Staying creative when AI has all the answers

Dave, when you were a kid, what was your favorite game to play? I don't know if this is my favorite, but this is probably a very telling of both of the culture. So like I'm first generation Chinese Canadian, the first 13 years I spent in China. So I tell people I grew up in Canada, but like I was born in China. So when we were young, we had no, we have no, like we had no tech, I know I've had no games, nothing. Yes. So we played with knives a lot. Oh my God, oh no. So a game that we had, and this sounds like extremely, we were not published, like we could have had toys, but like, okay, yeah, but we, there was a game that we played where we would draw a square in mud or like in dirt, and you take a small knife, and you try to, I guess I hit within the square that you draw, and then if you hit it, you cut the square in half, and then you pick up the knife and try to hit it again within the square. So like the size of the square reduces every time you hit it. And then I think that if I remember the rules correctly, it's just like to see who can keep heading the smallest area, surface area that you draw until nobody can anymore. So you, as a child, literally chose violence. I think this is like the most, you need to start disclosing this to your team. This needs to be in like the day for me to file, like figure out. If you want to know who you're working with, your, my childhood preferred game was knives. That is something. Well, let's hear yours. Okay, what did I was very into like make believe storytelling imagination games as a kid? And my dad was an excellent, like he was very like happy to just kind of go along. I think it's very telling that a game that I was really into was essentially kind of like play acting, all of the authority rules in like a school type of environment. So I would be the mom dropping off the kid at school. And I always would like really embarrass them. Like that was like a big thing. I would always like come up with these elaborate like hugs and dances and things to embarrass them. This being my dad in front of imaginary other kids. And then I would be like the teacher and I would give like so much homework and like just do everything I can to make it like a really painful experience. So yeah, just like kind of being the authority figure, I guess was my childhood game. So I think that's also very telling and should also be in my like read me file. That is so on brand like so consistently on brand since you're a child. Today we're going to talk about play. We have Ricardo Vasquez on the podcast and Ricardo is was actually asked us in his one of our one of our emails back and forth about this very question. So I think he will enjoy hearing our answers quite a bit. Ricardo is a head of product design at Stripe and I have worked with him before we worked together at a well simple. He's very kind, very empathetic, extremely lovely person as you will hear in our conversation. Great craft leader. And someone who I think like really embodies the spirit of play and it does not surprise me at all that that's what he wanted to talk to us about was played in product design and in UX because Ricardo is such a playful, optimistic person. Yeah, I could see that from the organization was a truly enjoyable conversation that could have also doubled as a parenting podcast. We also of course talk about AI, does AI help our hinder creativity, all of these topics we will get it too, so have a seat, grab your coffee and let's listen in. How are you doing? Gosh, you know, we have a big deadline coming up at the end of the month, so we're busy. It's yeah, yeah, we're always busy, we're always busy. But otherwise life is great, yeah, life is great. Glad to hear that. Well, we're very glad to have you here. Shall we get into it? Are you coming to design leadership summit? Yes, I will. Yes, I will. I'll be there. I'll be there. Amazing. So we'll be hanging out soon. Danielle, that's the last time we saw each other, right? Yeah. Last year at that, it's becoming like, I feel like it's becoming my like annual reunion with people where like I just see all of my old friends and it's so nice. Yeah, it is actually quite nice. I'm very excited for it, Ricardo, absolutely freaking thrilled that you're here. We of course used to work together. Well, simple. It was a dream. Let's start off with what's your what's your review of working with me? No, I'm kidding. Yeah, let's get into it. I want full details. I mean, maybe let's start off with you have, I want to say you are a low-key design celebrity because I feel like speaking at config is the qualification of being a design celebrity. How's it been being in the spotlight? And you've been talking about quality, which much appreciated getting some spotlight on that. How's your last few years been? Who we start there? How are you enjoying life at Stripe as well? It's fine. These are quality, Danielle, because I feel like in the world that we're in in Intek, there's this gigantic movement towards craft and towards taste and towards quality. I don't know if if I am one of the seldom few, but I believe that craft and quality extends beyond the pixels, extends beyond the border radius and the, you know, depth, visual depth that