50 episodes down and the lessons we've learned along the way

This is a special episode for a few reasons—it’s our 50th episode and it kicks off season four of Overtime! We had so many incredible people on the show last year that we’re looking back at 2018 and sharing some of our favorite clips.

We were surprised to see some common themes emerge over the year. In this episode, you’ll hear from past guests about how they’ve attracted the clients they truly want by sharing their authentic selves, how teaching can actually be a big learning experience, how side projects can be used to explore new directions, and a few more.

We hope you enjoyed listening to season three of Overtime as much we enjoyed making it. Have feedback for us? Share your thoughts in our annual Overtime survey.

This episode is brought to you by PageCloud, the world’s best drag and drop site builder. Right now, PageCloud is offering you the chance to earn up to $1,000 for building a PageCloud template. Sign up at pagecloud.com/dribbble.

  1. Overtime with Debbie Millman
  2. Overtime with Alana Louise
  3. Overtime with Tina Roth Eisenberg
  4. Overtime with Katie Dill
  5. Overtime with Pablo Stanley
  6. Overtime with Mary Kate McDevitt
  7. Overtime with Rob Generette III
  8. Overtime with Lauren Dickens
  9. Overtime with Tad Carpenter

Subscribe to Overtime on Apple Podcasts or Spotify. Or download the episode via Simplecast.


Dan Cederholm: They said it couldn’t be done, but here we are - episode 50 of Overtime. I’m Dan Cederholm. This is Dribbble’s official podcast. Actually, no one ever said it couldn’t be done, but here we are anyway - 50 episodes, a pretty cool milestone. And I feel so fortunate to be able to do this and host this show and basically learn from some amazing talent out there. I feel really lucky to be able to do this.

Dan Cederholm: This is a special episode for a few reasons. One, it’s our 50th episode. Two, it kicks off season four for us as this is the first episode of season four. And also, we’re going to be looking back today at 2018 as a whole and pulling out some of our favorite clips from all the interviews that we’ve done. It’s pretty cool because there are some common themes that emerged from talking to all the folks last year that were unplanned, and I thought that was really interesting - things like how to get clients that you want to get from side work. Learning by teaching was a big theme that popped up in several places, having a sense of humor and fun in what you do, persistence. There’s just a lot of stuff that came out of all the different folks that we interviewed.

Dan Cederholm: This episode is brought to you by PageCloud, which is an extremely cool drag and drop website builder, and I’ll be talking more about PageCloud later on in the episode.

Dan Cederholm: Oh, and before we get started, we want to hear from you. We want to make this podcast the very best podcast it can be in 2019. We have a short survey for you, a couple of questions about how you listen to the podcast, and if you have any feedback for us, we’d love to hear it. So check out the show notes in this episode for the link to the survey, and we’d really appreciate if you’d fill that out for us.

Dan Cederholm: Let’s get started with the first episode that we actually did a year ago with Andy J. Pizza. He’s host of Creative Pep Talk podcast. This is a good one to start off with because Andy starts by talking about finding his gift and how he found his gift and how you can too, and embracing what’s weird about you in order to make you unique and embrace your gift as well. So here’s Andy.

Andy J. Pizza: The thing that’s driven me since I was young even was this idea that … I think it’s best summarize that I always talk about this quote by Picasso where he said, “The meaning of the life is to find your gift, and the purpose of life is to give it away.” And I think that the meaning of life is finding your gift is the first part of that, and I think that in our society we think that you find your gift through a 30-minute career aptitude test, that you’re going to find the meaning of life in just a little navel gazing or self-reflection or a Myers-Briggs test or something. And the thing that I think has served me better than anything else is that I’ve always seen finding my gift as a journey, and I’ve never been satisfied with anything but the real thing. Even though I don’t feel like I’d ever properly tasted that exact sweet spot, I always felt like I had a metal detector that was telling me when I was getting warmer or when I was getting colder.

Andy J. Pizza: Basically, in that Picasso quote, I think you can extrapolate the definition of a gift. In my opinion, it’s what’s weird about you that other people want. I always say if you have something weird about you that helps other people, it’s a super power. And if you have you something weird about you that doesn’t, it’s an abnormality. I think a lot of creative people, myself included, have spent tons of time in a self-obsessed place obsessed with this weird thing that we’re into or this weird thing that we can do, and it’s more of an abnormality than it is a super power, which is a problem if you want to create a career on the back of it. If you just are doing it to express yourself and you’re not worried about or you don’t feel called to do it for a living, that’s fine. But for me, I always felt like it’s either this or I’m going to have to fake insanity and be taken care of in some kind of home because I don’t have anything else. This is what I know how to do. It’s the only thing that makes sense to me.

