Play
Categories
Tools
Questions
Blog
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.
When You Say "No"
Not everyone has tried a side hustle, and that’s perfectly okay. Some reasons include:
- They prefer focusing solely on their main job or studies.
- Lack of time or resources to pursue additional projects.
- They haven’t found a passion or hobby they want to monetize yet.
Best Follow-Up Questions
- What was your most memorable experience with your side hustle?
- Did your side gig influence your career or studies?
- What motivated you to start your side hustle?
- Have you ever considered turning your side project into a full-time job?
- Would you recommend trying a side hustle to others? Why or why not?
For more ideas, check out our category suggestions or use the icebreaker generator to keep conversations flowing smoothly.
Feeling the vibe? Start a game now and explore more fun multiplayer options with friends or new acquaintances!