8 “Would You Rather” Questions To Get Teens Thinking About Their Future Careers


Choosing a future career is undoubtedly a daunting task for teenagers. It is a decision that requires careful thought and contemplation. One great way to involve teens in discussions about their future careers is by engaging them in thought-provoking “Would You Rather” questions. Here are eight such questions designed to make teens give serious consideration to their future careers.

1. Would you rather have a high salary in a stressful job or a lower salary in a relaxed job?

This question helps teens think about the importance of work-life balance and how much they value financial prosperity versus their mental well-being.

2. Would you rather do a job that helps others but pays less or a job that has no social impact but pays well?

This question encourages them to reflect on whether they desire a purpose-driven career or prioritize financial stability over societal contributions.

3. Would you rather be your own boss or work under someone else’s leadership?

Considering this question allows teenagers to examine their aspirations, either as an entrepreneur building their own empire or as an employee climbing the corporate ladder.

4. Would you rather have an outdoor job with physical demands or an indoor job requiring lots of screen time?

Teens should ponder what type of work environment suits them best, taking into account long-term health effects and daily activities they would enjoy.

5. Would you rather work in your dream location but not in your preferred field, or work in your ideal field but not your dream location?

This question compels individuals to weigh the pros and cons of location preferences against their dream careers.

6. Would you rather constantly travel for work with few personal connections or stay rooted in one community while building long-lasting relationships?

Considering this query helps teenagers think about how much value they place on personal relationships versus exploration and adventure throughout their professional journey.

7. Would you rather have a stable 9-to-5 job with limited growth prospects or a less predictable job with significant growth potential?

This question makes teens evaluate their appetite for risk and whether they prioritize stability or potential growth in their professional life.

8. Would you rather work with people who are extremely smart but aren’t easy to get along with, or with people who are kind but somewhat inexperienced?

This choice tests if they would prefer a more competitive, skill-driven environment or prioritize teamwork, camaraderie, and a supportive atmosphere.


“Would You Rather” questions serve as both engaging conversation starters and insightful tools to aid teenagers in contemplating their future career paths. Encourage open discussions and careful thought about each question to guide them towards making informed decisions regarding their professional aspirations.