Andy J. Pizza: So I feel like the first half of my journey was just a series of science experiments. I’d have a hypothesis of what I think. Based on data I have, this is my hypothesis of what I think that gift is going to be. And I would do a personal project to test it out and invest in that path, and then assess how it went, and then press on or pivot. This is like looking back, it didn’t feel that clear to me, but now I have this system that I think about because I go on to try to help other people do the same the thing. And by no means do I feel like I’ve completely found it, but I definitely feel like I’ve made a lot of progress.

Andy J. Pizza: So anyway, all that to say that that was the process of getting to Creative Pep Talk.

Dan Cederholm: Okay, there’s a couple of cool things here - Andy finding his gift and then giving it away in the form of helping people through his Creative Pep Talk podcast. I think his journey in getting there is really inspirational and it reminds us that find what’s different and weird about you and turn that into a passion project. For Andy, that was his podcast. What’s cool is how he got there. He went on to explain how he’d never done a podcast before and how he started.

Andy J. Pizza: Directly after that moment was when I started to conceive of doing the podcast as it is now, and I’d never done a podcast up to that point. I was like I’ve got to figure out … basically, again, take this hypothesis and prove it with a project. And I just thought the only way I’m going to get momentum behind this and start getting invited to conferences and stuff is if I take the reins in my hands and create basically an online portfolio of talks.

Andy J. Pizza: I think as I went through mastering the art of the side project, which I haven’t done, but working on this idea of how do you make personal work that really pushes things forward in a direct, deliberate way. So one of the things that’s always happening is a portfolio proving that you can do what you want to get hired to do, and that was definitely a part of it. But I will say that more than anything, the reason why I think that there’s really some kind of magic sauce on this thing isn’t because of me at all. It’s just because it’s such a part of my passion and my history.

Dan Cederholm: And there it is, folks. You’ve got to be passionate about what you’re doing and what you’re creating and putting out in the world. That certainly comes through in Andy’s work for sure.

Dan Cederholm: Speaking of passion projects, we sat down with Jim Coudal last year, creator of Field Notes, Jewelboxing, Layer Tennis, a whole bunch of different side projects that Jim has been successful with. And it was really great to sit down with him and hear how he got to where he is, which as it turns out is a pretty good place to be.

Jim Coudal: We’ve been good at starting things and we’ve been pretty good at managing them, and we’ve been excellent at shutting them down.

Dan Cederholm: Wait a minute. Can you be good at shutting things down? Jim goes on to explain that it’s all about trying new things and then seeing what sticks.

Jim Coudal: Try stuff out and if it’s a moderate success, try to figure out how to make it a bigger success. And if you can’t figure out how to make it bigger, then go on to the next idea.

Dan Cederholm: I love this thought that not every business needs a business plan or massive planning behind it. It can just be something you want to try, something you’re passionate about that you enjoy that you want to see in the world, and then you see what works and what doesn’t work. This is how Dribbble started really. It was a side project and it grew. It was a slow road to grow and that’s okay. What’s cool, too, is that Jim goes on to talk about the definition of success and maybe redefining what that means. Success doesn’t necessarily mean that everything you create is going to be profitable or last forever. Sometimes you can get success just from the path of doing it and learning from it.

Jim Coudal: Things can be okay successful. You know what I mean? It’s not like, well, this is either going to be a success or a failure. And that’s not to say that we haven’t done plenty of things that have been abject failures too. But I think don’t underestimate getting out of bed and wanting to go to work as part of the equation of success or failure.

Dan Cederholm: Man, Jim is smart. Not everything has to be a “success” from the outside to be valuable. I love that. The path that we take to create things and try new things is oftentimes success in itself. That’s just wonderful advice.

Dan Cederholm: And this idea of persistence, this theme of persistence in trying, trying, trying until it works is a theme that carried over into one of my favorite episodes of last year back in February with Debbie Millman.