you're able to give something, it extends beyond that and into the definition of a problem. Who are we? Who are we here to solve a problem for why are we solving this problem? And also, have we diverged as much as we we we we need to? There is quality of craft in that. There's so much quality of craft in the things that are left on the sketchbook, in the things that are left in a meeting room or in a jam with, you know, with two people. That's quality. So I appreciate you bringing quality in the talk, a config I did focus on quality. Also not through the lens of additionally, aside from approaching quality from a lens of look at the beautiful animations that we can do, if we, you know, if you focus on the little bits that matter, quality also extends into a simple loading state, like loading something quickly, that is quality as well. So I've been, I've been, yeah, I've been on a, on a campaign crusade to mature my own thinking and my own understanding of what quality can be and it, I often end up talking about anything other than the pixels in the micro interactions, that's usually where I find myself. And by the way, Danielle, working with you was indeed a dream. And if I'm ever so lucky, I'll work with you again. I met Stripe nowadays, Stripe is on a mission to, or my group at Stripe is on a mission to invert our value proposition and to, to really start to bring additional jobs to be done, if you will, for our users to do. Our users or Stripe is, is incredibly well known for payments processing. Our thinking of a, of a pathway to allow users to do more than just process payments. What about storing funds? What about currency conversion? What about sending money to people all over the world? There are jobs that business owners, our users, have that it's, it's a, it's a very clear graduate, graduation path into, you know, let's say that the, the three of us, we own a, a book shop, a book store and we sell books. Of course, we're, we are processing these payments, but we have vendors all over the world with purchase orders because we're getting books from all over the world. We need to pay them. What does that look like? We also need to hold currencies and, and hold funds money in so many currencies. And also, now with the, the advent of, of crypto and stablecoin maturing to a point where, in my opinion, it is finally usable, you know, we've moved away from that crypto as a, as a, as a, like a, very, very risky endeavor and with, you know, mean coins, we move, in NFTs, we moved away from that into stablecoin as a foundational piece of financial infrastructure with, with things like everything, anything that is pegged by a fiat backed currency, that is something we're working on. So it's a brand new banking rail for us. And there's, there's a lot, a lot, despite it feeling like it's just financial technology, there's a lot of creativity, obviously, in that, in a lot of ways that we need to continue thinking and abstracting away complexity as much as possible. And in that, and through that lens, the creativity is endless. Kiering, you talk about, you know, Stripes mission and also your personal view on quality, I'm curious to, to just get your take on how do you, as a design leader, uphold that quality in the context of, which is also very relevant for one past word, in the context of acquisitions. Stripes has, you know, done quite a few over the years and more recently acquired open router is, you know, one could argue it's maybe a slight departure from what people's to understand the rules of stripes and products. strategy is, or like, admission, but just, yeah, just curious to get you to, because like one past where we've done our fair share of acquisitions over the years and, you know, being on the design leadership team, we also have to deal with a lot of trying to uphold the design quality bar, because the all these different companies come with their own stuff, right, different design system, design language, looks and feel and all that. So just like trying to merge the two together and get your take on that. Yeah, it's an incredible question, because I think it hits hits on an element of what do you keep and what do you like go of? I cannot, I can speak better of of this point, Dave, through my time at Dropbox, because I, that's one of the main things that I had to do at Dropbox was bring three brands together to one. Dropbox, of course, has a core product, right, file sinky share. But Dropbox, similar to other companies, they had acquired separate companies. Dropbox sign was one of them. Dropbox sign was a, again, let's call it a satellite product. And it hadn't up until that time, it hadn't been integrated into the experience. I found it and maybe this is the curious to hear you're both your take if you've gone through this, I found it incredibly challenging to to find a world where you could keep the essence of a, of a brand and infuse it into another brand. That was personally really, really hard for me to, to grapple with what I found equally challenging to do. But this is I think where the path leads us into like, what do we can keep versus what we can let go? The Dropbox, you were thinking about integrating an acquired product into the core product. You are already setting yourself up for failure. If