Events | Think Again

In the Open

Benchside conversations

In a time when our ability to connect emotionally, engage in civil disagreement, and empathise with others feels increasingly strained, reading and reflecting alone won’t fix it. That’s why I’m adding another dimension to Think & Think Again: a simple yet powerful initiative to bring people together to engage in meaningful dialogue, In The Open!

Here’s how it works:

Once a month: members of the Think & Think Again community meet up in person, in a park (starting with Centennial Park, Sydney, Australia).

The focus: In duos, discuss a theme or topic that purposefully invites nuance and further reflections. Members are invited to choose how to engage in these conversations:

Free Flow: An organic discussion around the topic.
Semi-Guided: One person considers the pros, the other the cons.
Guided: A series of pre-set questions to spark deeper reflection.

A Simple Reflection: a couple of days after the conversation, participants will receive reflective question in their inbox: How did it feel? What did you learn? What’s one takeaway? These reflections can be shared as testimonials to inspire others and potentially inform future themes and events.

Take it to your city

Think & Think Again isn’t just rooted in Sydney; we’re a community spread across the world. As our community grows, I’d love to see In the Open conversations spring up wherever members are. To make it easy, I’ve created a simple playbook for anyone who feels called to facilitate, and I’ll provide all the themes, materials, and guidance you’ll need. If you’d like to bring people together in your own city, reach out, I’d be glad to share it and support you along the way.

Previous events & themes

Is using AI in our work cheating or just the new common sense?

Tools like ChatGPT make tasks like writing, researching, and ideating feel almost too easy. But that ease can leave us uneasy. If we don’t use it, are we falling behind? If we do, are we cutting corners?

Directions to explore:

Why does using AI sometimes feel like cheating, even if the outcome is better?
If AI can replicate our skills, what becomes the source of our value?
What kind of thinking is worth doing ourselves, even if AI could do it faster?

Dialogue Playback

When is it okay to say you’re good at something?

We’re often taught to be humble; to let our work speak for itself, to downplay our strengths. But confidence and humility can coexist. So when does modesty become self-doubt, or confidence cross into arrogance?

Directions to explore:

Why does owning our strengths feel uncomfortable?
How do we teach kids confidence without losing humility?
In a new job or interview, how honest should we be about what we’re good or bad at?

What actually motivates us to act? Hope or outrage?

Some people say we need to see what is wrong to want to fix it. Others say change is more likely when we believe something better is possible.

Directions to explore:

Do stories of injustice stir action or just paralysis and guilt?
Can focusing on the positive make us complacent?
What kind of messaging actually changes minds or behaviours?

Our Is it OK series

This time, instead of diving into a single theme, we explored a series of questions. Some were light, some a little thorny, but all of them were designed to surface the kinds of dilemmas we often carry quietly, the kind where your gut might have an immediate answer… but sitting with it for a moment revealed a lot more nuance.

Here are the four that were picked, yesterday:

– Is it OK to not want to have children?
– Is it OK to change your mind about something you were once very vocal about?
– Is it OK to want external validation?

– Is it OK to ghost someone after one date?

Many more to come for the next sessions of "is it ok to"

What are we really signalling when we dress a certain way?

Dress codes are everywhere, at work, at school, at events. But what do our clothing choices actually communicate, and who decides what is “appropriate”?

Directions to explore:

Are dress codes about respect, identity, or control?
When does self-expression clash with social expectations?
Do appearances still hold power in a world that claims to value authenticity?

Bella

I just loved my second 'In The Open' event on Saturday. The theme was perfect - so many directions it could be taken in. It was a pleasure meeting the other members, and I can see that these events will be not only an opportunity for intellectual engagement but also for new friendships.

Oli

I was initially a little bit apprehensive about joining the in person group meeting and discussion, questioning what value I had to contribute. But honestly, it was the warmest bunch of people I could’ve had the pleasure of meeting, and I felt immediately at ease sharing my thoughts/perspective with the group. I liken Think And Think Again to a ‘book club for ideas’… It’s exercise for your mind, delivered in a social, outdoors setting. I’ll definitely be making this part of my monthly ritual moving forward.

Milly

I LOVED IT! I felt so invigorated after it, it was so so marvellous. I cannot wait for the next one. I was nervous before going because everyone seems so impressive but it was just the best conversation. I got the sense that it was a space where all opinions were welcomed, that there was no judgement, just a commitment to listen.