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Working from home: Quitting a corporate, freelancing, then failing at it

Sam: Where did you work?

Hayley (28): I was working in communications at a large retailer. Think David Jones, Myer, Woolworths, Westfield… you get the idea. Day to day I would be working on copy for their website, updating press releases about new products or business changes to go to the media. It was a vanilla job. A lot of the content I was producing was aimed at my demographic, but for me it just missed the mark.

Sam: How long before you decided that you wanted to freelance?

Hayley: I was looking at a campaign we were running on social media that had taken months to approve, and it was so vanilla. It ticked all the ‘boxes’ and at that moment that I realised I could not count on huge corporations to construct and ever approve content that myself or my friends would find appealing or useful or meaningful or complex. The amount of approvals required in a big corporate mean that no fresh idea would ever have a chance. They have no sense to “risk it,” and try anything new. It’s not really a complaint. It’s just the reality of working in a large corporate.

I used to write a few pieces freelance for a publisher, so I thought; why not make a career out of it. So I did.

Sam: What was freelancing like?

Hayley: I quickly realised that freelancing is impossible without solid relationships with editors.  I learned to be consistently kind and polite to all editors, even when they pissed me off. Maybe I am a precious creative! You need to realise that the people you will freelance for are really fucking busy and overworked and they aren’t dismissive of me or out to get me, even when that’s where my brain goes on a bad day. They also have a million-and-one personal challenges that you know nothing about. And yes, that includes the fossilized head of departments that sit in the corner offices. It’s just this time that you aren’t working in the physical office as them.

Sam: It feels like it must have all been a let down.

Sam: You kind of said, “fuck it! I am going out on my own,” but end up working for the same ‘man’ – metaphorically.*


Hayley: Exactly. It’s like, I had a good plan and it failed! It’s embarrassing. Everyone knows you’ve failed.

Sam: Did the ‘fear of failure’ impact you?

Hayley: Everyone knows you’ve failed. You get used to it. People say, “at least you tried,” a lot, and you know they mean well, but it’s hard to hear. It makes you scared to talk about your next ambition.

Sam: What advice do you have?

Hayley: Seeking out a creative career like writing means experimenting and taking a lot of leaps. Creative careers are clearly mapped out. You have to pick something and TRY IT, knowing that it will probably fail. But unless you are picking something conventional, like being a nurse – where there is a set trajectory – it’s just part of it.

Do you have a story to tell? I’d (Sam the Editor of The Footnotes) love to share your career story and your advice. Email me at:

We love interviewing people about their day jobs, their journey, their failures and their successes. This is the website that talks about careers, study and money without any ‘puff-spiration’. It’s real stories, from real people.

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