The routines of “successful individuals” are a hot topic. We are curious about a wide range of things: What do they eat? How many hours do they sleep? It’s through questions like these that we hope to uncover the secret formula to an extraordinary life — whatever that may mean.

So, what better person to ask about time than someone who’s explored this subject for a significant part of her career?

Madeleine Dore is the creator of Extraordinary Routines, an online publication that explores the daily rhythms of authors, entrepreneurs, philosophers, DJs, photographers, designers, and dozens more. She’s also a writer, founder of the Side Project Sessions, and host of the podcast Routines & Ruts.

Through each of her projects, Madeleine thoughtfully nudges us to embrace experiments, allow ourselves to flounder, and to create space for our passion projects to emerge.

In your interviews for Extraordinary Routines, you delve into daily rhythms and routines, getting to know your interviewees and their creative process. What are some of the biggest takeaways of your exploration into routines?

Something I learned early on is that the creative process has less to do with how somebody might schedule their time hour by hour and more to do with how someone’s motives or personal measures of success give shape to their days. A writer might sit at their computer for hours and produce less than one paragraph, but it’s the act of showing up and being patient with time that counts.

A creative’s output can’t be measured against a clock — part of the work is discovering our measures. That’s an empowering thing to determine for yourself. In a society that places so much emphasis on productivity as a measure of our worth, it can be difficult to determine your own set of priorities and milestones. It’s both a privilege and a courageous act to give the work time, to allow for space and quiet, to engage in the all-important act of doing nothing, to allow for just one paragraph on the page when we feel a perceived (or real!) pressure to write one thousand by noon.

That’s something I’ve noticed in my own creative practice — that these sorts of expectations can stifle us. Instead of making the most of the moment we have, we wait for the perfect swathe of time to begin. We can easily convince ourselves that there will be a better time to begin a project, new habit, or pursue a new career, or tell ourselves things like, “I’m not ready yet” or “I don’t have the skills yet” or “It’s too late to start” — but really there is no better time than the moment we’re in.

This has been my biggest takeaway from the interviews — that there is no right time, and you have to work with the imperfect chaos around you.

I’ve learned to become more comfortable with uncertainty, as well as overcome perfectionism. I’m slowly learning to seize what I have available rather than waiting for the perfect, neat pocket of time that may never arrive. When I’m putting something off, I’ll often put on a timer for two minutes, and that short burst of focus often turns into an hour.

“There is no right time, and you have to work with the imperfect chaos around you.”


You’ve written that, “Finding out how someone spends their day is not about glorifying flawless productivity or finding the perfect routine.” What value, then, is found from this exploration both for you as the interviewer and your readers?

The value, I hope, is in demystifying the creative process. For me, delving into the specifics of someone’s day has provided great comfort and assurance that I’m not the only one who procrastinates, experiences doubts, or falls into comparison spirals! From the conversations, you might glean something new you can experiment with, or you might experience a sigh of relief that you’re not alone in your fears, imperfections, or mundane moments.

It’s those messy bits that can be most interesting to explore as a creative. As Austin Kleon said in our conversation, “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 tension in their life.”

I wanted to dive further into the tensions, to show them in real time, and so I recently launched (another) side project and my first podcast, Routines & Ruts, to further explore the daily rhythms and inevitable stumbles in our creative lives. It’s about the days we find flow, and the days we go completely off track. It’s about resilience and rejection, motivation and procrastination, successes and setbacks — because I believe we can learn from all of it.

Ultimately, whether it’s hearing about how someone has “mastered” their routine or learning about a creative rut, it’s about figuring out what works for you, rather than trying to replicate someone else’s path or process.

“Ultimately, whether it’s hearing about how someone has “mastered” their routine or learning about a creative rut, it’s about figuring out what works for you, rather than trying to replicate someone else’s path or process.”

What is your relationship to routine, and how has this impacted your creative pursuits?

Despite my best efforts, experiments, and having conducted hundreds of interviews with incredible people on the topic, my relationship to sticking to a daily routine feels akin to building a Jenga tower only to see it tumble over!

