Work & School

Have you ever thought about starting your own business?

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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. Questions like this one get played across every kind of group on have.you — couples on a first date, coworkers at team events, friends on long drives. Each setting produces a different answer, which is part of why Have You Ever has stayed in circulation long after most party games get retired.

What do players say?

100%
of players said Yes
10 responses

Based on 10 answers so far, 100% of players say yes — making this one of the most common experiences players own up to.

Discussion starters

  • Who in the group is most likely to have thought about starting your own business?
  • 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?

Thinking about starting your own business can reveal your entrepreneurial spirit and aspirations. It’s a great way to understand someone’s ambitions and drive. Curious to explore more questions like this? Visit our classic questions library.

What This Question Really Asks

This question touches on dreams, motivations, and plans for the future. It can also highlight how someone perceives risk and opportunity. When you ask deep questions like this, you invite more meaningful conversations about goals and passions.

  • Are they entrepreneurial or risk-averse?
  • Do they dream of independence or stability?
  • How creative or prepared are they for new challenges?
  • Are they motivated by financial gain, passion, or both? Funny responses might emerge here.
  • It reveals their long-term vision and desires for their career and life plans.

How to Use This Question

Setting Tone Best for Tip
Friends game night Casual, fun Light-hearted sharing Encourage honesty and humor to keep the vibe friendly. Use group decider to pick the perfect question among many options.
First date Warm, thoughtful Getting to know someone’s ambitions Frame it to inspire optimism and dreams, making the conversation uplifting.
Team meeting Professional, open Understanding colleagues' aspirations Approach it as part of team-building, fostering a culture of innovation and support.
Family dinner Personal, heartfelt Discussing future goals and support Be sensitive to different perspectives and life stages, but keep it engaging and caring.
Party Light, humorous Breaking the ice and sparking stories Use humor to make everyone comfortable, and remember to ask casual follow-up questions.

When You Say "Yes"

  1. You’re generally ambitious and value independence.
  2. You see opportunities where others see obstacles.
  3. You’re motivated by passion and the desire to create something meaningful.
  4. You enjoy taking risks and are comfortable with uncertainty.
  5. You might be interested in exploring more about entrepreneurial journeys or related topics.

When You Say "No"

Refusing this question can indicate a preference for stability or comfort in current routines. It may also suggest a focus on existing commitments or uncertainties about future plans.

  • You prefer security over risk.
  • You might be more focused on personal or family stability.
  • You’re simply not interested in entrepreneurship at the moment.

Best Follow-Up Questions

  • What kind of business would you start if you could?
  • What motivates you most about becoming an entrepreneur?
  • Have you ever taken steps towards your business idea?
  • What challenges do you think you’d face?
  • Would you prefer to start a business alone or with a team?

Explore more question categories to keep the conversation lively and engaging.

Want to make this question part of a fun group activity? Try our play mode or gather your friends for multiplayer sessions and discover new insights together!

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