Clarity Cards; Handwriting and Reflection with Mathias Jakobsen
On life in New York City with a young family, the importance of journaling, handwriting and reflection plus the story behind his Clarity Cards.
Today’s guest is Mathias Jakobsen who is the creator of Think Clearly. Born in Denmark, he founded his first company at age fifteen building digital solutions for companies. Powered by digital, he later branched into fashion journalism and photography before moving to New York City where he worked as an advisor and consultant for startup CEOs and corporate executives. He has worked with Bloomberg, Google, Hyper Island, Carrot Creative, Holstee, The Wharton School and many more. Mathias talks about his love for New York City, how he deals with burnout, how he handles social media in his life, and about his Clarity Cards.
Links and Resources:
Welcome to the show, Mathias.
Thank you, Clare. It’s good to be here.
Tell us a little bit about your journey from Denmark to New York City.
The interesting thing to talk about here in the context of this podcast, specifically the topic of urban and cities, was that up until the second year in high school I saw really no purpose in traveling anywhere. I was fine where I was living. The only problem was that there were no mountains in Denmark. If I wanted to go skiing, which I really badly wanted to do when it was winter, it was hard to get the mountain to come to me. The only reason for travel was to go to the mountains. I would travel to Sweden or to France or wherever to go skiing. That was all, otherwise there were no purpose.
Then second year in high school, we had a week-long class trip to Barcelona. That was a major, major turning point for me. It’s because of Barcelona that I live in New York now. We were out and we saw all these things. A lot of it was interesting and was a good time, but particularly, the Sagrada Família, the Cathedral that is 200 years later still unfinished, designed by this famous architect. It was so moving. I was brought to tears by this building and the thinking and the idea, just everything about it. After that, I had this whole new commitment to go look for places around the world where I could feel at home in a different way. I went on vacation to France, to Paris.
My initial hypothesis was that it was about big cities because Aarhus, where I’m from, is a relatively small town. I went to Paris. I spent three weeks living in London studying in the London School of Economics for a summer. I went to New York on vacation with my girlfriend at the time, who is now my wife and mother of our three dragons. It was really this whole exploration of cities. Along that, New York was the place that just felt different from all the other ones. All the other ones felt like cities that were great and I feel very comfortable. For example, I’m very comfortable in London. In New York, I felt at home. We spent the next five, six years figuring out how we can move here.
What is it that you find really wonderful about living in New York?
It’s been more than ten years since we started the journey and we’ve been living full-time here for six years. I’m a citizen now, my wife is a citizen, our kids are dual citizens. I still struggle to explain exactly or at least to say it’s that. There are a lot of things that altogether combine into this. It’s actually quite interesting that I can’t point exactly to it and I’m trying. I get asked this question all the time, “What is it about New York?” Sometimes it’s just the feeling both practically, when I walk around, when I move around, it just feels very natural to me.
A huge part of it is the people that I’ve met here. I feel that I meet people and get to spend time with people that appreciate and understand diversity. There are a lot of talks about diversity where it’s very much about how people look; gender, origins and all that. That is part of diversity too, but there’s also a part of diversity that is how you think and what you believe and what you aspire to do and your scale of your ambition or how similar or dissimilar it is to other people. This is one of the places where I don’t feel I’m as weird as I feel in most other places. I feel that I am seen and appreciated for who I am when I’m here.
Tell us a little bit about the work that you do and how it’s influenced by living in this city where you feel you’re seen in a way that’s different to other places in the world.
The works that I do is also something I sometimes struggle to explain, but part of the work at least I can talk about. Part of the work is teaching other people to be and to try and to explore new things. It’s not so much teaching people a skill, it’s much more about teaching people a way of using a skill that they may already have from a place of exploration. I did a workshop this week on Wednesday in São Paulo in Brazil where the topic was visual thinking. Most people already do that without realizing it. They’re just not very confident in the way that they do it. They do it in one way. The reason they’re not confident in it is that they feel that the way that they’re doing it is not right or it’s not serving them properly.
The whole workshop is about exploring more broadly all the different ways that you can do this and learning to see moment to moment what is working, what is not working, going where it worked. You have a broader space of opportunity to try things and an awareness to choose and to realize what’s working quickly and what’s not working and then change it. A lot of people in those classes will ask questions like, “What are your best tips or dos and don’ts?” The things that are good in one situation can be really bad in another situation. If you draw very confident, you have a very clean, beautiful line, that can be great if that’s what people want. But it can also mean that everybody feels that it’s your drawing that it’s your visual and they don’t dare to engage with it. In those cases, you might be much better off having not such a beautiful, not such a great clear simple line. You might actually be better off being a little bit more messy because that invites other people to grab the pen and come into the collaboration. There are really no clear right or wrong, good or bad. It’s the awareness of it. That’s at least a huge part of the work that I do.