Sometimes I wake early, sometimes I sleep in, sometimes I maintain a consistent reading habit before bed, sometimes I scroll my phone till after midnight! I’m starting to think I might even be a little routine-resistant. My favorite days are the ones that unfold in unexpected ways, which perhaps makes me sound a lot more spontaneous than I am. Still, I do think there is so much to respond to in real time — your own energy, mood, desire, people, the weather — that a routine can sometimes interrupt or block.

Over time, I’ve noticed that I'm not alone in my shambolic schedule. Often when I invite people to be interviewed for Extraordinary Routines, they will agree with the caveat that they don’t have a daily routine!

All seasons are important — nothing in nature blooms all year round — and I think when it comes to our days and creative work, the ebb has as much significance as the flow.

For me, it’s these non-routines that are most interesting and maybe a more accurate depiction of how our days unfold. We all shift and change as our lives and work requires, and I’ve noticed it’s more sustainable to have seasons rather than set routines.

“All seasons are important — nothing in nature blooms all year round — and I think when it comes to our days and creative work, the ebb has as much significance as the flow.”

In building Side Project Sessions, which offer creatives dedicated time to work on tasks that they have put off, what value do you think external accountability provides?

We all face internal blocks such as procrastination, distraction, self-doubt, expectations, and perfectionism that can get in the way of making time for ourselves and our creativity. There are also busy schedules, financial limitations, responsibilities and pressures, discrimination, lack of resources or opportunity to consider too.

Whatever might be getting in the way, I do believe creativity can be accessible to us all. It’s what often connects us and makes us human, but it can also be scary. It requires asking ourselves big questions, or putting ourselves first, or opening ourselves up to ridicule or rejection. I don’t think we should eradicate fear or tell people to “just do it”, but rather sidestep it and find ways to be a bit gentler with ourselves and our progress. We need to get a little creative with how we find time and get started!

That’s where a little external accountability or “peer-pressured productivity” can be helpful for some. I’ve also found it’s easier to get into the zone when we are given parameters — in the case of Side Project Sessions, it’s a 45 minute working session and a 15-minute break. Over time, this helps people recognize how much they can realistically achieve in a set time, which can prove useful when tackling high expectations, perfectionism, or planning paralysis!

The sessions are designed to tell you when to start and stop, similar to having a personal trainer, but for your creativity. The hardest part is often showing up for yourself. I find once I arrive and get to work or take action, time and time again, I find myself asking why I put it off for so long! There’s a magic and momentum to beginning, and it can be so helpful to have that little nudge.

How has shifting from full-time employment to freelance life impacted the way you schedule or manage your time? What advice would you give to people newly working for themselves on adjusting to a freelance life?

When I first embarked on a freelance writing career, I had grand delusions of how I would structure my working day. With the freedom of not having to rush in the morning, I’d rise early, exercise, meditate, eat a healthy breakfast, stroll to a café to collect my morning coffee, then sit at my tidy desk and tap away on my laptop for the next eight hours.

Instead, I found myself binging on Netflix; snoozing well into the mid-morning; scheduling unnecessary "meetings" throughout the week that would disrupt my workflow; sitting on Facebook for hours; moving between cafes, libraries, coworking studios, and my home office to find the “perfect” working environment (and never finding anything just right).

Three years in and I still feel like I’m learning to manage my time as a freelancer, but I’m now a lot kinder to myself about the figuring-it-out process. My advice is borrowed from a dear friend and illustrator, Gorkie: allow yourself to flounder. We can be so quick to rush the learning process, but it’s only in time that we see the lessons and can figure out what works for us.

Also, freelancing changes your relationship with time and money. Each hour becomes billable, which can create a lot of confusion, pressure, or even doubt that you’re not doing enough or making enough. For me, it was essential to build up a safety net before going freelance and making mistakes, and I still have periods of dipping back into full-time work to build up finances when necessary. For someone who might be less averse to financial risk, that might not be as necessary, and instead it could be about meeting a social interaction quota.

Figure out the ballast that makes you feel steady or “enough” — be it a regular client, savings, a coworking space, a knock-off time for your day, and try to remember it’s okay to flounder and figure it out as you go.

“Remember: it’s okay to flounder and figure it out as you go.”

