Rachel Ann Lindsay

Rachel Ann Lindsay

  • artist
  • illustrator

Rachel Ann Lindsay is a freelance illustrator who is making a name for herself through her whimsical, continuous line drawings. Born in rural Ontario, Canada, Rachel moved to Toronto after graduating from Sheridan College’s illustration program. After a few waitressing gigs, Rachel got serious about illustration, quit her job, and dove into freelance work as her sole source of income.


Describe your path to becoming an artist.

It’s really not an interesting story. I figured out that I could draw when I was taking art classes in high school. It came really easily to me and at the time, I liked drawing everything perfectly. I loved English and art and at the end of school I just picked one.

Where did you grow up?

I grew up in the country outside of Woodstock, Ontario (Canada). Woodstock is the dairy capital of Canada and I grew up just outside of there, on a little dirt road. I would have given anything to live in one of the villages a few miles away where my friends lived, like Sweaburg or Oxford Center. That would have been a really big deal because they had ball diamonds and general stores there. Looking back though, I was lucky to have a childhood in the country.

Was creativity a part of your childhood?

I think I had all your standard childhood creativity stuff going on. I was crafty and made stuff for people. I spent a lot of time outside. It wasn’t anything out of the usual in terms of a creative upbringing. My grandmother was a painter and our house was full of her paintings, but I was never around her while she painted. My mom can paint too and my brother could always draw, they just never do it.

Did you go to college right after high school?

Yes, I went to Sheridan college in Oakville, which is right outside of Toronto and an hour and a half from my family. I had also applied to the OCAD (Ontario College of Art), which is in downtown Toronto. I was accepted into both of them and I chose Sheridan solely because it was out in suburbia and I was terrified of living in the city. I didn’t want to go anywhere near it. I was mostly afraid of public transit and getting lost all the time.

What is your degree in?

I earned a Diploma in Illustration. It’s different in Canada because college and university are two different things. I did one year of art fundamental classes and applied to the illustration program. I spent the next 3 years focusing on illustration.

I worked really hard in college. I had that fear coming from a small town. It’s one thing to be the best artist in your high school, but you think, oh, I’m going to an art college and everybody is going to be the best artist from their high school and I’m not going to stand out at all. I did my absolute best on every assignment.

Did you jump right into working as an illustrator after college?

I worked so hard in college and I feel like there were weeks where I didn’t sleep at all. When I graduated, I got an award for best in show and all that stuff. But after I graduated, I did nothing for a while. I waitressed, worked in bars. I didn’t draw for ages. I saved some money and travelled and got away from my art for a while. Then I started out really casually and got a few jobs, then gradually a few more.

Was there an “aha” moment for you when you knew that you wanted to do illustration?

Um… no, not really. I actually struggled throughout my illustration program. In the last year, we were required to do a work placement at the end of it for 3 weeks. A lot of people found internships with working illustrators or interned with magazines. At that time, I was thinking illustration was maybe the absolute wrong thing for me and I had to get special permission to intern at a gallery instead. I thought maybe I didn’t fit into the commercial art world at all. Working at a gallery showed me that I wasn’t a fine artist either. I think I was always more of an illustrator. I’m glad I did that internship. It showed me that I did want to be an illustrator even though I was worried I wasn’t cut out for it. I am more commercial than I thought.

Did you have a mentor? Who was it and how did they inspire you?

Yes. When I got out of school, I was waitressing, but doing illustration jobs here and there. Gary Taxali, an incredibly talented and successful illustrator had seen my work and contacted me. He was teaching at OCAD and asked me to come speak to his students and I said, “I can’t speak to your students, I don’t know what I’m doing yet.” He said, “No, come anyway.” So I did and we became friends and I used to call him my mentor and he hated it. He would ask me not to do that. But the truth is that he really was a mentor to me for a period of time. He was the only person I had around me in the flesh who was working and had this great career as an illustrator. Knowing someone who was doing it made it feel more attainable.

I credit him with really helping me kickstart my career in illustration. At the time, I was still waitressing on the weekends and there was one specific lunch where he said, “Rach, you gotta quit this waitressing shit because you’re not hungry enough. You always know that your rent is going to be paid. You’re never going to get anywhere. It’s going to take you ages because you’re not required to work hard enough for it. You have to get rid of this safety net.” I was pumped. It was a Friday and I went to work a couple hours later and just quit my job.

It was probably not smart at all and it was scary because I hadn’t saved or anything like that. I didn’t have a steady income from illustration yet. It was rough for 6 months or so. I even paid the rent on my credit card a couple times. It was bad. And then, it just came together. If he hadn’t really pushed me… I felt like he dared me to do that, I may have held on to that safety net for years otherwise. I don’t know if I would have ever felt ready to let go. That was maybe 8 years ago. God bless him.

That ties into our next question about risk. Was that your big moment where you took a risk to move forward?

That was it. I don’t know how I did it. Now that I’m older, and very much enjoy knowing my rent is paid, I think that was crazy. You gotta go through it though, I guess.

Are your friends and family supportive of what you do?

