Ryder Carroll

Interview by Madeleine Dore

Ryder Carroll: author & digital product designer

Full transcript

Full interview transcript

“Philosophy, as far as I’m aware, was designed to help you figure out how to live better and that’s exactly what I had been trying to do, but my answer was productivity. And I realised that a lot of my productivity ended up being empty and, though I could accomplish my goals, that didn’t make me any happier.”
– Ryder Carroll

Madeleine: I have long loved a list. There’s something so soothing about putting a pen to paper, checking off a box, planning a new week, a new month. I’ve had various dalliances with different notebooks and weekly journals, but since watching a tutorial on bullet journaling a few years ago, I have been a loyal follower.

If you’re not already familiar, the Bullet Journal is a customisable notebook used to track the past, organise the present, and plan for the future. There are countless Bullet Journal groups on Facebook and Instagram accounts with thousands of followers, all dedicated to the art of Bullet Journaling.

Mine is quite humbly composed with an erasable pilot pen, but it begins with a five-year plan. Then I create an annual list, so more specific goals, whether it’s personal or work or passion projects for the year ahead.

Then I’ll have monthly to-do lists, also accompanied by a habit tracker, which I will experiment with month to month. So it could be that this month I really want to focus on putting my phone away before I go to bed, or taking my vitamins, or tracking what time I’m waking up, and that’s a way for me to take the long view and see what habits I’m actually sticking with and what has been useful for my day-to-day life.

Then I move into more of a weekly to-do list with different deadlines, and then I also have daily to-do’s and notes and schedules and meetings and so on. If that all sounds a little bit overwhelming, perhaps it’s because, like any love, my affinity for lists can actually turn into a bit of an unhealthy obsession, and that obsession comes in the form of over planning.

For as long as I can remember, when I’ve begun to feel anxious or uncertain or overwhelmed, I will reach for a blank piece of paper and write a list. It could be a list of things that are hanging over my head, a list of life admin, a list of ideas, a list of deadlines, a list of dream careers, a list of people I admire or envy.

I think I’m trying to pinpoint what is missing and what I need to fill the void with. What I need to control. But, newsflash, there is no certainty and control is an illusion. In this way, my planning is interlinked with procrastination and perfectionism, and I suppose fear. Fear of uncertainty.

It’s not the planning that’s the problem, but this tendency to over plan. This tendency to really search for control. It’s, in some ways, a way to avoid starting that feels productive and a way to soothe ourselves from uncertainty, but also from possibility.

Life doesn’t quite work in this way. Even the plans I had for this month have morphed, let alone what will happen to the ones that I have for five years. As John Lennon put it, “Life is what happens to you while you’re busy making other plans.” 

And more and more, for me, the Bullet Journal is a way for me to reflect on what’s important. It’s teaching me to be more intentional with my lists, and therefore my life.

If there’s one person who understands intentionality and the possibility of the Bullet Journal, it’s this weeks’ guest. Ryder Carrol is an author, digital product designer, and the inventor of the Bullet Journal Method.

In this conversation, Ryder speaks about empty goals, the book writing process, and creating your own structure and pattern as a freelancer and independent creative. We also dive into a period of his life and career where he experienced what he describes as rut after rut.

As Ryder puts it, the Bullet Journal is almost a paper mirror. A way for us to track the ebb and flow of our lives and, most importantly, it helps reflect the deep reasons why we do the things we do.

So, to begin, here’s Ryder on starting with the small why’s.

Ryder Carroll: I think just asking that question about anything is really important because when we don’t ask that question every time we have to ask that question, it’s already too late probably. Why didn’t this work out? Or why is this goal feeling so empty? It can provoke some existential crisis. Why did this happen to me? Why is this happening?

And that’s real. And that will happen. But I started realising that, when I started questioning the smaller things in my life, I got more comfortable thinking about it in that sense. Like why am I taking this meeting? Why am I working on this project, these small things? Why am I working on this task?

And all of a sudden it became much easier to think through it that way and would relieve the pressure that you usually have when you question something that you’re doing. We don’t like doing that often because we’re so busy and focused on doing the thing, that we’d rather just complete it than challenge it.

So if you start with really small why’s, you get comfortable with challenging things and you can work through it faster as well. You don’t have to stop everything you’re doing and, when you’re asking why, you start getting a better birds’ eye view. You start compiling all this different knowledge, this self-knowledge, that helps you work quickly, work through bigger and bigger and bigger why’s.

