Jonathan Patterson

If you’re a product designer that’s been thinking about striking out on your own in 2024, then Jonathan Patterson is a name that you need to know. As a freelance senior product design generalist, he knows all about rolling with the changes in the industry, and about what it takes to stay competitive.

Jonathan and I spoke not too long after his presentation at AIGA Detroit’s IXD2 event, and he talked about the various projects he’s worked on in the fields of healthcare, education, and AI. He also shared his personal journey growing up with a passion for drawing, transitioning from traditional print design to digital products, and explained why he made the switch to full-time freelancing (and what he’s learned along the way).

Hopefully Jonathan’s story and his work inspires you to carve out your own path for your career!

Interview Transcript

Maurice Cherry:

All right, so tell us who you are and what you do.

Jonathan Patterson:

All right, so I guess I’ll give you the elevator pitch. I’m the invisible hand that crafts the products you rely on daily. Often we don’t know who’s behind the things we touch and interact with. And I mean that in the virtual and the physical, you know, whether it’s the buttons you click to play your favorite podcast or the home screen of a service that you subscribe to, I design and make sure everything is where you expect it to be and make it look good in the process. So I’ve got a BSA in visual communications from Kendall College of Art and Design, which is essentially graphic design. And over the years, I’ve slowly morphed my interest and my focus to kind of like pace or sometimes exceed where the industry is headed so I can stay competitive. But these days, I’ve moved completely into product design generalization. So instead of having one focus like user experience design, I do all of the skills that are closely related to design that launching a product or service usually requires.

As a full time freelance product design generalist, my goal is to really have a variety of skills that when you total them up, they make what I have to offer kind of more comprehensive and fine tuned than anyone who’s just doing one part of the product design stack. So, Jonathan Patterson, two decades of experience, first podcast interview. Let’s go.

Maurice Cherry:

Looking back at this year, what are three words that you’d use to describe how 2023 has been for you?

Jonathan Patterson:

I would say revolutionary, difficult. Well, this is not a word or more of a phrase. Kind of par for the course.

Maurice Cherry:

Okay. How has it been “par for the course”?

Jonathan Patterson:

Par for the course. Meaning there’s always something changing. Nothing stays the same, which is especially true in technology. Right. And I think any business owner, which as a freelancer, full time freelancer, I certainly look at myself as a business owner. But there’s always a challenge to contend with. So par for the horse means while we have certain types of challenges this year, there’s always a challenge to contend with.

Maurice Cherry:

Yeah. Well, the only thing constant in the world is change, as the saying goes. And I think those three words are a really good way to sum up 2023. I think for a lot of people.

Jonathan Patterson:

Yeah. Everywhere you look online, it’s people posting about the tech layoffs and their job being downsized or eliminated or can you help me get a job? That’s what I’m seeing a lot of.

Maurice Cherry:

Yeah. Do you have any goals that you’d like to accomplish for next year, like any resolutions for next year?

Jonathan Patterson:

I think one of the things that I’ve been sort of indexing on is just starting something, I suppose, of my own on the side. Now, while I have a lot of different fun side projects that I’ve done here and there, I think that’s probably one of my objectives for the upcoming year, is to start something maybe that is more official outside of the full time freelance product design work that I do. It could be a product or service. I have many ideas about what those could be. I keep a running list of things that I’m considering and just ideas that I’m vetting. I think that’s probably one of the focuses that I will put some thought around soon.

Maurice Cherry:

Now, you just did a talk recently. There was an event in Detroit called IXD2 put on by AIGA Detroit. Shout out to Carlos and the folks there. Tell me about the event. How did it go?

Jonathan Patterson:

It went well. That was a first annual, we’ll call it…it’s called IXD2, which is the interaction design Detroit conference, and it will be held annually. So I actually talked about how to stop ghosting your side projects and basically I gave five tips that I’ve used to kind of see my projects from start to finish. So it was actually a whole day of different speakers and panelists and workshops. So mine was towards the end of a twelve hour, probably around their day. But it went good. It was well received. It will continue into the coming years, as far as I understand.

So I’d be excited to go back or I was a speaker this time, but if I’m not a speaker next time, or if not involved next time, I’ll certainly be happy to attend it.

Maurice Cherry:

Now, was this a new talk that you created?

Jonathan Patterson:

It was, and it was relatively in short order too. I think that between the time that I came to understand that they were interested in perhaps putting on some type of event like this, and the time the event actually occurred was just a matter of a couple of months. So I kind of last minute put together some ideas and the presentation ended up coming together. I probably would have talked about something else besides how to stop ghosting a side project. But again, due to the time constraints, it’s just like, okay, well, let me see what I can do that will perhaps resonate with people. And as I also come to understand, I tend to try to get feedback from people after I do a presentation or a talk or something like that, just because it’s always good to be sharpening your skills wherever you can. One of the things I heard was that people liked the variety that my presentation provided. There was a lot of, as you might expect from the title interaction design.

There were a lot of presentations and talks about processes and user experience specifically into the weeds of those types of things. Mine was a bit more general and sort of lighter. So I heard that people like that kind of component of my presentation. And I’ll also say for anybody who perhaps is listening to this and who saw that presentation, that I did put a lot of emphasis on the design of the presentation itself, because so often I find that, and this is just an easy thing for us designers to fall into for some reason, that when you’re doing a presentation, you don’t necessarily design it to your best ability. Rather, you’re just so focused on the content that you sort of let the design go by the wayside. And I’m like, okay, I can’t let that happen this time. This is specifically a design conference, so I’m definitely going to make sure that I put equal focus on what I’m saying, what I’m presenting, as well as what it looks like. So the design, it’s kind of contemporary.

It’s of the times. Lots of interesting typography and visuals to look at us designers are a fairly fickle bunch. We like things to look pretty. So I’m like, okay, this is going to look pretty cool.

Maurice Cherry:

Do you do a lot of public speaking at conferences?

Jonathan Patterson:

I wouldn’t say a lot. I’ve probably presented just a handful of times. Really. I can count in one hand probably the number of times I presented, but I’ve had some local colleges who will ask, like accelerators or programs that colleges have that are related to product design or design will ask me to come and talk to one of their classes or something like that. So I’ve done that a few times. I was part of another AIGA event a few years ago before COVID where I talked about or I presented a case study that was the theme of the event, was like, case studies and case studies projects that you’ve worked on. So I presented then, which was a few years ago, and then, like I mentioned just a few weeks ago, with this most recent one. So not a lot, but I was happy to hear that.

Some of the feedback that I also got recently was that someone said that my presentation flowed very smoothly and they got the impression that I did it all the time. I’m like, well, thank you very much. That’s probably the best, most flattering compliment that I feel like I got this evening. So I was happy to hear that.

Maurice Cherry:

Nice. I mean, I hope you get a chance to give that talk at other conferences. I mean, you put that much time into designing it and you’re getting this great feedback, like take it out on the road.

Jonathan Patterson:

Yeah, you know what? Somebody else mentioned that. I think if the opportunity presents itself, I might do that.

Maurice Cherry:

So let’s talk more about you being a freelance senior product design generalist. You had mentioned that before. I was like, that’s a mouthful. That’s a lot. And according to your website, as well as what you just said, you are the invisible hand that crafts the products that you rely on daily. And you’ve been doing it for such a long time. I mean, almost 13 years. That is super impressive.

Jonathan Patterson:

Well, thanks. Yeah, I’ve worked in all sorts of industries on all types of projects. Early in my career I worked with on a bunch of apps in the education space that taught kids how to write or do math. I also worked on a project for the brand pull ups where I did a lot of UX and UI for an app that parents use to potty train their kids. Let’s see. Some other memorable projects that come to mind are product designed for a healthcare startup. This is akin to like Angie’s list for healthcare workers. I did iconography for OkCupid, where I created dozens of icons that reflect the interest and the characteristics that people show on their dating profile.

I did data visualizations for Brighthouse Networks, which was bought by charter Communications or Spectrum Charter, I believe. But more recently I’ve done work for this company called the Standard, which is this wellness and social networking app. They’re kind of still in this amorphous phase where they’re establishing their value proposition. I’ve helped this company called True Anthem. They’re out of California and they have this AI powered social publishing tool. And basically the gist of it is that large scale content publishers like the Associated Press or Reuters or NBC News give their social teams access to this dashboard where they can automate their social media posts and understand all of the analytics around what content performs the best and when to post it and where to post it to. So it’s this dashboard that integrates with all the popular social networking platforms. You know, Facebook, X, Instagram, et cetera.

Last, I guess I won’t forget to mention Ford. I’ve helped them on and off over the years. I’ve worked on their website, helping to think through different visual concepts to present features and promotions. I’ve also done a lot of work on what they call the build in price section of their website, which is the part where you customize a vehicle that you’re interested in buying. And that area of the site in particular is in constant flux, and they go through many iterations to push out even the smallest of changes. So I’ve helped with the UX and the UI there, as well as, again, lots of iconography for that section of their website. Yeah, I mean, that’s kind of the overview.

Maurice Cherry:

Now, you’ve mentioned a lot of different clients here and a lot of different sort of types of product design work that you’ve done. What are the best types of clients for you to work with?

Jonathan Patterson:

You know, I work on B2B and B2C types of projects. I tend to find the B2C ones a bit more, I guess, compelling to work on because the tone that you take in terms of the writing, the UX writing that you do for it, any kind of light copywriting that I might do, don’t get me wrong, I’m not a copywriter, but any of the. I think just the way that you approach a consumer is very different than the way you approach, like, a business product or service. Now, I definitely do both, but I think I probably get a little bit more fun out of the B2C ones. They’re just more room to, kind of…I feel like those apps and services are a bit, just more entertaining, if you know what I mean.

Maurice Cherry:

Is there any type of work that you want to do in the future? Like dream projects, anything like that?

Jonathan Patterson:

You know what, I have always been of this mindset too. I’m like, okay, it could be fun to work on in the entertainment industry specifically, maybe for some type of celebrity website or something like that. But then the more I think about it and the more I see how other industries work with certain types of media, I would imagine that it’s probably a more difficult ask to do some of that work quicker turnarounds, probably projects that you imagine might go a certain way, maybe don’t, because you’re answering to maybe people who have. Maybe my idea of what it’s like is totally different than what it’s actually like. I’m starting to think that that might be the case. So in the past, I’ve always thought that maybe I’ll work on entertainment stuff, but maybe not. I think what I have going for me now, which is a variety of types of work that come my way, is a great kind of mix because at times I’m working on very UX heavy work. Then, at other times, I’m working on very UI heavy work, and I think just the mix of projects is what keeps me most interested. It’s almost like you never get bored.

Maurice Cherry:

So you like to have that variety, it sounds like.

Jonathan Patterson:

Yeah. I think that’s one of the main draws to freelancing, is that you get to pick the types of projects that you work on in the mix. So if you’re ever feeling too much of something, you can say, okay, well, this next inquiry that comes in, I won’t take that, I’ll take this other thing, because my plate’s full in that other area. So, yeah, that’s definitely a plus.

Maurice Cherry:

One thing that we’ve been talking about on the show pretty regularly over the past two years is kind of how a lot of this new tech is encroaching upon the creative industry. Maybe encroach is not the right word, but it’s starting to infiltrate into the tools that we use, the way that certain businesses now offer new services, et cetera. I’m curious…with what you do, have you seen any trends or changes in the industry, particularly as it relates to AI or generative AI or something like that?