you're not thinking about the job to be done from the lens of the user, whenever company acquires another company, and that acquisition is just, is as treated as a, as a side benefit, or is treated as a, you know, complete separate product under the, you know, one unified flag. I feel like it misses a gigantic opportunity to find a home in the end to end experience of a user. Ultimately, think of that's where acquisitions make sense. That is also through that lens, through the lens of like, okay, well, in this end to journey here is where this acquisition helps solve a problem for our users and helps our users lives just improve the quality of life improve. And it's through that understanding that we can then begin to understand, okay, great, what are the things that we want to keep? What is the, what's the IP that we want to keep? What are the interactions that we want to keep? What is the environment that we want to continue to like move towards or like apply in the core product? And in that way, the core product can become, can augment. And instead of thinking of us like replacing one to one tool with another or one piece of software or another, we instead think about it as extending the playground. And I'm already heading into play there, but we extend the playground. That's in my, in my experience at, at a drop box, the, the most successful that we got to was, was thinking, these are not two different playgrounds. It's one, we just have to do our job in understanding what corners do we do we do we lengthen, meaning what problem are we solving for the user in their intent journey? I love that perspective for Cardo. We've absolutely had our challenges with acquisitions. It's like a such an amazing thing. I think, and at the same time, it takes at least like in my experience, typically years to truly integrate, not just product wise, but also teams and team culture. And to your point of this idea, like extending the playground, like the team seeing things that way, the team seeing us as one product and not multiple. And we still go through that with our acquisitions. And still like, I find these kind of surprising corners of the products like you, their products are so vast, the way customers use them, understanding all the different workarounds and understanding how customers think of the products and then how our customers making the connections in the ecosystem. It's very like it takes a lot of time is my experience with acquisitions and making it all make sense for the team. 100% and takes it takes patience as well, right? This is also my gosh, this is ever true about the creative process in our increasingly impatience towards allowing creative process to just be your absolute right, Danielle, in acquisitions, you can say that we can apply the exact same parallel into just solving a problem. This is where play becomes, I feel, this is where plays at risk, I think, in today's world. We are in a beautiful AI movement. I am calling it beautiful because there's wonderful things about it. But it's our application of it that I feel like we need to, we need to be mindful of, because it ultimately, I believe it closes the doors to that ability to play, it closes the door to patience, Danielle to to your point. There's this wonderful quote by, I have it seared in my brain. There's this child pediatrician, his name is Donald Winnecott. He described or defined the act of play as a child without hallucinating. A child puts out a sample of their dream potential into reality and lives with this, with this like dream reality, with this dream world in reality, which we, he's describing as effectively a bridge when a child plays on any one of us play. We reach into our inner world, our dream world, and we press a piece of that onto the real one. It's, it becomes this, this, this world or this timeline where two worlds are touching. And in those in that way, new things become possible. That's where innovation. I feel like that's like that's like the magic sauce. It's not the only way to innovate, of course, but it's, it's a way to innovate. It takes courage, though, it takes patience. And as adults, we end up naturally narrowing our focus. We end up naturally closing this door to this dream world. And instead of being attracted to exploring new environments, we're trained to concentrate on what we know, concentrate on what is relevant today, not to more today, what is relevant today. And this narrowing over vision increasingly makes us close-minded, closing the door little by little. I like to think about it as, as, I mean, we are systems, humans are systems. And we have many, many operating systems. But one lens to read us through is to, it's whether or not we are a system that exploits or a system that explores a system that exploits automatically. Nero's is focused to what appears immediately relevant to its goals. We're exploiting. We are, we're focused. We're getting things done, probably very quickly. A system that explores, however, adventures outwards. It gathers diverse information. It reads, analyzes information that could become relevant to solving the problem that the system has at hand. It could not. Regardless, it's a system that explores deals with the world with a level of curiosity. And there's no