What 100 Conversations Are Teaching Me About Human Connection
Written by Sarah Rosse, Guest Writer
What might I discover about myself, other people and the world if I intentionally made space for 100 conversations? We live in a time when we can communicate with almost anyone, almost anywhere – yet many of us still feel lonely, unseen or disconnected.
When I published my memoir, So, Who Are You Anyway?, I thought I was putting my story out into the world. What I hadn't anticipated was how often sharing my story would invite someone else to share theirs.
It happened in conversations with readers, during podcast interviews, at author events and workshops, and sometimes in completely unexpected places. Someone would recognise something in my story and offer a piece of their own in return. The circumstances might have been completely different, but there was often a moment of recognition — a sense that something I had said had given them permission to say, “Me too.”
What began as a way of continuing the conversations sparked by my book is becoming something much bigger: an exploration of what happens when we slow down, become curious about another person and genuinely listen.
I became curious about what was happening in those moments. What makes us feel safe enough to move beyond small talk? What happens when someone feels genuinely listened to? And how much do we miss when we're so busy preparing what we're going to say next that we don't really hear the person in front of us? I am guilty of doing that!
That curiosity became the 100 Conversations initiative — my commitment to intentionally make space for 100 meaningful conversations over 12 months.
I'm still somewhere in the middle of those conversations, so I don't have a neat list of conclusions to offer. Perhaps that's part of the point. I'm listening, noticing and allowing myself to be surprised. But already, a few things about human connection are beginning to stand out and they are making me think differently about the conversations we have every day.
Moving beyond small talk
I've never been particularly good at small talk. I can do it, of course, but I've always been more interested in what sits underneath it. I'd rather know what someone is excited about, what they're wrestling with, or what matters to them than spend too long talking about the weather.
As I get older and have developed a better sense of my own identity, I yearn for meaningful conversation. I feel nostalgic when I think about sitting down, being present and really listening and sharing with another person.
Perhaps that's why I've become so interested in what happens when we move beyond small talk.
One of the things I'm noticing through 100 Conversations is that meaningful conversation doesn't necessarily begin with a profound question. Sometimes it starts with something quite ordinary. The difference seems to be curiosity – asking because you genuinely want to know the answer, rather than because it's simply your turn to speak. The excitement of where an answer may take you is exhilarating!
A person might mention something almost in passing, and there's a choice in that moment. We can move on, return to what we planned to talk about, or become curious. Tell me more about that. What was that like for you? Why do you think that stayed with you?
I've also become increasingly curious about where these conversations happen and continue to explore this in my research. Some of my conversations have taken place behind microphones or as part of organised events, but others have unfolded over coffee, while walking, sitting beside someone or in the conversations that happen around the edges of something else. I've started wondering whether where we gather changes what we're willing to share.
Perhaps sitting across from someone with a coffee between us gives us permission to linger a little longer. Perhaps walking side by side makes it easier to say something that feels harder face to face. Perhaps sometimes it's the unexpected conversation, rather than the carefully planned one, that stays with us.
I'm learning that we don't necessarily need to force a conversation to become meaningful. Sometimes we simply need to notice when a door has opened — and be curious enough to step through it.
Listening can matter more than advice
If curiosity opens the door to a meaningful conversation, I'm beginning to think listening is what keeps it open. Listening sounds simple. We do it every day. But I've started to wonder how often we're really listening and how often we're waiting for the opportunity to respond.
When someone shares something difficult, there can be an almost automatic urge to make it better. We offer advice and look to reassure them. We search for something positive to say, or we reach into our own experiences and respond with a story that shows we understand. Most of the time, those responses come from a good place. We want the other person to know they're not alone.
I've certainly done all of those things. However, through these conversations, I'm becoming more conscious of what happens when I resist that urge and simply stay with what someone has said. It is not always easy to do.
Sometimes that means asking another question or acknowledging what I've heard them say. Sometimes it also means allowing a few seconds of silence to exist without rushing to fill them.
