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  • Writer's pictureRosie Fay

Sydney & Sydneysiders: A guide

Sydney is my old home, I haven't been on its shores in over three years!

I moved to Sydney in 2000 after my Dad got a job in its North Shore, working at a radio station. One of his colleagues had a house up for rent in the Northern Beaches, and that’s where our family ended up settling for the next 15 years.

Iconic Sydney

I moved more into the Northern Beaches when I hit 16, before this, I was going to school in the North Shore and socialising in the city areas. The one thing you learn about some Sydney areas is how quickly you need to ‘keep up.’ I’d had a unique upbringing, and quite often I felt left behind. It seemed like every woman I met was smarter than me. Richer than me. They all seemed to fit in easily, fashionably. Many people I knew barely worked or didn’t have a job at all.

The Northern Beaches life is a relaxed one, like many beachside areas of Sydney. Life often centres around the next nice day, where you can get out and enjoy the sunshine. Being fit is important to Sydney-siders. You’ll find most people on their time off being active – whether it be outside, in the water, or at a gym. Local shops and cafes are regarded highly, and nights out in Manly are common – since the city is so far away.

I often wonder where my life would have gone if I didn’t spend my early 20’s trying to earn as much as possible, whilst running around going from job to job to make it happen. I would have started my Digital Nomad career a lot earlier if I wasn’t so concerned about making rent each week. No matter how many jobs or side-hustles I did, I could never seem to ‘make it’, but then again, I was never satisfied. Maybe I was designed for something more.

Cathedral Cove Water Beach
My Balgowlah Home

I value Sydney for its health focus. By growing up in such an active place I value quality food and outdoor living a lot more than some of my European friends. I feel privileged I was able to enjoy such a beautiful part of the world.

READ: A digital nomad guide to Sydney


I don't really want to go back. I fear it.

I say this with caution, as last time I mentioned this on the internet I was bombarded with messages - outrageous claims and accusations on how I didn't know any better. I post this blog with caution - even though I think many of the people I knew in 2018 read my words.

I struggle to explain my frustrations without coming across as insulting. I carefully choose my words but no matter what, I seem to anger someone.... so I'm here, to be honest.

Keeping it Real

I filled my weekends up months in advance. Every time another one finished, I'd know what I was doing the next Friday - Sunday. My life centered around my friends and what they were doing with their lives. I put myself in the front and centre of every issue and concern; trying to be a fix-all, a dependable, or a guaranteed good time.

My Sunday Scaries seemed a bit more real back then. I had no backbone or boundaries I set with others, my self esteem at its lowest. No one would respond to my messages for hours. I struggled with the party being over and suddenly I was useless again. It was frustrating, as my job wasn't fulfilling and I seemed to be constantly striving for life, one that wasn't behind a desk.

My weeks repeated themselves in a groundhog day situation - work, gym, home. I know now the value of being alone and taking myself out, but in those days, I'd be wanting to socialise, to feel worthy. I got all my validation from others.

On my 27th birthday, I knew my decision to leave was right.

After coming back from NZ in 2015, I had a new friendship group. I fit in nicely but I was always the outsider, I never really felt welcome. My messages would go unread & unreplied. Why is it that I can see shows like FRIENDS on TV, but no one wanted to meet me in a coffee shop? In How I Met Your Mother - they hang out at the bar almost every night. I don't want to watch Netflix alone. Why can't I find friends like this?

Every year, September would roll around and I'd had spent most of my time and money around my friends for the year. Birthdays and celebrations I would always attend.

I'd kept my new visa a secret and asked a small group to gather together for my combined farewell/birthday - I knew once I left it would be a long time before I returned.

Every single person cancelled on me.

I felt like my world had actually crumbled. 27 or 7, no one coming to your party is a rough truth to face. I got hopelessly drunk with people from work and woke up near the airport on a randoms couch. Embarrassed as hell, head throbbing, I spent $60+ on an UBER Pool home.

My life was packed the following week whilst I put on a brave face for people.

I cried every night. But I knew it was the right choice.

I've lost a lot of people and friends since leaving the shores of Sydney. I don't get much support from home. A lot of people click through my Instagram and stalk my profile. It's weird to have the stalk without the support, but hey, that's Sydney for you.

I'm stronger now, potentially that has come with age and a lot of resilience travelling.

I have a few mantras that help me get through my darkest days.

  • FOR WORK: 'I have achieved great things at every job'

  • FOR MONEY: 'I always find ways of making money'

  • FOR LOVE: 'Look at what you have achieved. You are amazing'

  • FOR SELF-ESTEEM: 'I am enough.'

  • FOR SUNDAY SCARIES: 'I never cause issues at a party'

Silly for some, lifesaving for me.

I know that with this strength that when the time comes I will be able to travel home without anxiety. That I can be strutting the streets and swimming in the oceans again. I'll always treasure Sydney and my past but it will not belong in my future.

Until next time x

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