Debbie Millman: It’s very rare to have the Jessica Walshes and Jessica Hisches and the Timothy Goodmans who come out of the gate and hit the ball out of the park first pitch. It’s really rare. For every one of those, there’s probably 100 or 200 or 300 thousand people that are slogging away at trying to figure it out. And to those people, because I was one of those people, I say keep trying and keep trying with self-generated work. I don’t think it’s possible to make a name for yourself doing work for other people. I think that the way you make a name for yourself is doing original work on your own, which doesn’t mean you have to quit your job to do it. I was doing Design Matters while I had two full-time jobs, one at Sterling Brands and one at the School of Visual Arts. So I had a day job at Sterling and a night job at SVA where I’d been running a graduate program. So you make the time to do what you want to do.

Debbie Millman: And that gets back to the other thing that I say all the time, which is busy is a decision. If you say I’m too busy to make self-generated work or to make work that I feel is different or attempts to be original in some way, then it’s just not a priority. It’s just not something you really, really, really want to do because we somehow find the time to watch Game of Thrones, or House of Cards, or Homeland, or whatever it is. So if we have time to binge watch a TV show or spend three hours last night watching the Grammys, we have time to make work.

Dan Cederholm: Right. So keep trying but keep trying with self-generated work. I think that is excellent advice. It’s always worked for me. Don’t wait for big clients to come knocking on your door to create something. You can make up your own stuff, make up your own brands.

Debbie Millman: The way that I would guide people to try to do something for themselves is to do something where you don’t have to ask anybody’s permission for something, where there aren’t parameters put in place by somebody else in which to make something. And if you can sit down and try to do something with that lack of parameters, it might help guide you to something meaningful.

Dan Cederholm: I pressed Debbie on, well, is that work real if you’re just creating, say, fictitious logos or whatever? And she came back with a really great answer about what is real.

Debbie Millman: If you’re creating a graphic novel, if you’re creating some type of visual identity for something that you’ve created, how is that not real? I mean, I think that real is a subjective word. If you mean it’s not being sold in the marketplace and people aren’t buying it, well, then I don’t know that Design Matters would qualify because it’s free.

Dan Cederholm: Boom! You heard it from Debbie Millman herself, folks. The stuff you create is real. Even if it’s not for a client or for big money or whatever it is, it’s real. I just loved hearing that from Debbie. So create those projects that you want to see.

Dan Cederholm: And along those lines, we were talking with Alana Louise in another episode last year, and she shared how her lifestyle online and the things she shares on her Instagram - for instance, like her fly fishing and her adventures - being herself has attracted the type of clients that she loved working with - outdoor companies.

Alana Louise: Okay, this is my assumption because I’m not 100% sure why I got this lucky, but I think because on my Instagram I post pictures of whatever hike I did or whatever fish I caught that that attracts a certain group of followers. Then when they discover that I’m a designer, I think that’s when that type of work comes in. Right now, I’m working on a project with two outdoor companies that are collaborating on public land use, which I’m a complete support for because the water I fish in is public and I would love it to stay that way. It just gets people excited when they realize that I’m passionate about similar things.

Dan Cederholm: By being genuine about her interests, Alana was able to attract clients in those spaces and went on to work with really cool brands in the outdoor space.

Dan Cederholm: So I think take those bits of advice and put them together. Be true to who you are and your interests but also know that you have the ability to create your own work, your self-generated work that’s a reflection of the kind of work that you want to do.

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Dan Cederholm: All right, so what if you’re building products and you’re building teams that need to build those products? We talked to Tina Roth Eisenberg, a.k.a. Swiss Miss, back in August, and one of the first questions - and she probably gets this question a lot - was how do you do it all because she has so many side projects that have turned into real businesses, much like Jim Coudal. But how does she do it? We dug into it a little bit, and I think part of it is she does attract and hires really, really good talent and people that are on the same page as Tina. So here she is explaining that.

Tina Roth-Eisenberg: I mean, to be honest, I am someone who probably puts too much on my plate on a regular basis. But at the same time, all the things I’m doing are things I really care about and I want to see in the world. Then I think the luck I have is that I can get people very excited about the things I want to build. So I get to form really great teams around me that support what I want to do. Obviously, without that, I could not have built all of the projects and companies that I’ve done.

Dan Cederholm: So for Tina, her enthusiasm about the thing that she’s building has to rub off on those people that want to work with her and want to build those products with her.