Yeah, all of them. I have a terrific family. My parents… you know how parents are. They would be supportive of me no matter what I did. They have framed every promotional postcard that I’ve ever done. I say, “Guys, these are just postcards!”


Who has been the most supportive along your creative path?

I would say my sister, Suzanne, because she has always taken the most interest in my work. She is genuinely interested in my career and feels proud of me I think.

“‘You gotta quit this waitressing shit because you’re not hungry enough. You always know that your rent is going to be paid. You’re never going to get anywhere. It’s going to take you ages because you’re not required to work hard enough for it. You have to get rid of this safety net.’”

Do you feel a responsibility to contribute to something bigger than yourself?

No, none at all. Maybe I should. I feel very removed from that type of idea. I feel very responsible to myself to do things to the best of my ability that give me personal satisfaction. If I was drawing, and nobody knew anything about my drawings 5 years from now, that wouldn’t really bother me.

What do you find personally satisfying?

It’s so simple. I feel satisfied when I draw and I draw well. Whether it’s for a project or personal work, there’s nothing like that for me. You know what I mean as someone who feels really rewarded creating something that didn’t exist at all 5 minutes before you did it.

Of course, the opposite of that is drawing poorly, which is also a part of being a creative person. I’m not always drawing well. Sometimes I’m drawing like crap and that’s difficult. That’s tough. You either have to walk away if you can, or you have to keep drawing and drawing and draw through it. But I’ve realized over the years that that’s just a part of it and it makes it so much more rewarding when I draw something and it feels effortless. Drawing like that is like meditation.

Are you satisfied creatively? Where do you hope to be in 5 to 10 years?

No, not entirely, to be frank. I would love to be doing more personal work on a larger scale, like literally larger. I’d like to be doing larger scale drawings, maybe 5 x 5 feet. If I had unlimited time and money, that’s likely how I’d really be spending my life. That’s the dream… to be creating more personal work. Right now, I do personal drawings and they just stack up. What I’m not great at is marketing and all the things that get your work out of from the piles around your desk and somewhere better.

I think most of the people we’ve spoken with so far have mentioned they would like to be doing more personal work.

The irony of that for me is that when I’m really busy with commissioned work, is the time when I’m working a lot and really engaged in drawing. That’s when I feel like doing all my personal work. That’s when I really don’t sleep because I’m working and then I stay up after working because I feel like doing personal work. When I have periods where I have the extra time, I sometimes get totally away from it. When I have to draw, I want to draw all the time. When I’m not working, I take breaks from it. It’s probably not the smartest way to operate in life.

What does a typical day look like for you?

I don’t really have typical days as far as routine goes because of the nature of working freelance, but I do have typical mornings. I’m very attached to my morning routine. I feel passionate about the first couple hours of my day. I wake up kind of early, especially in summer. I’m a morning person. I wish it could be morning all day long. It’s likely because in the morning, there’s still so much promise about all the things you’re going to accomplish that day. You never do them all of course. But in the morning, it all still feels reasonable to believe that you will.

I have a dog (Davey) so I put coffee in my travel mug, go outside for a walk with him, come back. I usually eat the same thing every day. I sit at my table, eat, and read bits of my “morning books” (they’re ridiculous, don’t ask). Then I go to my computer and it’s email and whatnot. From then on, I have no routine. It’s completely contingent on jobs and what I have going on that day. I think that’s why I feel so fierce about keeping the little routine I do have… because that’s it.

You live in downtown Toronto. How does where you live affect your creativity?

I don’t know that it affects it as much as it probably is supposed to or should. I know I don’t utilize all the creative things happening in the city as much as I should. I’m lucky though that I live in an interesting part of town and I see a lot of interesting things and people on a daily basis. I’m a big walker, and I love to walk for hours all over the city, through all the various neighborhoods and back. I think, more than anything, living in this city, this great place, distracts me from my creativity. I think if I still lived in the country, I would get a lot more done. Truthfully, I’d spend a lot more time working.

“I’m a morning person. I wish it could be morning all day long. It’s likely because in the morning, there’s still so much promise about all the things you’re going to accomplish that day. You never do them all of course. But in the morning, it all still feels reasonable to believe that you will.”

If you could go back and do one thing differently, what would it be?

Oh my lord, I have no idea what to say to this. Can there only be one thing? I have hundreds. I would say, personally, this list is long… relationships, tattoos, haircuts, entire years of my life… the list is endless. Career wise, I don’t feel like I have that much yet. I hope I have a long enough and vibrant enough career that stretches over enough years that I can look back and have a bunch of regrets. But right now I don’t feel like there’s anything that stands out. Just small things, like jobs I quoted too low that still kinda kills me. But nothing big.

If you could give one piece of advice to another artist starting out, what would it be?

Whatever it is that you do, do a lot of it. Do as much of it as you can. And know that sometimes you will not do that thing very well and it’s not the end of the world, I think. What do you guys think about that?

No, that’s great advice.

It’s rough. Do you have periods where you sit down and you’re just not performing?