Jonathan Patterson:

Generative AI pretty much seems like it’s working its way into everything. ChatGPT has all of the, like, DALL-E and all of those types of services. Photoshop, just typing in something and generating it on the spot. It is totally changing the way that we work, the way that I work. Like many People, I think that we’re in this phase where we’re just trying to understand how do we make our businesses kind of bulletproof against some of these new technologies. I think at times people have this idea about, or this feeling that, okay, I can’t wait till things get back to how they were. They’re not going back. This is kind of like we’re here now. It’s just going to kind of keep on happening, and I don’t want to say get worse, but there’s going to be kind of more of this need to reinvent yourself, to come up with ways to stay marketable and relevant.

Maurice Cherry:

I mean, have you been using it any in your wor, or…

Jonathan Patterson:

No, I use ChatGPT for sure now. I tend to have it refine my work. So if I’m writing something, whether it be some text for a website or for anything, I like to use ChatGPT to refine my work instead of just be the kind of creator of it. I’ll say that one phenomenon that I do notice is that I tend not to recognize my writing. If chat GPT kind of manipulates it too much, and I think that might be, like, a phenomenon that people may start to realize. I’ve experimented with it, for example, commenting on a blog post or some type of medium article that I saw, where I’ve experimented with using ChatGPT to write my response haphazardly, type something out, pop it in a ChatGPT, have it, rewrite it, make it sound good, and then post it. Then go back and read it. Like a month, two months later, I’m like, okay, did I actually write that? I don’t remember writing that.

So that’s this phenomenon that I’m noticing with ChatGPT. So I use it, and I’ve learned to. Obviously, it’s still fairly new, or I’m new to it, but I try to use it more sparingly so that the work is my work, and I recognize it as such. But in terms of design work, not as much there. I’d say more in the lines of text. Right. I don’t feel like the image generators are exactly up to kind of the level that I would want them to be at. They’re helpful if you want to maybe change something small in an image, but they all had this overly smooth look.

If you try to generate an image from scratch, I’m sure that’s going to change in the future. But for right now, I don’t use it extensively in the kind of visual work that I do. It’s just not capable.

Maurice Cherry:

Yeah, we’ve had folks that have come on the show before that say they use it kind of like as a mood board or as inspiration. Like, it’s a great way to help spin up ideas. If you have maybe some ambiguity on where to start, it can kind of give you a nudge in that direction. But there still has to be discernment from humans, of course, the ones that are going to be using that stuff to decide how it should be used, if it should be used at all, if it should be changed, et cetera. So it seems like you have a pretty kind of discerning nature about how you use it.

Jonathan Patterson:

Yeah, most definitely. It’s going to change quickly, I might add, too. I think that there’s always this kind of impression that, like, oh, this is far off. Well, technology is kind of exponential in many ways, so while it’s not there yet, it’s probably going to be there faster than I expect. So I guess fingers crossed. I’ve got a little bit more time to be employed.

Maurice Cherry:

Well, let’s kind of switch it up a little bit here. We’ve talked a lot about the work that you’re doing. But let’s learn more about you, about the person behind the invisible hand, so to speak. You mentioned before we started recording you’re in the metro Detroit area. Is that where you’re from originally?

Jonathan Patterson:

Yeah, I’ve always been in this area. Went to school in Westland. I had a class in graphic design. I was, I guess, early on, though, I was kind of always interested in drawing by hand. That’s kind of where it all started, drawing on paper. Mortal Kombat characters. I remember when the Lion King came out, I got a computer. Then I started drawing in, like, Microsoft paint.

Lion King characters. Yeah. So I grew up in Westland or which school in Westland, rather. Then I went over to the Grand Rapids area for school for my degree, and after I graduated, came back and started working at this. I worked at J. Walter Thompson, which is this worldwide advertising agency. They have offices all over. So I was working on regional advertising campaigns.

That was technically an internship, but it was after I’d graduated and I was actually making money and working on projects. So it’s kind of strange, but that was an internship. It was after I graduated. So I did that for a year and then I started working. Once that internship ended, I worked at this full service ad agency, which is again, in the metro Detroit area, and I was doing all types of things. Any creative task that came through the agency, I had my hand in it. So they were full service. They did out of home, digital, print, radio, TV.

So I was the senior art director there, and I did that for about six years, and I decided to kind of break off and do my own thing.

Maurice Cherry:

Well, before we kind of get into that, I want to just kind of step back a little bit to talk about your time at Kendall, because I’m sure if you sort of had this sort of talent as a child where you really were drawing and into this sort of stuff, and then you wanted to pursue it enough where you went to school. Do you feel like your time at Kendall kind of prepared you for getting out there in the world as a designer?

Jonathan Patterson:

I do think it did. Again, things are constantly in flux. Right. Stuff that you learn. I was in college in 2004, so obviously things that I learned back then are not necessarily relevant today. But for the time. At the time, yes, it did prepare me. Now, that said, I did find that I had to, or I’m the type to push myself to learn new things.

So even though I did feel like some of the courses and things like that, I learned a lot, but I didn’t think that they were challenging me as much as I could challenge myself. So I would take it upon myself to kind of just do whatever I could to be learning new things and challenging myself. It’s a great program. I learned a lot there, but learning is never done. You have to constantly learn new software. Things that the programs that we were using back then practically don’t exist now, just things that you were doing then, just not relevant. So for the time, it was great. But I know much more now than I did back then.

Maurice Cherry:

No, I mean, that makes sense. I mean, if you were in college in 2004, I’m just thinking, sort of, what design tools were out there. I mean, I think everything was pretty much Macromedia or Adobe. This is before they, I want to say 2004 is before they merged, because I distinctly remember using fireworks, like right around that time. And I remember Dreamweaver first being Macromedia, Dreamweaver before it became Adobe Dreamweaver. But just in terms of like, I’m thinking, yeah, software and things like that, there’s so much changing in visual communications during that time period. I think also because, and maybe you saw this when you went out into the world after graduating, but companies were then starting to realize how to have a visual presence online. Prior to this, companies were still sort of trying to figure out, well, how do I get on the Internet? Should I be on the Internet? What should that look like? And by this time, like mid-2000s, companies are starting to figure it out.

They’re starting to sort of see how they can represent themselves or represent their brand or their product or their service online in a visual way.

Jonathan Patterson:

Yeah. So when I was in college, it was technically graphic design, so I only had, if memory serves one, maybe two. Two classes. Honestly, I think it was one class on web design or anything like that. So all of my other things were print focused.

Maurice Cherry:

Oh, wow.

Jonathan Patterson:

I did learn Quark, but I actually never used Quark outside of school, at least not to any degree. It was always indesign. Indesign was like coming on the scene right when I was going to school and graduating and things like that. So all of my education was really centered around print design. I had a couple of typography classes and Photoshop classes and of course all of your core studies, design fundamentals and all of those art history classes and things like that. So I used GoLive, which doesn’t exist anymore.

Maurice Cherry:

Oh, man, I remember GoLive. Oh, you just took me back with that.

Jonathan Patterson:

You know what? Their program was nice work, though. I loved the fact that it was like designing in Photoshop or Illustrator in the sense that you could lay something out on the canvas, then it turns it into the design. Honestly, I only had one Web design class, and it wasn’t until after I started working at that agency, after my internship, after college, where I really started doing more digital work and web work, everything else was like, up until that point was very traditional, advertising based. And that’s actually one of the reasons I did kind of make the switch to full time freelance, is because I’m like, okay, I want to specifically work on digital products, websites, apps, experiences, things like that.

Maurice Cherry:

Yeah. During that time, as you mentioned, you were kind of studying a lot of stuff with print. That’s another thing, is that the web was sort of changing from, I say, in the early days, it felt like a lot of the web was just taking whatever was in print and directly putting it on the web, whether that was a scan or whether that was a table based layout or something. And so it sort of limited, I think, a lot of expression that brands or companies could have. But then I’d say right around, not even too long after you graduated college, like 2005, 2006, things switched over to CSS, and then you could now float things across the page and change alignment in these ways that broke you out of this grid based kind of print format that I think a lot of early design was in. And it allowed you to sort of really kind of go outside the box with different types of design and things of that nature. So to me, it does make sense to freelance during that time, because if you’re working at a company, and I just know this because I did work at a company, when that happened, it is so much hassle to change things internally after you already have one set of processes, whether this is how it’s always been done or this is how we want to do it, as opposed to when you’re a freelancer, you can change on a dime if you need to. You can just focus on a specific type of product or a different type of service, but you can adopt and change, do things much quicker than larger companies or larger firms or agencies can.

Jonathan Patterson:

Oh, yeah, most definitely. And I think that you need to be able to do that. Right. I’ve had the kind of luxury of being able to experiment with. All right, so what interests me? What are people asking for? What are people reaching out to me for? And I have a lot of interest in terms of the design space. So while that may not work for everybody, it worked for me because back in the day, I had people, independent app developers, for example, making their first app for the iPhone and they need somebody to design it. That was kind of how I got my intro into designing for iOS was app developers reaching out to me saying they needed some design help. I’m like, this is fun.

Let me try this. So I did that. So my degree is in graphic design, but due to my wide range of interests, I have been able to kind of explore working in all aspects. And one of the things I’ve done is transition some of the skills that I’ve learned that apply to other design mediums into more marketable skills. So, for example, an ability to use Adobe illustrator very well and make cool looking icons, well, how that looks today for me is I use this program called Blender 3D. I wouldn’t call myself like a 3D artist. Rather, I’ll call them illustrations because I’m not focusing on how to make something technically accurate for 3D printing or for the architecture space,.right?

It’s more like, how can I add on this medium to enhance the product design work that I do, right. So if I’m creating a website or something like that, or an app, and it needs some cool animation or content to be designed that we want to manipulate, when the user hovers their cursor over it or taps it or something like that, that’s kind of where my skills come into play. So I try to develop this skill set of deliverables that can all work together.

Maurice Cherry:

Now, when you look back at your time at Quill, I know that was sort of what you mentioned prior, before we talked about Kendall a little bit. You wa ere there for almost six years. You were their senior art director. What sort of was the impetus for you to start your own business?

Jonathan Patterson:

Yeah, well, and to be clear, too, so I was the senior art director, but they were, we’ll say, a small to medium sized company. So it’s not that we had a ton of people there. So the reason that I decided to leave is what you were asking, is that right?

Maurice Cherry:

Well, I guess you could say that. I mean, unless that was sort of part of the reason for you wanted to start your own business, was that you wanted to leave.

Jonathan Patterson:

Well, I’ll say that I was just maybe starting to Plateau at the company. Maybe there wasn’t enough kind of upward opportunity. And again, I also wanted to focus exclusively on digital products and services versus having to work on prints and radio and broadcast. Also, I feel like I was capable of executing the types of experiences myself that the firm’s clients were looking for. So as is so often the case, pay was also starting to become an issue. And in the end, I felt like I wasn’t making enough as I could make, and I didn’t see much evidence that that would change. So that said, I did learn a great deal about the ins and outs of how to run a business. One of the most important lessons I got to see firsthand was how clients don’t hire you simply because you’re good at what you do.

