Skillshare Talks | Self-Taught to Self-Employed: Peggy Dean on Building Her Creative Career | Peggy Dean | Skillshare

Playback Speed

  • 0.5x
  • 1x (Normal)
  • 1.25x
  • 1.5x
  • 2x

Skillshare Talks | Self-Taught to Self-Employed: Peggy Dean on Building Her Creative Career

teacher avatar Peggy Dean, Top Teacher | The Pigeon Letters

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

    • 1.



    • 2.

      Self-Taught to Self-Employed


  • --
  • Beginner level
  • Intermediate level
  • Advanced level
  • All levels

Community Generated

The level is determined by a majority opinion of students who have reviewed this class. The teacher's recommendation is shown until at least 5 student responses are collected.





About This Class

Welcome, everyone! Thanks for your interest in my creative journey. I hope that you can take something from this raw talk and apply it to your own journey. Thank you for allowing me to be a part of it.


This short video is the first in our new Skillshare Talks series that shares footage from live conversations with our teacher community.

Join the Skillshare team at our NYC headquarters with Peggy Dean - a self-taught calligrapher, artist, and creative entrepreneur. In March 2018, members of our local community came together to hear Peggy's journey from teaching herself calligraphy to launching her own creative business. She speaks candidly about challenges she's faced along the way and offers strategies for overcoming hurdles to following your passion. 


Peggy, the woman behind the popular brand The Pigeon Letters, is a best-selling author and award-winning educator. Her work has been featured on NBC’s the Today Show, and she has collaborated with brands such as Daniel Wellington, Mixbook, and Wacom. Peggy also travels the world sharing her skills with others.

Whether you're searching for inspiration, ready to start your own business, or just a fan of Peggy, we hope you enjoy her honest and intimate talk."


Filmed and Edited by Gabriel Noguez


Meet Your Teacher

Teacher Profile Image

Peggy Dean

Top Teacher | The Pigeon Letters

Top Teacher

Snag your free 50-page workbook right here!

Hey hey! I'm Peggy.

I'm native to the Pacific Northwest and I love all things creative. From a young age I was dipping everything I could into the arts. I've dabbled in quite an abundance of varieties, such as ballet, fire dancing, crafting, graphic design, traditional calligraphy, hand lettering, painting with acrylics and watercolors, illustrating, creative writing, jazz, you name it. If it's something involving being artistic, I've probably cycled through it a time or two (or 700). I'm thrilled to be sharing them with you!

Visit my Instagram for daily inspiration: @thepigeonletters, and head over to my blog for more goodies curated just for youuuu.

I'm the author of the best selling... See full profile

Level: All Levels

Class Ratings

Expectations Met?
  • 0%
  • Yes
  • 0%
  • Somewhat
  • 0%
  • Not really
  • 0%

Why Join Skillshare?

Take award-winning Skillshare Original Classes

Each class has short lessons, hands-on projects

Your membership supports Skillshare teachers

Learn From Anywhere

Take classes on the go with the Skillshare app. Stream or download to watch on the plane, the subway, or wherever you learn best.


