I remember feeling confused the first time I read artist and designer James Victore’s words ‘freedom is something you take‘. I thought I am privileged to live in a first world democracy, of course, I’m free. My freedom was given to me at birth. I didn’t need to ‘take it’.  And yet in many ways, as a grown woman I didn’t feel free. I felt trapped by expectation, obligation, comparison, norms, shoulds and fear.

It took me a while to realise that indeed, my freedom is highly personal, and a result of my mindset, worldview and choices. Even when our basic human rights are met, we are not free if we don’t see ourselves as such. Permission to change, try and grow is something we grant ourselves.

In a parallel universe, you’ll read that this week’s leap taker Madeleine Dore was having a similar epiphany inspired by filmmaker and writer Miranda July. While Madeleine was working in her dream job, the side gig she had started was beckoning her to go deeper. So she claimed her freedom to explore it full-time. Not only did her Extraordinary Routines blog blossom, as did her corporate freelance writing. So much so, that she had to remind herself again that she could to claim her freedom to say no, in order to continue to exploring own creative work.

Staying woke to our freedom to choose matters. Because seemingly not making a choice is one. We owe it to each other to keep reminding each other of our freedoms and our choices because courage is contagious. And we could all do with a good dose of that every now and again.


The gorgeous Madeleine Dore, founder of Extraordinary Routines. Photo by Prue Aja Photography.

What did you want to be when you grew up and why?

When asked this question as a kid I would reply with ‘everything.’ I remember thinking I was so clever because I had somehow cheated the system and thought of an alternative all the adults with their singular job titles had somehow overlooked.

The feeling of wanting to do everything has never quite escaped me and when asked this question today I’m still not sure – ‘I don’t know, a bit of everything?’ At times the question can have me stumbling over my words, worried that ‘everything’ ultimately translates into nothing – or perhaps there’s a divide between the things I currently do and the myriad of things I want to be doing. But I think by definition creatives have permission to try it all, and it’s okay if that process is non-linear.

Madeleine Dore Extraordinary Routines

What did/do you study?

After high school, I went straight into a Bachelor of Professional Communication at RMIT before switching to study entrepreneurship at Swinburne. The degree took me abroad to Copenhagen where I completed my studies and dabbled in arts management. While I was studying overseas I took up some internships that brought me back to writing. For a while I would berate myself for this – I felt like my education was full of gaps from changing back and forth, but when I took up a role interviewing creative entrepreneurs it all feel into place. Nothing is ever wasted, it seems!

I’ve dipped my toes in a Masters of Creative Writing, Editing and Publishing, but gaining full-time employment as the Deputy Editor at ArtsHub in 2014 took over.

Madeleine Dore Extraordinary Routines

What has been your most scary/courageous leap you’ve ever made (preferably in your business/career/life direction)?

Quitting my ‘dream job’ at ArtsHub in June last year was certainly a scary one – especially because it was on somewhat of a whim. I saw Miranda July speak when she was in Melbourne and her words stuck in my mind: she explained how she continues to forget and remember, forget and remember, forget and remember that she is free.

There were things I wanted to try in terms of freelance writing, projects and Extraordinary Routines that I felt as if I couldn’t because I was trapped in a dream job. It sounds odd, but when things are going well, it feels completely against the grain to change them. We can get stuck in the rules we create for ourselves, or the made up version of our lives we think we should be living.

But the decision was made and I went about putting in safety nets – I had money saved for travel that I decided to allocate as a backup fund for the transition from full-time work to freelance. I was in a very privileged position in that sense – freelance writing can be precarious, but I had some room to experiment and ease into it.

The first day of my new freelance career I wrote a manifesto for quitting your day job which including some guidance including the wise words of Maya Mendoza: ‘No amount of security is worth the suffering of a mediocre life chained to a routine that has killed your dreams.’

Five months in and I had to stop myself in my tracks – I’d done just that, settled for security. I’d taken on some well paying corporate work so that I didn’t have to see my savings diminish. In the meantime, I hadn’t set about expanding Extraordinary Routines or my own creative projects. And so it begins again – a new plan has been set for 2017 that includes a full three months of only working on the interview project and seeing where it takes me.

Madeleine Dore Extraordinary Routines

What were you doing before you made your leap?

I was working full-time as the Deputy Editor at ArtsHub, but I could also trace back my leap to when I started Extraordinary Routines in 2014.

I was unemployed, suffering from a case of reverse culture-shock and house-sitting for a family friend. I felt pretty dismal having just come back from an exciting year abroad in Denmark, unable to find work while friends around me were making leaps and bounds in their newly formed careers. When I was overseas I was working for a local English newspaper and small art magazine – I missed interviewing and meeting interesting creatives and needed to find a way to bring that experience into my current life. Despite feeling low, I chipped away at launching Extraordinary Routines, which if we come full circle, helped me land the job at ArtsHub! I think once you find the momentum and confidence, you’re more aware and open to opportunities.

Madeleine Dore, founder of the inspiring and creative interview series, Extraordinary Routines. Photo by Prue Aja Photography.

Who have been the biggest 3 – 5 influences in your life, in terms of your career and doing work?

1. I have a strong curiosity about people – how they deal with each day, the highs and the lows, and what it really takes for them to produce something extraordinary. Often we see the end product or picture-perfect Instagram account, book launch, or gallery opening, but there is often doubt, fear, mistakes, failure and a real, often flawed human behind what is portrayed. I used to suffer from comparing myself incessantly, but since discovering other people have their vulnerabilities too, I’m less tough on myself.

2. I really enjoy hearing about side projects and seeing a friend or stranger build an idea from nothing to something. Whether it’s a painting, a funny series of images, or a publication, the process is fascinating.

