List #10: 30 Reflective Questions That Lead to Fascinating Conversations

30 Lists of 30 to Celebrate my 30th Birthday

6 min readAug 10, 2021

The What & Why Behind This Project:

This year I turn 30. And my gosh, I have been thinking about it a lot. I don’t know if it’s the pandemic, or the fact that this milestone is loaded with many societal expectations, but my mind has inundated me with reflections and memories from the past, with questions arising about my life choices and lesson learnt, about my expectations of being a human and about my desires for the future. And this combined with pandemic reflections has meant there has been a lot on my mind….🤔

I started writing a series of questions and lists of all the elements I wanted to capture and articulate. There were a lot, unsurprisingly; 30 years is a long time really! So I gave up on the 1 list idea that I normally write (30 reflections/lessons turning 30) and decided to write 30 lists.

30 Lists of 30, for my 30th Birthday.

Who are these lists for, you might wonder? I started writing reflections many years ago to get to know myself better. And when I shared these raw and real accounts with friends I discovered that what I wrote about my individual journey, touched upon something universally human. Beyond the masks and labels we wear is a messy, beautifully complex life, with highs and lows. And more similar to others than we might think.

So I share them in the hope that you too might feel something — intrigue, joy, resonance or maybe even difference — as you reflect on what it means to be a human. I recognise that my experiences are my own, that some come from a place of privilege and that they may not all be relatable or interesting to you. I know I can’t please everyone, so take what you can…(and let me know what lands!).

So, Back to Lists…

The Why Behind List #10: 30 Reflective Questions that Lead to Fascinating Conversations

Questions are like magic. They are the catalyst to a new world of thought, create novel connections between ideas and opening doors you never even knew existed. When I first started Trigger Conversations in 2016, I started collecting reflective questions that accelerated deep and meaningful conversation, to create the conversations menus. Over time, I became a bit of a question addict, reading through all the question cards, articles and books out there and my team and I started looking for (or crafting) questions that created novel (and not just meaningful) thoughts. The database has grown to 2000… here are a small sample with a variety of themes.

List #10: 30 Reflective Questions that Lead to Fascinating Conversations

What are you craving right now / what have you been craving this week?
If you had to wake up 1 hour early every day, what would you do with that hour?
Why do you have the ambitions you have?
What are, or would be, your faults as a parent? What do you hope parenting changes about you?
What piece of advice would you want everyone in the world to hear?
In what way are you a difficult person to live with?
If you could leave a microwave-sized capsule to be found 1 century from now, what would you put inside?
What is something you enjoy now that you never used to?
In what ways are you naive?
What is one thing that most people misunderstand about you?
If it harder to find a job you can love or a person you can love?
If your son was going to be stupid, ugly or boring, what would bother you the most? Would this be the same for your daughter?
In what way have negative travel experiences positively transformed you?
Do you think there’s any truth in the lines: ‘they fuck you up, your Mum and Dad. They may not mean to, but they do.’?
What personal vulnerabilities and flaws have held you back in your ambitions? In what way have these also been valuable in helping you reach your goals?
Who are you? What properties or attributes are distinctly you? Can you lose this property?
If you googled yourself in 20 years time what would you want it to say?
If you could let someone else live one moment from your life, which moment would you choose and which person would you share this with?
If you could wake up tomorrow having gained any one quality or ability, what would it be?
Based on who you are now, and where you have come from, how do you expect to be different in three years time?
How has the death of someone influenced the way you live your life?
What are you addicted to right now? Can you have too much of a good thing?
In what ways does the pursuit of ‘more’ affect your happiness and fulfilment?
What is the most loving thing anyone has ever done for you or you have done for yourself?
What aspects of your gender most support who you are? Which aspects don’t?
How do you relate to the edge of your comfort zone each day, and how has this changed over time?
What lessons could you learn from your childhood self that could benefit you now?
The curious paradox is that, when I accept myself as I am, then I can change” (Carl Rogers). What are you trying to accept within yourself at the moment?
What is the deepest loss you have felt that was not a death? To what extent do you recognise the impermanent nature of things?
How would you describe the financial philosophy that has led to where you are today? How has your upbringing influenced your feelings about investing?

☕ If you enjoyed reading this list and want to support my writing I would love a coffee!

👉 https://www.buymeacoffee.com/30Listsof30 👈

Your support will help me fund my PhD starting in October 2021 at the School of Design Engineering, Imperial College, London. The subject: Human Connection & Conversation Design. This research lab > interactionfoundry.com

Want To Read More Lists?

I’m publishing one list every day in August (and will add the hyperlinks below).

Follow me on Medium to read them.

Still Curious?!

💬 Watch my TEDx talk: Talking to Strangers: Having a Meaningful Conversation

📖 Read about some of my work recently published in Entrepreneur.com How to Become a Master at Talking to Strangers

✍️ Stay connected through Conversations With Georgie: The Home of My Thoughts as a Life-Long Learner. Curious. Deep. Exploratory. Real and Raw.

📧 Contact Me: Georgie@Triggerconversations.co.uk

List #10: 30 Reflective Questions That Lead to Fascinating Conversations

30 Lists of 30 to Celebrate my 30th Birthday

The What & Why Behind This Project:

So, Back to Lists…

Written by Georgie Nightingall