surprise that with AI, naturally, we, there's a quite aversion to seeing anything new because we're looking at it through the lens of a system that is exploiting what the inputs that we are giving it. So I think that this is where, sorry, I'm taking this so out there, you know, but I think that this is where the, the, the, the real risk is for creativity to lead into a world of the forgettable. I like to call it. Think back, both of you think back. And think back to a world where moment where you, you played with AI and it felt magical and you remember it and you know, like you feel it, you know, you were in the zone, you were in flow state, you could be, you could have one. But I would probably argue are what I would assume. I'm not going to throw a hypothesis here that it seldom it seldom that you, you, you, your mind chose to forget it because your mind wasn't really getting challenged. Your mind wasn't really getting blown up in beautiful ways. Think about the last time that you read a meaningful book, you can, I can think about when breath becomes there, this beautiful memoir that I read, I was crying on the train home when I was finishing the book, you immediately close your eyes and transport yourself to that world. It's, it's interesting how today we outsource memory in the creation of these memorable moments to technology. In it, in it, by the way, it's not just memory. For years, we've offloaded, I think these like very small jobs to, to, to tools. And it's, it's absolutely fine. We have a calculator and we've offloaded that to, to math problems. We have map quests, you know, years ago, now we have Google maps, great, that is our, our take up using technology to offload, you know, root and guidance. We, you know, technology handed a handle the task so that we could keep the thinking. We stayed in the driver seat, literally when, when, when, when, when Google maps is, is turned on, we stay in the driver seat, we check the work, and we steer the outcome. Hi, is, is different. AI is not a calculator. AI is not a piece of paper, because this is also a tool of, of cognitive offloading. There's a paper that was released recently, where researchers have coined a new term is not cognitive offloading that we're doing with AI is cognitive surrendering, where we're stopping, we're stopping the engagement of, of, of anything, and accepting the machine's reason. whole sale. We just accept it. There's no oversight on our part. There is no challenge on our part. There's no verification on our part. And that is the trap that use this way AI is the most powerful system of exploitation that we have ever built. The humanity has ever given us. It gives us the fastest answers. It gives us the safest answers. Not not always good. And it gives us the answer most importantly that already exists. So it narrows us to what is immediately relevant. And effectively, if we bring it right back to play, it it unless we use it in a different way, it immediately asks us to surrender that sense of play. But I believe the reason why I can continue to be optimistic about it is that I believe it is a choice. It is not a fate. However, you know, our choices surrender play while using AI. It is not a fate. And we are in a in a we can be in a wonderful position to take back the reins to use it for exploration. And as a parent, what you said is very resonant. Like I have two young kids and you know, their girls and they do a lot of play right now. I didn't say to stuff. I'm just like, that's not realistic. As an adult, in fact, who's you know, fight my urge not to suppress that. Like the I like the spectrum of you thinking Ricardo around balancing or maybe this tension between exploration and exploitation. As a leader, how do you how do you lead and coach your team in the day-to-day on that? Like how do you because as a business, you're absolutely right, right? We there is a part of what we do is exploiting all kinds of stuff we're doing with the very singularly focused goal that all the leaderships go as it were at the companies. Like we're maximizing value for the shareholders. Yes, man. Yep. But then as design leaders, the tension that we do is like we have to give the team space to your point to explore because it takes time, it takes patience to do these things and do them well. So as you know, you've been around the blots a few times, you have some big names on your resume. Like in your leadership career, how have you guided your teams through that tension? Yeah, there's two ways. Great question. There's two ways. The first is by admitting that efficiency is not free. Efficiency side effect is tunnel vision and the first thing of velocity, culture prunes or calls is a wasteful wandering. The creativity runs on. So absolutely agree with you. You know, we are here to to to move faster. But you can still admit that that efficiency is not free. So you can't fix that by telling people to play more because play me the container play needs time. This is where I, I already used this model, mental model, the playground. I frame the work to my teams. I frame the work as an adventure. Sometimes literally a hero's journey, I will use heroes journey, narrative structures. I'll say this is where we are. This is what we're we're about to do. What