1. Trailer: If it's something that you want bad, I hope you make it. Your excuses suck, you think they suck and you already know that they suck, you feel it, while you're ruminating and while you're sitting there, and while you're thinking about, you lose all that creative time and then it's time to go back to your office job, that you hate, and you hate your boss, because your boss won't let you text when you go to the bathroom. Nobody can be uniquely you. Whatever your style organically falls into, that's just what happens. I feel very strongly about this, that nothing will help you build your competence like owning your journey. I know this is cheesy, and it's like a blanket statement, but I wanted to resonate because if you can think of your truth, of why you want to do what you do, and fear can be there. You can accept fear, we just don't let it drive your action. 2. Self-Taught to Self-Employed: What I want to share some things that resonated with me through my journey. I've always been a non-dimensional thinker driven by rebellion and a lack of sense of authority. Not because I don't like authority, but because I feel like the way that my brain works towards better, like my way really works, guys, I wish she would just listen because I promise it works, but people don't work that way in a lot of employment situations. Then you get fired and then you work for yourself and then you figure it out. First thing I want to talk about is, this is something I couldn't. There's an art to art. Think about what that means to you. What's the art behind art to you? This could be a number of things this could have to do with personality, could have to do skill, it could have to do with all of these things that are like resonating. There's not a wrong answer. But think about this question. I'm talking about my journey, if you will. Before this, I have had more jobs than I am my age. Libraries [inaudible] a dry cleaners and I was detailing cars that decay like that's an auto plants in the North last time from but not things that made me happy. Entry-level didn't do college. It's like where do you go, what do you do? Creative minds and freelancers, unlike entrepreneurial instincts, are something that you don't really go on a path of a traditional job sense because you just find something you like. I think I'm qualified for this. They can train me. This is great. I think that I maybe I can build a career off of it and then you're empty inside. I mean it's true if we're going to be honest. This is what I did for eight years. I dabbled in art stuff. I've always been creative. I was then crafting and then I was and my mom put me through dance and I hated it. I was in ballet for nine years. I'm not a grateful person and I'm not flexible. I can point my toes really well. Identity point though. Anyway, from there I saw fire dancing one time and I was like, I am obsessed with as I have to learn it. I have always been self taught because like when you have that driving passion, you just instantly go into the whole mindset of like, I'm in a research. When you want to know something, you learn it, you find resources. That's something that you can never forget. Because like the minute that you dive into, the resources, just keep pouring in. Anyway, what happened with this was I ended up starting to teach. I did this for eight years and I taught for four. That was the first time that I really started seeing light bulbs go off in people's minds when you're explaining something. Although I do teach online and I love it so much, I think that because I've been resourceful, I've learned in a non traditional sense. I just teach the way that I learn for people who might ever have interests in sharing something or sharing and interests of your own. When you see a light bulb click, you start to yourself learn. Teaching is always learning, but when the light bulb goes off, it's just like you're like working your way. It's like a puzzle, a strategy that you're trying to figure out in each individual person. That's so cool. Can't even tell you it's so cool. Anyway, that's the first place that I started teaching. My body got really tired. My lungs got really tired because it's a lot of smoke. I decided to go to school for a while. I thought I wanted to reduce hair and makeup and ascetics and I did this for ten years. I know it seems like that makes me really old, these overlapped. I'm 31, that overlaps. But when I did hair and makeup, It was an art project all the time is always an art project and my favorite thing to do is behind the scenes style sheets. This is when you get together and photographer and a florist and a gowns, jewelry and in the model and then you take pictures and it's fun. It's great for your portfolio because then you have all these beautiful pictures of them comes into your slot and they do the boring like a line. You're like cool, you think I'm amazing because I did these pretty reidel photos. But anyway, so there's always an end goal in mind and I wanted to be published in style NEA pretty, it was like my end goal, like there couldn't be anything higher than this. I was like there are publish pieces of work and collaborations that I would do the other people and like white mag and harsh design, I'm sorry, but rather as a German is a big one. Then Oregon bride, things like this, but I'm like no, now this isn't good enough. I want styling pretty so I took my resources and things that I wanted. I'm like, this is something that I want, so I'm going to make it happen, period, bottom line. I decided to produce my own shoe. No idea what I was doing. I'm googling call sheets and I'm like, how do you make a call sheet? Who do you need to involve? I ended up doing a bohemian bridal shoot. I hired the models and I hired the photographers and the set designers, jewelry designers, there were floral anyway, the whole shebang, right? When we submitted it, it was submitted to style only pretty and they get thousands of sub missions that we have to share this. I'm so excited within four days they accepted. At that point, I feel like I pete and I was like, I don't need to do this anymore because the creative bind it just