Living in this environment, it’s still relatively niche in terms of work. Maybe part of it is being in big urban centers where even if it’s only relevant to one out of ten thousand people, I can still find enough people that are interested in it. That’s maybe part of it. The other thing is that living in New York from a global perspective it’s a very central hub. You can go almost anywhere in the world within a little more than twenty hours, you can get to pretty much anywhere from New York. Even though the world is round, the infrastructure that we rely on to get around with airlines has a massive bias towards a place like New York in a good way.
When you have been on a trip and you have landed back in New York, what do you do to reconnect with yourself and reconnect with the city? For instance, do you have a favorite walk? Is there a favorite secret location where you go and pick up a coffee or hangout with your kids and your wife?
I wish there were such a thing. Right now, it’s a little bit more like, Thursday morning I landed at 6:58 and I turned on my phone in the morning, we just landed. I get this text from my wife that our middle child, Unna, has been up between 2:00 AM and 5:00 AM and then other one was up. She just had this terrible night. It’s a little bit more like, “Okay, reality kicks back in.” It’s like, get in the cab, get home, and deal with whatever needs to be dealt with. There’s not so much romantically connecting with the city. It’s a little bit more cleaning up, wiping up, handling the situation.
Has there ever been a time in your career where you’ve really suffered with burnout?
Yeah. I don’t know if it really got to the point of burnout, but there was definitely a time around college years when I was living in Denmark and I was running my own company and in school, doing all these things. I definitely was affected by stress in an unhealthy way where I would get sick and just not deal with it in a good way. I’m not immune to it at all today either, but I’m able to detect the warning signs a lot earlier, which doesn’t mean that it goes away but I can at least know what it is much, much sooner. I know some of the things I can do to engage with it rather than just assuming that it’s nothing and that it will just figure itself out. That’s the main thing.
That’s one of the things that I think is so great about getting older. There are many things I do not think are great about getting older but at least the longer you’ve been in the world and the more experienced you’ve had of how you respond and what your body and what your mind does in these moments of acute stress and chronic stress. My experience at least, it’s certainly something I’m quicker to recognize and to mitigate, which sounds similar to you. Are there any specific tips that you could recommend for people in these moments? How do you carve out moments of stillness or quietness in your hectic New York life with a young family?
It’s totally possible and it is very important. Right now I’m very fortunate that I work primarily at a consultancy called SYPartners where we have this incredible, amazing office. For me, it’s a treat every day that I get to go to work in this place because it’s so not the hectic, noisy New York. It’s like a whole universe in and of itself. When I was freelancing and building my own things, it was a lot more like I had to explore and figure out. I found different hotel lobbies where they would have coffee service and meal service and stuff. It was legitimate to sit there even if you weren’t a guest in the hotel because it was basically just like a restaurant that was quieter. I found these little nooks, corners that were quiet. It’s not like there’s a ton of them in New York but there are enough, and when you find them you can find that peace and quiet space. That is super, super important. It’s not accepting the stereotype. People say, “New York is so loud.” Yes, that is what it mostly is but it doesn’t mean that it always is that. If you want that hectic-ness, fine. Go roll with it. But it doesn’t need to be that way. You don’t need to define your identity as, “I’m someone who lives in New York and I’m someone who loves the hustle and bustle.” I don’t necessarily love the hustle and bustle, but it doesn’t bother me that much. I look for and I find the places that have more tranquility.
What time of day do you most enjoy and why?
I like mornings. At least the beginning of the work day I like because it’s getting coffee and making a plan for the day and taking a little bit of a moment before meetings and emails and everything begins. I like that. The morning at home can be a little bit more like you’re just a waiter who has to serve breakfast and convince the VIP guests that maybe they should get out of the bathrobe and actually put on clothes. It’s a little bit more like manhandling, in a loving and caring way obviously. Mornings is definitely a favorite. Actually, there’s something special also about the evenings. I’m not a big night owl in general. There are these quiet moments also where the whole household has gone to sleep and I’m in the living room. I don’t turn on too much light and I can sit and read a book. I don’t want to sound like I’m somebody who just sits and reads a book. It’s just once a month that this happens. Maybe that’s why it’s also special, to sit on the couch until I pass out, and read a book.
That’s an interesting point for me to ask you about your relationship with social media and with time on the internet when you’re away from the workplace. That’s obviously bearing in mind that for so many of us, the workplace isn’t necessarily a physical place when we are walking around with mobile devices, which is where we can connect with work at anytime that we choose.