I do, the way that I that I help a team shift into that mindset, regardless of the timeline is that exploration is expected rather than then like the stolen. I mean, like you don't need to like, you know, quietly play. No, no, play is part of the process. However short, we still need to find however, the loop of heroes journey can be a Tolkien novel or it can be an novella by by someone. Give me an author, someone. That's still a very similar hero's journey structure. How big is a circle is really what we're talking about. What I challenge to teams and what I reframe for for companies that I get the pleasure to to support and to work on is that the circle should not just be aligned. Yes, the circle can go smaller. Sure. We can we can move faster, but play can ever be part of it. And I measure discovery differently from delivery because you cannot put a velocity number on exploration. So the urge to exploit never needs my help is another way of saying this. It's the urge to explore that fades unless I I protected. So my job is to be the fence around that playground and to say to others to say holders and to frame to say holders the value of both a creative output, the value of us spending time however short time in general rigging ideas diverging on ideas. Now this can give give us a bit of a risk. The risk is a designer genuinely exploring but becoming stuck. There is definitely it's a human element. We we can we can find ourselves in a loop where we're just playing diverging and not not converging, not adding value to shareholders. Exploring looks messy, but it has a direction. The person is is if if a designer is generating options widening and building on their ideas and they can tell me the why they're chasing even if the how is still messy. I am able to to to to understand where we're the the purpose of creativity. It's it's effectively like stuck in motion is stuck is is is is is someone in motion with no why. That's what feels like stuff. And as is if I'm able to understand the why around creativity, the right the why around why are we diverging here is effectively really the simple question to that if I notice that a team or designer has lost their why. Then I'm able to understand okay here's here's an instance of a human in the playground playing losing sight a little bit of the end goal losing sight of what is the story that I'm trying to tell what is the conclusion of this. And it happens this is what becomes risky for teams this is what becomes risky for for advocating for divergence not every problem will need divergence, but when it does, we just need to make sure that it is enabling a why the why enables the why enables the how effectively I love this line of thinking and I kind of want to ask you about the opposite problem, which is a problem I actually experience so I will benefit from this, which is the team and this even goes more broadly than designers struggling to be creative. I think being creative and being playful is very vulnerable and I can remember from like when I started my career as a designer, we did these like sharets, which I think is a bit of a lost art where they were basically like workshops where we would get in a room and sketch ideas and share ideas and do like very deliberate intentional divergence and I was always so terrified and it really just took like doing that repeatedly to become comfortable with imperfect sketches and imperfect ideas and and crazy ideas that really like don't make sense and aren't feasible, but just allow us to have a conversation that's interesting and what was amazing about those sharets and that like period of my career was that it wasn't just me, it was my PM, it was an engineer, it was a group of cross-functional people all coming together and like playing and being vulnerable and putting ideas out there and like people being like oh I don't want to sketch it so ugly and then of course it doesn't really matter right, like communicate the idea, you can use stick figures and draw a psychomic and we can have a conversation about it and I think even beyond AI that art has been lost maybe to remote work to some extent like just because we aren't in rooms together, we don't like there's a lot less sketching that happens, a lot less wire-framing, we are living in like high fidelity immediately and what I'm finding coaching my team and observing my team is that there is not like I think there's a lot of hesitance, hesitation to sketch to explore outside of AI, like exploration is starting in AI and starting in high fidelity and even before that it was starting in the design system, it was starting in Figma, so my question to you is like how do you coach people and how do you yourself kind of overcome the A, the vulnerability to be playful and creative and put ideas out there and B like how do you create space to do that in a way that doesn't feel, I want to say that feels low fidelity, that feels cheap because I think that right now there's a feeling that exploration is expensive and to me it used to always be in my mind well this is it's not expensive because it's like before we get into software but now everything starts to software, anyways rambling but I'm curious where is odds on that. I wish I'm hopeful that one day the nail will go back