An accomplished musician, actor, writer and entrepreneur, Clare Bowditch – an all-round high achiever – announces she’s terrible at painting. So last month she joined an artist friend on a painting retreat in Bali. “On a whim I said ‘OK’, and confronted my fear of painting and it was really refreshing. There were no rules. I couldn’t do it wrong, I couldn’t do it right.”

It is this, “clearing out the cobwebs” approach that Bowditch weaves into her project, Big Hearted Business. The tag line for the conference is: “We teach creative people about business and business people about creativity, in ways that make sense”. It’s all about getting left-brainers and right-brainers in the same room to learn from each other. That way they can use each others’ skills and help them realise each cannot be so easily stereotyped. “Creativity,” Bowditch says, “is just clearing away cobwebs. All of us were creatively competent as kids because we didn’t know what creativity was. It was just who we were, and most people get that bashed out of them.”

Although Bowditch’s creative streak was never repressed – she started writing songs at three and continues to do so more than 30 years later – when she first started touring as a musician, it was the business side of entertaining that crippled her. “I loved making music and I was playing in bands, but I was absolutely terrified at the concept of earning it for living. I was scared of concepts like marketing and money and even putting my face on a poster was absolutely paralysing.”

Nowadays, with an ARIA, a Logie nomination for her work on Offspring, seven albums behind her and having toured with Leonard Cohen (who reportedly proposed to her), it’s clear Bowditch’s paralysis has abated. And it happened with the help of her left-brained friends along the way. It was also her job, running a musician self-management and promotion course, that sowed the seeds of Big Hearted Business. She bought in experts of the industry to speak and pass on advice to the burgeoning musicians.

With a gap in her calendar last year, Bowditch launched the first Big Hearted Business conference to fill the gap she saw in the market for educating creative types about business (and vice versa) and helping both to build networks of support. She asked friends such as Design Files creator Lucy Feagins and writer Catherine Deveney to speak. With 180 people at Abbotsford Convent, the first conference, supported by ACCA and Mushroom Records, sold out in two weeks. “We pulled it off because of the communities that bubbled up and the way everyone helped each other.”

This year’s event, held at the Regal Ballroom in Northcote, will be double the size. The event is Labelled an ‘un-conference’. The food and flowers will be done by Joost Bakkar (who is also speaking) and the event will be styled by design studio Larritt-Evans. Jo Walker (editor of Frankie magazine), Danielle La Porte (Canadian author), Missy Higgins (musician), Pip Lincolne (shop owner and crafter), Beci Orpin (designer) and Bowditch herself will all speak in a two-day event that ends with a party.

But as Bowditch points out: “They are just the trimmings. The main thing is we want to get 500 creative people in a room together and build a community. That’s why we’re doing it again.”

The Big Hearted Business Un-Conference runs from May 3–4, 2014 at the Regal Ballroom in Northcote. Tickets are available here.