creativity, connection and ‘thingness’

a conversation with Madeleine Dore

Hello, hello! I am so excited to introduce you to Madeleine, because she’s one of my favorite creators on this side of the internet. Her writing explores themes like aliveness and ‘thingness’ — which we’ll get to! — in her signature style, observations that are clever, honest, and unpretentiously poignant. I hope you enjoy today’s conversation, and while you’re here, consider tapping the ❤️ button — it helps more than you know.

Madeleine Dore is a writer, interviewer and producer who explores what helps people foster creativity, connection and meaning in their everyday lives. I discovered her newsletter, On Things, this summer and it leapt straight to the top of my favorites: it offers a “place to ruminate on things, without feeling rushed towards an answer,” and to “navigate the various facets of…aliveness—the joys and the uncertainties, the tensions and the desires.”

Madeleine is also the author of I Didn’t Do The Thing Today, an internationally published book containing insights from hundreds of interviews captured in her project Extraordinary Routines and podcast Routines & Ruts. Her new podcast, A social life, with friends, explores “how we can better navigate the joy and the heartbreak of being a person in the world, with other people.”

In this interview, we chat about:

• Why social connection is so important — yet often the first to fall off our list

• Why perhaps more people should have imposter syndrome — and why it can be a good thing

• How to write into the gush and capture ideas as they’re most alive

I really hope that you a) enjoy our conversation, and b) go pore over Madeleine’s archives because they really are a treasure trove.

Without further ado…

Madeleine, hi! You’ve interviewed hundreds of interesting people about their creative lives, including some of my favorites: Katherine May, Mari Andrew, Oliver Burkeman, Heather Havrilesky.

I recognize the slight irony in this first question, as I’m now interviewing you for my newsletter. I was hoping you could share a bit about your process: How do you find these people?! How do you approach them, and what does it look like when an interview goes well?

When I started Extraordinary Routines back in 2014, I began by asking people I admired how they approached their days, beginning with friends and people I knew. The project just kind of snowballed from there, as a labor of love; I wanted to create a space that would help demystify the creative process, and to build a creative career for myself at the same time.

The project first travelled by word of mouth, and that created stepping stones to other people and interviews. I kept a wishlist of people I’d always wanted to speak to — of whom I’d read their interviews, or books, or had seen them on social media — and that list grew over time. One person leads to another, and so on. It’s funny how the same is true for books — I’ve found that writing one can lead to the next!

Once I finished writing my book, I found I missed writing what I was curious about. So when I stared On things I knew I wanted it to be as free as possible, as a space to explore my own curiosity and allow it to change. The name ‘On things’ allowed it to be broad and creatively open, yet grounded and organized along a cohesive theme.

The word ‘thing’ is also really interesting philosophically: it means the quality or state of objective existence or reality. ‘Thingness’ is really about exploring what it means to be alive. Which I hadn’t even realized when naming the newsletter, but now in hindsight, it fits perfectly!

As far as approaching people: if I don’t know someone very well, I will ‘gently arrive’ into their inbox, pointing out a mutual connection where possible to help build a sense of trust. I offer to come to them, and try to be accommodating as possible of their schedule; if we are meeting in person, I’ll often bring flowers or tea. And then I try to do the interview justice by writing it as beautifully as possible. 

When interviewing authors, I always make sure to read their book, and try to find unique tidbits so that I can bring new angle to our conversation that offers a fresh perspective with regard to my particular curiosity.

In some ways, the interviews always go well because I’ve found people always have something to offer you: you’re always learning through these conversations. In times where it doesn't go as well, it’s usually a result of energy — if someone is really exhausted, for example, or pressed for time. It can also be a lack of chemistry. But none of it is personal — that’s just how it goes sometimes.

I try to do the interview justice by writing it as beautifully as possible.

I’ve allowed myself to become looser with the structure of interviews; I always come prepared with questions, but also allow for the conversation to reveal something, and have learned to trust myself in that process. I allow my curiosity to adapt and change.

The interviewing itself has also evolved: from Extraordinary Routines a decade ago, to podcasting and building an online presence today. They now follow more of a theme, where I’ll ask specific questions, but fewer of them, and allow the conversation to unfold from there.

You’ve focused deeply on our relationship to productivity and creativity in your work. What has surprised you most about how we as humans relate to doing things, and doing things creatively?

