Alex DeSpain Staying Posi

Our guest today is Portland’s own illustrator and designer, Alex DeSpain. He talks about the most important lessons he is learning as a commercial artist, what he does to get more design and illustration work, and how to stay positive in not-so-glamorous times.

Interview by Cesar Contreras

Cesar: Pencil or pixel?

Alex: I would have to say do your sketching in pencil, polish it up in pixel. It’s a lot easier to edit.

Cesar: Nice. The whole thing with the name pencil versus pixel is that the pencil’s supposed to represent the analog side of things, whereas the pixel, digital. What is it that you are attracted most to?

Alex: There are pros and cons with using both tools. For me, I like to sketch with a pencil or a pen. I find there’s a lot less editing that happens when you’re working with the pencil. You just keep going. It’s like a continual stream.

Cesar: It’s like a stream of consciousness…

Alex: Yeah you just keep going. I don’t really like to erase. In fact, usually I’ll draw with pen often when I’m doing analog stuff. When you’re in Photoshop or Illustrator or doing it with pixels, you’re more in an editing mode as you create. It’s just a different train of thought I guess, for me.

Cesar: Are you a big doodler?

Alex: Actually tonight I will be doodling with some of my friends. We’re having doodle day.

Cesar: Oh nice.

Alex: We doodle every Wednesday. We meet up and a bunch of cool artists get together and kind of bounce ideas off of each other and have fun and just talk and doodle. It’s a good time.

Cesar: I’m sure it’s been very helpful getting together with other artists and collaborating with ideas. It sounds really cool. Who’s all involved in this?

Alex: We’ve got a group of maybe 60. But I’d say like 10 to 15 show up on Wednesday nights. And we’ve even had it as few as like one or two people. My friend Jeremy Pettis is the one who started doodle day, for what I know he’s the one who started it. I was invited by Jason Sturgill.

Cesar: Sturgill!

Alex: So many great creatives show up like Steve Alexander who will come to doodle day, and my friend Derek Moore and Jeremy Mlodik and Sam Spencer. There’s so many I feel like I’m afraid I’m going to forget somebody.

Cesar: Well yeah you just mentioned 60. I mean that’s more than a handful. Has it ever been up to about 60 attendees?

Alex: I have not been to a doodle day were there have been all 60. Some people will show up maybe once or twice and I won’t see them for a few weeks. And they’ll be there the next week.

Cesar: That’s awesome.

Alex: Yeah. There are those diehards who are there like every week.

Cesar: Yeah, I can imagine.

Alex: Yeah.

Cesar: You mentioned sketching, doodling, pencils, pens. Can you tell us what it is you do? And gives a little back story. What led you to what you do?

Alex: I’ve been drawing since I was a kid. My mom’s a graphic designer and I think that that had a big impact on me. I spent a lot of time working as a custom framer when I was going through school and I worked at Michael’s. So we would take things off of the floor and bring them back to the shop and experiment with them.

Cesar: So you made a lot of your own frames for your own work.

Alex: I mean, we did stuff like my friend Eric showed me how you could take plastic figurines and cut them in half, like a cow and a butterfly and then glue them back together and put them on the shelf.

So there are a lot of like weird experiments that I did as a framer at Michael’s that I probably shouldn’t have been doing. But I got to experiment with a lot of mediums that way and I think that fueled my fine art experimenting in a way.

Cesar: What other mediums and any tools?

Alex: I was learning about frisket and resin and all kinds of things. Oil paints and acrylics and just pretty much everything that Michael’s has in stock. At some point I have experimented with it. Yeah, I guess I showed a lot in art shows and I worked as an assistant at a gallery in Portland when I first got here. It was right before I decided to go back to school for design. I don’t know there’s something about graphic design and the clarity and I’ve seen its real impact on people.

Cesar: Where did you live for Portland?

Alex: Before that I was living in Texas doing the custom framing and just making fine art. I had a drafting table and I was really into watercolors and watercolors mixed with pen and ink. Just really detailed illustrations and they are deeply personal.

Art for me was a way to kind of heal my own personal, I guess trouble or issues, or process things that were difficult in life. I would just draw. It’s like a meditation, I suppose. But yeah I’ve been doing that for a long time.

Cesar: You and I previously had a conversation and you mentioned that you lived in several places before landing in Portland. What influence did your experience have on you personally and what influence does it have on your work?