To be clear, it’s not like all of a sudden you’ll have the answer all the time, but you get in the habit of asking the question, which, in my experience, has resulted in me working on far few things.

MD: It’d be lovely to hear what you’re working on now. The book came out in 2018. What is your main focus? What are you thinking about?

RC: After the book came out, I spent a long time going on different tours and speaking to different people, which, for me, was one of the first times that I could actually connect with my community in person. It’s funny because it is an analogue methodology after all, but the entire business and company is run online.

A lot of what I work on is just trying to create new, different kinds of educational material to help people see how Bullet Journaling applies to their life. When I started off, I used to say it can be whatever you want it to be, and for some people that was great, for other people that was really overwhelming. It’s like, I don’t know what I want it to be, what I need it to be. I need you to tell me how this is going to help me.

And that’s fair as well. There is that fear of the blank page. It’s infinite potential and opportunity. Where do you begin? So what I’m trying to work on right now is helping people see themselves in these different use cases.

MD: Yeah. Coming back to the Bullet Journal, I always like to keep the very first page blank because I don’t know what to do with a blank page, and then I can feel I can move on and start filling out the pages. But limitations can be really powerful in that sense. So, does that mean that a lot of your day is spent writing?

RC: It depends on what I’m working on. The thing that I love most about Bullet Journal as a company is there are so many ways I can go with it and a lot of these projects that I’m working on require different talents, so I’ll focus on whatever I believe to be most impactful for the community, and that will have different phases. So there will be the ideation phase, the design phase, the execution phase, the marketing phase.

So it keeps me switching between different hats, if you will, and that’s what I love most about my career as a product designer as well. I liked working for agencies because I could always work on different things. I try to have the same model with my own business because I see all my different projects as different products, whether they’re a product or not. I approach them as products.

These products are designed to solve very specific problems for my community, so the notebook allowed me to transition to doing more Bullet Journal work and, in that process, I started learning more about community questions, engaging significantly more directly with the community, and people’s questions started changing. 

Rather than, how do I deal with recurring tasks or how do I deal with project management, people would start asking questions like, what is a meaningful goal? Why should I be working on these things? 

And these are questions that I find fascinating as well, and I would get more and more of these questions and, rather than answering them individually, I was like why don’t I create something that could show people why I use the Bullet Journal? Now just how I use the Bullet Journal, but what it could be. And, over time, that’s what gave rise to the book.

MD: It’s a great book. It really does pull together so many snippets of psychology and philosophy. What was the book writing process like for you? Did you use a Bullet Journal to map it out or make notes? How did you pull everything that you’ve learned together?

RC: I’d never written a book before, so it was a real learning process. The best way I can describe writing a book is a book is a being. At the very beginning, it is an infant. It has no idea what’s going on, but it’s there. It falls over, it doesn’t know how to walk and, over time, it starts to grow, and all of a sudden it becomes an adolescent and it starts disagreeing with you and you don’t really see eye to eye and it has its own opinion about things, and eventually it becomes a peer and you start talking to each other. Ideally, one day, it also surpasses you.

The thing is it would be hard for most people to remember every single thing they put into their own book and have that in their mind at all times, so in some ways I was trying to create something that was better than me on an everyday level, if that makes sense.

MD: Yeah, that means you can refer to your book when you need it.

RC: Yes, and I do. There’s a tremendous amount of research that went into that and that’s stuff that I can’t keep in my mind at all times. The thing that’s so beautiful about writing a book, which is the same benefit that I see in Bullet Journaling, is that everything is trapped on the page. Everything’s captured there. And you can start to identify patterns.

Especially in the process of writing a book, you are exposed to so many things and writing and weaving all these ideas together not only helped me think more clearly, but also allowed me to discover things that I hadn’t known going into the process.

One thing in writing the book is that I investigated the benefits of handwriting because I wanted to see if there are any. I felt like they were, but that’s not good enough for me to share with the community. It’s like, I think so, so that’s the way it should be. No, I wanted to have really informed opinions, so I did my best to find sources that would tell me whether or not this was the case, so I got to learn more about the science behind the thing that had helped me in practice but I had no idea why.

MD: That must be such a nice feeling to see that reinforced through research. What are the benefits of handwriting?

RC: The ones that stick with me are, one, pattern recognition. When you’re writing by hand, you’re engaging your mind and your body at the same time in a way that you’re not when you’re typing or even writing on a screen on a tablet. So though they’re similar processes, apparently this is significantly more potent and so a lot of times you’ll be able to start identifying things that you may not have before.