It’s a challenge. For me, it goes through ways. It relates even back to what I was saying before about my work, helping people explore rather than trying to find the right way. There’s a right way in a moment but you won’t know if it’s the right way. Even if it is, you won’t know if you’re just committed to one and you’re just doing one thing. It’s the same thing with social media. I’m not too worried about finding the right balance or when is the right time or how will I do it or how will I not do it or why will I not do it or all that. For me, I let it go through cycles. In some cycles I’m very deliberate and intentional but also very much in it all the time.
I will use an app like Buffer. That way you can schedule tweets and Facebook posts and basically fill it up with all ideas and let them trickle out with big questions or big ideas, whatever is on my mind. It’s also generous in a way. It’s sharing a lot of stuff. I don’t mean sharing as sharing an article that makes me look smart and shows people that I read The Economist. It’s more about sharing ideas and sharing myself and being open and asking questions and sharing difficult moments and opening up to the fact that parenting is not always the images on Instagram where the kids are smiling. Sometimes it’s also a lot of crying and a lot of moments where there is no good solution here. There is no magic bullet. You’re in it and there’s vomit everywhere both literally and figuratively. That’s the thing. Then I’m on it all the time. It’s the first thing I do in the morning and it’s the last thing I do before I go to bed. It’s an integral part of how I live day by day, week by week. And I like that. That’s an interesting form of being especially when it gets really, really open and honest and genuine and loving and caring. I found a few things that standout.
I shared a moment with a challenging weekend with the kids. I ended up making a whole new friend who reached out and he turned out to be a psychologist living near Amsterdam in the Netherlands and we connected. Now, I feel like we’re becoming friends. We see each other in Skype relatively frequently now. It was all because we connected over this moment that I posted on Instagram. That’s magical that that can happen. That’s magical because it’s a new relationship. I’ve also had these magical gatherings on Facebook where I’ve asked a question or shared something around. I remember a specific post where I shared it around my using of melatonin as a sleep aid and was asking people. It became this opposite of trolling. People with very different opinions but were genuinely listening to each other, contributing. Medical doctors who were sharing what they knew from the latest research around this, both for long-term and short-term use. It was people that were just open and were like, “Me and my husband, we do this every night and we’ve done this for years. We know that maybe there are risks but we just find that it is so delightful to do.” It was such a gathering of people that were all my people but they didn’t necessarily know each other. That’s one part of it.
At other times, I need to get a little bit of a break from it. It doesn’t need to be a hard divorce and I delete my account. It can be as simple as just not posting a lot because then there’s little bit less. Then I get disappointed every time. Right now if I open Facebook, I’m disappointed because nothing has happened because I didn’t do anything previously. The last thing I did was I checked it and nothing had happened then either. It goes through these phases. Sometimes I’ll delete the apps from my phone just so that I’m less likely to engage with it. The interesting thing is not to find the right space in the middle. The interesting thing is to observe myself and where I am. For example, to your question before about stress, if I notice a stress pattern in myself, that’s one of the easy ways to cut something that is overly stimulating, to just chill it with the social media for a while. That’s one thing. Then go for a run. Those are probably the two first buttons that I push when I notice a stress pattern in myself.
I love the story of expressing vulnerability online and how that’s potentially opened up the possibility of a lovely new friendship that you’re rewarded with from that moment of vulnerability and connection. That’s a wonderful thing and it’s wonderful that we’re talking today. We’re in different countries on different continents. I love what the internet and social media can do in terms of how it can connect us. It’s also really important for us to tune in to what’s important to us at any given time, which is what I’m hearing you say similarly, to know when to pull back and to know when engaging feels good. It feels like the right thing to do at this moment. One of the next questions that I’d love to listen to your answer on is, where would you live if you didn’t live or couldn’t live in New York?
There are a few places. We’ve talked about this also, my wife and I. The most obvious one right now would be to go back to our hometown because then we would be closer to the grandparents, our own parents. We’re fortunate that we’re both basically from the same place. Both of my parents and my wife’s parents, they all live within easy driving distance from each other. If we move back there, our kids would have all of their grandparents very, very close by. That’s something we talked about. It’s also when we talk about that, I still cannot fully imagine what I would be working with if we live back in our hometown. Last time I was there, I was there in November of last year, I literally had this moment walking down the street close to where we used to live, I just felt this pressure on my chest. I think I can’t breathe. It’s a little overly dramatic. That’s how it felt for at least a minute when I was there.