They hire you because you’re capable of doing the work and you’re a likable person. You seem like you’ll be fun to work with. But the agency was, again, small to mid sized. So in a sense, I kind of, like, shadowed the owners, and I was able to learn how to talk to prospective clients and write proposals and run meetings and all of the other things they don’t teach you in college.

Maurice Cherry:

I think that’s fair. You get to a point where you feel like you could do this yourself or you could maybe do it better and you strike out on your own, and that’s what you did.

Jonathan Patterson:

Yeah. Well, again, too, people were. It made it easy because people were reaching out to me in my personal email and saying, hey, can you help me with this? Can you help me with that? I’m like, okay, well, maybe I should try this.

Maurice Cherry:

Yeah, I completely understand that because that’s the same way that I started my business. I was working at, at T and honestly hated it and just really felt like I could do better. I felt like I did reach that plateau where it’s like, I don’t know if this is going to get any better for me anywhere else. There were other issues there, too, just in terms of the staff, but in terms of just your personal fulfillment as a designer, I knew that I could be doing better work than this and could possibly be getting paid better, but this can’t be. The high point of my career is having a 15 minutes lunch break on a twelve hour shift. I can’t do this. Right.

Jonathan Patterson:

Well, I will say, though, too, at the time, it was in college, I was working at retail jobs, and that’s never fun, especially as a design person. You want to be doing work, that’s like, what you’re going to school for. So when I got that job, for the time that I was there, it was generally like, okay, this is where I need to be. I worked hard. It wasn’t that I wasn’t making any money, I was making good money. But I’m like, okay, I can make better money.

Maurice Cherry:

Yeah, totally. I get it. I 100% get that. How were those early years?

Jonathan Patterson:

Of business freelancing, early years of business. They were good. I would say that back then, I found myself working on a lot of smaller projects. Right. Projects that can be completed in a couple of days or a few hours versus these days. It’s like, okay, it requires a week minimum, or several weeks or several months. So back in the day, it was a lot of like…there were times where I’d be working for seven days a week.

I’m like, okay. I’d start getting stressed out because I’m like, okay, too many small projects, constantly working. I was making enough money, but the problem I had back then was too many small projects. Once you start running out of time to work on them, then you get stressed. So as the years have ticked by, I’ve slowly kind of expanded the scale of projects that I work on. And sometimes there’s some ebb and flow there, right? It can be very busy. Sometimes it can be a little bit slower. But I would say in general, the scale of the projects have changed over the years.

Maurice Cherry:

How do you approach a new project? Like, say you’re working with a client or something comes across in your inbox? What does that intake process look like?

Jonathan Patterson:

I think probably the more interesting part would be like, maybe my creative process. So it kind of starts with just asking a bunch of questions and understanding the problem to make sure I’m solving for the right thing. Suffice to say, there’s this extensive fact finding, goal setting, and planning process. But maybe the creative process is a bit more, I’d say, unique or just my own. It starts with taking inspiration from everywhere I watch movies. I think that medium inspires my creative process a lot. I think it’s so different from product design that it makes it easy to come up with an original idea based on a narrative that I saw. I think probably the most compelling creative ideas come from the mixing of unexpected connections that you can make between topics that are not already connected.

It’s almost like the magic comes from bringing those two concepts together in a novel way. But I try to take inspiration from everywhere and bring that work into the product design work that I do. In addition to that, I think, of course, surfing the web daily, you just come across things that naturally will someday work their way into inspiration for a project that I’ll work on. So I keep like, boulders of interfaces and websites and illustrations and animations on my desktop to kind of just refer to. I do consider myself in the business of selling ideas, so I’ll say this. Too often clients are eager to spend a budget if you hit them with something that kind of strikes their imagination, and having my go to folders that I can inspire myself from is a good starting point. So, actually, one of the things I’ll do to jump start a creative process or get a project off the ground and up and running is kind of like, after I have a meeting or a phone call with a prospective client, I will send them this preliminary or kind of like cursory email with some creative ideas, and that’ll get their wheels turning. And then the next thing I know, I’ve got them asking me to send a full proposal.

And then we’re often working on a new project.

Maurice Cherry:

When you look back over, I don’t know, let’s say, like the past, we’ll say five years, we’ll roll the pandemic into this. What would you say is the biggest lesson that you’ve learned about yourself?

Jonathan Patterson:

Biggest lesson I’ve learned about myself. I don’t know that I’d learned anything new. And maybe that’s because I’ve been freelancing for way before the pandemic started. Everybody was kind of like, clamoring when it all went down, getting their office set up, trying to understand how to freelance or work remotely. I’m like, I’ve been doing this for ten years at the point that the pandemic started. So that was easy for me. I felt like…I’m like…I’ve been social distancing for ten years now. I already had everything set up, my billing software, my processes were in place.

I was able to experiment with different ways of working with clients. Do I work with them on a retainer? Do I work with them on a fixed price? What’s my rate? Do I sign NDAs ahead of time? Or do I never sign NDAs? That was one of the things that I’m getting a little off track, but I think maybe a little bit relevant. I think that I very much enjoy the. Am thankful for the fact that I was able to see what works and what doesn’t work, which is different than working for somebody else. Right. When you work for somebody else, they tell you what you can say in your email to the client. They tell you how to Bill, they tell you the process that you have to structure your files through. Those are all things that I got to do my way or just trial and error.

I think there’s something to be said for the ability to see what works and what doesn’t work for yourself.

Maurice Cherry:

Right?

Jonathan Patterson:

Again, I guess that wasn’t new to me, but that was something that I imagine a lot of people probably started to get wind of when the pandemic hit. And what they learned about themselves is probably some of those things that I had learned up to that point.

Maurice Cherry:

But you’ve been good. You’re good.

Jonathan Patterson:

Yeah, I’ve made all the mistakes. I think that one of the things that I have learned over the years was that not everybody communicates the same way. I think that I have a very. In the past, I probably was much more direct than people that people tend to be like, if I have a question about something or if I just legitimately think that the client needs to hear some particular feedback, I would just say it. But I learned that, okay, sometimes you can’t just say it. You have to ease them into it. And that’s something that you can’t if you’re working for. I guess to bring my sharp point to this idea, it’s like when you’re working for somebody, they tell you that you can’t say this when you’re working for yourself.

You can try it and see what happens. And I certainly did that. So I made all the mistakes, but I think I’m better for it.

Maurice Cherry:

I got you. I feel you. Okay, so what are sort of the next steps of growth for your business? Like, where do you want to take it?

Jonathan Patterson:

I want to take it. I think that I have always wanted to remain in, I guess, a small business. Like, I don’t have any employees, and that’s by design. I think with employees comes other headaches. Right. You have to make sure that, well, I don’t know. I don’t have any employees, but I’m just guessing. It’s like you have to pay for insurance and all of those other things.

Many more expenses, overhead. It’s just a much different, kind of, like a ballgame. I feel like I would be managing people more than I am doing work, which is what I do now. When clients reach out to me, they’re looking for something to get done. I think my business is, I’m happy with kind of where it’s at. I’ve helped other clients of mine who say they’re like, oh, I wish I would have gone your route and not hired employees and just stayed small. So many fewer headaches to contend with. I had an attorney who I did work for who told me that.

So, yeah, I think just based on my experience and things that I’ve heard, I think it’s just as easy to stay small.

Maurice Cherry:

Yeah. Where do you kind of pull strength from? Like, what motivates you to keep doing this work?

Jonathan Patterson:

Well, I’ve always been a creative person. I think creativity can manifest itself in many ways. Right? So while I don’t think I’ll do product design forever, I will always be in the creative space. So, for example, I used to play the piano for many years. I took classes in school. I took them outside of school. My mom hired somebody to take me to get lessons from. So I’ve done music oriented endeavors.

I’ve, like I mentioned, had an interest in drawing by hand. I then kind of transformed that into graphic design. Now I’m in product design. So I will always be in the creative space, in the digital space. I think there’s so many foundations to design that are transferable, right? So all of the foundations, color, scale, contrast, repetition, light, texture, those things can apply to interior design, print design, furniture design. So I very much see that I will be in some creative space now. Which one? That is in the future. I’m not sure for the time being it will be.

It’s going to definitely be product design. But I think in the long term, I could see myself going into something probably in the fine art space, right. I think my career, for the most part, up until this point, has been commercial design. Right? It’s about how to sell a product or a service or get somebody to take an action based on. It’s less art. Granted, there are a lot of visual components to the work that I do, but at the end of the day, it’s not art because we’re selling something or making something or convincing people or educating people on why they want to buy a service or a product versus art or a personal expression that is more about self expression. Right. So you think of sculptures or paintings or woodwork or something like that.

So I think in the future, my interest will probably be more in the focus on things that are not, like, consumer focused.

Maurice Cherry:

Okay. Where do you see yourself in general in the next five years? I mean, I know we kind of talked a little bit about where you want to take the business, but when you look in the future, based on where you are now, what kind of things do you want to be doing, especially with.

Jonathan Patterson:

I’m very interested to see all of our AR and VR experiences start coming into play. I know that there are a lot of mixed reviews on how that’s going to look in the future of the metaverse and all of that. Personally, I’m interested in working in that space. I think it’s just going to be so new. Right. A lot of the work that we do in UX and UI design today for screens is there are many design patterns and tried and true methods to pull from. I’m interested in establishing and working in and setting up kind of new paradigms and principles and patterns for devices that are upcoming.

So I’m very excited about the Vision Pro. When that comes out, I’ll probably start to tinker around in that space. I’ll have to give me one of those when it comes out, start designing. And I do imagine maybe a similar kind of pattern as to what I experienced before, where if I’m offering services that are tailored toward developers who are creating products for vision Pro, they probably need some design assistance with it. So that’s kind of me keeping up with the times. It’s how can I tailor my services to be in demand and where the market is going? Which is one of the reasons I actually had an interest in three D. One of many reasons I’ve had an interest in 3D in the last few years is because I saw or I read that these types of experiences are coming and I want to be able to be able to create assets and just work in this space. So yeah, that’s an area I’m very excited about is VR, aR, that type of work.

Maurice Cherry:

Well, just to wrap things up here, where can our audience find out more information about you, about your work? Where can they hire you? Where can they find all of that information? Online?

Jonathan Patterson:

Definitely at my website, which is jonathanpatterson.com. I am on X – @jonpatterson_. That’s J-O-N underscore Patterson, of course. Linkedin.

Maurice Cherry:

All right, sounds good. Jonathan Patterson, I want to thank you so, so much for coming on the show. Thank you really, for kind of diving deep into your business and kind of exploring why you do what you do what you do in terms of services and things of that nature. I think it’s important, especially now at this time, when people, for one reason or another, might be out there trying to find their next path or like what the next thing is that they’re going to do to really sort of see what someone who has been out here doing this for a long time is doing. So they can maybe look at how they structure their work or their business. But I think what you’re doing is great. I know you mentioned something about sort of having the work speak for itself and being the invisible hand. I’ll tell you that once you start speaking, that kind of goes a little bit out the window.

Yeah, I know, because the work doesn’t have a mouth, you do. So it’s like, as you start getting out there and speaking more. And I think certainly as people really see more of you, as well as the work, you’ll take off for sure. I mean, certainly what you’re doing now is really great work, but I’m excited to see where you go in the future. So thank you so much for coming on the show. I appreciate it.