Tina Roth-Eisenberg: I think the secret sauce here is if you’re someone who’s really enthusiastic and can ignite that fire in someone else and then they come on and they want to build that thing with you, then this is possible. Right?

Dan Cederholm: I also asked Tina how do you find these people? How do you find these people that are just as passionate as you are about the thing that you want to build? Here she is shedding some light on that.

Tina Roth-Eisenberg: I mean, I feel like the things I want to build and see in the world, if you want to work with me, you have to connect with who I am on a very, very deep personal level. I always say you have to share a North Star and the same values. But when you find those people, and you give them freedom, and you let them bring themselves into work … I’m a very trusting person to the point where it’s almost sometimes I’m like, “Wait. Tina, you trust people way too much.” But what happens out of it is trust really breeds magic. When you hire capable, smart people and you have the same values, and you agree on that thing you want to build, and you both see the value and you feel like it makes the world a little better, and then you let them run, then there’s real magic that happens.

Dan Cederholm: Trust breeds magic. That’s really important to remember. I know I have trouble letting go of things and delegating and all that. But Tina makes a point to find those people that are passionate and trust them.

Tina Roth-Eisenberg: Well, I think it goes into the same thing again as I said before. I feel like the reason I was able to attract the remarkable team I have is because I’m very enthusiastic about things in the world. I’m a confident person, but I’m not just confident and I feel like the joy that comes out of enthusiasm is contagious. So enthusiasm is contagious, and contagiousness is what you need when you want to assemble a team that keeps going and when you hit bumps that you … So I’m a big believer that enthusiasm goes along with joy, and I’m a big believer that you need to create environments that are very joyful.

Dan Cederholm: Passion, enthusiasm, joy, trust. These are all important things to building good teams and building good products out of those teams.

Dan Cederholm: Now, you have this passionate team and how do you make sure they stay passionate and stay happy? We talked to Lyft’s VP of Design, Katie Dill, back in November and she had some really interesting thoughts about recognition within teams in an article she wrote about how she applies this book, The Five Love Languages, to making sure that managers in design teams are recognizing their team members in ways that they want to be recognized. And it turns out not everyone wants the same things.

Katie Dill: You might consider yourself a fantastic manager and you go out of your way to make sure that people know when you appreciate them and the great work that they’re doing, and you’re tapping yourself on the back thinking, “I’ve done a great job here.” Then at the same time, you hear from the same person saying that they feel like they’re never recognized. And it’s that moment where you realize they’re perhaps seeking something else. You might have thought just giving them a pay raise was enough, but they actually might find that hearing encouraging words from you matters way more than their salary or that just the autonomy to take on a project on their own without so much leadership oversight is what they’ve been craving and not tangible salary benefits.

Katie Dill: So you really do got to just dig into that a little bit because basically, we’re all different and we all speak a slightly different language. It’s totally fine that we do, but if we understand what the other person’s preferences are, we can better cater our conversations so that they can resonate more.

Katie Dill: And in the article, what I’m laying out is I compare it to the five languages and I offer a recommendation of what these five languages are in the workplace - things like encouraging rewards, further autonomy, visible impact, etc. - and explain what each of those things are and how you might see that want in the people on your team. Then I also do try to make the point that people want all of these things probably but in different amounts, and I think the real key is trying to understand what are the things that are the primary drivers and motivations for folks. And that will help you understand how to really drive home your messaging when you’re trying to provide recognition, appreciation and encouragement to your team, which I think hopefully all managers know is a really important part of getting a team excited and driving towards the right things and frankly, just fulfillment in their job. We all want to know we’re doing the right thing, so we need to hear that from our peers and our managers.

Dan Cederholm: Last April, we talked to Pablo Stanley, a really talented illustrator, UX designer, educator. And he had an interesting analogy around being in a band and how that relates to working well within teams.

Pablo Stanley: I always say, “Hey, start a band. Start a band.” In retrospect, I understand all the things that are learned by having a band when I was starting as a teenager and all those things. Obviously, in the moment, I didn’t know that this was going to be helpful and useful and in the future me. But in the present, I’d remember just if you have a band, you have to overcome all the differences that you have. Probably the drummer likes heavy metal and that’s their thing, and the guitarist really likes Latin music. But at the end, you have to find a common thing, and you have to find something somewhere in the middle where everyone is satisfied and everyone’s happy and everyone’s enjoying what they’re doing.