Once you commit to an idea, how do you stay on track? What tools and practices help you manage time effectively?

When it comes to personal projects, something that helps me stay on track is remembering... I make the rules! I have a tendency to fall into a comparison trap and tell myself that I should be sticking to a certain content schedule or interviewing a certain number of people each month, but for me Extraordinary Routines and other projects are very much labors of love, so I can add to them and explore when the curiosity is there.

I certainly still struggle with staying on track and managing deadlines and personal projects, which is part of what drove me to start Side Project Sessions. I wanted that time, accountability, and quiet moments to put my creative work first.

As for tools, I’m a big fan of bullet journaling to keep track of goals. It’s also a great way to track what I’m putting off, and decide whether it’s still a goal that’s relevant to the things I want now, or whether it’s time to let it go.

In 2019, I started reading The Artist’s Way by Julia Cameron. The morning pages exercise is now a staple in my routine (which is otherwise quite un-routined!) and helps with clarity and seeing my blocks and sticking points reflected back to me.

And finally — and this is probably the hardest “hack” of all to master — I’m trying not to take it all so seriously. I’ve got a long way to go to put the fear of disappointment or failure or people not liking something to the side, but those glimpses of time where that all fades into the background is an unparalleled joy! A labor of love should be just that — love, curiosity, lightness, and delight.

You’ve said you like to look at habits as puzzle pieces. What are some “habit puzzle pieces” you have found work for you?

Over the years, there have been different puzzle pieces that have helped habits fall in place, and it changes depending on what my focus is or what feels like a fit during any given season.

For example, I recently embarked on a six-month sobriety stint. My drinking, like my habits, has always been ad-hoc, but when I did drink it would often have a negative domino effect on my days.

I wanted to experiment and see if eliminating alcohol would have the reverse domino effect on my days. Perhaps it’s no surprise that it worked a treat — starting from the evening, not drinking alcohol made it easier to put my phone or device away at night and pick up a book instead. I had the clarity and focus to read, but without the dulling of alcohol I was also more attuned to when I was tired, and so I started to fall asleep at a decent hour.

With better sleep, I had a clear head in the morning to stick to my new journaling habit. I also made healthier food choices as the discipline of not drinking brought a thirst for discipline in other areas. Feeling healthier, I could put more effort into exercise and eventually built up to running 5 km for the first time in my life!

Reading before bed or running for that extra five minutes might sound small. Still, given the difficulty I’ve had in the past with incorporating them into my daily life, this slow and steady accumulation of habits has felt sort of remarkable. It has taught me that building habits has less to do with self-control, and more to do with making it easier for yourself by finding the starting piece to create an almost effortless knock-on effect on your day.

“Building habits has less to do with self-control, and more to do with making it easier for yourself by finding the starting piece to create an almost effortless knock-on effect.”

As a freelancer, what strategies have worked for you in determining when to say “no” and when to say “yes,” especially as you build your business?

A “yes” comes easily — I can feel the excitement, I’m compelled to tell someone close to me, or I might even let out a little squeal of excitement. Those moments are what we cherish as freelancers and creatives!

A “no” is more difficult to discern — often concealed with confusion and doubt. Something I’m learning to implement is to give my responses space if it’s not a “heck yes” immediately. I often default to saying yes out of politeness or fear of never being asked again, but sitting with it for 24-hours won’t hurt anybody, and it gives me a chance to check-in and get a better sense of what I actually want. You can create a mess for yourself when you say maybe when you want to say no!

A helpful tool to determine when to say yes or no can be to test whether it checks two out of three of the following boxes: Does it pay well? Will it be fun? Will I learn something or meet a new connection? Sometimes it can be helpful to pretend you’ve made the decision already, and check-in with how you feel. Do you feel burdened by the yes, or maybe regret over the no?

Other instances might require you to flip a coin and go with the flow! We have less control over the outcomes of our decisions than we think — and you never know what might change your course. Often it’s what pops up without any decision-making, planning, or warning at all.

What makes you feel like you’ve spent your time well?

Time well spent is when an ordinary day, for no rhyme or reason, feels extraordinary! A commute where I don’t look at my phone, a coffee with a friend who has news, a new song to love on my Spotify Discover.