Jonathan Patterson:

Yeah, well, thanks for having me.

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Chris Dudley

Chris Dudley is an artistic powerhouse. He’s been a working artist for over 25 years, creating everything from children’s books to commissioned drawings (and he teaches art as well). His latest book, Lil’ Boogaloo Shrimp and the Clean Sweep is inspired by the iconic 80’s movie Breakin’, and features the OG Boogaloo Shrimp himself, Michael Chambers!

Chris gave me the rundown on the new book, and we talked about his creative process and what draws him to illustrating portraits and children’s books. He also spoke about growing up in Grand Rapids, Michigan, the benefits on staying there for his career, the keys to his longevity, his work with Hudson Dawn Publishing, and dropped some great advice on work/life balance and staying inspired. You’ll definitely be a fan of Chris after you hear his story — I know I am!

Interview Transcript

Maurice Cherry:
All right, so tell us who you are and what you do.

Chris Dudley:
Well, my name is Chris Dudley and I am the creative director for Chris Dudley Art. I really focus on art and illustration.

Maurice Cherry:
How has 2023 been going for you so far?

Chris Dudley:
Actually, it has been going amazing. The scope and range of projects that I’ve been working on have been just straight fun. The recent project has been Lil’ Boogaloo Shrimp and the Clean Sweep, which is with Michael Chambers, who’s famous from the breakdancing movies franchises, and it’s been amazing.

Maurice Cherry:
Yeah, tell me some more about the book.

Chris Dudley:
Yeah. Well, it’s, I think, the first book of its kind. Scoured the internet, and I haven’t seen a book like this. One of the first books I’ve ever seen that focuses on breakdancing. The premise behind the book is that it teaches kids responsibility and priority using breakdancing. And also, it highlights, there’s a shout-out of a lot of the actors from the Breakin’ movies, Adolfo Quiñones, Bruno Falcon, and sadly, we lost both of them recently, and just all of the main characters from the breaking movie, but also a lot of other individuals.

And in addition to having that subject matter about breakdancing, because a lot of people think it went by the wayside, but it’s still hugely popular and also, it will debut in the Olympics in 2024. And so, it’s still a huge thing. There’s a shout-out to the Olympics in the book. Actually, the final spread, everybody’s breakdancing in Paris with the Eiffel Tower in the background.

Maurice Cherry:
Oh, nice.

Chris Dudley:
Yeah, I haven’t seen a book like this yet.

Maurice Cherry:
Nice. Congratulations on that.

Chris Dudley:
Thank you. It also, if I could add, it’s more than just a children’s book, it gives kids a little bit of history about the background of breaking, its roots in New York. Also, gives some terminology of breaking, like what a freeze is, what a go down is. So, it’s a little bit more than just the story.

Maurice Cherry:
Nice. I remember this was back in 2005. When was I working there? Yeah, 2005, I was working for the State of Georgia here in Atlanta, working at the Georgia World Congress Center. And I remember we had just hired this white girl as a PR rep or something. And I mean cute, short, bubbly white girl. I was like, “Oh, she seems really nice.” And the weird thing, well, not the weird thing, but as I was talking to her and I asked her what her hobbies was and she was like, “Breakdancing.” And I’m like, “You’re a breakdancer? You look like a UGA sorority grad. Come on, you’re not a breakdancer.” And sure enough, it would be in a sort of weird way, but sometimes she would do moves just in the office just to show us that, “Yeah, I am a breakdancer.”

Chris Dudley:
Gotcha.

Maurice Cherry:
She invited me to a few events that she was breaking at and-

Chris Dudley:
Oh, nice.

Maurice Cherry:
It was so weird because sometimes we’d be in these board meetings, in a legit boardroom with chairman and stuff, and then someone’s like, “Oh, you’re a breakdancer. Why don’t you bust a move for us?” And I’m like, in a way, this is so embarrassing, but also, it’s like, well, at least you’re not asking the Black person to do it, so I’m not… Let me sit back and watch the show.

Chris Dudley:
Gotcha. That’s awesome.

Maurice Cherry:
Yeah. And I think you told me that part of what you’re doing with the book involves a crew or something here in Atlanta.

Chris Dudley:
Yes, they’re in Georgia. I think they’re near Acworth, the Rockwell Dance Academy. And it’s interesting that you mentioned that the young lady there was a breakdancer, but the Rockwell Dance Academy is led by Honey Rockwell and Orko. Honey Rockwell is a staple name as a B-girl. Actually, just last year, they were both inducted into the Breaking Hall of Fame. And so, B-girls definitely have a place as well. I mean, she’s one of the most well-known. She was with the original Rock Steady Crew in South Bronx, New York.

Maurice Cherry:
Oh, nice.

Chris Dudley:
Yeah. We partnered with them and we’ve got some things in the works. So, it’s really exciting to have that Georgia connection going.

Maurice Cherry:
Yeah, we’ll make sure to put a link to the book also in the show notes, so people can check that out. Aside from this new project, how are things different for you this year than they were last year?

Chris Dudley:
It has been just ramping up with projects. Last year, obviously, we had a steady flow of projects, variety. This year, the children’s books have just been packed. I mean, I’m booked out with children’s books, booked out away. So, it’s fun where you complete one project and then you can look forward to the next one. But I’ve got, I think, four or five that are already in the queue, confirmed. And so, I look forward to working with each of those authors as well.

Maurice Cherry:
Nice. I mean, with everything that you’ve got going on now, what does the summer look like? Is it more work or you got any plans?

Chris Dudley:
Yeah, a little vacation, a little relaxation I would do with the family for the summer. I’ve got three girls and my wife, so we’ll get a little relaxation in, but some work too. Especially with the release of this book, Lil’ Boogaloo Shrimp and the Clean Sweep, we’ve got some events planned this summer as well. Some here in Michigan with the Children’s Museum and another bookstore, and actually, a local breakdancing crew.

Actually, Michael Chambers there in Los Angeles, July 29th, I believe, he’s got an event with Barnes & Noble. So, I may be flying out there to support him on that. But yeah, we’ve got a lot going on this summer. Then coming out of summer, we look to get in, we’re going to be partnering with some schools to get the books into schools as well.

Maurice Cherry:
Very nice. So, you got a lot planned coming up.

Chris Dudley:
Yes, sir.

Maurice Cherry:
Let’s dive into Chris Dudley Art. I mean, you just mentioned you’ve got a bunch of these projects that are lined up. What does your creative process look like when you’re working on a new project?

Chris Dudley:
Yeah. Well, they all start similarly because we do a little bit of design work. We’ve designed some logos and so forth. We’ve got a team that does that. But also with the illustration, I like to start out old school with sketching. That’s how I learned to draw. So, that’s part of my creative process with every project, is starting out with sketching. I mean, I can go into the meat of doing a children’s book, if you like.

Maurice Cherry:
Yeah.

Chris Dudley:
Okay. It’s basically we get a manuscript and it goes through an approval process. We don’t just take any manuscript. It’s got to… Just to be real with you, when I read the manuscript, if images start popping into my head, it’s a go. If they don’t, it’s probably not a go. And that’s just nothing against the author, but it has to resonate with me because it’s got to be a fun project that I’m looking forward to doing.

And so, from there, the manuscript checks out and we want to bid on that. From there, we will establish the illustration description. So, that’s what imagery is going to go along with what portions of the text, especially if it’s a children’s picture book. And once we nail that down, I’ll do sketches. And that’s where you establish the composition. Well, actually, prior to that, we design the characters, the main characters, and see exactly what they’re going to look like. Is it a eight-year-old African American boy, or does it have to be a little girl who’s three years old and she has a puppy?

So, we have to figure out the dynamics of the characters. What are they going to look like? What time period are we in? Are we in the 2000s? Are we in the ’80s, like with our recent book here? And so, we establish a character and then we do composition sketches of establishing what each scene is going to look like. And those get approved by the author along the way. So, they’re heavily involved with the creative process, so that I don’t just come up with the finished project and then hope they like it. They’re involved along the way so that there’s no surprises on either end.

Then from there, we go to final sketches. We start to flesh out this is exactly what this spot illustration or this full page or this spread is exactly going to look like and the details of it, if there’s need to be background and so forth. And from there, after the client approves that, we do the line work. That’s where we finalize it almost… Well, you’re familiar with how a coloring book looks where you have the simple black lines.

Maurice Cherry:
Yup.

Chris Dudley:
We finish out the book looking like that. That way the client gets to see, okay, this is exactly how things are going to look before we add color. In that way, any adjustments can be made along the way, if need be. So, they approve each process, and then we get into the color theory, because you can’t just throw colors onto the imagery. It has to make sense visually. Also, colors such as red is going to attract attention. So, you wouldn’t just arbitrarily use that just because you want it red. And sometimes, that has to be explained to the client as well, because they may think, “I want to paint this in a blue.” That, well, based on color theory, those won’t work with the composition.

Then we just move toward the formatting process, and then the text is added. And I take the text into consideration as well though when I’m designing the composition, so it doesn’t look forced later. I make sure I allow spacing for that. But yeah, that’s how we move through a project. Then from there, it goes to post-production, and then we have a book.

Maurice Cherry:
So, it’s way more than just art and illustration.

Chris Dudley:
Oh, yeah.

Maurice Cherry:
You’re really seeing it through the entire process, entire publishing process.

Chris Dudley:
Yeah, from concept to completion is what we’d call it. Yeah, from the initial idea to a finished book.

Maurice Cherry:
Yeah. I mean, you mentioned getting the clients involved with it. I’m pretty sure this is probably maybe not an exhaustive process for them, but how is it for them being able to see the book come together step by step like this?

Chris Dudley:
It’s amazing because it’s no secret most people haven’t learned the skill of being able to draw, let alone to illustrate, which is there’s a difference because with illustration, you’re telling a story with the imagery. And so, when you flesh out a character for a client, it’s so satisfying because they have it in their head, but they can’t see it. And so, when you can present that to them, it’s like, “Yes, that’s exactly what I want.” It’s just so gratifying for them. Then to see that character then doing things throughout the book, their eyes just light up. So, it’s a pleasure working with them and again, keeping them involved in the process.

Maurice Cherry:
Now, it looks like you do a lot of children’s book illustrations. What draws you to this genre?

Chris Dudley:
Well, having kids. Like I said, I got three girls. They’re a little bit older now into late teens, mid and late teens. But I actually spent, and actually people can go look at my website at chrisdudleyart.com, I spent about 15, 20 years doing almost exclusively realism. I mean very detailed graphite drawings. I did art shows and juried exhibitions and all of that. And so, I used that knowledge actually as I segued into, I still do some of that, but the children’s books, reading books to my girls. And I actually had to learn how to illustrate better. I knew it a little bit, but I had to really dive into it. So, I’ve been doing that for the past 10 years now, and it’s taken over really.

Maurice Cherry:
How do you stay organized with a lot of these projects? Because I would imagine as you’re saying this whole process, do you do just one book at a time? Are you juggling multiple books? How do you keep all of that managed effectively?