Alex: I think it was really the people that I would meet and the landscape and just the social climate. Growing up I moved a lot and that’s just kind of how it was. And that’s what I got used to.

Cesar: Let’s talk about your work for a bit. You have a lot of line work, really cool line work. It looks like you do most of that line work with a brush pen. Do you do most of your work in brush pen? Am I completely wrong about that? Or what are your favorite tools? And what tools do you use on a daily basis?

Alex: Sure, I do use a brush pen for my black and white work. That’s all ink in my brush pen, analog traditional. But I like for my digital work to very much look like my analog work. I want that sort of blurring of the lines where you’re not entirely sure if it was done traditionally with a brush pen or if this was done on a computer. And often I’ll work in Photoshop with custom brushes.

Cesar: What are some of the custom brushes you use if you don’t mind me asking?

Alex: I actually only use one custom brush for the most part. And it’s a Frenden brush.

Cesar: Frenden?

Alex: Yeah.

Cesar: This is like your go-to brush of choice when it comes to, like, Photoshop.

Alex: Yeah.

Cesar: Cool. Do you use a tablet?

Alex: Yeah I have an Intuos 4.

Cesar: Sweet.

Alex: Yeah I like it. I’ve used the Cintiq before where you draw directly on the screen.

Cesar: Yeah, yeah. What do you think about it?

Alex: There’s something about that that I don’t like because the thickness of the glass, I guess, where the pen isn’t actually exactly on.

Cesar: It’s almost like an optical illusion.

Alex: Yeah it kind of messes with me. I’d much rather look at the screen and know that that little cursor is exactly where my pen is. It’s like synced that way for me.

Cesar: Yeah. I’m looking at some of your physical products here and I see that you’ve collaborated with the Valley Cruise Press.

Alex: Yeah.

Cesar: They’ve got pens, buttons, and other artwork of yours that has been produced into these physical products. How did that collaboration start?

Stay Posi by Alex DeSpain for Valley Cruise Press

Alex: Yeah, Valley Cruise Press. They’re awesome. Yeah I made a stay posi enamel pen which is short for stay positive. And a silly goose pen because, really, I sent them a bunch of designs and they picked what they liked and moved forward with it. I thought might as well just reach out and see what happens. And he was interested and I don’t know, I just really like all the artists that they work with. And they seem like a really great company.

Cesar: I like especially the one you first mentioned, the stay positive – or stay posi – pin and boy is that something we should keep reminding ourselves these days.

Alex: Not easy. Not an easy thing to do.

Alex: Really, I made that as a reminder to myself because I have a hard time staying positive. Everything seems so, especially right now, pretty negative. I don’t know, I don’t think much happens when you’re just focused on the problem. You have to be focused on the solution too.

Cesar: And be the solution.

Alex: Yeah and for me I read in the news all the horrible things that are happening and it really gets me down and makes me angry. But I realize I don’t want to be just an angry person who’s down. I want to try to do something about it. For me, I just do what I can. It doesn’t help to just be a grumpy jerk.

Silly Goose Pin by Alex DeSpain for Valley Cruise Press


Cesar: So what kinds of things do you do to get yourself up and stay positive?

Alex: I try to just make sure my attitude is in check and make sure that I’m not taking myself that serious all the time. And making sure that I laugh and find humor. Instead of always looking for the cracks, spin that energy and focus more on what’s positive and what’s good in people. We all have our issues, we all have our problems, but at the heart I think people want good things to happen.

Cesar: Yeah.

Alex: The struggle is real, you know?

Cesar: It is.

Alex: It’s not like you just decide to be positive and that’s it. You decided that’s it, you’re done.

Cesar: It’s a constant evolution. You have to keep on working at it.

Alex: Yeah and the stuff that pulled me out of it was art and music and there are books and people – other people with their message. If I could do that for others that is what I want to do.

Cesar: Man, I appreciate it. I really do. And I think you’re doing it.

Alex: I’m also a weirdo.

Cesar: I think we all are. Or at least I am too. [Laughs]

Alex: That’s why I make those super psychedelic bizarre illustrations sometimes that are really goofy. For me, it’s just fun to make those and it’s not so serious.

Cesar: Yeah, I love it. It’s colorful, psychedelic, out of this world. It’s just, it’s crazy but it’s so good.

Alex: Yeah I get psyched on seeing that kind of artwork. And that’s what I love and that’s why I love to make it sometimes.