Tina: Yeah, you feel like everything is terrible and you want to rip up your sketchbook. Then you have these moments of genius where you think, this is amazing, but what if I can’t do it again?

Yes, that’s exactly what I’m talking about where it’s like, well, that was nice while it lasted, but it’s over for me now!

(all laughing)

We all go through those times, it’s just part of it.

Is it important to you to be part of a creative community of people?

I think that it should be important. I don’t know a lot of other illustrators or artists personally. I used to know a lot of musicians. I just signed up for Twitter. Someone told me I needed to be doing that and I can see the benefits of it, but it doesn’t come naturally to me to be a part of a community like that.

I think I also need to make an effort to look at more art. I went through a period in college where I didn’t look at a lot of art. In illustration, when you’re in your second year, it becomes really important that you find your style. It’s a huge deal and a lot of pressure for students. What I noticed was that everybody was looking at old source books and trolling through the galleries and literally taking bits and pieces of other peoples’ work and cobbling it together. I felt really strongly that I didn’t want to do that and I went sort of the opposite way and as much as possible, didn’t let myself look at any illustration references. I wanted to feel confident that what I was doing was completely my own. And that worked for me. But as a result of that habit of just doing my own thing, I actually feel pretty uneducated about what’s going on in illustration. I want to be more involved in what’s going on out there now because I’m confident in what I’m doing and am not concerned about being overly influenced at this point in the same way that it’s easy to be influenced when you’re younger and still searching.

Ryan: I feel like your work does have a really original feel to it. Maybe that’s part of the reason it feels that way, because there’s not a lot of outside influence? Nowadays, we’re all so connected and we see everybody’s work and compare our own to that.

Maybe… (chuckling) Let’s say that that’s true. I think I’m just behind, that’s what it is. I still draw on paper. I bought a tablet a few years ago. I thought, ok, this is going to change my life, I’m gonna draw everything on this thing. But it didn’t feel like paper and pen to me and I just couldn’t get on board with it. I’ve never used it.

Ok, now for some lighter questions. Current album on repeat?

I’m not an album on repeat person, but I have a song right now that I can’t quit playing. It’s by an Australian band, Gotye, and the song is called “Somebody that I used to know.” I listen to it 100 times a day.

Ryan: Yes! (laughing)

Do you know it?

Ryan: Yeah, I was playing it for Tina a while ago. She didn’t like it.
Tina: Yeah, it wasn’t my favorite.

Have you seen the video1 for it where he’s standing there being painted on and the girl comes up? I’m crazy for this song.

Ryan: Yes, I love the video!
Tina: It’s not that I don’t like it, I just wouldn’t listen to it over and over.

Okay, but you gotta listen to it one more time and listen to the way he says the word, “cut.” It’s amazing.

Tina: Okay, I will. Promise.2


Favorite movie?

I can say what I don’t like. I don’t watch scary movies at all. I don’t watch anything sad. When my friends say, “Oh, my god, have you seen The Notebook? I cried my eyes out.” Or, “You should watch Marley & Me, I cried and cried.” I think, I’m not gonna do that, why would I want to do that?

Favorite food?

That’s easy. Apples. I know every type, I’m apple crazy.

Black & white illustration by Rachel Ann Lindsay
Black & white illustration by Rachel Ann Lindsay

One last deep question. What kind of legacy do you hope to leave?

Um… If I’m just throwing out wishes, I would love to have some incredibly massive career as an artist. I don’t want to discredit commercial art because I really like commercial art right now. I love advertising and I like working in it. But I think down the road, I would love to be known for my personal work on a large scale. That’s no kind of answer. That’s everyone’s answer… Oh, I’d love to be a massively rich artist. Just put me down for that. That sounds good.

Ryan: Wait, I do have one more question. You don’t have to answer, but I’m looking at all of your work and it looks like you do it all in one stroke, like you don’t even lift the pen.

Yeah, that’s right. There are some drawings where there are two figures and each is its own line. I remember when I was younger, in the first couple years of school, I liked to be very precise. I was a painter and I liked to do portraits. Everything was super realistic and I felt like that was so common. If I wasn’t going to be the very, very, very best portrait artist in the world, then I didn’t want to do it and I needed to find something that would be more original. So I went out of my way to try to find different ways to draw. I did exercises that forced me to be looser and not so tight. These are exercises you would do as a young art student, like drawing with your left hand or giving yourself a time limit. I started drawing in pen because I couldn’t erase and correct mistakes. I had to really commit to the drawings. Then I gave myself the limitation of not lifting up my pen.

I remember in my senior year of college, when I told my teacher, Paul Dallas, “This is no good, it’s all broken up. I lifted my pen up here, here, here, and here.” He responded by saying, “There’s no tribunal. There are no rules. You can lift your pen up.”

It was a self imposed restriction and now, it’s how I draw all the time. I like whimsical drawings, but it didn’t come naturally to me in the beginning. It’s something I had to learn how to allow myself to do.

You could’ve fooled us!interview close

Black & white illustration by Rachel Ann Lindsay
Black & white illustration by Rachel Ann Lindsay

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