Chris Dudley:
Well, some of them will overlap a little bit, but it depends on what phase of the process. Honestly, for me personally, the most challenging part is the initial part, coming up with the concept of what the imagery is going to look like. Because once you’ve established that, you then created a roadmap for yourself, and then it’s just following the roadmap. It’s almost like plotting out your course somewhere. That’s the hardest part, where am I going to go with this? But then once you plot out the course, okay, now, it’s just following this path that I’ve laid out.

And there may be some tweaks along the way. And with that, it’s important obviously not to overbook. We’ve all heard the same under promise, over deliver. And so, really, we really focus on with my team, especially my assistant, not making promises that would be too difficult to even try to make happen. Then you’re disappointing clients. So, books, I won’t work on two or three at the same time, but they may overlap. Like okay, if I finish this portion, now I can maybe bring in, but they’ll have different deadlines. I don’t have it where they’re all due at the same time. Keeping it balanced, yeah.

Then we filter in some other relatively smaller projects in there while I may be working on a book, like a one-off illustration or a design project. But I like to really focus on that client’s project, so they get the attention that it needs.

Maurice Cherry:
And it’s important to note, as you’ve alluded to, you have a team. So, this isn’t a one-man operation.

Chris Dudley:
Exactly. I could not do it by myself. I did in the past. Obviously, it was just me. I started, well, way, way back before it was Chris Dudley Art when I was 18, 19. And it was just me, invoicing and trying to figure all this stuff out. But I realized later is that it stifled creativity, doing all of those other administrative tasks. Now, I still do some, but by and large, I want to save my brain for the project.

Maurice Cherry:
Yeah. I think, as you said, starting out on your own, you want to try to do everything or try to tackle everything because you’re just starting out. You want to establish yourself. But eventually after a while, in order for you to really be able to go further, you have to give up some control. You have to build a team. It’s just a necessary part of being able to scale the work that you do.

Chris Dudley:
Exactly, exactly. Yeah, it’s necessary.

Maurice Cherry:
Let’s switch gears a little bit here and learn more about you. You talked a bit about starting out. You were born and raised in Grand Rapids, Michigan. Tell me about what that was like.

Chris Dudley:
Yes, it was fun. My interest in art started very young. I had a couple of cousins that drew a little bit. One was just phenomenal, phenomenal artist, and it amazed me that he could do that with a pencil. And it wasn’t daunting like it may be to some people. And in school, I always drew. I remember back in, I think I was maybe in kindergarten or first grade, and a little weed of mine, it was like a stalk of grain or something that I drew, it got accepted in the children’s exhibition at the Grand Rapids Art Museum.

And so, it’s like that was a “first juried show” and it was accepted. And so, it’s going to be on display Downtown Grand Rapids at the Art Museum. And so, when my mom took me down there to see it and to see it displayed, it was just awe-inspiring. They had the artwork separated by grade level. So, mine was in the first, second-graders. And I remember walking and seeing, I remember the stuff like it’s yesterday, seeing the 12th graders. Obviously, their art advancement was far beyond my level, but it was so amazing that it was possible, and it just sparked that that’s possible. I didn’t have the skill to do it, but it didn’t deter me. It made me understand that’s possible. I can get to that level. And so, that’s where it began.

Maurice Cherry:
And it sounds like your family also really supported you in this too.

Chris Dudley:
Yeah, family has always supported me. Even teachers, I joke about it now, they would let me draw in class as long as I did my work, obviously. But yeah, I’ve had a lot of support over the years.

Maurice Cherry:
How has it been working and cultivating your career in the same place where you grew up? I feel like a lot of folks we have on the show may have, of course, started out one place and then ended up moving somewhere else, and that was where their career or their work flourished. What does it mean for you to still be in your hometown doing this work?

Chris Dudley:
Well, it’s taken some time. I started out with, it was Dudley Graphics actually, when I was 18, 19. And I was doing T-shirt designs and it was all by hand. I didn’t know graphic design or how to use a computer or anything. So, I was drawing things and even drawing lettering and so forth, and later rebranded. Actually, when I improved my drawing ability, I was okay, but I wanted to learn how to draw much, much better. And so, in my 20s, I said I want to learn this and really buckled down and improved my skill, but had obviously some success with that, dealing with some businesses and so forth.

But later, that’s when I started doing juried art shows. And I felt that if I could get into a juried art show, that somewhat vetted my skillset. Then some of these were hard to get into. They were hard to get into. So, that gave me a little boost of confidence. Then figuring out how to make it sustainable, like you said, in your hometown and doing projects with companies. I actually did a whiteboard animation with a pharma, very large, I can’t say the name, but pharmaceutical company. And so, finding avenues then how to make it sustainable.

And I was able to explore a lot of different avenues of art. I mean, it was design. It was drawing. There was a little bit of animation work with some of that, but to make it more sustainable even here locally. But then things did branch out where I started getting a little attention from those outside of Michigan. I worked with an author actually in Georgia, and just some throughout the States. And that’s when it’s like, whoa, it opens you up to that global market.

Maurice Cherry:
Yeah. Do you think it’s been a benefit to you to still do this work in Grand Rapids? Have you thought about, “Oh, well, what if I was in New York?” Or even in Detroit, if you stayed in Michigan?

Chris Dudley:
Yes. I found it as a benefit because it puts me in a position to, it sounds cliche, but to give back, if you will, to the community versus when you move away, you’re not in touch with that local community anymore. So, I’ve been able to be in contact with local artists that I know and local authors, because I work with a lot of authors here in Michigan. So, to be able to meet them in some instances face to face, you can’t replace that. It’s worked out. It’s just worked out for me to stay here in Michigan and still have some of those connects outside.

Maurice Cherry:
How big is Grand Rapids? I’m trying to think population wise, how big.

Chris Dudley:
Ooh, offhand, I guess I should know this, right?

Maurice Cherry:
No, no.

Chris Dudley:
Actually, it’s the second… I didn’t know I was getting a geography lesson here. It’s the second-largest city, obviously, behind Detroit. I mean, it’s growing too. It’s continuing to grow. Yeah.

Maurice Cherry:
No, I mean, I’m curious about that because I’ve had folks that are on the show before that aren’t in these big metropolises. They’re in smaller cities like Raleigh or Grand Rapids, like you mentioned. I think I talked to another illustrator in Detroit. Oh, his name escapes. I think it’s Sean Bell or something like that. But talking about the benefit or one inherent benefit of being able to do this work in a smaller community, I won’t say small, but smaller than a big city, is that in a way, because you grew up there, people know you, so there’s that sort of reputation. But also, you help serve as a beacon for the next generation to see that what you’re doing is possible where they are. They don’t have to move somewhere else or go somewhere else to achieve-

Chris Dudley:
Exactly.

Maurice Cherry:
… the kind of success that you’ve achieved.

Chris Dudley:
Yeah, exactly. That is the key. And a lot of it is about developing your skillset, really getting your work seen. And so, with the internet and so forth, I’m not old, but I grew up without the internet. But now, you have these different vehicles that you can use to have your work seen really all over the world.

Maurice Cherry:
Yeah. Before we get into that, I want to stay a little bit in the pocket of Dudley Graphics because I think it’s important for our audience to really hear about what it was like to design really before personal computers and Photoshop and all that sort of stuff was really a thing. Tell me about your early career of Dudley Graphics because that was roughly between what, ’96 and 2005, 2006, something like that.

Chris Dudley:
Yep, exactly. Yeah. I started out, man, I was 18 and I became a broker with a T-shirt company and I was doing the designing. And like you said, it was all by hand. I mean, it was freehand drawing. Then I would ink it and I would take actual ink drawings to my screen printer to get the camera ready, iron it and so forth. And so, if I had to make an adjustment, it was all by hand and cutting and pasting and whiteout. I did not know how to use a computer. I didn’t have one. So, it was the early days.

I remember when I first got a computer and trying to learn it, but I didn’t really have the correct software. Then had thought, “Okay, how do I input something in my computer?” So, I had to try to learn a scanner and it was crazy. One thing that really helped, I actually worked at a Kinko’s, which later became FedEx Kinko’s, and which is now FedEx office. And I got a lot of training actually in graphic design and just how those things worked. And that really helped me with launching Dudley Graphics.

Again, it was just in the design and T-shirt realm because my drawing ability honestly was, I would say, above average, but above average was to be average person who doesn’t draw. So, I had a ways to go as far as learning how to draw better. And that’s what prompted the rebrand, is I felt, “Okay, my skills are way better than they were. So, I can go with this art thing.”

Maurice Cherry:
Oh, you took me back there with talking about Kinko’s. I remember that fondly.

Chris Dudley:
Okay, yeah. Yep. Yep.

Maurice Cherry:
Yeah, during that time, I was in high school, right around that time. I was 18 in ’99. So, a little bit later than you were, but I did come up also in that time of life before the internet. I mean, computers actually when I was a kid were almost like a toy.

Chris Dudley:
Exactly, yeah.

Maurice Cherry:
At least that’s how they were marketed or pushed. It was like, oh, this is the fun thing you do at school in your free period or-

Chris Dudley:
Exactly.

Maurice Cherry:
It would be VTech. The company VTech had all these personal computer things. I had this big thing called a Precomputer 1000 that had a one-line screen on it. It had a full keyboard, but had a one-line screen and it had a handle on it so you could carry it with you. I think my mom wanted to throw that thing out the window because it could also make sound. And so, I was learning sound because I also grew up playing music, being a musician. So, I’m learning how to play sound and code on this thing. And I know she wanted to launch that thing out the window most days.

But I say all that to say it’s so different now when you look at schools. And even, I think, just the general conversation around technology for children and designs. It’s certainly something that people try to push their kids into as a viable career field or a moneymaking thing or something like that. Really back then, especially for Black folks, there was not a lot of examples. You had, what, Dwayne Wayne on A Different World. Maybe somebody that was featured in Black enterprise if you had a subscription. So, there wasn’t a lot around, oh, computers are a thing that you can use to build your career. It wasn’t a thing. And I feel like for listeners they should, especially younger listeners, it just wasn’t a thing.

Chris Dudley:
Yeah, it wasn’t. It wasn’t. I think, what is it? What would you say? 2000s before, I think, when the internet came out for everyday people and people still didn’t have a computer in their home. Whereas now, most people do. But you think about to have grown up or have grown up at a time where that you didn’t have internet at home, you didn’t have a computer at home even. So, totally, it was a different era.

Maurice Cherry:
Yeah. Or if you had an internet at home, it was via mail order CD.

Chris Dudley:
Yeah, AOL.

Maurice Cherry:
You get a AOL CD. You get a NetZero disc in the mail or something like that. And that’s what you use-

Chris Dudley:
Exactly.

Maurice Cherry:
… to get on for like… I remember getting those things and it’s like a thousand free minutes.

Chris Dudley:
Exactly. Oh, my gosh. Yes, I remember that too. Then you’re waiting five minutes to connect, just listening to that dial-up sound.

Maurice Cherry:
And it ties up the phone. So, if someone’s on the internet, someone also can’t be on the phone in the house.

Chris Dudley:
Exactly.

Maurice Cherry:
Yeah, it was a whole thing. So, I used the computers at school and I learned it at school. I designed my high school newspaper, for example, and we used PageMaker. We’d use a double PageMaker.

Chris Dudley:
PageMaker.