to a day where we can move into more analog methods, ways of being creative, I completely agree with you, I don't think we're there yet no matter how much we push it speed to Dave's point is going to always be the vector here so as much as I look I bought colored pencils the other day because I myself am trying to move into more analog ways of working but that's not a repeatable path or a scalable path for designers. I think number one, number one and Danielle Yunnan know this well it starts by building teams with high psychological safety. The reason why I love talking about children, I have a toddler myself, so it's I'm in that era of my life is and I'm learning Dave to your point I am learning from from the two-year-old that I have because the two-year-old that I have is always open to wonder. The two-year-old that I have is always open to they don't see boundaries, he sees an opportunity, he doesn't fear failure, he plays with that instead. This is all parenting and podcast. Welcome, welcome to parenting, if we bring just imagine if we brought that level of innocence. and intention into our daily work. Well, I mean, my gosh, there's no limit to solutions we might discover. So it first begins with creating a team, a connection with this team that has a high degree of psychological safety that comes with courage, that comes with leading the charge and saying hi. Like folks, like I tried this out, it didn't work. But gosh, that I ever learned something cool from it. And a little by little, you're starting to shift this culture towards a culture that welcomes that celebrates the path that someone took regardless of the destination. And another way of saying this is a failed iteration. That is absolutely key. The second part is, OK, well, how do you coach it? First is set to cultural tone of the team, a tone that can be healthy, irrepeatable, and self-sustaining. The second lens is, I don't want to go against the grain with AI. I think AI can be the key to creativity here. Danielle, you said something completely real and true. And that is that creativity or sorry, divergence exploration is starting in AI, is starting in Cloud Code or in Chagypatia and CodeX. Like that's where designers are starting today. I don't want to fight against that. That is the movement that is, again, this is a tool that people have, the key though. Let's talk about the key. Let's imagine that AI is a doorway. And that AI is a doorway into your creativity. The key that you're using to that door, depending on the shape of that key, it opens a door into a different world. The key that we are using today is a key that I am focused on. Just give me the solution. I don't care. Let's build a prototype. Let's go now. I've got to go A to B, build it, go. That's the key that we're using now. The key that I strive to reframe for designers on my team is to have that key feel different. To have the key be a pathway to creativity instead. It's AI never changed. It always was. It depends on how you use it. It depends on your application of AI. This is why you come back to the key. How are you opening this door? Are you opening this door in a world where in a way that divergence occurs? Or are you working through, again, this system of exploitation? I build a cloud skill and we can post it in the show notes. It's called Play Partner. Play Partner is exactly what I want AI to do is a partner that plays a game with me that hands me 100 babies so I can go hunting for the one that surprises me. It's not that the skill that I created is not here to think for you. The why remains human, it remains yours. It is always. However, the skill is here to play. Think about us in a basketball court with just with us in a ball. It's fun, we'll shoot some hoops. But what if there was one more person? Oh my gosh, now we could run like some drills and now we could be a one-on-one, one-on-one. It becomes a more meaningful game and hopefully a more memorable one. So that's what-- yeah, that's what I think. AI can indeed be the key to creativity. To some degree, if we're being honest as leaders, we-- because I keep thinking about this parent-to-child analogy, right? I'm just going to double down on this parenting podcast now. We're making a pivot. Whereas, to your earlier point of Ricardo, as our kids grow up, we, as parents, start to tell them these are the things you can't do. And some of it is obviously everything's about intention. But what we're trying to do is we're trying to protect them from the world. Because we have now experienced the world growing up as adults. Yes. If I extended a parallel analogy to workplace, I think a lot of the suppression comes from us as leaders, as well. I mean, to some degree, we're trying to protect our teams from what's happening around us that we're seeing. But also, I think our leaders are doing the same thing to us, which is like, you can't do this, and you can't do that, because of X, Y, Z, E. But I do have-- yes, yes, and to your common date. If we think back of the three of us, think back as children, the way that I view the world, I would remember Mimic and Marl. And through that, inspiration came much more easily. I would marble at the mundane, the very simple things, the simple things like how a box closes in itself. With