. It might not always be integrity, and that’s OK too.
But whatever you do, don’t pretend you’re playing a different game than the one you’re in. Don’t be aimlessly aimless. Own your intentions, lest someone else own them for you.
Here’s the thing though: Optimizing for something doesn’t mean you’re doing it well. A lot of us are out here making the best of a broken system—and we still manage to clown ourselves in the process.
When Survival Becomes a Bit
Most of us try to navigate this mess with good intentions. But integrity doesn’t come with a user manual. Corporate theater, layoffs, ladder-climbing egomaniacs? Sometimes we need to improvise, rationalize, and yes, even compromise.
We become one of the idiots.
Some of us bail. Some climb. Some endure. Some seek to appease. Some care too hard for too long and watch their sanity crumble like old biscotti in lukewarm coffee.
Sure, these archetypes are meant to be funny. But they’re also uncomfortably familiar. You’ve worked with them. You’ve been them. You might be one right now. That’s OK though. The point isn’t to mock (though mock, we shall). It’s to name what’s happening so we can do something about it.
So with empathy in our hearts and snark coursing through our veins…
Meet the Idiots
🏃♂️ The Bailer
Their Aura: Confident, well-networked, and done putting up with your shit. Always two weeks away from a better offer.
Core Delusion: “Everywhere else must be better than this.”
Secret Weapon: Leverage. They’ve built enough capital to walk when the vibes are off. Existential clarity to say “nah”.
Achilles Heel: Bail too often and risk becoming “🚩 The Resume Red Flag”, another idiot archetype.
Signature Maneuver: Dropped their two-week notice like a mic. Left with a smug grin and a Substack link in their goodbye Slack message.
They’ve built something in their career they’re actually kinda proud of. They’ve seen the rot before and trust their gut when it shows up again. Why suffer through it when you can leave on your own terms? But this is a luxury, not a lifestyle. Burn too many bridges and you might find the next one is out of service.
“If I wanted to compromise my values, I’d stay—but I’ve got three offers with better comp and fewer headaches, plus my Substack is kinda popping off.”
🧗 The Careerist
Their Aura: Unnervingly agreeable. Always one meeting away from their “big moment”. Gunning for that next round of skip-level praise.
Core Delusion: “I’m definitely getting promoted next cycle.”
Secret Weapon: Fluent in corporate theater. Loud in Slack, silent in impact metrics.
Achilles Heel: Actually kinda bad at the job. Lacks both teeth and taste. Terrified of being outshined.
Signature Maneuver: Subtly corrects your typo in a public Slack thread to look helpful. Quietly CCs your skip as an FYI “just in case”.
They’re not a high performer—they’re a hall monitor with a calendar full of “quick syncs”. Obsessed with optics, allergic to impact. So concerned with being seen as promotable, that there’s no time for actually doing anything worth promoting them for. The ladder is their deity. And they’ll step on your head for a glimpse at their prophet.
“Let’s circle-back on that after we ladder it up to leadership and have more time to double-click!”
😵 The Endurer
Their Aura: Quiet resignation. Tired. Burnout in business casual.
Core Delusion: “I can’t leave. Not yet.”
Secret Weapon: Pain tolerance. Perceived loyalty. Knows how to disappear into their work and keep their eye on the prize.
Achilles Heel: The system isn’t changing, and neither are they.
Signature Maneuver: Adds color to the roadmap while disassociating in a staff meeting.
They’ve got reasons to stay. Really good ones2, if you ask them. Upcoming parental leave. Rumors of an acquisition. Market conditions. A sinking feeling that all jobs suck anyway and their side project is going to take off any day now. So they wait. And wait. And wait.
“I’m just waiting for my shares to vest. And my bonus. And for the market to recover. And for…”
🤝 The Appeaser
Their Aura: Spiritually beige. Big nothingburger energy. “Thanks for the feedback!” on loop.
Core Delusion: “Neutrality is leadership.”
Secret Weapon: Fluent in passive voice. Exceptional at playing both sides. Can sit through an entire meeting without saying a single useful word.
Achilles Heel: No one knows what they stand for. Neither do they.
Signature Maneuver: Says “great point!” to two directly conflicting viewpoints in the same meeting. Again.
Not evil. Just lost in the sauce. They want to make everyone happy, but end up making no one anything. They’d personally shake hands with a sea monster if it meant avoiding a difficult conversation.
“It’s important we create space for both sides, even if one of them denies your humanity.”
🧨 The Professional Caremad
Their Aura: Righteous, intense, and low-key on fire.
Core Delusion: “If I care hard enough, I can fix it.”
Secret Weapon: Charisma, conviction, and a bullshit detector with hair-trigger sensitivity.
Achilles Heel: Teeters between changemaker and burnout case.
Signature Maneuver: Hijacks the status thread with a principled manifesto on systemic rot. Everyone claps. Leadership opens a doc titled “Performance Concerns”.
They’ve been around. They’ve seen some shit. And they’re not gonna let your OKR and values theater rend their soul. But the cost of caring this much? It’s high. They’re just hoping they can stay in the fight long enough to make it worth it.
“You asked for ideas, and I gave you fully-formed systemic autopsies with root causes and corrective action plans: Our interview process is broken, our leveling rubric is a joke, and onboarding is a slow descent into chaos. That’s just foreplay.”
It’s All Rigged, But That’s Not an Excuse
Yes, the systems are broken. Yes, incentives are misaligned. Yes, people get ahead for the wrong reasons and burn out for the right ones.
But if you want to lead with integrity, you still have to play. You just have to play on purpose. That means knowing when you’re making tradeoffs and owning them. It means seeing the game for what it is and not pretending that you’re above it. It means holding your values close, even as you wade through the muck of politics, performance reviews, and power grabs.
You can be any one of these idiots. You probably already have been. You’ll be one of them again soon. That’s fine.
Just don’t lie to yourself about what you’re doing and why you’re doing it.
🏃♂️ Don’t pretend your exit is taking a stand when you just didn’t like the vibes.
🧗 Don’t say you’re optimizing for impact when what you’re really chasing is status.
😵 Don’t call it “strategy” when it’s really self-preservation.
🤝 Don’t confuse making everyone comfortable with making a difference.
🧨 Don’t wrap your ambition in a blanket of virtue and expect it to keep you warm.
The cautionary tale isn’t that the game is rigged. It’s that most people never stop to ask: “Do I want to win this game, or do I want to play a different one?”
I kid. We’re all optimizing for different things at different points in our careers. It’s OK to optimize for climbing the ladder sometimes. It’s OK to optimize for increasing your salary, too.
Sometimes they actually are really good reasons. This is where the capitalism angle hits the hardest. It’s not fair, it just is. Money buys freedom. Sometimes you’re playing survival games rather than strategic ones.