Throughout these projects, I was interviewing people who I deeply admired, and thought had it ‘all figured out.’ But actually…I was surprised to learn over time that no one really knows what they’re doing, or has it figured out, or has the ‘secret’ to pass onto you! These people who I put on a pedestal also shared my own feelings, insecurities, and guilt associated with not feeling creative or productive enough.

The expectations we put on ourselves are extraordinary and oftentimes unrealistic…I’ve learned that in my work and creative life, it will never feel like enough until I decide it’s enough.

One of my biggest takeaways has been that the expectations we put on ourselves are extraordinary and oftentimes unrealistic. Striving and ambition can propel us — but they can also deflate us in how we think we’re not measuring up. So I’ve learned that in my work and creative life, it will never feel like enough until I decide it’s enough.

I think we can all hold things more lightly, and focus on just taking one step at a time. That’s the only thing we really can do. Starting where you are, working with what you have and what’s around you.

Your new project, A social life with friends, takes a warm, curious, and honest look at our social lives and what it means to “be a person in the world, with other people.” I adore the podcast and would love to know — what inspired it? How do you see it evolving?

While compiling the lessons from Extraordinary Routines into my book, I noticed a common theme: people who were successful in their creative careers would often admit that they were too busy for friendship. We know how important connection is, yet it’s the first thing to fall to the bottom of the to-do list. So kind of naturally, I’ve turned from looking at our working lives to examining our social lives.

I’m also at a fascinating time in my personal social life: I’m in my mid-thirties, in a time of transition, which has provided rich ground for exploration. The project is on pause at the moment, though I’m hoping to resume the podcast and newsletter soon and am exploring potential book ideas!

People who were successful in their creative careers would often admit that they were too busy for friendship. We know how important connection is, yet it’s the first thing to fall to the bottom of the to-do list.

I so admire how you have built a vibrant career centered on creative community, which has allowed for curiosity and exploration (see: path of the hummingbird). Can you walk us through how you got to where you are now: what sparked your interest in writing, and our creative lives? What stepping stones have emerged along the way? What’s been hardest, most rewarding, and what’s next?

I studied a degree in Journalism, and switched to Entrepreneurship and Innovation midway through — I thought maybe I’d start a business related to secondhand clothing! I finished my degree in Copenhagen, where I stumbled upon an agency that interviewed creative entrepreneurs. I made a video asking to be intern, and they said yes! I then became the editor of Rebel Times, which represented the fusion of writing and creativity.

When I came back to Melbourne, I knew I wanted to continue having conversations with creatives, and to keep on writing. I hoped to land a job as a journalist, but it was hard to get work, so I started my own personal projects in the meantime. These side projects allowed me to build a portfolio, and to learn how people made creative careers for themselves.

I eventually landed a dream job as deputy editor at an arts publication, which I think shows that your own side projects and labors of love can lead to creating the job you want. I started writing a guest column in a well-known publication, which led to more momentum, and began running live events, interviewing people all the while and freelancing on the side. Through organizing the Side project sessions events, I was able to continue building community. 

Your own side projects and labors of love can lead to creating the job you want.

It can definitely be challenging to make time for your own projects, especially when they are labors of love. While they have given me a profile to freelance, the income is up and down; at times, I’d feel the panic set in and would jump back into a 9-to-5 for a bit. 

There’s also the uncertainty of investing time into what you’re curious about without knowing if it will lead to anything. It can take a while to begin; sometimes I’ll have an idea for years, before eventually getting sick of myself and starting on it. And as a team of one, the work — hosting, researching, producing, editing, marketing — is not always sustainable, so I will often put things on pause when it becomes too much.

It’s helpful to remind myself that these are labors of love. And to let them be like that: as love.

It’s also good to remember that personal projects tend to ebb and flow. Sometimes we have time and curiosity; sometimes we don’t. When we remember that, and allow space for it, we open ourselves to opportunities and give ourselves the grace to pick up projects and put them down. 

Now I’m dreaming up: what comes next?

It’s always worth it to put something into the world, because you don’t know who might be listening or where it might lead.

I think the most rewarding parts are the surprises, the things you can’t plan for — like a book deal, or certain opportunities that will spring up out of nowhere. It’s always worth it to put something into the world, because you don’t know who might be listening or where it might lead.