For the kids and the grandparents, that would be something. We’re considering it; to deal with that sense of not being able to breathe, what the hell would I do. Actually what I’m trying to do is just have a little bit more of a presence in Danish media. I want to pitch a weekly column about family, life in New York and see if there’s any Danish publication that would pick that up and just have a few maybe talk or two talks every year in Denmark just to have a little bit of presence on the distance. Because what that could do is it could potentially mean that a potential employer could reach out and say, “We actually have this job that would be perfect for you. Would you consider moving back?” That would make it a little bit more tangible. It’s less moving back to our hometown and then all these questions. It will be like we would move back and that would be the job. That’s actually one of the strategies for that. Of other places I’ve visited in the past couple of years, I feel that both Buenos Aires in Argentina is a place that I’m very drawn to, and also Mexico City, even though I’ve been there for a couple of days and have only really seen one neighborhood. Especially the architecture, there was just something about that that really, really spoke to me.
What about in Argentina?
Similarly, the architecture is a thing and the people. I can’t quite describe what it is but there is openness and the generosity of being in-touch with emotion in a way that most people here are not. There’s something there that I like. Actually, the same in São Paulo as well. I don’t feel at home in São Paulo, but I do a little bit more in Buenos Aires. The people actually have the similarity and that these are countries with lots of uncertainty on the political, economical scale. It’s the normal. I’m not saying that there’s no anxiety but I’m saying that the threshold for anxiety is at a whole different level. The comfort and ambiguity is a lot higher for people there. I resonate with that. People are just chill with it in a different way.
I’m interested to know about how much of your identity is linked with being a New Yorker versus someone who is originally from Europe versus someone who’s a global citizen?
Part of moving to New York, that whole ten-year phase that I talked about from the dream and until we moved and began really settling in here, the identity part came before we actually moved here. My first Twitter handle was @mathiasnyc. This was 2008, so that was three years before we actually moved. I made it a part of my identity that I was moving to New York. I would literally say it like that even though I didn’t know when or how or if it would even happen. It has been a huge part of my identity. I remember a trip to Lisbon where I came back and landed in New York airport. The plane touches down and the captain comes on the speaker system and he’s like, “Ladies and gentlemen, welcome to New York International Airport. On behalf of United and this New York-based flight crew, we want to thank you for flying with us. For those of you who are visiting, have a great stay, and for those of you who live here, welcome home.” I was like, “That’s me.” It was just so good. In those moments, it’s definitely been a huge part of my identity.
I’m trying to be aware of the fact that I feel most of the problems I face are not actually problems of the world. Most of the things it stresses me, most of the things it disappoints me, most of the things that causes anxiety are usually when I’ve become too invested in some part of my identity that is then challenged by something. I’m trying to be very aware of whenever I make my identity too solid in any direction. For example, this whole idea of being a New Yorker, if I was too invested in that, I wouldn’t be able to look at my situation and say, “What’s actually best for our kids? Is this actually best for our kids?” Right now I think it is. If it becomes an identity thing or at least if it becomes too much of an identity thing, there’s a huge risk of losing the clarity of what actually is going on.
You just mentioned the world clarity there, which is such a great point because I wanted to ask you about your Clarity Cards and the genesis of those and also the genesis of your really spectacularly beautiful handwritten newsletter, which is the only handwritten newsletter that I received in my inbox and one that I really enjoy reading. I’d love you to tell us a bit more about how those two things evolved.
The handwritten newsletter came out of the consulting work that I was doing before the job that I’m in now. You mentioned it in the intro when I was consulting with startup CEOs. A lot of the work we were doing together was around clarity. Their reality was a small team trying to build something that hasn’t been done before. There was no manual. There were no guidelines. There’s lots of best practice but the best practice are of the people that have come before you that were doing something different. A lot of what you’re challenging is maybe if those best practices are actually the best practices. You don’t want to go there necessarily. You’re both trying to think long-term and dream big and make something that’s a compelling vision that will allow you to raise more funds. At the same time, you’re executing every day and everything is going wrong all the time. There’s not a lot of room for clarity in that. A lot of what we were doing together was this work of just taking a moment, taking an hour, two hours, stepping outside of the madness and looking at that. We would use tools that were more conducive to that. A lot of it was hand-drawn to get away from the distractions and the scream.