You start seeing relationships between different ideas. It also embeds the information that you learn, that you actually write, deeper. A lot of studies I found were comparing students that were typing their notes versus handwriting their notes and almost, without fail, the ones that would write their notes would have better recall during an exam, but also afterwards they would be able to remember the information significantly longer because they had imprinted it more deeply in their mind.

And I found that to be true as well because most of my career I was a digital product designer, but I’d always come back to my notebook because it allowed me to engage my mind in a different way. I could feel things moving around up there in a different way.

So memory, pattern recognition, and then also it allows you to gain distance from your thoughts in a different way, and that’s why journaling is used to treat many different kinds of mental conditions, so OCD, PTSD, and a lot of that comes from people taking their thoughts and writing them down by hand. 

There’s something very personal there and I find that to be true in my life as well. It’s not just about writing down a bunch of notes, sometimes it’s about untangling some kind of very challenging idea or notion or feeling, and it’s interesting how much easier it is to think through those things when you write them out.

One of my favourite lines is that you write in order to learn how to think, and I feel that to be really true. Not just with Bullet Journaling, but in the process of writing the book.

MD: Yeah, absolutely, and it’s about thinking on the page as well. I do stream of consciousness journaling practice and what I love about it is how I surprise myself because I get to see my own conscious mind on the page, and I love the reflection element of the Bullet Journal for that reason as well. 

A lot of the Bullet Journal is about intention and reflection, and so I’m curious to hear about how you approach your days, whether you’re quite routined as a result of being someone who is quite reflective and intentional, presumably.

RC: Well, that’s the thing, people always think that I’m some mega-productive person, but the Bullet Journal exists because I need it. And I still use it all the time. It just helps anchor me. It provides a way for me to fight against my instincts in some way. It’s like, oh, I just want to work on this, or I’m just going to work on that, but no, I have a list of things that I need to do, and I check them off.

So my routine loosely is based on trying to tackle the thing that has the highest priority that I want to do the least. I do that first thing in the morning. Whether it’s fill out documentation or deal with some kind of inventory issue, that’s the last thing I want to do in the day, so I put it first because willpower is the highest then.

MD: Yeah, it’s like eating the frog quote. Mark Twain used to say that if you eat a frog first thing in the morning, then that’s the hardest thing you’ll have to do all day.

RC: Yes, exactly like that.

MD: So in terms of putting that at the start of your day, what does the morning look like? Do you wake up at the same time every day?

RC: Yes, I roughly wake up around 7, 7:30 naturally, no matter how late I stayed up, so that’s something I had to deal with. I don’t know why I’m programmed that way. So I wake up and usually the first thing I do is meditate and journal. Actually I journal and then I meditate, which I find that journaling actually helps my meditation practice because my mind is so full when I wake up in the morning, I kind of just declutter it.

MD: Ah. I’ve always wondered about the order of that. There you go.

RC: For me, it works that way because I know, as soon as I start meditating, all those thoughts are going to get in there. Meditation isn’t about not having thoughts, but I feel when I write things down before I meditate, I have less thoughts.

MD: You’ve cleared the clutter for thoughts that might be new thoughts.

RC: I think so. I feel like that helps a lot. Plus I also just feel ready and prepared when all the thoughts are written down. It’s like the plan for the day is ready. Here are my priorities, here are the things I didn’t want to forget. Okay, now let’s take a moment and think. Journal, meditate, and then, depending on the day, I’ll either go to the gym or I’ll just start emailing immediately.

But I try to make sure that I’ve checked in with myself before I engage, before I go online, so that’s helpful.

MD: And when you say check in with yourself, does that mean doing the AM reflection that you talk about?

RC: The AM reflection. So when I journal, it is the AM reflection. I go through my previous pages and make sure there’s no open tasks or, if there are, are those a priority for the day or not? And then, again, declutter my mind and then mediate. So that’s the way to get my mind ready for today.

MD: And the days that you skip that, does the whole day feel like a domino effect?

RC: Sure. It’s one of those things where, when I don’t Bullet Journal, which happens from time to time, and for the last couple of years I’ve been writing about the Bullet Journal, talking about the Bullet Journal, Bullet Journal, Bullet Journal, you know, it’s too much of anything. You can’t eat cake all the time

So sometimes it’s just like, I don’t want to. I just don’t want to do this anymore, and then things start to fray and I realise why it is part of my life. When I don’t have the tool around, all of a sudden, I forget things, or I don’t do things, or I feel like I’m forgetting something.