3. Annie Dillard’s words, ‘How we spend our days is, of course, how we spend our lives,’ are a constant reminder that our life doesn’t begin when we find a new job or partner, or in five, ten, or fifteen years – it’s happening now and our days ultimately shape our lives. There needn’t be pressure to do everything right now, but it’s important to pay closer attention to your choices.

4. This may sound a little morbid, but a current influence on my own daily work is thinking about mortality. I believe reminding ourselves of our own death can serve as a motivator and help us prioritise what we do each day – nothing kicks you out of a bout of procrastination like reminding yourself of your own death! I started an Instagram account @moralitymusings to collect famous quotes and thoughts on the subject.

Madeleine Dore Extraordinary Routines

How did/do you overcome/work with the fear that comes with leaping? How do you decide to choose courage?

When creating Extraordinary Routines, it was a friend’s gentle push that helped with my leap. I think it helps to have some objectivity in these types of situations – someone who is not experiencing the fear to offer a bird’s eye view and let you know it’s not as difficult as your making it out to be. I highly recommend finding an accountability buddy for this very reason!

What motivates me to keep leaping – public speaking, dabbling in events, testing out new blog formats, conducting life experiments – is a fondness for bravery and doing something new, even just for the story! I’ve learned to stop worrying about what other people think and simply try new things in order to make life more interesting.

And again, remembering I’m going to die! I can’t help but think of poet Mary Oliver: ‘Tell me, what is it you plan to do with your one wild and precious life?’

If the privilege of leaping is available to you – even if you don’t quite have the bravery yet – leap!

Madeleine Dore Extraordinary Routines

How did you fund your leap?

Starting Extraordinary Routines involved getting a Squarespace website and buying coffee for the first interviewee. Today I fund the project and photography through my freelance work.

I had the backup fund for when I quit ArtsHub – and I used that to calculate a ‘burn rate.’ I put together all my expenses, then modestly estimated what I thought I could earn each month so I was able to see how long I could survive. I’ve been lucky that I haven’t dipped into my savings since freelancing – but again, that’s perhaps a sign I’ve been playing it a little safe with taking on corporate work!

Madeleine Dore Extraordinary Routines

What’s the biggest upside to making the leap?

You’ll meet new people and create opportunities you would never have imagined. I was out to dinner recently and realised the majority of the people around the table were people I had met through Extraordinary Routines.

I’ve taken part in writers’ festivals and given a talk at one of my favourite events Creative Mornings as well as had new writing opportunities open up just through putting the project out there.

Even little leaps in your day to day life can change how you view your world. There is so much we do each day that we are unaware of – in fact, by the time we reach the age of 35, eighty-five percent of our behaviours are unconscious, making our personality almost set in stone. So when we do something just a little out of the ordinary like take a different route to work, we are jolted out of ourselves.

In a way, we can constantly take leaps just in our minds by changing our thoughts, moods, and attitudes. This has been a big lesson for me, and Epictetus said it best: “Do not seek to have events happen as you want them to, but instead want them to happen as they do happen, and your life will go well.”

Madeleine Dore Extraordinary Routines

What’s the biggest downside to making the leap? And how do you get through it?

The ever-present feeling that it’s not quite what it could be. It’s easy for the mind to fall into a cycle that tells you you’re not living up to your own expectations. I try to keep that in check, and instead of focusing on what I’m not doing, appreciate what I have accomplished.

What might be your next leap?

I want to keep experimenting with new formats, whether that be a podcast or book! I also have a few ideas for a new interview series and exhibition, so tinkering away with that.

Madeleine Dore Extraordinary Routines

What are your favourite words to live by?

I keep a spreadsheet filled with my favourite quotes by authors and inspirational tidbits I find.

Here are a few:

“Develop an interest in life as you see it; the people, things, literature, music – the world is so rich, simply throbbing with rich treasures, beautiful souls and interesting people. Forget yourself.” – Henry Miller

“All I ever really want to know is how other people are making it through life. Where do they put their body, hour by hour, and how do they cope inside of it.” – Miranda July

“The more you know what you really want and where you are really going, the more what everybody else is doing starts to diminish.” – Alain de Botton

“There isn’t time – so brief is life – for bickerings, apologies, heartburnings, callings to account. There is only time for loving – & but an instant, so to speak, for that.’ – Mark Twain

And finally, the ultimate leaping mantra:

“Never work for other people…always, always remember that the reason that you initially started working was that there was something inside yourself that you felt, that if you could manifest it in some way, you would understand more about yourself and how you co-exist with the rest of society… And the other thing I would say is that if you feel safe in the area that you’re working in, you’re not working in the right area. Always go a little further into the water than you feel you’re capable of being in. Go a little bit out of your depth and when you don’t feel that your feet are quite touching the bottom, you’re just about in the right place to do something exciting.” – David Bowie

Madeleine Dore Extraordinary Routines

A piece of advice for someone with an itch to leap?

Start small and don’t let imperfection, comparison or expectations get in the way. Remember it’s your project, your leap, your life and your rules. Allow yourself to be pleasantly surprised by even the tiniest of steps.

Right now I’m:

Hearing: Lianne La Havas – saw her perform recently in Melbourne and she’s been on repeat ever since
Eating: Boiled eggs with butter (I’m on a bit of a butter craze since trying Bulletproof Coffee! – a mix of filter coffee, grass fed butter, and coconut oil!)
Drinking: Prosecco, always
Reading: Yassmin’s Story by Yassmin Abdel-Magied
Loving: Themed dinner parties


Dear friends, what freedoms might you take this week?


Kylie x

p.s. Purchase your copy of The Leap Stories book to access exclusive content only available in print, including a provocation for your own leap. Buy Now.