Cesar: Yeah totally, man. Who are your top 3 favorite artists? They could be past, they could be current, they could be contemporaries, people you’ve worked with.

Alex in the studio

Alex: Yeah. That’s a difficult one. Well I know who’s up there for sure. It’s obvious that I love his work and that would be Geoff McFetridge.

Cesar: Yes!

Alex: Also I really like Matisse and the more fine art. I know Geoff’s in fine art also but more traditional like Matisse.

Cesar: I was just looking at Matisse’s work. He had these cutouts.

Alex: So good and it’s so simple and pure in the way and just clear.

Cesar: Yeah.

Alex: Very clear. And I have to pick one more?

Cesar: I mean you don’t have to, but I am curious.

Alex: I really like Brian Chippendale’s art from lightning bolt.

Cesar: Ooh I’m not familiar with him.

Alex: It’s super wild and really great. Oh I forgot to mention Ray Pettibon. I really like Ray Pettibon a lot. Aside from all my friends who I’m spoiled by, super creatives here in Portland. I think those are my top there.

Cesar: What time during the day do you put out your best work? So for instance I’ve noticed lately the best time, when I have the best ideas, when I put out the best work, is around 10:00 in the morning. And I’m probably good until, I don’t know, noon. Do you experience something similar on a daily basis?

Alex: You know, I used to be a work at night kind of guy. But yeah from about 10:00 to 2:00, those are really great hours. I don’t know why. I’ve tried different times, but I like to get a full night’s sleep.

Cesar: Yeah 10:00 to 2:00 is definitely my sweet spot too. I mean my mind starts to wander anytime after.

Alex: Since I work from home now, I feel like I’m always kind of ready to work now. So I could make dinner and then afterwards think, yeah I probably have a couple of hours I could just go and work.

Cesar: It’s that blurry line between work and home life. But it proves that you enjoy what you do.

Alex: Yeah. I feel like work and life are fused together in a lot of ways.

Cesar: I know that you used to be part of See Saw Club there in the Ford Building in Portland with Jason Sturgill, Kate Bingaman-Burt, some great, great artists. Will Bryant was there too before he moved back to Austin.

Alex: Totally.

Cesar: What were the most important lessons that you learned as a commercial artist, whether it’s putting out work, whether it’s getting the work? What was it that really stuck with you?

Alex: I think I learned valuable lessons from each of them in different ways. With Kate I learned about staying on track and how to keep going with a theme and sticking out for a long period of time. Just stick to a theme, develop it. Don’t just do something randomly and just be random all the time. Like it’s hard to follow that. Kate had her daily drawings where she would draw everything that she would buy. And she did this for, I think, 8 or 9 years.

Cesar: Yeah, about eight years.

Alex: Yeah. And at the end of it she had this huge collection. This awesome set of drawings. For me, I thought that was really inspiring like just the amount of work that she produced with this one theme. I learned a lot from Kate. Kate was a big mentor and I still ask her questions and learn from her. Will, I learned about just how to be nice. I mean I am nice, but Will …

Cesar: You’re terrible, man. [Laughing]

Alex: Will is super nice and he is one of the nicest people that I’ve ever met. I found that to be really inspiring. And the other thing is that he is a serious artist, but he doesn’t necessarily make serious work.

Cesar: Or take himself seriously.

Alex: Yeah. I thought that was so great or that is so great.

With Jason I learned about how to dive more into research, how to find inspiration, how to stay inspired, to push yourself out of a comfort zone and to try new things and be more experimental. I think those are the most valuable things that I picked up while I was there.

Cesar: What about in terms of getting more work?

Alex: Yeah I would say that they taught me to actually be active in the community. Like, not to just email people. Actually show up to things. Go to events, get to know these people, know who they are, care about them, care about what they’re about. Don’t just email people. Treat people like people. That was really important.

Cesar: Any particular events that you’ve attended that really stick out?

Alex: Design Week Portland is a big one. Creative Mornings. There are a lot of events that happen that artists, or designers, or illustrators will just put on themselves. Going to those and supporting other creatives and just being there is really important. And talking to people face to face.

Cesar: Yeah man, thanks for sharing that. That’s one of the most important things for sure and that’s one of the things that I’ve learned in the last 4 years is to just be there, be present. Show up.

