Should I Quit My Job? A 7-Question Test Before You Resign
Almost nobody who asks "should I quit my job?" is short on feelings — they're short on structure. These seven questions separate a bad week from a bad fit, and tell you which one you're actually in.
The 7 questions
1. Is it burnout or is it boredom?
Burnout means you can't do the work. Boredom means you can, easily, and it costs you nothing. Burnout is often fixed by rest or a boundary. Boredom almost never fixes itself — it's a signal you've outgrown the role.
2. Is it the job, the manager, or the company?
A bad manager is a transfer away. A bad role is a re-scope away. A bad company is the only one that genuinely requires leaving. Most people quit the company when the actual problem was one layer smaller.
3. What's your real runway?
Count the months you can cover fixed costs without income. If that number is under six, the decision isn't 'quit or stay' — it's 'how fast can I build runway or land the next offer while employed'.
4. Has this feeling survived 10 days?
Write the date you first seriously considered quitting. If the urge is still there ten days later, it's a signal. If it disappeared by Wednesday, it was a bad week, not a bad job.
5. Did you actually ask for what you wanted?
Most people quit having never made one direct, specific request — a different project, a title, a raise, fewer meetings. If you haven't asked once and been refused, you don't yet have data.
6. Is this a one-way door?
Could you get an equivalent role back within six months? For most jobs, yes — that makes it reversible, so decide fast. If leaving burns a visa, an equity cliff, or a rare industry relationship, slow down hard.
7. The 10-year test
Ten years from now, which version stings more: having left and it not working out, or having stayed another three years in the same seat? People overwhelmingly report the second.
Still 50/50? Pressure-test it.
Career decisions are where blind spots hide best — sunk cost, identity, what your parents will say, the offer you're comparing against a fantasy. Tridecide runs your exact situation through 13 AI critics (devil's advocate, 10-year regret, pre-mortem, second-order effects, survivorship bias, base rates) and returns one calibrated confidence score instead of thirteen opinions.
FAQ
Should I quit without another job lined up?
Only with runway. Rough rule: months of savings > realistic search length + 3. Quitting first also weakens your negotiating position — recruiters treat employed candidates differently.
Will I regret quitting?
People regret inaction on career moves far more than action. The exception is quitting impulsively during a bad week — which the 10-day rule above filters out.
How long should I stay before it "looks bad"?
One short stint explains itself. Two in a row starts to need a story. Neither is a reason to stay somewhere that's damaging you.