Challenges

Questions are organized by level from beginner to advanced. A printable PDF of all the questions is available at the bottom of the page.

Beginner (A1-A2)

1. What is something your friends or family think is easy, but you think is hard? What makes it difficult for you?
2. Do you like to try new foods, or do you prefer to eat the same things? What is an example?
3. What is one thing you want to get better at? How do you practice?
4. Have you ever helped someone with a problem? What did you do?
5. Is there a sport or activity you tried but found too difficult? What happened?
6. What is the hardest thing you have ever done? How did it go?
7. Who helps you when something is hard? What do they do?
8. What is something difficult you learned to do? (Cooking, driving, swimming, etc.) How long did it take?
9. What did you find hard when you were a child? Do you still find it hard now?
10. When something is difficult, do you keep trying or stop? What do you usually do?
11. What is the scariest thing you have ever tried? Did you like it?
12. What is something you are working hard on right now? How is it going?

Elementary (A2)

1. What is a challenge you faced? How did you deal with it?
2. What are some fun or interesting challenges a person could try?
3. What kind of challenge would you like to try? Why does it interest you?
4. Do you have any heroes that have done something amazing? What did they do?
5. What are some normal challenges people face?
6. What is a personal challenge you would like to accomplish in the next 5 years? What steps will you take?
7. What is the biggest challenge you’ve faced while learning English?
8. What personal challenge have you put off but want to try soon? What is stopping you?
9. What challenges have you faced in your career or when looking for a job? How did you handle them?
10. Do you find challenges in general to be exciting or do you dread them? Why?
11. Do you like easy things or hard things? What’s good about each?
12. Are you a patient person or do you give up easily? What’s an example?
13. What is a challenge you are facing right now? How are you dealing with it?
14. Do you like doing things that are difficult? Why?
15. Have you ever failed at something and then tried again? What happened?
16. What is the most challenging part of your week? Why is it so hard?
17. Have you ever moved to a new place? What was the hardest part?
18. What challenge do many students face? Why is it difficult for them?
19. Have you ever surprised yourself by doing something you thought was impossible? What was the situation?
20. How often have you quit something because it was too hard? What made you stop?

Intermediate (B1)

1. Some people think that facing challenges improves a person. Do you agree or disagree? Why or why not?
2. What is a tragic event you remember hearing about? What were you doing when you found out?
3. Do you think someone is a better person after they have been through a challenge? Why or why not?
4. Should people make their children have easy lives with few challenges or make sure their children face challenges? Why or why not?
5. How do you stay motivated when facing difficult challenges?
6. How has education helped you overcome some challenges?
7. How do you challenge yourself to try new experiences and activities?
8. Do you find physical challenges like sports easier or harder than mental ones? Why?
9. Do you think overcoming challenges builds empathy for others’ struggles? Why or why not?
10. What advice would you give someone feeling overwhelmed by life’s challenges?
11. What is a creative way you have solved a challenging problem before?
12. What is more satisfying — finishing a physical challenge or solving a difficult mental problem? Why?
13. Do you think competition brings out the best in people when challenged? Why or why not?
14. What do you think of reality shows where people compete in challenges?
15. What is harder for you: speaking to a group of people or writing something important? Why?
16. Do you think facing challenges makes people stronger or just more stressed? How so?
17. Do you think people today face harder challenges than people 50 years ago? What has changed?
18. Some people seek out challenges on purpose, like running marathons or climbing mountains. What drives them to do that?
19. How do you decide when a challenge is worth the effort and when it is better to walk away?
20. How has your approach to handling challenges changed as you’ve gotten older? What experiences shaped that change?

Upper-Intermediate (B2)

1. What are some challenges you think the next generation will face?
2. What challenges does your community face? How could these be addressed?
3. Do you think technology has made life easier by solving challenges or harder by creating new ones?
4. What challenges do immigrants in your country face?
5. What are the three biggest and most common challenges that people all over the world face in their lives?
6. Compare how your generation handles challenges versus how your parents’ generation did. What is different about the approach?
7. What role does failure play in professional success? How much failure is necessary or helpful?
8. What are the implications of living in a society that glorifies overcoming challenges? Are there downsides to this mindset?
9. How do financial challenges affect people differently depending on where they live? What are some examples?
10. How has the way people deal with mental health challenges changed over the past 20 years? What do you think about those changes?
11. Some companies deliberately give employees difficult challenges to help them grow. What are the risks and benefits of this approach?
12. Why do some people seem to handle challenges better than others? What factors make a difference?
13. How does living through a major crisis, like a pandemic or economic collapse, change the way a society thinks about challenges?
14. Many people say ‘what doesn’t kill you makes you stronger.’ Do you think struggle is actually necessary for personal growth, or do people romanticize hardship?
15. Why do wealthy societies still report high levels of stress and dissatisfaction, even though many basic survival challenges have been solved?
16. In many cultures, people are expected to handle challenges quietly without complaining. How does this expectation help and hurt people at the same time?
17. Some of the most successful people credit their failures for their success. Do you think failure is genuinely useful, or is this just something successful people say to make a good story?

Advanced (C1)

1. People often say they want work-life balance, but many still work long hours, check emails on vacation, and sacrifice their health for career success. Why is this gap between what people want and what they actually do so hard to close?
2. Every generation seems to think the next one has it easier. Why does this pattern keep repeating, and what does it reveal about how people remember their own challenges?
3. In many countries, people are expected to figure things out on their own rather than ask for help. How does this attitude shape the kinds of challenges people end up facing, and the ones they avoid entirely?
4. Social media is full of stories about people who beat impossible odds, the single mom who became a CEO, the refugee who became a doctor. How do these success stories change the way society treats people who are still struggling?
5. Some challenges, like poverty or discrimination, are passed down through families for generations. What makes these kinds of challenges so much harder to break free from than individual ones like learning a new skill or getting fit?
6. Why do people seek out challenges even when their basic needs are met? What drives someone to quit a comfortable job to start over, move to a country where they don’t speak the language, or take on a project they know might fail when they could simply stay comfortable?
7. When someone shares their struggle story on social media to inspire others, how might that backfire? Who benefits and who gets hurt?
8. Some people choose to do hard things for fun — climbing mountains, doing extreme diets, living without technology for a month. But for others, daily life is already a struggle. When does choosing difficulty become a luxury rather than a necessity?
9. How has the digitization of difficulty, from gamified apps to algorithm-driven learning, changed what it means to face a challenge? What is lost and gained when challenges are optimized for engagement and measurable progress?
10. When a country faces a major crisis, governments often gain more control over people’s lives. How do societies decide when that control has gone too far?
11. Climate change, aging populations, and political division are all happening at the same time. How do these overlapping challenges make each one harder to solve?

PDF: Download a PDF of all the questions