Johannesburg

A community of conversation: Q&A with A StrangerKind founder Madi van Schalkwyk

27 May 2025
Catch A StrangerKind, a volunteer-run initiative centred around the power of curiosity, at The Linden Market’s winter edition on Sat, May 31 and Sun, Jun 1, 2025. Buy tickets here.

“When last did you ask a truly open-ended question?” A StrangerKind (ASK) founder Madi van Schalkwyk put this to us when we caught up with her via a series of rapid-fire voice notes. It makes one pause. “We all assume we’re curious,” she continues, "but an honest assessment might reveal we’re not quite as open-minded or as all-embracing as we like to think."

The power of curiosity

A StrangerKind's founder Madi van Schalkwyk. Photo: Supplied. 

In our short but heart-warming conversation about the wonderful ‘community of conversation’ that she has built, curiosity is a word that came up repeatedly. Perhaps she’s making up for lost time. “I wasn’t brought up to be naturally curious,” van Schalkwyk reflects. “I grew up in a conservative Afrikaans family in the Free State. I didn’t have a lot of exposure to people who were different from me in any way – religiously, ethnically, culturally, or even when it came to their life experiences.”

It was during her studies at Open Window (a higher education institution focused on creative fields) in Centurion that she became exposed to a whole world of differences. “I think it caught me off guard how much learning things about other people would change me.” The power of curiosity and open conversation sits at the heart of A StrangerKind, an initiative and event series that has a presence in Johannesburg, Cape Town, and Bloemfontein, and that is set to launch in Gqeberha next.

For folks who are allergic to small talk but love diving deep with other people, this is just what the doctor ordered. In a world of digital oversharing, many of us still feel an acute lack of meaningful connection in our daily lives. A StrangerKind is a balm.

Creating a family of changemakers

A group of A StrangerKind volunteers at The Linden Market. Photo: Supplied. 

At a StrangerKind events, ASK is a volunteer-run network (about 150 strong at the time of writing) where attendees are able to choose a topic that resonates with them and sit down with a stranger for a 40-minute conversation around it. It’s radical in its simplicity and goes to the very root of what it means to be a human. “Curiosity is such a potent tool for change,” says van Schalkwyk, who describes A StrangerKind’s volunteer network as a “family of small changemakers”.

The topics are about as far-reaching as you can imagine. Volunteers include a single mother, a teacher, a whisky connoisseur, a motorcycle fanatic, a conspiracy theorist, someone with ADHD, someone who grew up with a deaf parent, and an accountant. The topics plumb the depths of the human experience, from ex-gangsters and recovering addicts to people of every religious persuasion, “and pretty much everything in-between”, van Schalkwyk says.

“If you take a screenshot of Johannesburg, it is such a beautiful representation of what diversity is and can be. It’s a beacon of potential for so many people – people go there to make a difference, to chase their dreams. Joburg has this underlying current, this urgency to find our purpose and pursue the best version of ourselves.”

Launching A StrangerKind

Tracing the origins of A StrangerKind, van Schalkwyk cites two major catalysts: “Having an existential crisis in my mid-30s, and also being really good at ruining family dinners,” she jokes. While her professional background is in visual communications, having worked as a graphic designer for close to two decades, a sabbatical forced the realisation that she wanted to do something significant with her life, pursuing things that energise and excite her.

“When I looked back at what that was, it was often interesting conversations – possibly a little bit of the taboo topics that we never get to talk about, understanding the human need for connection and community and why it is sometimes so difficult, and spaces of curiosity,” van Schalkwyk tells us.

The lesson that family dinners weren’t the ideal forum for conversations of this nature was hard-won for van Schalkwyk, who was prompted by a friend to find a different outlet. This eventually led to her founding A StrangerKind – a name she adopted for her initiative in 2021, although it has been operating since 2017.

We all need spaces where we’re allowed to be curious about things we don’t have a lived experience of, and the grace to make mistakes on our quest toward deeper understanding.

Transformative stories

At A StrangerKind event in Observatory, Cape Town. Photo: A StrangerKind via Instagram

“I don’t think I’ll ever get used to how incredibly well received the format is,” says van Schalkwyk. “There’s an urgency around people wanting to talk about something difficult, but they don’t know where to do it.” Stories have an impact. One-on-one conversations, and hearing and seeing one another, can be transformative.

A conversation that crops up continually at A StrangerKind events is around grief. “I find it fascinating that grief is such a human experience that we all go through at some point, whether it’s the loss of a parent or even a relationship or a season in our lives, and yet we don’t know how to talk about it,” van Schalkwyk shares. “To have someone on the other side who can hold that space, ask questions, and be interested in someone’s experience of loss is incredibly beautiful to witness.”

It may seem counterintuitive that strangers are able to elicit such a deep response in one another, but this is part of the magic of ASK. Because you’re sitting across from someone you may never see again, you’re able to take more risks. These can be very rewarding. Of course, all of this applies closer to home, too. “We assume we know the people around us, and so we stop being curious about them. I think there’s so much opportunity to also deepen our relationships back at home,” van Schalkwyk encourages.

Community roots

Van Schalkwyk lives in Cape Town, but spent 10 years of her life in Joburg. “If you take a screenshot of Johannesburg, it is such a beautiful representation of what diversity is and can be. It’s a beacon of potential for so many people – people go there to make a difference, to chase their dreams. Joburg has this underlying current, this urgency to find our purpose and pursue the best version of ourselves.” And yet, van Schalkwyk admits that in a city, life can feel segregated. Longing to really deepen the sense of community and belonging is something she found herself looking for in Joburg, and this is part of what led her to the work she’s doing now.  

Van Schalkwyk’s work with ASK has completely changed the trajectory of her life, who she is as a person, and how she sees the world. “I’ve been doing this for seven years, and I’ve been fortunate enough to hear pretty much every volunteer’s story,” she says. “I’m always proven in some way [to] still have preconceived ideas about others. It has prompted me to challenge myself in empathy. It reminds me how complex every person’s story is [and] allows grace for other people, but also then for myself.”

Surprising questions

The one question she loves to ask the most? “What’s the one thing you wish people would ask you more about?” is a favourite of van Schalkwyk’s because of its revelatory potential, always yielding surprising results. “I think this is quite a potent and open-ended way to not only send someone on a journey within themselves, but also to give them an opportunity to share something that could drive a conversation deeper.”

Link up with A StrangerKind at The Linden Market

Have surprising conversations with strangers at The Linden Market. Photo: A StrangerKind via Instagram.

Several of A StrangerKind's volunteers will be at The Linden Market's winter edition on Sat, May 31 and Sun, Jun 1 from 11:00 – 14:00. It will be looser in structure and more social than a typical ASK event, with volunteers equipped with conversation starter cards going around the market to prompt exchanges amongst market-goers. That said, you’re welcome to ask a volunteer what their story is and sit down with them for a longer, one-on-one conversation.

Explore the winter edition of The Linden Market here and buy your tickets here
 

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