Work & Career Dilemmas
Careers, bosses, and the grind, served up as impossible choices.
Sneak peek
- Would you rather sit at a desk all day every day — or stand on your feet all day every day? Everyday Medium
- Would you rather love your job but never get promoted — or hate your job but climb the ladder fast? Career Path Medium
- Would you rather have a mentor who actively undermines you — or have no mentor at all and figure it out alone? Career Path Medium
- Would you rather give a brutally honest exit interview — or give a polite, sugarcoated exit interview? Career Path Medium
Answers stay hidden — no spoilers for your crew.
Difficulty mix
How to play
- The host reads a dilemma out loud: "Would you rather A… or B?"
- Tap A or B on your phone. Nobody sees your pick until the reveal — you can change it until then.
- The reveal shows the split (e.g. "68% would rather A") and who picked each side. Time to defend yourself.
- Majority scoring: land on the bigger side for +100 (a perfect tie gives everyone +50). Minority scoring flips it — the brave few score.
- Watch for Contrarian rounds: the scoring flips for that one dilemma.
About Work & Career Dilemmas
Work & Career Dilemmas is a Would You Rather pack with 57 prompts covering work, rated PG (family friendly). Careers, bosses, and the grind, served up as impossible choices.
The difficulty mix is 100% medium, so it suits a regular bar trivia crowd.
It is one of the newer packs in the library — be the first table to take it on.
More Would You Rather packs you might like
General Knowledge →Play Work & Career Dilemmas in three steps
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1Open a game night
Pick a pack on your phone — a QR code appears.
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2Everyone scans
Friends scan with their camera and pick a name. No app, no sign-up.
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3Play & keep score
Questions pop up on every phone; scores update live.
FAQ
How do I play Work & Career Dilemmas at a bar or party?
Tap “Play this pack”, then put the QR code where everyone can see it (on your phone, a printout or a TV). Players scan it with their phone camera and answer on their own phones — no app, no sign-up. TipsyRounds runs the timer, reveals the answers and keeps score.
How many prompts are in Work & Career Dilemmas?
57 prompts.
Is it free?
Yes. Hosting, every game and every pack are free, and players never pay or sign up.