Pablo Stanley: I think that’s something I learned as being in a band. And you have to be persistent and you have to be really good at practicing. If you want to do good in a show where you present your music or you are exposing you’re vulnerable on a stage in front of people with a microphone, you want to practice a lot. You want to become great at your craft, and you only do it by being really good with your scheduling and being really good with communication with your band. And I see a lot of parallels with working with a team, with a product team where you have different roles in a team where it’s the front end. The designer is the project manager or the product manager and the engineer and the back end, and all these people that are working towards the same goal and probably there’s a lot of differences between them, but at the end, they all are trying to play some tunes in front of people and they want to do a good job at it, and they want to be proud of what they’re doing.

Pablo Stanley: That’s something that I always say, hey, if you have the time … I mean, it doesn’t have to be a band. For me it was a band because I suppose I’m the creative type, whatever that means. But some people, I don’t know, they’re probably into sports. So join a team and actually learn. It’s another thing that you will have to practice a lot to become good, and not practice by yourself but also learn how the rest of the team works, and what do they like and how does that affect you, and how can you help them reach their goals because if they reach their goals, they can also help you reach your goals too.

Dan Cederholm: So joining a band or a group or something that helps you understand what it means to work well within a team is super great advice, and it’s worked well for me for sure. But Pablo, tell us about how you really feel about drummers.

Pablo Stanley: Usually drummers will be … I don’t know. They are kind of snowflakes. Is that how you say it, snowflakes? You have to be very careful with a drummer and not hurt their feelings because the drummer, they know they’re super important. They know it. They know that that band is nothing without the drummer. You can play, you can go to a show … I mean, if you are in a punk rock band, that’s one of the things, that you can go in a show and it’s like one of our guitarists is missing, but it’s okay. We’re going to play because we’re punk rock. Let’s do it. But you cannot do that without a drummer. You cannot just go out there without … because then what is it? You need that beat. And they know they’re really important and you have to take care of them. So sometimes, if you’re a drummer, stop being a jerk. And I suppose, don’t be the drummer in your team too. Sorry. Be the drummer but don’t be a jerk drummer because drummers are really important, and they’re the ones that keep the beat.

Dan Cederholm: Now, we’re onto a theme that popped up several times, and that is learning by teaching and the fact that you can teach while you’re learning something and you don’t need to be an expert. This is a topic that really resonated with me because it certainly mimics how I got to where I am with really sharing and learning as I was going along. It helped me actually learn the thing that I was trying to explain. Pablo kicked it off for us here back in April and explains how he learned by teaching.

Pablo Stanley: Me sharing, I do have some selfish purposes behind this, and it’s because it helps me learn better. And probably by being open, I let other people be more open, too, and probably I can learn from them. In a way, that’s the selfish part of it where I also want to learn from others. Also, when you’re sharing your process, when you’re opening the box and telling everyone, “Look. Look what I did,” then you’re being vulnerable. You’re opening up yourself. Then it helps you be of the mindset that number one, you have to be more careful about what you do, too, and you have to understand it better. If you’re going to share it with other people, then you have to deeply understand what you’re doing because then you cannot teach without understanding a little bit of what you’re teaching.

Pablo Stanley: So when I started doing this, it was because of that, because I wanted to learn. And it sounds weird, but by teaching, I was actually learning because I was forcing myself to deeply understand how this thing works, and then I can explain it to other people. Once I understand it, then I’m able to put it in a way that other people can understand it too. So in a way, that’s my personal way of learning. By teaching others, it forces me to understand things.

Dan Cederholm: I just love this advice that you don’t need to be an expert, just dive in. Start sharing what you’re doing while you’re learning it. I mean, it’s actually the reason why all these YouTube channels are huge that my kids watch. It’s because it’s fun and it’s interesting, and I think it’s easier to learn something from someone that’s also in the same boat as you and that’s learning maybe at the same level that you are.

Dan Cederholm: We also talked to Joshua Davis, an amazing visual artist that’s been around for decades really. He made a big name for himself in the Flash world and is now doing some amazing programmatic, artistic things. He talked about how it’s okay to give your stuff away and how it’s beneficial for him to contribute to open source.