I read somewhere once that anxiety is the residue of things that you’ve forgotten. I don’t know if that’s true or not, but it certainly feels that way. So all of a sudden, I’ll be like, okay fine, and I get right back to it and I just feel better. It’s a form, not only of productivity, but for me it’s self-care and it keeps my mind clearer and more focused.

MD: I’m assuming that you work from home or have a home setup. What are the benefits and the bumps of working from home?

RC: When you work for yourself from home, I would say the bumps are that you’re never not working and you’re always in the office. I would say, for me, one of the things that I found really challenging also was that I miss having a team that I’m surrounded by. I think that’s something that you don’t realise how important it is until it’s not there.

There are plenty of people who work in teams and they just take for granted, this is work, this is how jobs work, which was most of my career as well. Even if they’re people you have to work with that you don’t like so much, the thing is that you are interacting with different minds, which changes the way that you think as well.

That’s what I loved about being a product designer. I would be in a room with people that had the same skills that I did and they would help me learn because they would help me identify things that I wouldn’t have seen on my own, and that’s something I miss working for myself, by myself. I don’t think I learn as quickly, and that’s why it’s really important for me to be engaging with the community because I learn things from them all the time. There are parts of my practice that are directly taken from them.

In the future, I would like to establish a team that I’m in direct contact with, just because that’s really important.

MD: So at the moment, there’s people that might be remote?

RC: Yeah, I have a distributed team. They all focus on different things. We have customer support and social media, and just odds and ends that can be done from anywhere, and that’s incredibly helpful to me but it’s just not the same thing. Maybe I’m old fashioned but I like being in the same room with people.

MD: Yeah, and I guess you’re really touching on what’s tricky about being either a freelancer or someone who works for themselves or a creative, is that you don’t have your structure imposed in the container of 9 to 5. You have to really figure it out for yourself, when you work, when you switch off. In some ways, do you think that the Bullet Journal could be helpful for people who might have to create that structure?

RC: I can only speak for my own experience and what I’ve heard from my community. The thing is that, when you work for yourself, you’re not aware of your own patterns a lot of the time. It’s easy to work forever. You’re working all the time, every day.

MD: Or not at all, as in my case.

RC: Or not at all, depending. But the thing is that you might. I feel like when you’re not working then you feel guilt or you have shame, so you’re aware of that. But when you are working, you don’t really experience that because you’re doing your thing. This is what you do, this is who you are, you identify with it in a very different way.

And I feel like, in my own practice, I’m like, oh my god, I haven’t gone out and met any of my friends for a long time, I haven’t made any room for play in my life because I’m seeing how my days are unfolding. I haven’t talked to anybody, not for work, in way too long. You can start sealing yourself into your own business, if you will, because it means so much to you. You identify with it in a way that you wouldn’t another job.

So I feel like you can become much more aware of your own patterns and habits, and I certainly have as well. So, okay, at six, I’m going to go do something not work and with other people. That kind of thing. The work can wait, and I feel like that’s part of the mindfulness and reflection as well.

Or sometimes you feel like you should be doing something and then, upon further reflection, you realise that it really doesn’t serve a greater purpose or you appropriated that goal or that mission from, I don’t know, something you saw on YouTube or Instagram. It’s like, oh, this is how I should approach this, or this is what I should want for my company, and upon further reflection, I just shut that down. That’s not why I’m here, that’s not why I’m doing this.

And so my Bullet Journal is very much like a paper mirror. It reflects back what’s going through my mind and what I’m allowing into my life and, when I check in with myself that way, again, I try to work on less and less things. When I’m not working on anything, that’s a different problem. That’s a whole different thing. That can happen as well, but generally speaking my issue is that I’m working too much and that’s not necessarily a good thing.

MD: Yeah, it comes back to asking yourself those little why’s, and one of my favourite tools in the Bullet Journal, which people might not be familiar with, is the migration. So whether it’s monthly, coming up to that monthly reflection and seeing what you might have put down for November and then seeing that, actually, why is that on my list? Is that because I think I should be doing it? And being able to check in with yourself with that.

I think that’s really key. It also, for me, really helps to see when I’m setting expectations that might be too high on what I’m either capable of in a given month, and it also really has exposed to me over time, the paralysis that can come with over planning, and I wondered if you could speak to how planning can actually be procrastination?