I actually think imposter syndrome has its purpose. We can embrace the fact that we don’t know, that we are beginning, and that it’s okay to be learning, and failing, and even to have self doubt, as long as we move along with it. The key is to not let it stop you. Imposter syndrome is just an indicator that we still have learning to do!

It can also occur even when we do know. Remember you don’t have to push through; instead you can acknowledge it, know that it’s very normal and move forward anyway. Maybe more people should have imposter syndrome! As in, the humility to admit when you don’t know, or are just starting out.

I like to take the attitude of an experimenter: if you’re experimenting, you’re using the experiences you’ve had to inform the next decision, while being open to what’s possible and to trying new things. It’s all about finding the middle ground between being grounded in your past experience, and curious about new things.

What advice would you give someone who’s contemplating a creative project, or wants to rekindle their creativity, but doesn’t know where to start?

Start where you are. And don’t put the pressure on! If you’re feeling stuck, you can take the idea off the table for a bit. When I was feeling really stuck with my idea for a book, I put it away for 6 months, and then all of the sudden the idea for a proposal popped into my head.

So much of the work is unconscious. Things take time they take; trust the process, and that these sorts of things have their own timeline.

What is some of the best writing advice you’ve ever received?

There’s a quote by Walt Whitman that I love: 

“The secret of it all, is to write in the gush, the throb, the flood, of the moment – to put things down without deliberation – without worrying about their style – without waiting for a fit time or place. I always worked that way. I took the first scrap of paper, the first doorstep, the first desk, and wrote – wrote, wrote…By writing at the instant the very heartbeat of life is caught.”

So, write into the gush! Meaning: when an idea arrives to you, write it then. By the time you return to it, it might feel stale. Write into the river as it’s flowing. Write in imperfect moments — on the bus, on your phone, in a notebook — so you can capture the ideas while they’re alive. I try to write about whatever feeling I’m having as I’m having it, and come back around to it while it’s fresh. 

You recently wrote that until your move to London, your adult life has been “imbued with impermanence,” spent “in sharehouses, furnished sublets, housesits, or staying with family and friends.”

What do you think has drawn you to a more wandering existence? Where have your travels taken you, and what have you learned — about yourself and the world — along the way?

I’ve pursued freedom; it’s always really appealed to me. If I don’t have things, then I can be completely untethered. For me, it’s about making the most of what I have: I do have freedom, so how can I make the best of it? What’s right about my life that I can use — in contrast with friends who might have mortgages or pets or children, for example?

I have recently felt a shift towards something that feels more grounded and committed. I can see the benefits of what happens when you stay and cultivate something, even if it’s imperfect. Part of me is curious about the flip side. So I’m now in the middle of both, in limbo. It’s funny — we get this longing for freedom, and then when we have it, we crave stability. The grass is always greener, I suppose; we are cyclical creatures. 

Bonus round: what’s your favorite… 

• Show: My Brilliant Friend. It’s a tale of friendship, and shows its psychological inner workings.

• Way to spend a Sunday: Sunday is a beautiful workday for me! I’ll usually go for a long run, then come back and have a delicious breakfast. I’ll go through things I’ve saved from the week for reading, watching, listening, and compile them into the newsletter. I’ll usually finish by early afternoon, and then have friends over or do something else social, like go on a date, or go to a movie. I’ll also try and do some batch cooking and grocery shopping!

• Author: If I ever feel very ‘wobbly’ and lose sight of things, or compare myself to others, I try to turn my mind to poets. One of my favorites is Marie Howe. I also adore Amy Krouse Rosenthal, who wrote Encyclopedia of an Ordinary Life, which is incredibly moving and quirky; she’s also written memoirs and children’s books. She wrote a really stunning column for Modern Love in the New York Times, You May Want to Marry My Husband. She’s such a vibrant writer, and shows that you can do what you want to do, and write what you want to write.

• Snack: Cheddar cheese on apple slices! I call it ‘cheese apple.’

• London hang spot: The Barbican. It’s an art center with a cinema, theater, and cafe — but also brutalist building where people live, with gorgeous plants and balconies. It’s my go-to meet up spot when people are in town! In Sydney, where I spent a lot of time before London, the Bronte Beach Baths are a perfect spot for moonrise.

• On Things post: I walked a loop of the same park every day for a month, and wrote a diary on that: The repetition of things. Separately, one of my favorite Substacks would have to be The Lunar Dispatch; it’s essentially a love letter to the moon.