Joshua Davis: I got this argument years ago when I was doing it with Flash, and people would say, “Why are you doing this? Why are you giving away the FLAs?” Most people didn’t realize that if I gave something away, I would get it back 50 times and 50 times people trying other things. So I was learning. I was learning because it’d be like, oh, shit, I never thought to do that, and that would end up fueling more of the creative process. So open source is very valuable in the sense that people do contribute, and they contribute outside of what you know. So they’re going to do things that end up informing you. So it just means that the inspiration is always moving.

Dan Cederholm: Right. So by sharing as you’re learning something, sharing it with the world, giving it away, Joshua is explaining that he learns from that. And that’s the power of the Web really and the power of numbers out there.

Joshua Davis: If you are willing to give stuff away, people are going to give back to you. Literally, I have sketch books of ideas that are spanning years of ideas that I still haven’t gotten to yet.

Dan Cederholm: Right. There’s just not enough time.

Joshua Davis: There’s not enough time. There’s not enough time to embrace all these paths that people have helped point me into certain directions. Open source does that. Open source says, “Hey, you have one simple idea. People will give you that idea back with 50 mutations.” So there’s never a moment where I say, “Oh, I have no idea what I’m going to do today.” That’s never happened to me.

Dan Cederholm: Back in November, we talked with Mary Kate McDevitt, an illustrator and letterer, and she reflected on how teaching helps her refine her own process and put a microscope more on the way she creates work in a way that wouldn’t have happened if she wasn’t teaching.

Mary Kate McDevitt: I mean, I’m really terrible at analogies, and the ones I come up with, I always talk myself out of it because they’re too basic. But I’m always like it’s like math homework. You have to show your work. How did you get here? And that’s what that class is all about. It’s basically just taking a sketch and just really carving away at it.

Mary Kate McDevitt: But when I did that class, it made me realize how I enjoy teaching and how making yourself reflect on your own process is really important. So when I was creating the outline for the class, I would be doing something and anytime I was like, “Oh, I wonder if people don’t realize this one little detail to create a drop shade,” or something like that. Any little tips and trick that you can spell out a little bit more clearly for students is really helpful. So it was really nice to just take a step back and look at my work from a bird’s eye view basically.

Mary Kate McDevitt: I’d say with teaching, it’s like I’ve laid out my own set of rules to follow with each project I approach. So if I feel like I start straying from my own process, then I’m like, “Oh, better go back and do a revision,” or something like that. It’s helpful to know that you have these set of steps that you have to follow, I guess. And the personal projects are usually ones where I don’t follow it basically at all. I start with something where it’s like I want to draw birds and I’m going to do a drawing about birds. Then I start drawing and something pops up. There’s no brainstorming. There’s no really crazy amount of sketches. So I like having the personal work to loosen up a little bit and not be so precise and have to follow up because it can feel restricting if you feel like you’re just only following this one process each project. It’s like I want to let loose a little bit.

Dan Cederholm: Not only is she learning by teaching, but she’s also using personal work as an opportunity to continue to experiment and refine that process that she has.

Dan Cederholm: Speaking about learning on the job, we talked to Rob Generette, III, about his first teaching job at a high school and teaching photography and how he’d never taught photography before. He had to learn it and he sort of put the challenge back to the principal.

Rob Generette: The film process, I mean, I had to learn it. As a matter of fact, during my interview, I told them, “Yeah, I can learn it in two weeks.” And you should have saw the look on my principal’s face like, “Oh, really?” And it was almost like, “Oh, challenge accepted. I’ll take you up on that.” And I learned it in two weeks. Being that it was a new school, I had to put all the enlargers together. I had to set up the dark room. I had to unpack all the chemicals. So as I would unpack the chemicals, I would learn the nature of the chemicals and where they fit within these different processes.

Rob Generette: As far as putting the enlargers together, it prepared me for if there was some troubleshooting to do or if one decided it wanted to malfunction. Even though somebody had to cause it to malfunction, I would know how to fix it because I put them together basically.

Dan Cederholm: That’s amazing - learning it in two weeks, being able to teach it, but then having it so fresh that you’re able to troubleshoot things that happen. Rob went on to talk about what teaching meant to him.