Time well spent is when I keep the promises I made to myself. Be it a promise to start or finish a personal project, or to go for a long walk, or to sit in the sun and do nothing — the “well” part is ever-changing.

Time well spent is when internal or external expectations slip away and I take joy in doing the work rather than focusing on when it will be done.

Time well spent is being open to the moment.

“Time well spent is when an ordinary day, for no rhyme or reason, feels extraordinary.”

Time well spent can also mean wasting time!

Sometimes when we think about spending our time well, we think about maximizing our time, causing us to worry that we are wasting it, not doing enough with our time. This belief that time is something that can be wasted can be harmful to creative projects and following our whims — what if it’s a waste of time? It can also be exhausting — if we worry about wasting time, then we might not take the breaks, rest, and moments of respite we need to sustain ourselves.

I think the surest way to squander time is to worry about wasting it. We need to waste time, we need to follow our whims, we need to see where something may take us, and we need to rest.

In the words of Arnold Bennett, “The chief beauty about the constant supply of time is that you cannot waste it in advance. The next year, the next day, the next hour are lying ready for you, as perfect, as unspoilt, as if you had never wasted or misapplied a single moment in your career. Which fact is very gratifying and reassuring? You can turn over a new leaf every hour if you choose.”

Imagine you’re reflecting at the end of a day where you felt that your time was well spent. What did you do? How did it feel? How much time did you spend doing it?

“Routine” version:

  • Restful, uninterrupted sleep. (7.5 hours)
  • Make a pot of herbal tea and do morning pages journaling. (1 hour, morning)
  • Read the obituries like Maira Kalman to remember to seize the day! (30 minutes, morning)
  • Dance to Bossa Nova music like Mari Andrew. (30 minutes, morning)
  • Hop onto my hypothetical treadmill desk and write like Heather Havrilesky. (3 hours, morning)
  • Receive and respond to a life-changing email. (30 minutes, midmorning)
  • Go for an (effortless) 5km run. (1 hour, midday)
  • Attend to emails, life admin, maybe even sort out a cupboard drawer (1 hour, early afternoon)
  • Dabble on a side project. (2 hours, afternoon)
  • Visit my favorite fresh produce market and chit-chat and browse like like Julia Busuttil Nishimura. (1 hour, afternoon)
  • Enjoy a conversation with a stranger. (30 minutes, afternoon)
  • Take a nap like Ken Done. (30 minutes, late afternoon)
  • Have a pot-luck dinner with friends. (3 hours, early evening)
  • Switch off my devices and practice the piano. (30 minutes, evening)
  • Shower and do some evening stretches. (30 minutes, evening)
  • Read in bed. (1 hour, late evening)

"Rut" version:

  • Sleep. (9 hours)
  • Repeatedly hit the snooze alarm. (1 hour, morning)
  • Feel guilty for sleeping in. (30 minutes, morning)
  • Fall into a comparison spiral scrolling Instagram. (3 hours, morning)
  • Take a short-cut to alertness and drink 3 soy lattes and skip morning pages. (1 hour, morning)
  • Intermittently stare at a blank Word document. (6 hours, morning to afternoon)
  • Avoid the gym. (1 hour, early afternoon)
  • Craft an overly-ambitious to-do list. (30 minutes, afternoon)
  • Eat slices of cheese intermittently. (30 minutes, afternoon)
  • Finally shower and sit in my bathrobe. (1 hour, late afternoon)
  • Go back and forth about going out for dinner or staying in. (1 hour, early evening)
  • Wallow in FOMO. (1 hour, evening)
  • Drink too much wine. (3 hours, late evening)
  • More phone scrolling in bed. (1 hour, late evening)
  • Reflect on the day, decide you don’t need to feel guilty for doing nothing — you don’t always need to be on, to wake up early, to be productive, to be in the world. You’re not a failure just because you didn’t meet the ideal version of a day only you set for yourself. Time is yours to spend, each hour unfolding without judgement from the last. Sleep. Be. Do nothing. Turn your mind off, and embrace it. 1 fleeting minute, just before you doze off.