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Irresistible Festivals: Interview With Sydney Writers Festival CEO Brooke Webb

Irresistible sat down with one of Australia's most important literary bosses to find out what she's most looking forward to in the 2025 Sydney Writers Festival, and in the literary scene beyond that.

April 7, 2025
Brooke Webb Photographer: Belinda Rolland
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Brooke Webb is the Chief Executive Officer at the Sydney Writers’ Festival. For the past 27 years, she has held senior and executive-level roles, leading the creation of commercial theatrical productions, concerts, and festivals, working both within Australia and internationally.

She has worked with global entertainment companies, multinational corporations, state governments, not-for-profit organisations, local councils, and private SME agencies. Her diverse experience includes serving as the Artistic Director at Cirque Du Soleil (Canada, North America, South America, and the Middle East), Executive Director – Concerts and Touring at Universal Music in New York City (USA), Resident Artistic Director on The Producers collaborating with Mel Brooks, Susan Stroman and the US Creative Team (Australian Tour 2003–2005).

She is now well and truly settled at the Sydney Writers’ Festival, so Irresistible caught up with her to find out what’s on her not-to-miss list, and why feels so inspired in the heart of the literary world. 

Sydney Writers Festival

Can you tell us what you are really looking forward to in Sydney Writers’ Festival 2025
Brooke Webb:
I am really looking forward to The Art and Science of AI with Jeanette Winterson and Toby Walsh. AI is it’s own beast, but Jeanette Winterson is probably one of my favourite writers. She’s so eloquent and poetic. I love the idea of a scientist and an artist together and I couldn’t think of a better pairing . Its really hard to find people who can meet in the middle like that.

I’m really interested in cancel culture and so I’m looking forward to catching A.C. Grayling’s talk about that.

Maggie O’ Farrell’s Hamnet has got to be one of my top 10 books. Nobody knows much about O’Farrell. She’s so mysterious, so that’s so exciting.

Colm Toibin (photo credit Reynaldo Rivera)
Charlotte Wood (photo credit Carly Earl)

We have a session called Pen Pals with Michelle Brasier, Virginia Gay, and Chloe Elisabeth Wilson. It is going to be so much fun.

I think Marian Keyes is funnier than a stand-up comedian. I’ve read all her books. That is going to be a delight.

Colm Tóibín is one of the most brilliant orators you’ll ever see. I love how the Irish value the artform of writing, and in the Making a Writer session he and Charlotte Wood will be discussing what countries and states need to do to support their writers. 

I am so excited for the Dame Harriet Walter session. Her new book about what Shakespeare’s women might have said is going to be fascinating. 

I’m really curious to hear Matthew Walker’s session on Why We Sleep session with Matthew Walker. It’s so relevant to all of us.  

Sydney Writers Festival
Chloe Elisabeth Wilson Photo Credit Giulia Giannini Mcgauran
Matthew Walker

Do you remember the first time you went to Sydney Writers’ Festival?
I didn’t grow up in Sydney, and my early work history was over in Europe and the USA, so I was late to get here. My first experience was only in 2016, when I saw Gloria Steinem. Where do you go from there? I was amazed at the feeling of community that came from the festival. I still am. That’s what really attracted me to work at the festival. 

Where did you grow up then?
My dad was in the Navy, so it was a lot of places. My formative years were in Darwin, and I grew up all over Australia. Adelaide, Melbourne, Canberra. There’s something that happens to you when you’re in high school in Canberra as I was, by 18 you’re out of there. Or you stay your whole life. I left and I went to Europe for 5 years. I studied puppetry in Prague. I took every weirdo job that there was, and eventually came back to Canberra. I didn’t feel like I really fitted in there anymore so I moved to Melbourne. I’ve moved all over Australia again. Really I’ve never stopped.