The newsletter grew out of that. It was taking some of the ideas that came up in that work and making them into almost little journal entries with a few drawings, a few ideas, and started to send it out. The first people that subscribed to it were my own clients. Then it just grew a bit unexpected, I would say, very rapidly after that. That’s the origin of that. For me, the whole handwriting thing is weird because I stopped writing by hand in eighth grade because somebody had told me that I had bad handwriting, and I had really bad handwriting and I hated handwriting. I thought it was painful, I thought it was useless. I started doing everything on a laptop. I was the first in my class to have a laptop to school every day. I did all my homework on a computer so I could print it out rather than do it by hand. I literally stopped in eighth grade. I didn’t write by hand for the next twelve years.
How old were you in eighth grade, for non-Americans listening? Were you a teenager? Younger?
Yeah, a teenager; maybe 13, 14, something like that. It wasn’t overnight. It was over a year maybe that I eventually phased out all handwriting. By the age of 15, I didn’t write anything by hand anymore, nothing, zero. I spent the next decade of my life basically living inside of a computer. Everything had to be on the computer. I had a very advanced phone for the time. There wasn’t anything called push notifications, but I could get text messages whenever I got a new email. The experience of getting constantly buzzing something in your pocket, not just for text messages but text messages that were indicators that I had emails coming in. Then I could use my phone to dial up to the internet and download those messages and respond to them everywhere. I really lived for ten years inside the internet.
This is also where it eventually will lead us to the Clarity Cards. The realization eventually was that I didn’t actually enjoy it anymore. It was too much madness. It felt like a loss of agency ten years later. I was like I’m not really in control of this. I just sit in front of this thing and it takes me places, but it doesn’t feel like me and where I want to go. It’s more like I’m babysitting a machine and the machine wants to me do all these things. It wants me to install updates. It wants me to go here. It wants me to go there. Whenever I go here, it also takes me here and here. I’m not in control. Handwriting and reflection which is really the process of the Clarity Cards support is breaking away from that. It’s working with tools that don’t have distractions built-in in a way you realize that you’re generating everything. The blank page does not have an agenda. If you don’t bring focus and some effort to it, nothing is going to come. You can sit in front of a computer with no effort for hours because it just keeps giving you a little thing that you can click on and then the next and then the next and then the next; all these micro-moments.
The Clarity Cards came out of these years of journaling by hand after I tried to step out of the computer for a while. A friend of mine helped me see that what I was doing was asking a lot of similar questions to myself and journaling and writing about it. He was like, “Other people need to do this. Let’s make a tool that helps them do that. We can just lift these questions out of your notebook and turn them into a deck of cards.” I was like, “Sure, that sounds great. Thanks for the idea. Now you want me to go and do it.” He was like, “Yeah, let’s do it now.” He stood up. His name is Dave Gray. He’s an amazing author by the way. His latest book is Liminal Thinking. He’s a great guy. He gets stuff done because he stands up and he picks up the Post-it notes, “Let’s make the questions.” This was in the middle of dinner. He gets the Post-its, he gets a sharpie and we threw the notebook that I had with me that day. We list out maybe 45 questions and sort them into four groups. When I came home I just put them in into sign and gave them a type treatment and ordered a prototype from some company in China and suddenly they were a thing.
Mathias, I would love you to tell us what it is that you’re curious about right now and why.
I’m curious about different things. One thing that I’m very curious about is where it’s going with humans and machines together. There’s a lot of talk about AI right now. Most of what’s happening right now to me feels extremely predictable. There were books written. Jeff Hawkins wrote On Intelligence ten years ago. He basically predicted all the breakthroughs that are happening now. Ten years ago he was like, “This is going to happen when these two lines cross each other.” That’s now. He knew that. It doesn’t seem the whole machine learning thing but that seems relatively obvious. There is a social and societal part of this that has yet to play out and that’s when we begin really applying this in ways that radically begin to displace and change jobs and what’s going to happen there. What does it mean really then to be human? How do we coexist with this? What’s the role of love and kindness, for example? Those things become ever more interesting as more and more of the even creative work can be done in interesting ways in collaboration with algorithms.
I saw a short film the other day where the script was written by a machine learning algorithm. They still had to interpret and play it and give humanity an emotion to it, but the end result of this collaboration was amazing. It was truly wonderful. There is something really, really interesting to explore there for all of us and what it means. What does it really mean to be human in this world today? Not just human with my notebook and free from distractions but also the humanity we talked about with social media where you’re plugged in and you’re human with thousands of people at a time. In a scale, you can experience compassion and generosity and love and kindness at an unprecedented scale. Seeking that out, I’m also extremely curious about what that does, what that feels like, what that means.
Where can people find out more about you and your work?
Googling Mathias Jakobsen will probably be a good place to start. You can also go directly to my own website thnkclrly.com.
Mathias, Thank you so much for being a guest on the Urban Curiosity podcast today.
This was super fun.