Maurice Cherry:
And I know we started off trying to use Quark and those-

Chris Dudley:
Yeah, QuarkXPress.

Maurice Cherry:
That software would come with these big… I mean, these instruction manuals could choke a horse. It would be so thick, and it’s like a textbook. How am I supposed to read through all this to figure out how to use this software on this thing? And eventually, we’re just like, “We’ll just do it by hand.” It’s just easier to print and cut-

Chris Dudley:
Exactly.

Maurice Cherry:
… and copy and all that sort of stuff. So, I know what you mean about having that not necessarily on the job training, but you learned through application. You didn’t necessarily go to school for. You learned by doing or you learned by working almost like an apprenticeship in a way.

Chris Dudley:
Yeah, definitely, definitely. And along with that, just to add briefly, is that in that manner, you learn what you need because all these programs, obviously Adobe Photoshop, it’s so deep that even the experts don’t use everything, right?

Maurice Cherry:
Right.

Chris Dudley:
But I think a lot of us artists and entrepreneurs may… It can be daunting, but you may realize that I only need five functions from this program to run my business. I don’t need to know all 5,000 and shortcuts and all that. And so, it’s really finding what you need, and okay, that’s all I need from this program. Then it’s worth it for me to have it to run my business.

Maurice Cherry:
Right. And the chokehold that Adobe and Macromedia back then as well, the chokehold that those products had on the burgeoning digital design industry cannot be understated. I never thought I’d see a day where Photoshop is almost not derided, but I know a lot of designers now will use Figma over Photoshop. There was a time when they would use Sketch over Photoshop. I never thought I’d see a time when Photoshop would fall out of favor because it was everywhere.

Chris Dudley:
Yep, yep. And also, I think a lot of people are still upset about the subscription model. But I guess I get it. You get the updates. You don’t have to come up off of $900, which a lot of people couldn’t back in the day anyway. Or they’re working on old versions of Photoshop and there’s, like you said, a lot of options now. I do a lot of illustration in Procreate on the iPad Pro.

Maurice Cherry:
Yeah. I think Adobe knew that their software was being pirated left and right. I didn’t buy Photoshop until the subscription came out. Everything before them was some cracked version off of LimeWire or Kazaa or whatever that I hoped would not give my computer a virus. And sometimes, it would. But that’s how I ended up learning because I was like, “I can’t afford.” Even when I had my business, I was like, “I can’t afford the cost of this. I’ll still use this cracked version because it works. It does what I need it to do.” Like you said, it does the five things-

Chris Dudley:
Exactly, exactly.

Maurice Cherry:
… I need it to do. Why would I pay this astronomical amount of money for this piece of software if I can’t use every single part of it?

Chris Dudley:
Yeah, exactly.

Maurice Cherry:
Yeah. Now, you’ve been a working illustrator in this industry now for over 25 years. For you, what have been the keys to sustain that longevity? We’ve talked just now about how technology has really changed the game. How do you still keep current and maintain yourself in this industry?

Chris Dudley:
First thing is skillset. When it comes to art, you have to have the skillset and it’s not… Obviously, no disrespect to anyone, but a lot of times people think about art as it’s just a feeling and you just express yourself. And there are some aspects of art that are that way, but there are rules and fundamentals that you learn. Composition, you have to know anatomy. There’s so many things and you have to learn that stuff before you can just venture off and draw your feelings if you want to say. And so, I really focus on that skillset, learning those things.

Also, art is a different pursuit in that everyone else has to be… They understand that I got to be good at it first before someone’s going to hire me. If you were a baker, I got to be able to bake cookies good first. So, you’re going to be baking a lot. If you’re a singer, you have to show that you can sing. If you’re a writer, you have to write the book. But oftentimes, artists, some artists, new ones anyway, feel, “Well, I want someone to hire me to draw something.” Well, you have to show them that you can draw.

And so, I think a lot of artists don’t have enough of a body of work to show for someone to hire them, so that’s what I… I didn’t want to do that. And early stages I went through were, okay, you want someone. Then I realized that, no, you have to be drawing and producing things so people can see that you know how to do this thing. And when I took that approach, things really just really started to take off. And it can’t just be your practicing. You need to do a project from start to finish. People can see that you can do that, the highest level you can do at that time. And so, that’s what’s really helped me.

Maurice Cherry:
So, working in public. Like they say in math class, show your work. That’s what’s really been a big key for you.

Chris Dudley:
Yeah, yeah, and being able to show that you can. It’s not waiting to be asked to do it or waiting to be hired to do it. And that’s what a lot of artists do. Again, no other industry is that way. You know that you have to have this skill at a high level before someone’s going to ask you to do it for pay. But sometimes, artists just wait. I’m waiting for someone to hire me. I’m just sketching in my sketchbook. Well, no, do a project. Even if you “hire yourself” to do a project, show that you have the chops to do it.

Maurice Cherry:
How has tech impacted your work? Of course, we’ve talked about Photoshop and things like that, but lately, over the past almost nine to 10 months now, the conversation has largely been around generative art and Midjourney and DALL-E and all this stuff. Yes. How does that, if at all, incorporate into your work?

Chris Dudley:
I have switched over. I’m almost… Well, I still draw because I love the tactile aspect of just traditional media. Actually, I’m going to be teaching a paint class this week, but the majority of the bulk of my work is digital now. So, I’m drawing on a tablet. And with regard to art, that’s… Well, if I could add, one funny thing to me is, in the art community, drawing hands because of their nature is difficult for just about every artist starting out. And so, one hilarious thing to me is that AI art can’t draw hands either, and that’s something…

I knew someone who, well, just recently they produced a book. And I said, I’ve looked at it like, “Wow, that’s a nice image.” But then I started, just from my trained eye, started to break away. No, this is AI. Again, not to discredit it, but I could tell right away it was AI produced. Then I looked at the hands and they looked atrocious, like claws. And I was like, “Oh, yep, I was right. That’s definitely AI.”

And so, I don’t think, I don’t see it as a battle per se, but I use digital aids, if you will. Sometimes, I’ll even create a scene with poseable characters if I’m looking for a certain pose. And I might take a picture of that and then use that as a reference. So, I’d use some different aids, but I think you have to have the skillset. The tools can’t make you an artist. So, you got to have the skillset behind it. People can’t think, “Oh, hey, I’ve got Midjourney now. I’m an artist all of a sudden.” No, you still need a certain base of knowledge and ability to be able to then use those tools to actually create art.

Maurice Cherry:
Yeah. I was watching some video. I think it was from Wired, and it was an AI artist detailing their steps. And it’s all writing for the most part because you have to get the prompts specific in order for the thing to generate and all that sort of stuff. And it was fascinating to see it come together, but it didn’t feel like art. It didn’t feel like the creative process, especially with something as I think intimate as hand drawing something. There’s more that goes into it than, I think, just a technical skill. I mean it’s creativity. It’s emotion. There’s a lot of specifically, individually, intrinsically, fundamentally human things that go into the creation that the computer just can’t do. It can maybe-

Chris Dudley:
Exactly.

Maurice Cherry:
… try to replicate it from other sources. And of course, there’s been talk about how these engines crib from other artists, but it’s not the same. I find a lot of AI art has a specific look. It’s like heavily shadowed and it’s a very specific look where I’m like, “Yeah, that’s AI.” It doesn’t feel like it’s from a person because people’s art styles are so varied and different.

Chris Dudley:
Exactly. And it’s very static as well, and some of it’s… I mean, obviously, you’ve got a trained eye to be able to see that but not to, I don’t want to sound condescending, but to a person that just says, “Oh, I like pretty things,” but they’re not into art or know, they don’t know art, they could just see an image and, “Wow, it’s a pretty image.” But if you’ve got a little bit of a trained eye, you can realize, “Oh, it’s okay. It’s nice. But it’s a static image. There’s no emotion.” Like you said, you could feel that it doesn’t have that human element to it. It’s just produced. It’s like a mass-produced restaurant versus a high-end restaurant or that little mom-and-pop shop that puts love into the meal. So, you can tell the difference.

Maurice Cherry:
Yeah, like a McDonald’s hamburger is going to be different from-

Chris Dudley:
Exactly.

Maurice Cherry:
… the Smashburger place or something like that.

Chris Dudley:
Exactly, exactly. And there’s a reason that there’s always going to be that Smashburger. Yeah, you have the McDonald’s customers, but there’s a lot of people that says, “No, I don’t go to McDonald’s. I rather pay a few more dollars for a real burger.”

Maurice Cherry:
And I think, for you, because the work that you do involves the clients in the process from start to finish, it would almost feel like introducing AI into it, one, sort of cheapens it in a way, but then two, I could see how it could make the client think, “Wait a minute, I could do this myself.”

Chris Dudley:
Yeah, exactly. Definitely could, definitely. And I don’t think it’s going to… Who knows with technology, but there’s just what I see certain elements that AI just can’t do. You have to be able to, just with what I do with illustration, you have to be able to change the POV. Am I going to go with a bird’s eye view or worm’s eye view? What about the expression on their face? And AI can’t do that now. They can’t take a character and then put it through all these emotions and all these angles and add these other el-… You can’t replace the human element, like you said.

Maurice Cherry:
Yeah, AI can’t get inspired.

Chris Dudley:
Exactly.

Maurice Cherry:
It can’t get inspired from a work or a piece of music or a feeling. It just tries to recopy and regenerate from whatever it’s been fed into their model.

Chris Dudley:
Yeah, yeah, definitely.

Maurice Cherry:
So, we spoke about just social media and these platforms and stuff. How do you approach marketing and promoting your work? Are there specific strategies that you found to be pretty effective?

Chris Dudley:
I really try to let the work speak, but also letting yourself be known as well. Because people do, that’s something I realized, they do like to know the artists behind the work. So, periodically posting a picture of yourself with the art and so forth, or even doing a little video or something. Everybody wants, I want a million followers and so forth. But then I started realizing I don’t need a million followers. I’m booked out with work, and I don’t know how many I had on Instagram. I don’t even think a thousand, but I’m booked with work. I have more work than I can do.

And so, that really changed my whole thought process of… Then I don’t want to be putting all my energies or time just into social media when I want to put that into the creative process, and it has worked for me. It has worked. I focus on my skillset and focus on putting projects out and more work comes. And so, I think having the presence though, obviously, is so crucial. Having a website, I think, is very valuable because it really gives a place where this is your work and you’re not competing for attention on social media platform, but then you could have those platforms that direct people to your site as well.

So, I think it’s necessary in today’s age, especially with the visual aspect of doing art, but focus on the work though. Don’t spend all of your time social media marketing, and then you forget to actually be producing artwork.

Maurice Cherry:
Right. Because the followers don’t necessarily translate into work. It may translate into visibility.

Chris Dudley:
Exactly, exactly.

Maurice Cherry:
Into more eyes on it, but it doesn’t necessarily mean that… And also, you may be attracting the wrong type of clients or the wrong type of people.

Chris Dudley:
Exactly, exactly.

Maurice Cherry:
The tire kickers and the low ballers and stuff. They see what you do and they don’t get the value in it. They just see it and think it’s something that could be potentially easily replicated.