Jeanette Winterson (photo credit Sam Churchill)
Toby Walsh
So does Sydney feel like home now?
I think there’s something that happens as you get older. You don’t have the same energy to move around and pack up your house. I have too much stuff now! I moved to New York when I was younger, and I was working as Artistic Director of Cirque Du Soleil. It meant moving to Montreal. I ended up with two bases. As I get older I want to own furniture and know where everything is. I moved back to Sydney in 2013. I did live in Hobart for a couple of years since then. But Sydney is probably now where I’ve lived the longest, and my family is here, so Sydney does feel like home now.
Harriet Walter (photo credit Sim Canetty-Clarke)
Marian Keyes (photo credit Dean Chalkley)
How would you describe the Sydney Writers Festival community?
If we think about the whole ecosystem, we’re thinking of writer to writer, writer to reader, and reader to reader. It is a really broad community around the festival. I think particularly over the last three years, we have deliberately and strategically grown the breadth of programming. We’re not just talking to one community of readers, its several. There are so many varied demographics in the people who come. And we are growing. Last year there were many second and third generation Australians coming for the first time, and people for whom English isn’t their first language. This year Sayaka Murata and Asako Yuzuki will be speaking in Japanese and  Mariana Enriquez will be speaking on Spanish. Her event was one of the first event to sell out. We are doing more and more to remove any kind of barriers to attending the festival. It’s such a joy to do that. Diversity is so important to us. Literature can sound exclusive. But there are stories everywhere. 
Maggie O'Farrell Photo Credit Dasha Tenditna
A.C. Grayling
Do you have a job or mentor that pushed you in a certain direction, or gave you the confidence to take her big leadership roles?
I wish I could narrow it down to one person. If I’m honest, there have been more people that I haven’t enjoyed working with, when I’ve thought ‘I’m not going to get even, I’m going to jump ahead of you.’ I have also had the great fortune to work on incredible projects throughout my career, and with people that have defied any sense of gravity and said ‘this is just what I want to do.’ I find that really interesting. I’ve always wanted to make really good stuff, that breaks the mould, that’s exciting and fun and has heart and beauty. My background is definitely not exclusively literature. I’ve worked in PR marketing and comms, before I went into the dark arts of theatre. I studied at NIDA. I was working with Mel Brooks on The Producers and Julie Taymor on The Lion King. I worked with David Gilmour, casting Grease in the West End. I worked with some of the most important musicians of our generation at Universal Music, from Bon Iver to Sonic Youth. I’ve always worked with incredible artists and now I find myself in the literary world. It’s a very different art form. Full of very passionate people. I’ve always been a big reader but my passion for supporting authors is next level now. Trying to create pathways for paid employment for authors is, I feel right now, my life’s purpose.
Michelle Braiser
Virginia Gay
What inspires you so much about writers?
Writers are primary producers of the arts, there’s no question. But it is also ridiculously hard for writers to be full-time writers. We do have a tendency to undervalue the craft of writing. Writers earn an average of $13000. They’ve typically spent five years meticulously crafting a book. If we don’t do something now to support them, in 20-30 years time it wont be a viable career for people. When you read something that can blow you away and move you, that needs to be supported. Writers have the ability to articulate something that is so intangible. With Jeanette Winterson it feels like she’s channeling something from the gods. I want to highlight that we have to value it. Providing writers with time and space to write and create is so important. Imagine what would happen if we could give writers a salary. 

Sydney Writers Festival 2024 photos credit Jacquie Manning

Who is your local hero of Sydney Writers?
We’re fortunate that we have a really great relationship with Richard Flanagan. I love how fearless and courageous he is. I’ve just gone back and read Question 7 for the third time. I was told once you’ve never really read a book until you’ve read in three times, and Question 7 just gets more poetic and prophetic each time. 

Which other literary festival would you love to go to?
The Hay Festival is straight after us so it’s so hard to go. I’d love to go to Edinburgh, Brooklyn and Frankfurt Book Fairs. I don’t really have a sense of the scale of it, but I’m desperate to get to  the Jaipur Literary Festival. I know I’m going to love it. 

Sydney Writers’ Festival runs from 19–27 May 2025. 

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