Alex: Yeah. I think also be a self-promoter and don’t be shameful about it. It might at first seem king of awkward to email somebody that you’ve never met and say, “I really like what you do. Here’s how I would like to participate. This is what I have to offer,” and just putting yourself out there. That can be hard. That requires a lot of belief in yourself to do that all the time. And how do you harness belief and how do you keep it going, especially with all the rejection you face as a freelancer? It can be very like disheartening.

Cesar: It hurts.

Alex: Yeah, you spend all this time with all this thought. You put together a presentation and you email it to somebody, and you hope it’s the right person. And you never hear anything back. That can be frustrating after awhile. Makes you kind of question am I doing the right thing? But sometimes it’s just about finding the right person to work with.

Cesar: Or even the right time.

Alex: Yeah timing. Persistence is what will pay off.

Cesar: Yeah. Sometimes when you reach out to someone or a group of people, you might not reconnect until later down the road. Maybe even years down the road and they might approach you and say, hey Alex I really like your work. I would like to work together. And you’re thinking didn’t I email you like 4 years ago about that one project?

Alex: Yeah totally. It’s kind of a mystery. I think people are just referring each other and that’s how it happens.

Cesar: How do you overcome those moments when you know you’ve been rejected from a potential project? I would just grab a big drink and pass out.


Alex: It’s note easy at times. At least you got to practice, I don’t know. Or at least you know…

Cesar: Yeah, we learn something from that. I’m sorry for interrupting. I’m a big fan of Robert Greene and he wrote this book, Mastery. I don’t remember if it was a book where he had mentioned this or an interview.

Illustration for Lush Cosmetics by Alex DeSpain

There was a point where I was just reading the book and I’m like, “I’ve got to listen to more of this guy.” It’s so fascinating. He said something along the lines, and I’m totally paraphrasing here. But he said that every shitty experience that you have, every crappy job, every low point of your life is a lesson.

It’s really important to keep note of your experiences and what you’ve done and where you’ve gone and these kinds of things. And just learning from them.

Alex: Yeah I think there’s always room to improve and improve how you do something.

Cesar: Sometimes it just isn’t your time.

Alex: Yeah. You could put the best work out there that you have to offer and you’re right, it might just not be the right time. And patience is a part of it and just waiting for the right time to come around.

I think it’s helpful to remind those people that you are still interested in working with them. Send them an email, follow what they’re producing, let them know what you think about it, let them know that you’re still interested in working with them and staying persistent.

Embrace wherever you are right now because there are great lessons to be learned in it.
– Alex DeSpain

Cesar: Yeah. Don’t dismiss them. You never know.

Alex: Yeah.

Cesar: What areas are you trying to get better at? It could be anything.

Alex: Yeah I think that I’m trying to be more clear with my work and more thoughtful and more intentional. I’ve been experimental with my work for a long time and I think it’s good to be experimental to a degree.

Cesar: Totally.

Alex: But right now I’m really focused on creating work that is as authentic and from my heart as I can make. Making work that means something to me and working with people who are on that same page.

Illustration by Alex DeSpain

Cesar: Well said, my friend. Well said.

Alex: You know, like I think I’m more selective about who I’m collaborating with too. Because collaboration can be a tricky process at times.

Cesar: How so?

Alex: Just making sure who I’m collaborating with is on the same page.

Cesar: What kind of missteps or bad elaborations have you experienced that made you think I’m not going to do this ever again?

Alex: I think it’s good to collaborate with somebody who doesn’t have a superiority complex.

Cesar: Maybe someone that wants to take over a project completely.

Alex: Right and then take credit for everything. Yeah, I’m not interested in those kinds of collaborations. I really want my opinion to matter to the collaborator or my expertise to be considered when I’m collaborating.

Cesar: What is one thing you wish you knew about at an earlier stage of your career that you know now and why?

Alex: I would say that it’s easy to compare yourself to others and that is a trap. Everybody is on their own path. Good things take time to develop so just keep at it.

Doodle by Alex DeSpain while joining Pencil vs Pixel

Cesar: That’s something that I keep on reminding myself.

Alex: I just want to say that we’re all dealt a different hand in life. We’re not all dealt the same obstacles. And to love the struggle and to love the obstacles because they will teach you lessons that you’ll be able to use later on in your careers.

And so just embrace wherever you are right now because there are great lessons to be learned in it. And don’t listen to anyone who’s trying to discourage you from doing it. If you know it’s right for you, do it.

Cesar: Thank you, Alex!

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