RC: Sure. I think planning and perfection go hand-in-hand. You create this perfect plan, and this is how you’re going to do it and you’re going to write four hours a day for the next month and then your book will be done, right?

MD: Yeah, easy.

RC: Easy. I don’t know, for me, I’ve stopped setting goals that way. For me, the way I see goals is that they’re lighthouses. They’re not a target, right? A ship never steers towards the lighthouse. He uses the lighthouse in order to make its way and orientate itself, so my goals are the direction that I want to head, but I’m not going to get to that place. And seeing goals that way allows me much more latitude in how I approach the thing that I’m trying to figure out or work on.

So, for me, the most important part is focusing on the process all the time. It’s what am I learning, what should I be moving towards, and course-correcting constantly. At this point, other than very few things in the real world, like somebody needs to be opening this door on August 16th to accept a delivery, other than that, my goals are much more about what am I learning and to give me some direction. 

And that has allowed me to also be much less hard on myself because, as long as I’m working, as long as I’m showing up every day, I will make progress and maybe the deadline will have to shift, which is a blessing and a curse when you work for yourself because you create your own deadlines. I would say I’m not good at that. 

My deadlines are really hostile towards me. I expect so much of myself and then that works against my ability to actually motivate because I’m like, oh, I’m so behind on this thing. But now I think again, what is the purpose? Why am I doing this? Am I working on it? Am I making progress? And that way, if I focus on just showing up every day, then that’s enough.

MD: Yeah. Love that, and it ties into another concept called sprints Bullet Journaling, and I loved how you were very clear about however long you think it will take, double it. So that can be really helpful.

So if we return to your day, you spend the morning emailing and prioritising. What happens when you hit lunchtime or the afternoon?

RC: Lunchtime for me is like recess. Depending on my workout schedule, sometimes I go out and grab food and eat out or prepare lunch at my place, and then I can do whatever I want for an hour. I’m just allowed to surf YouTube or read whatever news that I want to, but there’s no restraints. I have an hour of not having to focus.

I eat and I watch. Ideally, I should just be focusing on eating, right? That’s the mindful thing to do, but I feel like I spend so much of my time trying to focus and concentrate, I really like the idea of just blocking that off for a minute.

So I have an hour just to do whatever I want and then I get back to work. After lunch, I usually keep the latter part of the day open for things that I do want to do, the things that are really creative. 

The way I set up my day is in the morning I work on things I don’t want to do. These are the vital things, if you will. Things that are not fun to do but are really mission-critical down the road and I know that, if I don’t do them in the morning, I’m not going to do it in the evening. It’s why I work out in the morning. I just won’t work out in the evening. I know that about myself because I’ve tracked it.

So these are the things that I’ve gleaned. I’ve tried all these different things and here’s where the hit ratio is much higher. And in the evening, I try to do the stuff that’s much more fun for me, so it’s something that I look forward to.

On the best days, the things that are mission-critical and the things I love to do are the same thing.

MD: Yeah. Can you give us an example of what that would be?

RC: Writing. So when I was writing the book, that was the mission-critical. That was it. That year, I really spooled down everything else. I just focused on the book and I realised that, for me, there’s certain type of writing, when I started writing the book, I’d have to literally get up, no habits, no anything, I’d just walk over the computer and start writing because my mind was still really fuzzy and foggy and very creative and generative and that was a great way to start getting the material I needed to write.

But then later, my writing habit would change to later on in the day when I started having to sculpt what I had written, so my habit would change depending on the phase of the book. But usually writing in the morning is something that I just really like to do. I can write easier and it’s more enjoyable and I’m not as hard on myself because my mind is not as critical at that point. The gears are still not really catching.

So that’s something, and also design work. I really like waking up and doing my AM reflection and journaling and then using that to immediately hop onto getting into design work, which is, to this day, one of my favourite things to do.

MD: So do you still take on freelance clients for design work? Or it’s design work for Bullet Journal?

RC: It’s all Bullet Journal design work. There are many different things that we’re working on right now. I still see myself as a product designer and it’s nice to be able to spend time with this thing that I’ve based my whole career around. It’s not the focus for me anymore, but being a designer can be helpful in so many different ways and I feel like a lot of Bullet Journaling is about design but it’s got lifestyle design about designing your mind, about designing your life, and designing your days.

MD: And it’s interesting to hear how you got into, specifically, digital experience design because it wasn’t what you set out to do for your career. And it took a bit of a stumble, a bit of unfortunate circumstances to redirect you, or direct, you here. Do you want to speak about that time, which was your first year in New York?