the four lids, it creates a latch. Puzzled me for hours. It continues to puzzle me today. Or where we would focus on-- again, we would marble at the mundane, a water tab. I would close it just so that one drop of water would release. And I would spend seemingly-- would felt like hours. My two-year-old does the same thing this time with anything with wheels. He'll just-- he'll open up the dishwasher, and he'll pull back a track, and he'll just move it back and forth. And just look at the circling, the rail. Move back and forth. Marbling on the mundane is something that you're absolutely right. We kind of like move humans to not do that. Don't spend time on the mundane. It's not going to bring any value. Don't spend time just focusing on that. Create. Do something. Let's-- you have a goal. That can definitely be exposed into teams. The way that I enjoy healthily fighting against the urge towards efficiency is by leaning into it a little bit to an extent, and that is by mimicking, by rewarding the act of mimicking. Let me give you an example or a story. There's this one human. Her name is Wendy Chen. Wendy Chen used to work at Google. I don't know the years I can't remember. But after Google, she decided to take a one-year sabbatical. And that one-year sabbatical, in that one-year sabbatical, she had one goal. And her goal was to tie one new knot every day of the year. So it was a 365-day project, one knot every day for a year. So at first, she exploited. She mimicked-- she mined every knot tying technique, guide, book that she could find. And with that, of course, she mimicked. She was just copying what she was seeing. But soon, with that act of mimicry, she became something else entirely. She became a system of exploration. So it began as mimicry turned into invention. She wasn't copying the world anymore. She was adding on top of the world. And this is where we can, again, go back to AI. Because Wendy stopped asking the existing forms, existing knots, for answers. And she's starting inventing brand new forms that never existed. She never went back to tech. Wendy never went back to tech. She's now an artist. She has installations, rope installations, all over the world. And that's, I think, one of the opportunities that we have to continue instilling in our teams is, yes, mimicking, marveling in the mundane. Those at face level might not seem very productive. But let's start with mimicking. What are we seeing out in the world that we can first mimic and then start to invent something new on top of that? It's a similar model that, as Austin Cleans, artists steal. See like an artist? There we go. See like an artist. It's a very similar type of thinking, probably, a different mental model, but very, very similar frame of mind is creativity can start by stealing. Let's copy. Let's mimic. And then from that, let's invent. OK, we're going to get into our lightening round. So we ask a set of questions to all of our guests. And the first one is, what's the best leadership advice you've received and why? Very early in my career. I think I was two years into my career. I had a bout of overconfidence in my craft. I thought I was just, just, didn't know, I thought it was the best designer ever, you know, as one does. And I'm sure you were for what it's worth. No, no, I had my gosh, did I ever have so much to learn? I moved from a startup, a 24-person startup. That was the first year of my career, maybe first two years of my career. And from there, I moved into 150-person startup. That shift from a 24-person startup where there were only two designers. It was me and one other person into a, you know, into my eyes, a much more mature company. I mean, it was now 150 people. I think the design team was probably nine or 10 humans. I was like, OK, well, yeah, this is a place where I can do it. I can make it. That place was FreshBooks, FreshBooks Cloud Accounting. I spent some time there. And I'm incredibly grateful for my time at FreshBooks. The first three weeks at FreshBooks were really hard. Really hard for me. One of the first things I did, I was a designer that was able to code. So I submitted a PR to change the color of the links in FreshBooks.com and the landing page. The link color was blue, like 0, 0, 0, 0, 0, FF, like that hex code blue, like blue, like Microsoft 95 blue. My gosh, was that ever ugly, right? And plus, FreshBooks already had a blue. They had a blue that, the brand is blue. So a very small change, one change has changed the variable of links, the link color, and I submitted a PR and I was super proud of myself because I'm an artist and of course, it's better. KC, the director of product at the time, KC came to me and said, hey, I noticed that you submitted a PR, that's great. You got your environment set up, awesome, awesome. Bring me back some research. where users were there's a need for users. We might some research and we'll merge it. We'll merge it as long as we effectively we find user need. At first I was like in my mind I was like, but what are you talking about? Like this is objectively a better blue. You know, again me being overconfident. We weeks came by, weeks went by and Casey and I were talking and I was like, I don't know, I don't know. I don't know if this is the right company for