Dreams?
What are they good for anyway?
Oops. That’s just the cynical middle-aged man in me speaking. Bad Ian.
Anyhoo!
However jaded we might be, we all have unfulfilled ambitions… hopes that we quietly stash away.
While it’s important to be pragmatic, you don’t want to end up regretting the “what ifs” later down the road.
“What if I had the courage to try that career out?”
“What if I had gone ahead and quit my job?”
“What if…”
In this article, I will share a list of dream-related questions for fun or deep conversations.
You can use these questions to help reignite someone’s dreams — or even your own! (I use many of these for my own reflection anyway.)
What makes me uniquely qualified to write about this?
Over the last ten years — across three continents — I’ve started conversations with thousands of strangers. I’ve also interviewed well over 700 people for my projects (namely a street journalism project and a book).
Speaking about my experience talking with strangers at TEDx!
In other words, I’ve asked more questions to spark meaningful conversations than most people.
I can’t guarantee that my conversation starters will work every single time, but I’d like to think that I have a better gut sense of great vs. blah questions.
When and how to use these questions
No hard rules per se, but here are a few suggestions:
- Ask questions about someone’s dreams after you’ve built some rapport with them. As these questions can go fairly deep, an acquaintance might feel uncomfortable about sharing their honest thoughts.
- Ask one question at a time. Gauge their response before going deeper. If they seem disinterested in the topic, switch to something else instead.
- Balance between asking and talking. Make sure that you share your answer to the same question, or comment on their answer, so that the conversation doesn’t become an interrogation 🙂 I’ve been guilty of that.
- Most importantly, modify the questions and brainstorm new ones based on what sounds/feels most natural to you.
Why is that important? Different people have different ways of saying things. The more you can tailor the conversation starter to your tone of voice, personality etc., the easier (read: less awkward) you will find using it. To make this more usable for you, I’ve tried introducing variations of the same question 🙂
Dreams conversation starters for adults
Professional dreams
- What’s your biggest dream as a <professional e.g. doctor, marketer, entrepreneur>? // What’s your craziest/wildest professional dream?
- What is the biggest/craziest dream you achieved in your career?
- What’s stopping you from achieving your career dreams? (follow up to #1, or if they are already talking about their dreams)
- What would you like to be known for?
- If you could choose a hobby as a career/business, what would it be?
- If money wasn’t a concern, what passion of yours would you turn into a career/business? What is it (and why)?
- What did you want to be when growing up?
- When you were a kid, what was the coolest job?
- What’s your dream job/business?
- If you could be in any career, what would it be?
- If you could wind back time, what career would you choose? // If you could wind back time, would you be a <professional e.g. doctor, marketer, entrepreneur> again?
- Fill in the blanks: In 10 years, I will be working as a ____ because I love ____ / I’m passionate about ____
- If you could wave a magic wand, what’s the #1 professional/entrepreneurial dream you want to see fulfilled?
- If you have a magic lamp, what are your three career wishes? Only three 🙂
Note:
- You can easily follow up by asking “why” — it just depends on their level of enthusiasm.
- Questions about choosing another career (ones from #8 to #11) aren’t necessarily the best at industry conferences — they likely attract the more committed professionals in the field, and you don’t want to come across as questioning their career choices. Exception: the person seems to be doubtful about his/her career choices.
- Some people find it too cheesy to talk about dreams. You can always swap the word “dream” for “aspiration” or even “goal” (that might change the nature of the conversation though, since goals are typically much more defined.)
Personal dreams
- What’s your biggest/craziest dream in life?
- What is the biggest/craziest dream you achieved in life?
- What’s stopping you from achieving your dreams in life? (follow up to #1, or if they are already talking about their dreams)
- What would you like to be known for outside of work?
- What legacy do you want to leave behind?
- How do you want your family and friends to remember you?
- If you didn’t care what others thought about you, who would you be? // What would you do?
- If you could wave a magic wand, what’s the #1 personal dream you want to see fulfilled?
- If you have a magic lamp, what are your three personal wishes? Only three 🙂
- What’s your dream lifestyle?
- If you could go on any adventure, what would it be?
- Fill in the blanks: In 10 years, I will be living in ____ because I love ____ / I’m passionate about ____
- What would be your dream city/country to live or travel in?
- What’s your dream <possession e.g. house, car, handbag, etc.>?
- Given the choice of anyone in the world, whom would you want as a dinner guest? (source: Arthur Aron’s 1997 study)
Note:
- You can easily follow up by asking “why” — it just depends on their level of enthusiasm.
- While some of these questions aren’t directly asking about dreams, they will reveal one’s deepest wishes in life. The key is getting them to imagine outside their usual reality 🙂
Dreams conversation starters for kids or students
- What do you want to become when you grow up? // What do you want to become after you graduate?
- Who’s the coolest person you know and why?
- If you could be anybody in the world, who would it be?
- If you could wave a magic wand, what dream would you want to see fulfilled?
- If you have a magic lamp, what are your three wishes? Only three 🙂
- What’s your dream lifestyle?
- What would be your dream city/country to live or travel in?
- What’s your dream <possession e.g. house, car, handbag, etc.>?
- Draw your dreams on a piece of paper!
Note: For the love of God, don’t be that guy/gal who’s trying to get kids to grow up faster 🙂 Have fun with these questions!
Literal dreams
- What’s your happiest/funniest/saddest/scariest/weirdest dream?
- What’s your most meaningful dream?
- Have you ever had the same dream again and again? (Would you want to?)
- Have you ever had a dream that felt so real?
- Have you ever dreamt of a family member or friend? Who was it?
- What’s the #1 dream that you always remember?
- Have you ever been able to move in your dreams?
- What if you could control your dreams? What would you do?
- What if dreams are actually real? (What if reality is just a dream!?)
(Here’s the science on dreams, along with a list of questions and answers.)