RC: I moved to New York the year after 9/11 and I moved here to actually start an internship of my dreams. There was this company who worked on title sequences and originally I wanted to do music videos, but by the time I graduated college, that wasn’t a market anymore. There was no money in that. 

But title sequences started to become really popular and there was something I loved about that it was both graphic design and filmmaking in one. So I got an internship with this company run by my hero at that time and when I showed up, I called them and was like, when can I begin? They were like, oh, didn’t anybody call you? I was like, what do you mean? I just moved to New York with everything I own and got an apartment.

They were like, yeah, sorry, we’ve downsized, this and that, and so I spent the first 14 months in New York unemployed, looking for work in one of the worst job markets in recent history. It was another unemployed art major, and then eventually I took the first job I was offered, which was working as a production assistant at a very big publishing company. 

For the most part, I designed order forms. It was a miserable job because these order forms were hundreds of thousands of lines of just titles of books. Nobody knew how to do it properly and the technology wasn’t there, so something would always go wrong, and I feel like it was a job that people were hired into because they needed scapegoat.

All these different people were like, uh, we don’t know how to do it, you do it, and everybody before me had left that job running. It was so miserable that it forced me to make a decision, and that decision was I have to become more valuable. I continued looking for work and I didn’t have anything to offer these employers that made me special.

And that was a really hard thing to hear because in college I did well and I was proud in the work that I created, but in New York nobody cared. This is an incredibly cutthroat city in that sense, especially when it comes to talent. Everybody’s really good. Especially back then. But I had nothing that I could offer my employers and so I started taking night classes and web design.

This new job of web design, something that wasn’t even offered when I was in college. I took my tiny salary from this production job and took night classes until eventually I learned how to build websites and then I would start taking on freelance clients and I did that until I could finally leave.

MD: It’s amazing how… I’m really passionate about side projects and how they can often shape our career. It is the thing that makes it special, us special, in our careers. It’s also often the thing that’s most meaningful to us, too. It really opens up surprises, I think, and I think maybe the lesson there, I’m not sure if you agree, but that those ruts in our life can actually be quite potent for learning or redirecting, and sometimes we need to fall into the rut to be able to see where we want to go. 

Was that helpful for you in that time? I know that there was the story about the flooding in your apartment and you lose your whole portfolio, which would be, I’d imagine, quite a creative rut.

RC: Yeah, so not very long after getting the news that my internship disappeared, the place that I was staying flooded, so I lost all of the materials I was using to get a job. Not that they were helping much anyway.

It was just a rut after a rut. All I wanted was a job. Okay, here’s your job. Oh my god, all I want is a different job, this is terrible. At least I could pay for my food and pay for rent, but at the expense of my wellbeing.

It was such a bad job and I worked with people who made coming to work very, very hard, to the point where I was actually scared of going to work because you never knew what was going to happen or you were going to be playing for. It was a bad, bad situation. I felt much worse having a job that I hated then not.

I don’t know if you can actually compare those. They’re two different kinds of very real misery, but, over time, I just realised that if I don’t make a change, if I don’t do something about this, there is no lifeboat. It’s like Seth Godin’s thing, there is no lifeboat. You build your own. And that’s what I set to do.

And I did that by taking classes and learning about this thing that was just interesting to me. It wasn’t so much about web design, but it was about this new way of telling stories. That’s what web design was for me. It wasn’t about creating a website, which that’s fine as well, I learned how to do that, but I would go online back then, 2002 or something like that, and people were creating these little movies or interactive experiences. I was like, wow, this is really interesting because that hadn’t really existed like that before. And they were terrible. Using GIFs, the technology wasn’t there yet, but the potential was there, and that fascinated me.

So I just started with the basics. How do I get things online? And I built my own portfolio, and that portfolio, A, couldn’t get flooded out, and, B, helped set me apart from all the competition and eventually I fell in love with making websites. When that got old, I started building digital products, which were significantly more complicated, and they were different kinds of narratives and puzzles.

I used a lot of that learning to form the Bullet Journal. There are a lot of different agile approaches that are used inside the Bullet Journal, except rather than focusing on a product, you focus on your personal life. So your life becomes the product.

MD: It’s just a great example of small steps as well. I’m sure it would’ve been impossible for you to make the goal of be the creator of Bullet Journal. Do you think that, if you could go back to that younger self that had the portfolio flooded on the floor, that you’d be quite happy with where things ended up?

