Yes — designed to be. Use it for off-sites, onboarding, and team dinners with confidence.

Will my boss find out something?

Only what you tell them. The skip button exists for a reason.

Good for school reunions?

Excellent — half the questions are about school disasters and the answers age beautifully.

Work & School

Have you ever had a side hustle?

👥 Play with Friends

Why people ask this

This question works because the yes-or-no split always surprises the room — someone answers in a way nobody expected, and the conversation starts from there. Work and school questions are popular because everyone has the same bad-meeting and dumb-detention archetypes — recognising them in someone else’s life is the whole point. What makes this format durable is that a no can be just as interesting as a yes. 'No, but I once…' or 'No, and here is why not' opens a conversation the question never directly asked for. The best sessions are ones where the follow-up runs longer than the question itself.

What do players say?

62%

of players said Yes
8 responses

Based on 8 answers so far, 62% of players say yes — making this something the majority of players have actually done.

Discussion starters

→ Who in the group is most likely to have had a side hustle?
→ What's the full story — and who in the group is most surprised by your answer?
→ What is the worst meeting you have ever sat through?
→ What is the dumbest reason you have been in trouble at work or school?
→ What is the strangest job interview you have done?

Asking about a side hustle can reveal a person's entrepreneurial spirit, work ethic, and how they manage their time outside their main job or studies. It’s a fun way to uncover hidden talents or stories of hustle and determination.

What This Question Really Asks

This question delves into your experiences with side gigs and personal projects beyond your main employment or education. It helps uncover:

If you've ever taken on additional work to make extra money
Whether you enjoy or struggle with balancing multiple commitments
What kind of skills or passions you pursue in your free time
If you've ever turned a hobby into a source of income
Your attitudes toward entrepreneurship and side businesses

How to Use This Question

Setting	Tone	Best for	Tip
Friends game night	Lighthearted, casual	Getting to know amusing side hustle stories	Use a playful approach to encourage sharing, e.g., "Have you ever tried turning a hobby into a side job?"
First date	Friendly, warm	Discovering passions and entrepreneurial spirit	Frame as curiosity about passions to keep it engaging
Team meeting	Professional, insightful	Learning about colleagues' side projects or interests	Ask in a way that respects privacy but encourages openness, like "Have you ever explored a side hustle?"
Family dinner	One-on-one, intimate	Sharing personal endeavors	Be supportive and show genuine interest
Party	Fun, spontaneous	Sharing funny or surprising side hustle stories	Keep it light so everyone feels comfortable opening up

When You Say "Yes"

You’ve taken on additional work outside your main job or studies.
You’ve turned a hobby or passion into a source of income.
You’re comfortable juggling multiple commitments or roles simultaneously.
You’ve experienced the challenges of managing time and resources in your side hustle.
You’ve learned new skills or discovered hidden talents through your side projects—consider exploring other kinds of side gigs.