“Adrian, should I just quit this stupid job?”
I’ve heard that question more times than I can count, from senior PMETs in their 40s and 50s, usually on a Sunday night when the Monday Morning Blues are setting in, sometimes with a resignation letter already sitting in their drafts folder (To send, or NOT to send…that is the question!)
And honestly, some of those jobs really were stupid… demanding bosses who took credit for everything, restructurings that made no sense, diabolical back-stabbing colleagues… the list goes on.
But after two decades as a headhunter and #CareerStrategy coach, I’ve noticed a pattern among the people who regret leaving. Most of them had perfectly valid reasons to go, but a terrible process for deciding when and how.
That’s why I keep going back to the book, Decisive by Chip and Dan Heath. They describe a decision-making process called WRAP, and it’s built to defeat the four villains of #DecisionMaking, and it fits the “should I quit?” dilemma remarkably well.
Before we get to it, one important caveat – When You Should Simply Walk Away
There are three situations where I won’t ask you to run any framework at all… physical danger, psychological harm and ethical compromise.
For everything else, the difficult boss, the stagnant pay, the soul-crushing boredom, run it through WRAP.
1. Widen Your Options: Stop Asking “Quit or Stay?”
The first villain the authors identify is Narrow Framing. The moment you ask “should I quit or not?”, you’ve shrunk a major life decision into a coin toss with only 2 options.
In their research, the Heaths spoke to two people agonising over whether to leave their jobs. Neither had considered the obvious third option, which was to change the job itself… talk to the boss, reshape the duties, ask for a different project.
This is where your 6 Career Moves, from our book “Your 7 Career Currencies”, comes in. Exit is only one of six moves, and you can also Accelerate, Hover for a set period while you sort out your priorities, Downshift to buy back time, or Pause with a sabbatical or no-pay leave.
Even a so-called dead-end job can be an asset if you’re building a side hustle or prioritising family, provided you chose to stay there deliberately and didn’t simply drift.
Try the Heaths’ Vanishing Options Test. If resigning were completely off the table, what would you do to fix the situation? Most people find two or three options they had never considered.
So be honest with yourself… how many options are on your list right now?
2. Reality-test your Assumptions: Beware the “New Girlfriend Syndrome”
The second villain is confirmation bias. Once you’ve decided your job is stupid, every bad meeting becomes evidence, and every headhunter’s call sounds like Odysseus‘ Siren Call.
On our podcast, Yen and I call this the “New Girlfriend Syndrome”. The new role looks luminous, with the bigger title, the regional scope and the charismatic hiring manager, while your current job’s flaws look glaring. Six months in, you discover the unrealistic targets, the constant travel and your new boss’s real operating style. The grass is greener on the other side… because of a layer of fertiliser six feet deep.
Here are three ways we test our clients:
- Ask the disconfirming question. If the problem you’re unhappy with were corrected tomorrow, would you still want to leave? If the answer is no, that symptom is the presenting complaint but the real issue lies somewhere else.
- Get neutral advice. Your best friend will tell you to go for it, your boss wants to keep you, and the headhunter wants the placement. Look for someone experienced in your field who has no stake in what you decide.
- Test before you jump. The Authors call this “ooching”, running a small experiment before you commit. On the podcast we told the story of a professional who quit to become a content creator, spent over three thousand dollars on equipment, and went live to an audience of exactly one. Validate the fantasy job as a side project before you bet your income on it.
3. Attain Distance: Are you running TO something, or running FROM something?
The third villain is short-term emotion… and we’re all guilty of it at some point in our career.
Every career move is driven by Push factors (like the toxic boss, the pay or the politics), and Pull factors (like the scope, the team and the growth). When push is high and pull is weak, you’re about to jump from the frying pan into the fire.
In Your 7 Career Currencies, Yen and I wrote about Joan, a private banker who quit in frustration to open a hipster café. She discovered the exact same problems she had run away from, in a new form and with worse pay 🙁
Two tools from Decisive help here. The first is 10/10/10: how will you feel about this decision in 10 minutes, 10 months and 10 years? The second is asking what you’d tell your best friend if they were in your shoes, because most of us give far better advice to others than we give ourselves.
Your frustration is useful data… it just makes a terrible plan.
4. Prepare to be Wrong: Don’t get too Cocky
The fourth villain is overconfidence. Everyone who resigns believes the next job will be better, yet the Heaths cite a study in which doctors who were “completely certain” of a diagnosis turned out to be wrong 40% of the time. If doctors can be that wrong about a diagnosis, you can be wrong about a job offer.
A climber on a vertical cliff never lets go with both hands at once, and always keeps one hand or foot anchored before reaching for the next hold. In career terms, that anchor is a Career Pivot, a strength you already excel at that transfers quickly into your next job, like your functional expertise or your industry knowledge.
Debbie, a lawyer who switched to teaching with no anchor at all, found herself in a role that clashed with her temperament, and she hated it.
Then set tripwires, the Heaths’ term for pre-agreed triggers that force you to act. For example: “If nothing has changed three months after I’ve spoken to my boss, I start my search.” Take things one step at a time, ok?
So, Should You Quit Your Stupid Job?
Maybe… the job (and your boss!) might well be stupid, but the way you quitt doesn’t have to be!!
Widen your options, test your assumptions, get some distance and plan for being wrong. If you still want out after all four, go, and go with a strategy, because a planned exit gives you leverage in the market while an emotional one often buys you a more expensive version of the same problem.
If you’ve quit a job before, I’d love to know which of these four villains got to you… and what you would do differently today. And if you’re standing at this crossroads right now, this is exactly the kind of decision I help #SeniorPMETs work through.
#CareerStrategy #CareerAgility #SeniorPMETs #DecisionMaking #CareerTransition



