5RW | You Hate Your Job
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Illustration by — GLC
TL;DR:
It’s What’s Missing → 73% of executives feel disengaged—not because work is hard, but because Purpose, Progress, and Agency are absent.
Industrial Hangover → For 100 years, we’ve been drinking the Industrial Kool-Aid, managing knowledge workers like factory workers.
Inevitable Decay → When P/P/A disappear, you survive instead of thriving. Teams turn inward. Culture calcifies—the best leave.
It’s You, not Them → Don’t wait for permission. Define your purpose. Measure your progress. Claim what you can control.
Hate is Great → Hate means you still care. Flip it 180°: Chaos → Clarity. Frustration → Momentum. Powerless → Ownership.
😓 My most successful friend hates his job.
After five years, I finally caught up with Kim — a close friend whose career had skyrocketed.
Big title. Great salary. Dream company.
“So how’s the new role?” – I expected a success story.
Instead, he took a sip of his coffee, looked at me, and said,
“Man, it sucks so bad. I f***king hate it.”
He wasn’t joking. And he wasn’t alone.
Over the past few months, I’ve heard that same line from multiple friends — all leaders, all thriving on paper, all quietly miserable.
Why?
Here are Five Reasons Why… 😫 You Hate Your Job
I — It’s What’s Missing
Kim’s words surprised me.
This was the job he’d worked for years. The one he dreamt about.
I expected him to complain about how complex, demanding, or political it was.
But that wasn’t it.
“It’s not what I do,” he said. “It’s what’s missing.”
What’s missing are the three things every high performer needs to thrive:
Purpose → Knowing why your work matters and what it moves
Progress → Feeling you’re getting better at something meaningful
Agency → Believing you can actually change things for the better
Without these, even apparent success feels hollow.
According to Gallup 2024, 73% of executives feel disengaged at work.
The higher they climb, the emptier it gets.
As Kim put it:
“There’s no amount of perks, pay raises, or promotions that can fix that.”
II — An Industrial Hangover
Photo by Christopher Burns on Unsplash
[Second cup and a croissant]
We started debating about what might be causing this mess.
For 100 years, we’ve been drinking the industrial Kool-Aid.
We still manage knowledge work, like factory work — linear systems, gated information, fixed hours, seeking predictable outputs.
High performers end up under-challenged, over-controlled, and stripped of authority.
They’re told to “own outcomes” but given zero real power to influence them.
As Forbes 2025 called it: “The Under-Challenge Crisis.”
Kim sighed,
“I feel like all I do is put out fires and try not to get screwed over.”
He smiled when he said it, but it wasn’t funny.
“Maybe I should just quit. But then what? I’ll probably end up in another BS job.”
That broke my heart.
III — An Inevitable Decay
I asked Kim, “Do you still like the work itself?”
“Oh, I love the work,” he said. “I just hate how I have to do it. The biggest problem is that I’m not growing in any meaningful way.”
Growth is exponential — but so is decline.
There’s no such thing as neutral. You’re either compounding or decaying.
When purpose, progress, and agency vanish, here’s what happens:
You stop striving and start surviving.
Teams turn inward, culture calcifies, innovation dies.
The best people leave; the rest cope.
Then leadership tightens control, which only accelerates the decay.
IV— It’s You, Not Them
Photo by Tim Mossholder on Unsplash
“Can I be blunt with you?” I asked.
“Always.”
You can change it.
But no one’s coming to do it for you.
We act like we’re entitled to better conditions, but better conditions are built,
not granted.
Creative leaders operate from abundance — not scarcity.
They obsess over what can be created, not what’s missing.
Selling change is like selling online: most clicks don’t convert.
The average conversion rate is 2–4 % (ConvertCart 2025).
That means you need 98 'nos' to get 2 'yeses'.
Kim groaned. “That’s insane! I’m supposed to get constantly shut down?”
I nodded while taking a sip.
“That’s a way of looking at it or… You can learn from every NO. Every rejection is data. Every pushback teaches you how the system works. If you quit now, you learn nothing.”
He gave me “The Look”— Go on!
Progress isn’t permission. It’s persistence.
The reps are the work.
So, if no one’s giving you purpose, progress, or agency, create them yourself:
If no one is telling you why your work matters, define it yourself.
→ Purpose: Identify what metrics your work truly moves.
If no one is showing you growth, measure it yourself.
→ Progress: Define what you are deliberately getting better at this month?
If no one is giving you authority, claim what you CAN change.
→ Agency: What’s one thing within your control you can change this week?
Meaning compounds through micro-ownership — small acts of initiative that rebuild momentum.
“…I am the master of my fate: I am the captain of my soul.” — W. E. Henley [Invictus]
V — Hate is great
“Yes, But…” I stopped him before he could reply.
“Hate is great,” I told him. “It means you still care.”
It means you have standards.
It means you see the gap between what is and what could be.
Compliance is the real enemy.
Flip it 180°:
If you feel Chaos → Seek Clarity: Pick the battles you can win
If you feel Frustration → Create Momentum: Small wins compound into real change
If you feel Powerless → Claim Ownership: be your own engine for growth.
When you reclaim purpose, progress, and agency for yourself and your teams.
You create an environment where you can grow, influence, and matter.
Despite all adversity.
That’s the moment you become Invictus — undefeated.
Kim stared at me intensely. Then smiled.
“Alright, man,” “Coffee’s on me.”
These are Five Reasons Why… You Hate Your Job.
Something I wish I had.
When I stepped into my first leadership role, I also hated my job at times. I felt powerless and frustrated in total chaos.
That’s why I built the Creative Problem-Solving Playbook—the guide I wish someone had handed me.
It’s designed to help new leaders shift from scarcity to abundance and from compliance to creativity—so you can spark curiosity and lead with confidence from day one.
1 Million Creative Leaders by 2030
Our mission is to enable and empower a new generation of leaders. To do so, we have created a community, workshops, a podcast, and…
4 Playbooks to Help You Lead with Clarity & Confidence
Every new role brings the same challenges: time, decisions, focus, and complex problems. These Playbooks are the tools I wish I had as a new leader.
1. Own Your First 100 Days → Start strong, set the tone, and build confidence fast.
2. Take Control of Your Time (TMXI) → Reclaim 10–20% of your week and protect deep creative work.
3. Make Better Decisions (DMXI) → Cut through complexity and move from hesitation to action.
4. Solve Complex Problems (CPSXI) → Reframe challenges and spark ideas that drive innovation.
.Be Irreplaceble!
In a world with all the answers.
We must ask better questions!
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