RC: I can’t complain, no. I feel incredibly privileged to do what I do now, and as a product designer, the goal is to build things that help people and the whole thing about the Bullet Journal is, of all the things that I’ve worked on, that’s the thing that helps the most people, so I love doing what I do.

I think it’s really important to state that, even when you run your own business, there are plenty of things you’re going to hate doing. Things that are just so far removed from your curiosity, but that’s just what it takes. But even with all that, it’s fantastic.

Part of me wishes that I could’ve told my younger self what was going to happen, but the other part is like, you don’t want to mess with that because maybe they wouldn’t have been as hungry.

MD: Yeah, exactly.

RC: It’s like, oh, it’s going to work out just fine. It’s more like, well, it will work out just fine if you work it out. And that’s really, I think, everything that I’m proud of today was in some way really hard.

One, in my own experience, I had to have those experiences in order to appreciate everything that came next. Even when I had jobs that I wasn’t blasting out of bed in the morning to go to, I knew that they were orders of magnitude better than the first job I had, or than being unemployed.

Having that base level of gratitude made my work better because I wasn’t spending all day like I have seen, where people are like, why am I doing this? Why do I have this job? Well, the first thing is, you should be grateful that you have anything. And that base level of gratitude has helped me, but it’s also made me much hungrier, knowing how bad it can get.

MD: So, I guess to come back to your day, it must mean that you sleep well?

RC: That’s funny that you mention that. I don’t. And I realised that, so earlier this year I read Why We Sleep. It’s making the rounds right now, it’s a fascinating book. I was like, hmm, I should track how well I sleep, and as soon as I started tracking my sleep, I realised that I don’t sleep.

And this is one of those things where becoming self-aware is really important. As far as I was concerned, I went to bed, I woke up, fine, done. I never really had a problem with insomnia or anything, but when I started realising how many hours I was actually sleeping, I was like, ooh, I need to start changing things in my life.

This was an unconscious problem, so I’ve started tweaking things and it has got better, but it’s a work in progress.

MD: How much are you sleeping on average then? Or what interrupts your sleep?

RC: That I don’t know yet. That’s TBD, but I’d say I average between 4.5 and 5.5 hours of sleep a night, even though I go to bed at any time. But I’ve definitely changed my schedule to get better at that, and chances are very unlikely that I’m part of the 2% of population that can get by on that kind of sleep.

I think a lot of people, especially entrepreneurs and people who run their own businesses, like, I’ll sleep when I’m dead. I was like that as well, but the more you read, the more you realise, well, the more you work, the sooner you’ll die. So it’s an important thing to have a balance and, for me right now, this is one of the challenges that I’m trying to work through and I’m trying to be as mindful and intentional with my choices about this.

For example, my PM reflection marks the end of my day. That’s when I go screenless. So once I sit down with my notebook, I try not to be in front of any screen for an hour before I go to bed, and that, in itself, has been kind of a revelation because what do you do for an hour you go to bed?

The answer is so many things, right? Maybe learn how to play an instrument or you can actually sit down and read. All these things that were just kind of lost because of just checking your phone unnecessarily over and over and over again, which ends up making it harder for you to sleep, which makes you more tired, which makes you less productive, which makes you check your phone even more. It’s just this terrible cycle.

So, for me, I have AM and PM reflection as my digital detox window. And that’s been really nice.

MD: I like that. Do you also still have a ritual that is tied to remembering that we’re all going to die?

RC: I do. I usually wear a black band or a watch and that’s my memento mori.

MD: And that ties into that reflection time as well? Or just at any moment?

RC: Any time I check my watch. Or that I see it, or I feel it. I try to keep something on me that is unexpected in some way, like maybe it’s a coin or something, but every time I bump into it, it just triggers my mind. It’s like, okay, why are you doing what you’re doing? That kind of thing.

Or when you get super upset, it’s really nice just to hold that item. Just be like, this is not important. Because, when things get rough, a lot of times it becomes pervasive. You didn’t get along with somebody at work or something happened in your apartment, countless things, and all of a sudden, it’s all that’s on our mind.

Sometimes it’s really hard to remember that this will pass. It’s not pervasive and it’s taking up way more room than it should.

MD: It’s nice to take that birds-eye view and think about whether you’ll even worry about this in a year from now.

RC: Yeah, I feel like the time where we remember that often is when you have either a close person in your life who experiences a tragedy, or you do. There’s a moment of clarity after that happens. You’re like, wow. Things are okay.