Rob Generette: Yeah, I credit teaching to that attraction, that draw that I have. Being a teacher, whatever you’re in public or you’re doing something of that nature, it adds a warmth to the whole experience because I got to know my demographic. I got to know what’s comfortable for them. I got to have my transitions, my segues, and I got to have a certain flair to deliver whatever message it is that I’m trying to deliver, whether it’s verbally, if it’s written or either visual. I put all of those different tenets and elements in effect whatever I go up there. And most of the time, I don’t know what’s going to come out of my mouth until I watch the audience walk in.

Dan Cederholm: So for the last theme that I thought we’d touch on in our wrap-up of last year is the importance of fun and play and having a sense of playfulness and a sense of humor in the work that you do because if we’re not having fun, then why are we doing this at all. Here’s illustrator, Lauren Dickens, sharing how fun and playfulness is important in her work.

Lauren Dickens: It’s definitely somewhat intentional. I love making people laugh and I like surprising people too. I also like surprising myself, and when that happens while I’m designing is probably one of the best feelings you can have as a designer when you can step back and be like, “Wow, that’s really something there. I’ve tapped into something here.” That’s a really incredible feeling. So it’s really not like I start a project and the goal that I’ve set for myself is that I want to make people laugh. It’s really about finding the connection between whatever I’m trying to communicate conceptually and then tying the visuals back into that, almost like an infinite loop if that makes sense.

Lauren Dickens: So injecting, yeah, some wit into the work, and basically, these larger concepts I think really help the work resonate with people and keeps it interesting for me doing the work because if you’re not having fun, then why be doing what you’re doing?

Dan Cederholm: Amen. Also, it’s a tough world out there, and how do we real with real serious topics day after day after day? Here’s why Lauren uses humor in her work.

Lauren Dickens: It’s kind of a lighthearted way to take on these really tough issues. As a human being, I would say I tend to use humor as a tool in a lot of ways or at least humor to talk about deeper things. So I think that it’s number one, a really great exercise for me to really gather my thoughts. The world we live in is such a touchy place right now, so trying to inject a little bit of humor into these concepts and trying to get a laugh out of people or to bring people together in that way I think is a step in the right direction because it’s hard to be serious all the time about these things, even though it’s important.

Dan Cederholm: For Midwest native Tad Carpenter, adding fun to his routine involves creating a challenge for himself, drawing a sun every Sunday. And he’s been very dedicated to this and has drawn almost 200 of these suns, each in a unique style. Here he is explaining the inspiration behind that.

Tad Carpenter: Once a week seems like a very achievable goal for me. The way I look at it, for me, play is so unbelievably important in my work and the value of play. A huge part of what I do is really try to remind myself how lucky we are to do this. I feel like I never feel more alive sometimes … This is the saddest thing I’ve ever said. When I’m actually creating something, there’s a feeling I get from that that is something I wish I could bottle up. And that’s kind of what it is, is me getting to make and play for myself and not for a client, not for a specific deadline even really, but letting me just make things for myself and just explore new styles, explore new mediums. And at the bottom line, what it is is it ends up being practice also for me. And we forget to practice our craft. It really was me trying to find a way to make something for myself and purely explore and do things for myself.

Tad Carpenter: But as things went on, I started seeing different needs and different avenues on how this project is starting to come into people’s lives in some way potentially. It’s just a fun thing that I do, but the bottom line, what I hope is that through that work, it shines, for lack of a better term, a little ray of light on their life that day they see that thing, that object when it comes into their lives. I’m a firm believer that as designers … I mean, the bottom line if you really cut through all the crap with design is we’re here to better the human experience. That’s what it is bottom line. Yes, navigation and communication and all these things, but at it’s core, design is here to better the human experience. And to me, I hope that these little exploratory things that I get to make and have fun doing can free people from any concerns they might have that day or just make them have a little smile. That’s what you hope your work can potentially do.

Dan Cederholm: Right. So I think this is a perfect note to end on, to remember that we’re lucky to be able to do what we do and to create and try to make people happy. Don’t forget to fun. If you can’t have fun in your day job, then create your own fun on the side.

Dan Cederholm: I want to thank you for listening. Thank you for listening to our 50th episode. It’s a fun look back at the whole year. I’m really excited for this next season. Season four is going to be wonderful, and we’ll see you back here in a couple of weeks. Please make sure you subscribe to Overtime, and we’d appreciate it if you’d rate and review us on Apple Podcast or wherever you listen to podcasts. Thanks again. We’ll see you soon.

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