Actually, going back a little bit to the AI conversation, one thing I thought that was super interesting is when people started getting those AI art, AI generated avatars out, how many people were, I guess complaining, but they were like, “Wait a minute, you paid for that? You paid for that? You paid how much for that?” Some people. Well, the cost wasn’t what it would cost you to actually commission an artist. It was much, much, much cheaper, maybe $5, $8.

Chris Dudley:
Exactly.

Maurice Cherry:
$20.

Chris Dudley:
Exactly.

Maurice Cherry:
For several images, not just one image. And it was so funny seeing people like, “You paid for that? You paid money for that?” I’m like, “If you were to pay an artist to do it-

Chris Dudley:
Exactly.

Maurice Cherry:
… you would pay the artist. Do you expect it to be free?”

Chris Dudley:
Yeah. Oh, man, that’s a whole other story too, because art is no other industry, well, maybe photography possibly, but no other industry do people expect you to work for free because people think it’s just maybe some God given talent so you’re supposed to share it for free. And there’s times, obviously, where you’ll be giving with your skillset. But you don’t go to a mechanic and say, “Hey, if you fix my car, I will tell all of my friends that you’re a great mechanic and that’s going to get you some more work.” But people do that to artists all the time. It’s hilarious, man. It’s hilarious.

Maurice Cherry:
I’ll tell you from doing this show, they do it to podcasters too. They’re like-

Chris Dudley:
Yeah, exactly. Yeah.

Maurice Cherry:
“Oh, you’re just talking to a mic. All you’re doing is just press and record. That’s it.” No.

Chris Dudley:
Exactly.

Maurice Cherry:
There’s so much more that goes into it.

Chris Dudley:
Yeah, they don’t see the art behind it.

Maurice Cherry:
Then when you try to show them, they feel like, “Oh, well, this is too much.” Once they get an idea of what the process is and how it is a skilled thing, then it turns them off. From then, it’s like, “Well, now you know.”

Chris Dudley:
Yep, exactly. And to speak to what we’re touching on, that’s what, again, versus just I want to become a social media marketer, that’s what has gotten more work, focusing on the work and then the relationships that I build with my clients. And when we onboard a new author and they see what’s involved, they see what you’re doing to bring their vision to life, that has gotten me more work than marketing on social media.

And so, that’s when it’s that shift of, “Hey, I’ll post and I’ll talk about stuff.” Plus, I’m not a salesman per se, so I’m not trying to hard sell, “Hey, come buy my book.” No. Here’s we created this book. It was a fun project. You can look at it a little bit. And people have bought from that versus me trying to hard sell them. And with regard to more work because then that author speaks highly of the experience they had working with you. That has gotten me so much more work where I have other authors call so and so.

I just finished up a book with Erica Flores, first time author. It’s been an amazing process. That has led to more work. And so, focusing on the skillset, and obviously, your working with clients far exceeds just trying to beg people to buy your products online.

Maurice Cherry:
Yeah, I 100% agree with that. And also, because if you’re focusing on social media, as we’ve seen fairly recently, these platforms can change at the drop of a hat. If you’re busy trying to chase the algorithm, if you’re busy trying to market or make your work fit into whatever this opaque algorithm is in terms of visibility or something like that, it takes away from the work. I think we certainly see it with people that create content for video, like YouTubers, TikTokers. It’s a lot to try to figure it out. And even on maybe non-video platforms like Twitter or Instagram, Instagram is still pictures, but a lot of Instagram now is video.

Chris Dudley:
Yes, it is. It is.

Maurice Cherry:
Then with Twitter and this Twitter Blue, they’ve changed the weighting of how people see your work unless you pay for a subscription. The platforms have gotten so, I don’t want to say unreliable, but they certainly have gotten so caustic and to the point where you can’t really depend on those to get the word out or to get the work out.

Chris Dudley:
Exactly.

Maurice Cherry:
It helps. It still is a megaphone, but you can’t depend on just that to be the thing that propels your work or propels you into whatever the next level is.

Chris Dudley:
Definitely. And that’s why, like I mentioned, having your own website is so crucial. And again, I started before the internet. Well, not just before the internet, but when the internet was starting out, it was before all of the social media platforms. And so, I had a website even way back then. Whereas I see a lot of artists now that pretty good work, but they don’t have a website, and it’s just shocking to me. And they think, “I’m just going to get all kinds of work from Instagram.” Maybe if you were in the inception, but if you’re starting out right now and thinking, “I’m going to start an Instagram and get all kinds of work” and you don’t have a website, it’s not going to happen.

Maurice Cherry:
Yeah. I know even from just trying to reach artists or folks to have on the show, it’s always tough to get them on if they don’t have a site, because even if I send them a DM, the way that the filtering is, they may not ever see it, if I send them something on Instagram, if I send them something on Twitter.

Chris Dudley:
Exactly.

Maurice Cherry:
If they even allow you to send them a message, and it’s like, “Well, do you want people to contact you or not?”

Chris Dudley:
Exactly.

Maurice Cherry:
What’s the point? Yeah.

Chris Dudley:
Exactly.

Maurice Cherry:
How do you balance your artistic pursuits with your personal life and responsibilities? You mentioned your marriage. You’ve got three kids. How do you balance all of that?

Chris Dudley:
Well, again, with booking, I don’t just accept any and all projects. I’d be with a privilege to be in that position where I don’t have to take all work that comes my way. I can be a little choosy and making sure that I’m prioritizing that time with my wife. We just hit 25 years.

Maurice Cherry:
Congratulations.

Chris Dudley:
So, that’s a huge milestone, and with our three girls and prioritizing that time. I love doing this. Obviously, there’s a monetary component to take care of my family and so forth. But I often think about too is that there’s time that I can’t sell a client. That’s for my wife and for my family, but then often think, but the time that I do sell you, if you will, you’re not paying just for that project. You’re paying for the time I’m not being with them.

And so, when that clicked in my brain many years ago, that changes your margin, that changes the value of what you’re offering. And time to ask me to not be with my wife and my girls, like I said, some time I can give you, but the time you’re going to take from them, it’s worth something to me. So, it’s got to be important. That’s why the project has to resonate with me. So, that’s how I really keep that balance.

Maurice Cherry:
That is so deep. That is probably one of the deepest things I’ve heard on this show, and I’ve been doing this for 10 years.

Chris Dudley:
Wow. Wow.

Maurice Cherry:
No, seriously. It’s like you’re not just paying for my expertise and time; you’re paying for time away from the people that I care about. That’s deep. Wow. That resonated with me. Thank you. Wow.

Chris Dudley:
Yeah. And with that, if I could just compound on top of that, it’s where, obviously with projects, you’re not paid in hourly sense, but a lot of people understand the concept of getting paid hourly. So, if you ask the person that, would you not spend time with your family for five bucks an hour? Most people would say no. And so, if you just keep going up the ladder with the amount, there may be a threshold where people would think about it. But that starts to help you to appreciate that there’s a value add there. That I’m not just going to not spend time with my family and exclusively give mental and emotional energy to your project for any amount. No, there’s a value thing to that.

Also, like we touched on earlier, I forget the book that I read, but they said that don’t spend time doing something that you could pay someone else minimum wage to do. Obviously, when we’re starting out, and that’s what has almost changed my brain. And that’s what made me, like we talked about earlier, we put together a team. And I’ve got assistants and people that handle that because it just doesn’t make sense for me to do something that I could pay someone 10, 15, 20, 30 bucks an hour to do when, my time, I could be doing something that makes way more than that. You get what I’m saying?

Maurice Cherry:
Yeah.

Chris Dudley:
Yeah, it doesn’t add up. But a lot of people think, “Well, I’m giving away money. I can keep that.” Yeah, but your time is a non-renewable resource, so you got the time that you do sell, it’s got to be at the right price.

Maurice Cherry:
Yeah, and I think that becomes even more important, especially when you have a family, when you start getting older, when other members of your family start getting older. There’s no amount of money that can buy that time back.

Chris Dudley:
Exactly, exactly.

Maurice Cherry:
When you look back at your career, is there a particular moment or a particular experience that stands out to you the most?

Chris Dudley:
Man, I have a few. And one, I would say, is when I get an award at a juried art exhibition here at Downtown Grand Rapids. That was a very nice privilege. And like I mentioned, starting out with Dudley Graphics, and my drawing ability was not up to par by any means, any stretch. And so, to work hard to improve my understanding of light and shadow and composition and all of that, to get to the point where to be accepted into the juried exhibition again. And you’re paying to have your artwork reviewed and they can just send a no. To get accepted, to get the award, to have my work purchased and so forth, that was a milestone where I felt, “Okay, I’m pretty good at this.” Then it really gave me the confidence that I can take this to other levels.

Maurice Cherry:
What’s the most important lesson you say you’ve learned throughout your career as an artist?

Chris Dudley:
Again, sounds cliche, but to truly stay humble. Humility is something that can slip away. And that’s why I say it’s stay humble because it can be a constant fight for all of us. You’re this imperfect person, but to really strive to maintain humility and never stop learning in your craft. And so, even when I meet with clients now, I tell them, I say, “Yes, you’re hiring me because I have a skillset that you don’t have, but I want to do what’s in the best interest of the project, not what’s in my best interest.”

So, if you have an idea, even though you can’t draw, please tell me. If you can defend your idea, because I’m looking at as an illustrator, I need to be able to defend my choices that I make artistically that, oh, the composition is this way because of that, that way because of this. But if someone shoots an idea to me and I realize that your idea is better than the one I had, hey, let’s make the change to make the project better.

So, that humility, even the face of you have a skillset that someone else doesn’t have, but that doesn’t mean that they can’t suggest something that’s better. So, that’s what I really strive for. And never stop learning. I feel like I’m decent at drawing and I’ve been learning this craft since I was a little kid. And some days, it feels like I can’t draw. Like, “Man, what are you doing?” And other days it’s like, “Oh, you’re pretty good. You got this.” But yeah, never stop learning and never think you just got it down.

Maurice Cherry:
Now, all of your daughters can draw too. Is that right?

Chris Dudley:
Yes. I jokingly what they say, joking but not joking. I made them learn how to draw, and there were times with each one of them. My oldest is almost 20, almost 20, 16 and 15. And they would see me drawing and I would teach them how to draw. I didn’t tell them that it looked good when it didn’t when they were young. I didn’t crush their feelings, but if something was off, I told them. I didn’t just put it on the refrigerator just because they drew it type of thing.

There were times with all of them that there were tears. And I would ask them, “Do you really want to learn how to do this?” And with tears in their eyes, each one of them, it’s like, “Yes, I do, daddy.” And it’s like, “Okay, you see that the eye is crooked. How do we fix it?” And it’s helped them to really grow. And if I could share just a brief story with that.

Maurice Cherry:
Yeah.

Chris Dudley:
When I was teaching my oldest how to read, it dawned on me that this is hard because if you can picture this, you know how we write, the kid learns how to write the alphabet. What I did was, so to make an A, there’s three lines that you use to make an A, right? Then there’s one line and two bumps to make a B. And this curve line to make a C. So, what I did was I wrote an A, but I kept all the lines. Just imagine doing the first line on this part of the page. Second line over here. And I did the whole alphabet that way on a piece of paper and it looked like a jumbled mess.

