Madeleine Dore is a freelance writer and founder of the website Extraordinary Routines, an interview project that uncovers the routines of artists and entrepreneurs. She’s also responsible for the event series Side Project Sessions, in which people meet regularly to work on whatever they’re putting off – from novels to tax filling.

Illustrated by Inês Medeiros

THE “OK, WHAT’S THE NEXT STEP?” MOMENT

What was your “OK, what’s the next step?” moment?

In 2014, I was 25 years old and I had just arrived back to Melbourne after a year living and studying abroad in Copenhagen. I studied journalism, entrepreneurship and innovation. In my final year of my degree, I was doing internships with a creative agency called ArtRebels and a local Danish newspaper and had really enjoyed the opportunity to interview creative entrepreneurs about how they got their start.

Coming back to Melbourne, I struggled to find opportunities in journalism, especially in arts journalism. I dabbled in freelance copywriting and even did a short stint at an art gallery, but I was feeling despondent, and unsure of how I was ever going to pave the career I wanted. It felt like I was behind, that I would never measure up to my peers, and the creative career path felt very mysterious. I remember sitting with my mum at the dining room table with my head in my hands, worried that it will never work out – in that moment, she gently suggested I stop looking at what everybody else was doing and make a list what I want to do.

“If there were no restrictions, where would I want to be in five years?”

I wrote down ‘writer and editor’ – and here we are, five years later and I’ve been a deputy editor, and now a freelance writer with a growing event series so there are some nice surprises in there!

So after you followed your mother’s advice, “Extraordinary Routines” was born. Can you tell me more about that decision?

Out of guidance or out of comparison, it’s hard to say, I looked to a close friend who I had studied journalism with and observed how starting her own side project (a zine) had an incredible impact on her career – it gave her a portfolio, a niche, and something to explore and be curious about. I was driven to do the same, so I thought about what I was most curious about – creative people, and how they shaped their days to make time for their work. So I started the interview project Extraordinary Routines – it was my next step in building something for myself – if you can’t find the job you want, create it – but it was also a way to demystify the creative process and find out first-hand how people built their careers. 

The project then lead to getting a job as the deputy editor of the online arts news website, ArtsHub – and I’ve kept Extraordinary Routines up ever since!

But how was the process from brainstorming to execution?

The idea for Extraordinary Routines was like a hidden seed for some time – I’ve long been drawn to that question ‘what’s typical day’ in magazine articles, and have pestered friends to tell me about their morning routine or what they eat for lunch for many years, I just didn’t realise it could be an interview format in and of itself. 

So when I sat down to really think about what I want my side project to focus on, it started to sprout. I love writing lists and brainstorming, so I sat with a big piece of paper and just unloaded everything from my brain, wrote down names of people I would want to interview, wrote a list of questions and what I would need – a logo, a website, a voice recorder – and then I started by interviewing friends.

Illustrated by Inês Medeiros

Even though I knew I wanted to pursue the project, I still had a lot of fear and resistance. I had conducted the first two interviews in January 2014, and didn’t share them till June 2014.

It was a friend’s words that finally got me over the line: “Done is better than perfect”.

So I put together the Squarespace website and shared the first interview that day – sometimes you just need that bit of accountability! I realised I wanted it to simply exist, it didn’t have to be incredibly polished and perfect as I could build it as a went. It’s been incredible to keep it going all these years – however ad-hoc my publication schedule may be – and have a platform to speak to people I feel inspired by.

The project has since evolved to include life experiments and musings – I was learning so much from the people I was interviewing and I wanted to try things out on myself, experiment with my own schedule, and share thoughts on the themes that were bubbling up.

What helped you stay focused on the project?

What helps me stay focused is remembering I make the rules. I can still fall in the trap of comparison and tell myself that I should be sticking to a strict content schedule or interviewing X amount of people each month, but for me it’s very much a labour of love, so I have to remember that I will add to the archive when that curiosity is there. Maybe if there was more structure – or routine! – it would be different, maybe better, maybe not, but I am learning to do what interests and works for me when it comes to passion projects!