Silence can feel uncomfortable. In conversation, we can interpret it as a gap that needs fixing. Yet I've noticed that sometimes the pause is where someone decides whether to keep going. When we fill that space too quickly, we may unintentionally close the door just as they were considering opening it a little wider.
My own experiences have shaped the way I think about this, too. There have been times in my life when I haven't needed someone to solve what I was experiencing. I haven't needed advice or reassurance that everything would be okay; I have simply needed someone willing to sit alongside the uncertainty and hear what I was actually saying.
Perhaps being heard isn't the same as being helped – but sometimes being heard is exactly the help we need.
I'm learning that good listening isn't necessarily passive. It requires attention, patience and sometimes restraint. It means being curious enough to ask another question, but also knowing when not to ask one. It means resisting the temptation to make someone else's story fit neatly inside our own. Perhaps most importantly, it communicates something very simple: What you're telling me matters.
That thought has become increasingly important as I've continued these conversations, because often the moment of connection hasn't come from having the same experience at all. It has come from recognising something of ourselves in someone else's story. Through several of the conversations I have had, two very small words keep appearing: ‘me too’.
What the conversations are teaching me about myself
When I set myself the challenge of having 100 meaningful conversations, the number gave the project a shape. It gave me something tangible to work towards and, perhaps more importantly, a reason to intentionally seek out conversations I might otherwise never have had.
I also went into this project thinking communication was something I understood. After all, we communicate every day. We talk, ask questions, share stories, send messages, exchange ideas. I've spent much of my personal and professional life communicating with people. How hard could having a conversation really be?
It turns out there is a difference between communicating and connecting. The further I travel into this project, the more I'm realising how much I still have to learn.
I'm noticing when I ask a question because I'm genuinely curious, rather than because I already have an idea of where I want the conversation to go. I'm learning to ask another question instead of immediately sharing my own experience. I'm becoming more comfortable with pauses and silence. I'm noticing the temptation to fill the space, offer advice or find the right thing to say.
Arguably, most importantly, I'm learning to pay more attention to the person sitting opposite me.
Perhaps that's been one of the biggest surprises. Meaningful conversation isn't necessarily about being a good conversationalist. It isn't about having interesting things to say or knowing the right questions to ask. Sometimes it requires doing less – listening longer, allowing silence, following someone else's lead and being willing to let the conversation go somewhere you hadn't anticipated.
I'm also discovering that connection doesn't always look the way I expect it to. Some conversations are immediately deep and personal. Others wander there slowly and some may never move beyond what appears, on the surface, to be an ordinary exchange. Yet even those conversations can leave something behind – a question, a feeling, a different perspective, or a moment that returns to you days later.
I started 100 Conversations wondering what I might learn about other people. I hadn't really considered what the conversations might teach me about myself. I am excited to report that I'm still learning.
I don't yet know what conversation number 100 will teach me, but I'm beginning to suspect that meaningful connection isn't created by having the perfect words. It begins when one person is willing to ask, another feels safe enough to answer, and both are prepared to stay for the conversation.
So perhaps the invitation isn't to go out and have 100 conversations. Perhaps it's simply to start with one. I ask you to consider: ‘What might change if this week, you moved one conversation beyond small talk?’
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Sarah Rosse, Guest Writer
Sarah Rosse is an Australian author, storyteller and journal coach with a deep curiosity about the stories we carry and what happens when we create space to share them. Her memoir, "So, Who Are You Anyway?", explores identity, caring, mental health and finding yourself again through journalling. She is currently undertaking "100 Conversations: One Question. Countless Stories," a year-long project exploring human connection through meaningful conversations with people from all walks of life. Drawing on lived experience and more than 30 years working in the community and disability sector, Sarah is passionate about creating spaces where people feel heard, seen and connected. Her work invites us to slow down, listen more deeply and become curious about the person behind the story.