me. He said, well, do me a favor. And here's where the piece of advice comes in. Tomorrow leave your ego at the door and that's, he walked away. At first I was like, what, what are you talking about? I have no, but of course I did, right? Of course I did. And that one comment reframed my early career and through that I became a humble designer. I became a designer that that observes first, then acts that asks why instead of here's the answer and it really framed my early career. I love that story and I have to say, I think there was like a period of time, I don't know if this is necessarily true anymore, but like the FreshBooks School of Product and Design produced amazing people. That's also where I started my career and it just like was so instructive and like to your point, so deeply humbling, such a humbling place to work with a lot of like rigor in the process that was just very humbling. And it, I think it just built really, really great judgment. So I love that story so much. - Completely agree. - Oh, Allison came from there too. - Yeah, Allison is on our team now. Allison Garcia, so I know it's amazing. - From Jabber. - Yeah. - Oh my gosh. - Yeah, Jabber Shopify and FreshBooks. - And FreshBooks. - Wow. - Wild stuff. Okay, our next lightning round question is, we love this one, shout out a work bestie and that's been there for you as a leader. - Oh man, I'm gonna shout out a long standing, design partner and our friend. His name is Toby, Toby Negale. He's a designer at Shopify. He's been there for nine or 10 years, I think at this point. Toby and I are at opposite ends of the design spectrum. We, you know, regardless of, let's not get too deep onto the design spectrum of what it is, but Toby is an incredible, incredible design mind that is focusing on, that when we were worked together would focus on a technical aspects of a solution. He would like iterate and innovate in ways that I continue to believe, my craft would never get me there. It was never that strong as a designer where I find that my skill set complemented his, is that I found a lot of joy and a lot of purpose in storytelling and bringing people along the journey of what we were doing at Shopify, which was reimagining point of sale, framing the why, framing our story and then, of course, like leading teams through divergence because we were the creators of an all new, the all new POS system, but we needed multiple teams to come help us. It became an incredible partnership and it's like the best example in my career where I found this like Yin Yang effect and two designers with, with a seemingly opposing skills because, you know, no designers is the same. Seemingly opposing skills coming together and becoming this unit that, like, he would lean on me for certain things, I would lean on him for certain things. It's, yeah, it certainly marks some of the high moments of my career thus far, has been working with Toby and, yeah, we continue to be friends to this day and, yeah, even in the music, didn't it? Like, he would like, we would sit side by side, he would listen to metal and I would listen to Broadway, you know, like, just that's how, that's how different we were and in it worked and it continues to work and, yeah, he's now a dear friend. - Awesome, go Toby. For a second, I thought you meant Toby, the CEO. - Toby, the CEO, yeah, everyone does, yeah. Yeah, he's Toby with the Y and we say that Toby, CEO is Toby with an eye, so yeah. - Last, let me round question. - Side projects or passion projects or just like any plugs at all, maybe you're hiring, if you have a passion project, the 204 downloads of your hub will help you go viral. - I'm not gonna talk about a side project because my side project at this moment in time is raising a human being, so shout out for that, but I will shout out one quality as a whole. Human, if you are watching this or listening to this, please do not forget to read, read, buy a book, go into a world, like, submerge yourself into a world as someone else has written and then through that, find creativity, find purpose. So it's the call to action is broad, it's just go and read, don't read a PRD for God's sakes. Go read, go read a book that sends you somewhere, the teleports you to a new world. That's my wish for anyone to listen to this. - Oh, if you're reading a PRD or downtime, we can't help you. - No, and it's definitely, I generated. I love that plug, that's great. - Thank you so much, Ricardo. This was such a delightful conversation, dare I say such a playful conversation, and I think we were all accessing our inner child. Thank you so much for coming. It was truly such a pleasure. - Dave, Danielle, thank you. Thank you, and hey, I'm honored. I'm honored that you're reached out to me. - Thank you so much for listening. - You find all the links, projects, and resources we mentioned in the show notes. - If you enjoyed this episode, subscribe wherever you get your podcasts and share it with someone you think would love it. And don't forget to check out our subsdaq, Dear Danielle and Dave, for more. - If you have questions, feedback, or you'd like to collaborate with us, or be a guest on a future episode, drop us a line at [email protected]. - Until next time. 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