Illustrated by Inês Medeiros

ABOUT EXTRAORDINARY ROUTINES

You’ve mentioned in an interview that it’s cathartic to get to know the behind-the-scenes and see that your idols also snooze their alarm ten times, have breakdowns and feel lost. Is that the core message of Extraordinary Routines?

The core message is that we are all just figuring out, we all stumble, and there is no such thing as the perfect day or perfect career or perfect life. So often we are only privy to a curated version of someone’s work or life, but I’ve found the interview format to be a great way to illuminate diversity of creative experiences – the lack of routine, the burnout, the challenges, the floundering, the emotional, mental and financial strains – and I have a lot of respect for the subjects who have shared these internal struggles candidly with me over the years.

I learn something astonishing from every interview. Recently, Austin Kleon’s routine has really inspired me – he reserves the morning for creating, and the afternoon for more admin. There is also a great flow to his work – he does a daily post, which then forms his weekly newsletter, and the themes over time result in a book or a talk.

He talked a lot about embracing your rough edges, tensions and flaws: “We’re so obsessed with life hacking and with becoming these productive, shining examples of ourselves, but so much of good creative work comes from being a person that has tensions in their life.”

And nowadays, what helps you keep on track?

Over time, I found that working around people, working in short stints and taking regular breaks is key to productivity – as well as learning to be kind to yourself and remembering things take time.

Many of my work activities and approaches have culminated in the event series Side Project Sessions – I kept hearing how easy it is to put off deadline-free personal work, and how creative ideas can often fall to the bottom of the to-do list.

These sessions remind me of so many important lessons – do more with less, done is better than perfect, just begin, do a little, take the break, rest, reflect, show up. 

I also regularly bullet journal to keep track of goals, and early this year started doing The Artist’s Way by Julia Cameron. The morning pages is now a staple in my routine (which is otherwise quite un-routined!) and helps with clarity and tapping into my blocks. Highly recommend!

HOW TO START A PROJECT?

What do you think stops most people when it comes to starting a new project?

I think there are a lot of internal ways people stop themselves from starting, but it’s also important to acknowledge some of the external ways too – financial, restricted time due to varied responsibilities and pressures, discrimination, lack of resources, opportunity, or education.

With or without those external blocks, there are internal blocks many of us face. It could be self-doubt, it could be procrastination, it could be perfectionism, it could be indecision, it could be self-sabotage. Fear has many guises – and what has helped me is to ask why the block serves me. For example, perfectionism serves me because it means I can delay putting something out into the world, and therefore delay potential criticism. It keeps me “safe”. Now that I know that’s why it’s there, I can navigate it, and even ask why I need to be safe – maybe I would derive more joy from being courageous, for instance.

Pain and failure are part of the process but, after all these years, if someone asked you “Where should I start?”, what would you reply?

Illustrated by Inês Medeiros

Always start with your curiosity. Don’t worry if it will be good, if it will be popular, if it will be a success. All of that is subjective anyway. Think about if something interests you and makes you feel alive. If not, you may as well watch a wonderful show on Netflix.

You don’t need a project or to be productive every moment to be a worthwhile human being, so really think about what it is you want to do for you. 

When you find what you love or what makes you light up, it doesn’t always make it easy – you will still find blocks, fear will still come up, you will still put things off. That’s okay too. Remember thinking is part of the process. Things take a long time, and sometimes the best thing you can be doing is staring out the window or dilly-dallying!

If you need a list to organise your ideas, great, but otherwise, pick one task and begin. Set a 45-minute timer and go. Explore. You can write one word, draw one line, send one email. The important thing is to begin – and let momentum do the rest.


NEWSLETTER + E-BOOK “How to start a project”

Thank you for reading this interview! I truly appreciate it! Inspired by this interview with Madeleine Dore, I created a short, and free of charge, workbook on how to start a project. If you’d like to have access to it and the newsletters, subscribe here:

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