Leadership

Rosie Waterland has come to terms with not winning an Oscar

The author and comedian on chronic illness, self-blame and what workplaces get wrong about mental health.

By Melanie Dimmitt

Published 12 March, 2026

Leadership

Rosie Waterland has come to terms with not winning an Oscar

The author and comedian on chronic illness, self-blame and what workplaces get wrong about mental health.

By Melanie Dimmitt

Published 12 March, 2026

Rosie Waterland grew up with a very specific goal. She wanted to win an Oscar for best original screenplay. 

“It came from the one thousand nights that I had spent as a very scared little kid in my room, in a very chaotic life, with my little TV on, taping episodes of Seinfeld and then writing down the scripts,” says Waterland at the FW Leadership Summit.  

Years later, once she had established herself as a professional author, writer and comedian, a Hollywood star with an idea for a screenplay saw Waterland featured on Australian Story

“They got in touch with me and asked me to meet them for lunch – and it was truly just one of those unbelievable, ‘I can’t believe this is happening to me’ [moments],” she says. 

“So I said yes. And then, I just couldn’t do it. It was at a time when I was incredibly unwell mentally and I kept telling her, ‘Yeah, I can do it’ and she was very gracious about it. [But] I kept missing deadlines.” 

Waterland is speaking with FW’s Jamila Rizvi onstage at the Summit. The duo are good friends and co-authors of Broken Brains – a book they delivered late to their publisher. Four years late. 

“But we did say to them, look, you can’t agree to publish a book by two chronically ill people about chronic ill health without expecting there to be some delays due to some chronic ill-health, right?” 

“A lot of people see the mental health side of things as the person’s fault. I’m prone to those prejudices, too.”

Waterland has complex trauma and PTSD from her childhood. Rizvi is a brain-tumour survivor. And as their book explores, their respective illnesses – one physical, one mental – tend to receive very different responses from those around them.

“The reason we decided to write Broken Brains was you came to visit me when I was getting inpatient healthcare for my mental health, and you talked about how when you first got diagnosed, within seven days, you had a freezer filled with lasagnas,” Waterland recalls. 

“And I said, oh, you know, I’ve never got a lasagna.”

Rizvi shares that while she looks back on the darkest days of her illness with sadness, not once has she felt like it was her fault. Waterland cannot say the same. 

“I’ve often seen it as my own fault. Still now, to this day, it’s hard for me to shake those biases and feelings.” 

Back when Waterland was working on her Hollywood project, it was exactly that thinking – that it was her fault, that she just needed to try harder – that saw her watch this opportunity of a lifetime slip away.

“I couldn’t understand why I was having my dream handed to me on a silver platter and I was unable to do the work, and I kept denying that it was happening,” she says.

“I was at a point where I wasn’t dealing with my illness in the right way. I was just ignoring it going, ‘Sorry, I’ve got an Oscar to win. Today wasn’t a good day, but I’ll get it done tomorrow’. That’s not practical. I had to really let that dream come crashing down the way it did.” 

Waterland learned to work with her challenges once she stopped waiting to overcome them – a moment that was never coming. 

“I needed to start thinking a lot more intentionally about how I work and accept my illness as part of my life, rather than just wishing it wasn’t there,” she says.

“It’s about figuring out – some people don’t like this word – what some ‘limitations’ might be and how to work with them,” she says. “That’s the stuff I found it really hard to be honest about.”

Still today, Waterland turns to advice Rizvi gave her as her manager, when the pair first met while working at a women’s media company. 

“You said to me, ‘make a Rosie-shaped hole that no one else can fill’,” she says. And now, at the helm of her own podcast company, she says the same things to her employees. 

“As a boss, you also need to create a space where they can do that amazing thing that no one else can do. They need to create their own shaped hole that no else can fill – and you need to make sure that they can do that.”

Image credit: Vienna Marie

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