But then I thought that I’m asking my daughter to figure this out, learn how to put the lines together, so that they can make all the letters. Then we asked them to learn the name of the letters, the sound of the letters, how to put them together to make a word, how to put those together to make a sentence, a paragraph, and then you got to do it with math. And I thought, “Man, learning how to draw is easier.” Then the thing, Maurice, is that there’s no reference for that. They have to learn it though.

Maurice Cherry:
Yeah, you have to.

Chris Dudley:
And so, when it hit me that, okay, if you can learn how to read, how to write and how to do math, you can learn how to draw. Then this is a soapbox of mine, but I won’t belabor it. But when I realized that, I realized, okay, my girls can learn how to draw. They’re going to learn how to draw at least the basics.

And another thing, at a class that I got to teach, and I’ll keep this short, is that I told someone, they said, “Well, no, it’s just a talent.” I said, “Well, yeah, you can have a little bit of ability, but it gives you maybe a one to three out of a 10.” But I said, “We make kids for 13 plus years learn how to read, learn how to write and learn how to do math. Everything else is optional. If we made you from kindergarten to 12th grade, you had to draw every year and you were tested on it, everybody would leave school knowing how to draw at least decently.”

But if your kid said, “Ah, it’s hard.” You say, “Okay, quit. Let’s try and play saxophone or try soccer.” But if your kid says, “I’m struggling with reading,” you’re going to learn how to read and we make them do it. And so, that dawned on me. I was like, “Okay, my girls will learn how to draw.”

Maurice Cherry:
I really like that way of looking at it. And you’re right. I mean, as kids we start off with, I think, a lot of applied art education. In kindergarten and whatever, there’s finger painting, there’s drawing and there’s coloring. I remember being in elementary school and we would get these sheets of paper that have it’s blank at the top, and then there’s lined rules at the bottom for writing. And you had to draw something at the top and then tell the story at the bottom of it.

I actually still have them. I still kept all of my mine from being a kid. But the older I got, I remember art stuff just kept getting phased out, phased out, phased out. I had taken gifted courses. I think they called it enrichment back then, but they were gifted courses. And it felt like those were the only times when I got to do something that felt creative because everything else was towards some specific application. Like you’re learning English to learn how to read and how to write. You’re learning math for those applications and stuff like that.

And just the older you get, even if you are really into art and drawing and stuff like that, it’s increasingly treated as a hobby and not as also a fundamental thing to understand. It’s just the world that we live in because as you alluded to, well, you didn’t allude to this really in the interview, but before that we talked about this, everything is designed. Everything that we use in the modern world has went through some lens or filter of design in some capacity. The chair we sit in, the clothes we wear, the picture we write with.

Chris Dudley:
Exactly.

Maurice Cherry:
All of those are designed. And because we interact with these designed things on such a regular basis, almost on a subconscious basis, we know when something is not designed well.

Chris Dudley:
Exactly.

Maurice Cherry:
We know when this pen is bad or this shirt doesn’t feel right. We know that. We may not have the language for it, sort of speaking what we talked about with English and math and stuff, because that’s not really taught to us as we get older.

Chris Dudley:
So true. So true. And I remember someone asked me, “Oh, what do you do?” I said, “I draw and do illustration.” And the look on her face. And she said this to me, man. She said, “You might as well have told me you could fly. You can draw?” And she was just so shocked. And I’m like, “Yeah, I’ve been drawing and learning this for decades.” But what I’ve found is that artists, well, specifically with visual artists, we’ve done it before there was any incentive to do it. And so, that’s what I think makes it so amazing.

It’s like when someone sees someone that can do back flips and do all this stuff, but they’re not in the Olympics, they’re not getting paid. It’s like, “Wow, how did you learn how to do all that?” They did it because they loved it. And another point I’ll make is that it shows that, if you’re given the right incentive and you can do it because of the right incentive, that shows that you could do it all along.

I’ll use the example sometime. Usain Bolt, fastest man. He’s run the 100 meters in 9.58, I think it was. Now, if someone says, “Hey, I need you to do that in a year. You need to be able to run a sub-10 100 meters. I can’t do it. Right? There’s no amount of money. I can’t do it. But if someone says, “Okay, I need you to learn how to draw by next year decently and I’m going to give you $10 million.” What happens? You start practicing every single day. And guess what? At the end of the year, you’re going to be pretty decent at drawing and get that $10 million, which means you could do it all along, but you didn’t have the incentive.

Yeah, so as artists, we learn. We love it, so you learn how to do it and then later, you make a few dollars from it. And it seems amazing because most people, like you said, they veer off that creative path. Then you get older where you need money, and then I haven’t learned how to draw, so no one’s going to pay me with the skillset I have now. So, I got to go work over here and make some money. But yeah, it’s a awesome thing. Everybody can learn how to draw, but it’s cool being one of the few in the world that can.

Maurice Cherry:
Do you have a dream project or something that you love to do one day?

Chris Dudley:
Dream project? Well, actually, one of my dream projects is a book that I wrote. The book that I just finished up, I’m the author and illustrator and the collaborator with Michael Chambers. He’s featured in the book, but I’m actually the author and the illustrator of the book. So, it’s my book per se. But my dream book, actually, I wrote a couple of years ago, and I have just got around to illustrating my own work. This one is called Duddles and the Big Dilemma, and it is a book about that very thing we just discussed about learning to draw and how everybody thinks it’s magical, but it’s more work than just talent.

And it’s amazing to me is that in the book and it explains it, no one says you’re just an amazing gifted plumber or an amazing gifted carpenter or you just naturally know how to whatever. But when it comes to the arts, people want to put this fairy dust on it. Whereas, what is it, I think Malcolm Gladwell is in his book Outliers, he said that you’ve never seen someone who is good, but they haven’t put into practice, in the work, deliberate practice.

And so, that’s one of my dream projects is to finish that, the illustrations for it and really get that book out there. It’s called Duddles and the Dilemma. Well, I won’t want to give a lot away. I’m going to finish this project probably within the next year or so, and there’s a series to the book as well. But it’s about him realizing that it’s not all fairy dust. You got to put in work to learn to draw. It’s not a magical thing, and that’s just the truth of it. And a lot of people don’t want to believe that, but I wish there was just a download that gave me all this knowledge that I’ve learned over the last 30 plus years. I wish it was that easy, but yeah.

Maurice Cherry:
Yeah. So, to that end, what do you see as the next chapter of your career? What do you want to do in the next five years or so? What do you see yourself?

Chris Dudley:
Yeah. Well, more books. Right now, as I mentioned, we just launched the book with Michael Chambers, Lil’ Boogaloo Shrimp and the Clean Sweep. And so, I see the direction of doing more art talks and events with kids. We are actually partnering with a nonprofit here locally. I mentioned about the breakdancing school there in Georgia, but there’s one in Colorado that we’re going to be touching base with. And so, I think that’s going to really be exploding. We’ve already talked to Rockwell Dance Academy about a book project, and so, that’s on the horizon. And in the next couple of years, just more books. More books, man.

Maurice Cherry:
More books. Well, just to wrap things up here, Chris, where can our audience find out more information about you, about your work, about the books? Where can they find that information online?

Chris Dudley:
Well, my website is chrisdudleyart.com and that’s where you can see my portfolio, my body of work and anybody can reach out and contact me directly through that. But my books are available through hudsondawnpublishing.com that I’m connected with, hudsondawnpublishing.com. And that’s where all of the books that I’ve illustrated are available. And that’s been awesome being connected with them. I actually designed the logo. And my oldest daughter, she launched the publishing company. She put a team together. I was joking around about it, designed a logo. She launched it during the pandemic. Got with an artist and made a book and got it out. And I was like, “Wow.”

Maurice Cherry:
Wow.

Chris Dudley:
And so, since then she has worked with, wow, probably 10 authors. I’ve illustrated a lot of the books, but she’s working with, I think, five new authors right now and that’ll be on that site. So, yeah, it’s been awesome. She has printeries. It’s established printeries locally in Michigan actually, in the west and east side of the state. Got warehousing. So, she’s taken that to the next level beyond what I ever thought that could be.

Maurice Cherry:
That’s amazing. It’s a whole family operation. It’s a family affair.

Chris Dudley:
Yeah, definitely, definitely. Yeah, hudsondawnpublishing.com.

Maurice Cherry:
Awesome.

Chris Dudley:
And actually, the recent book, you can read the intro of the book right there online.

Maurice Cherry:
Okay. Yeah, we’ll definitely put a link to that in the show notes.

Chris Dudley, I want to thank you so, so much for taking time out and coming on the show. I mean, it always warms my heart to talk to people that have been doing this kind of work for years on years on years because the longevity in just this industry is something that you don’t really see from Black creatives. You can get burned out. We can get discouraged, et cetera. And it really feels like you have found a method and a calling and a passion in this work, and you found a way to not only sustain it for yourself, but also for your family and for the community that you’re in.

I think that is something that is super inspiring. I think any artist wants to make sure that their work has an impact in the world. And most certainly, I can tell just from your passion about it and how you talk about it and just the quality of the work, that you’re making an impact in the world with everything that you do. So, thank you so much for coming on the show. I appreciate it.

Chris Dudley:
Well, thank you for having me. It’s been such a privilege. I truly appreciate and look forward to touching base with you soon.

Sponsored by Brevity & Wit

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Brevity & Wit is a strategy and design firm committed to designing a more inclusive and equitable world. They are always looking to expand their roster of freelance design consultants in the U.S., particularly brand strategists, copywriters, graphic designers and Web developers.

If you know how to deliver excellent creative work reliably, and enjoy the autonomy of a virtual-based, freelance life (with no non-competes), check them out at brevityandwit.com.

You might not think of Detroit as a city for tech, but web developer Aisha Blake is helping change that perspective. She works as a web developer for Detroit Labs, fosters the next generation of tech speakers through Detroit Speakers in Tech, and her story of what drew her to the city is one that you’ve gotta hear.

Aisha and I talked about how a goalball tournament was the catalyst for her journey to Detroit, how couchsurfing opened up her up to an entirely new community, and she shared the the one piece of advice which has helped her accomplish so much in life in such a short amount of time. According to Aisha, we all need to feel comfortable with trying new things, and I think you’ll come away from this conversation feeling inspired to do just that!

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Kevin White calls himself a “UX strategist”, but that title barely scratches the surface of what he does. Aside from his work as a senior experience designer, he’s also a talented illustrator, a design educator, and a devoted family man. But according to Kevin, his origin story as a design professional is an example of what not to do. (Naturally, I had to know more about this.)

We started off talking about the ubiquity of UX in today’s modern design industry, and from there Kevin goes into the early days of his career, and we take a slight detour to discuss social media, sound design, branding, and even the historical archives of the Internet! We touched on a lot of topics in our conversation, but I think what stands out the most is that there is no one true path to becoming a designer. Learn more about Kevin in this week’s interview!

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This week’s interview is with none other than the venerable Craig Wilkins. Craig is one of the country’s leading scholars on African-Americans in architecture, and he’s an academic, activist, and author. He can now add one more “A” to his long list of titles — award winner!

I spoke with Craig fresh off his National Design Awards win, and we talked about a number of things — his love for Detroit, what made him get involved in architecture, where he sees design education in the future, why design organizations struggle with diversity, and more. It’s a far-reaching conversation that I think you’ll enjoy regardless of your design discipline. Enough from me though…press play and enjoy the interview!


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