Or if you’ve just gone through some kind of scary medical procedures and you wake up the next day, then all these problems at work just don’t seem that important. And it’s hard to keep that top of mind, and I think that takes training and practice and a big part of what I try to do with Bullet Journaling is to train my mind to remember things that, overall, make my perspective more helpful.

In terms of my routines, the thing that I need is novelty. So every month I try to either add or subtract a habit and see how that works, so things are new and fresh. I realise that my ability to sustain a habit is directly aligned with how interested I am in that thing, and that no matter how interesting something is, over time it can fade in its novelty. 

So I always try to change something up every month and I give things, usually 30- or 90-day trials, which also makes life interesting and fun. It’s like, oh, I’m going to cut out this thing from my diet, or I’m going to work out this many days, or play has to become a priority this month. Like, every day you have to play for half an hour and learning how to define what play means and just these little exercises in life to make things interesting. 

I need that, and so I feel like that helps me with my habits and routine. So you routinely change your routine. If that makes sense. 

MD: I love that. Well, it’s experiments. It’s wonderful. I open to life experiments myself, and one of them was to have no social life for a month and see how that actually influenced my day because I found that I’m a very introverted person, but I find that I was spending about 20 hours per week with people, whether it’s going out or dinners and so on. And that’s a lot of time with people for someone who needs a lot of alone time. 

And so it was a great way to realign how much time alone I need and also saying no to other people so that you can say yes to yourself was the biggest takeaway. So feel free to play with that one.

RC: Saying no is definitely a big one. Yeah. I mean, the thing that’s interesting about saying yes to things is you’re not just saying yes to possibilities that may or may not align, but you’re also saying no to resources. That’s the thing. It’s not just potential other projects you could be working on, but as you said, it’s emotional resources or mental resources.

So saying no, that’s something that I don’t have a problem with so much. I’ve got a lot better at saying no because I’m very careful with how I allocate resources, if you will. But it works in both directions, too. Like why are you saying no? Why are you saying yes? And trying to link it back to what you want to get out of this. Is this something for you? Is this something for them? You can’t say no to everything and making that choice, I think, becomes much easier when you’re aware of what you’re trying to accomplish or what you need. 

This isn’t like a huge life goal, but it’s like, I want to have better friendships. Then okay, you should say no to the business meeting and yes to that friend from back home that’s not going to help you become wealthier or this or that or the other thing. It’s just somebody that you love, spending more time with them. 

That’s more important right now. You can build your business a little bit later. So I think, when you’re aware of what you need in your life, or what drives you, that’s an easy way to figure out what to say yes to or no to. Easier. Not easy. It’s always hard to say no to big opportunities.

MD: Yeah, and to people. It’s hard to not feel like you’re hurting someone with a no.

RC: That’s true.

MD: One of my favourite lines in the book was, “Find music in the mundane”, and I was wondering what ordinary, small moments are bringing delight to your days?

RC: I think that’s the beautiful thing about the days. You never know. But I think that you can’t know if you’re not paying attention, so I find a lot of them when I’m bored, and boredom is relatively uncommon in my life, but sitting on the subway or waiting for a train, or something like that, I start trying to find something interesting.

And all of a sudden you can. Maybe it’s somebody’s funny little hat or the way that some couples bickering and they’re obviously angry at each other, but they’re both also smiling. These tiny little things that help you connect with the world around you.

Or sometimes it can be manufactured as well, for example I was doing dishes the other day and, as I mention in my book, it’s not my favourite thing, but it had been a really busy day, it’d been a really hard day, and this was this one thing that I could just control and be with. 

So I put on music that I liked, and I was scrubbing these pots, and it was nice. It was just a way to relax. And it’s doing the dishes, but all of a sudden you could smell the soap and I was using my hands. I’d been using my mind all day, and it was just changing my context. And I find that very hard for me to do, and I try to do that as much as I can. 

Change context when you’re in autopilot, and I think one of the people that’s taught me this more than anyone is my mother. Every time I go out, I don’t see her very often because they live overseas, but when we go out with her, we’ll be sitting somewhere and she’ll be like, look at the way that light is hitting that table, like a napkin. She’s a master at seeing the music in the mundane.

I’m just sitting there waiting for my lunch, and she’s seeing this beautiful angelic ray of light that’s lighting up the glass in a certain way and casting some kind of rainbow pattern. I wouldn’t have seen that. But because of her I’ve looked for it more and more and more, and feel like in most cases you can find something that is beautiful in the world around you if you allow yourself to see it.