like, "Come on, you get to a point and you get, you're just like, well, wash my hands, what's next"? It's just what happens. I think that's okay. I don't think that you ever have to be stuck in one thing.That's where I've been always really nervous about my brand because I started with calligraphy. It's like, am I a calligrapher? Because I really want to insert drawing. I did that, it worked. It's a test. Then I inserted watercolor. That's working. Urban sketching was my big like is this going to go over to Will, I don't know, it's not really that crowd. What I've noticed is that when you integrate things that don't necessarily fit well, it's amazing how many doors it opens. I never knew I would have an interest in this. Now this whole world is opened and then those doors open from there and there and there. Basically get your hands really dirty. Something happened in my life. Rejection is a huge trigger for me. I don't do well with rejection. I had some things going on with my job that weren't so great. I was like, let's channel this energy somewhere else. Because my coping mechanisms were not great. You have this kind of mindset, then it's like you have this impulsivity and it's like, well, what are we going to do from here? I started looking up just different random projects. You Pinterest for hours, but then I'll get into that later. I found Skillshare just randomly on a Google search and I'm like, okay, it was a teacher for this class that it was completely unrelated to what I do. But I joined and then from there, Skillshare sent out an email for teachers contests like I had at the time been learning modern calligraphy on my own, researching because there weren't many resources available at that time. I took what I learned in ninth grade traditional calligraphy class, blended it with this, did really bad while it was so ugly and early growth. Rather example because man, you would have been like, why are we listening to this girl? From there, I blended it together and then skill sure. I sent out this challenge and I'm like, okay because I was okay at that point, people were asking like what is this? Then I want to share it I love doing it. You share what you're excited about. I was like, okay, fine. I've always been interested in teaching. I taught before, not this, but fine and so I won which was like, is this a joke, like a raffle like type of thing where you just picked the name. But it was really encouraging for me because I'm like, okay, done, let's roll with this. It was just like that simple. Within a couple of months, I became one of their top teachers about a year and a half later. Now, I have over 20 classes. One of the questions that comes up is, "How do you know when to stop your job and when to do this full time?" I was at the time working at aesthetics bar, "brow Betty". It's not in quotes, it's actually called that. I was slowly reducing my days and it was nerve-wracking and like I go down to three days a week, I'm just not going to do yeah, there's going to be fine. That was when I was starting to teach on Skillshare. Then my first chat came and I was just like an extra zero here. Excuse me. What is this? I felt it out and wanted to see consistency. Nothing's predictable when we work for ourselves. But I started to see a pattern and it was a growth. It wasn't a significant growth, but it was growing over three months, four months. I went down to two days. Then I decided I wanted to write a book. It's been on my bucket list forever. I'm like, what? Yeah, let's write a book. Let's make this a book. Brush lettering. I started to write it and I noticed that I was so in my head and I was sitting in the back at my job and I was just like working on the thing and then a client would come in. I love people. I loved hands-on. I love dealing with clients, but I would dread it. I'm just like I hope my appointment cancels. Stupid.So much is here because I was like so involved in this passion project. Then of course you're with the person that's great, but you get it. Finally I realized that this today's week, although that doesn't seem like a lot. That burden was sitting here knowing that I couldn't devote my energy into what I wanted to be doing. Was I making enough to scrape by without that job? Sure, do I quit and do I chance it and is this really scary, or do I stick with it for awhile and watch growth? Although I'm impulsive, I'm very careful and calculated when it comes to survival, who isn't? That's why we're scared. But I pulled the trigger and within a month my income tripled. I really wanted that to resonate because it's what you put your energy and two comes back tenfold. It's incredible. It was really scary. I published a book and then I published another book, and then another book. Within their first month they were bestsellers and I was like what's happening? I think, it just goes with what you put your energy into. How does all of this happened? Burning question, here's the thing and this is the thing with fear. The only person standing in your way is you, the only thing standing in the middle of yourself and the goal, yes, you have to take staircases. It's not a jump, it's not a bridge. It's work. But all of those stairs, his is so like cheesy that I'm using this metaphor, analogy thing. But is all of the stories that you're making up as to why you can't do it. Your excuses suck. They do. You think they suck and you already know that they suck. You feel it. My excuses still suck. I have them all the time and they're really bad. Let's get rid of them by talking about them. I don't have time. Let me tell you something about time. I don't have it, but you make it. If it's something that you want bad enough, you make it. What happens when your kids get sick? Somehow you find the time. Where was it lost that you make time for you and like your passion in doing something that you love. Because the more that you put that off, the less it's going to be accessible. The more you get into this routine of thinking, rejection is going to happen. Rejection is why I'm successful. You're going to take baby steps and as you learn, you might fall into some traps, the inspiration trap. You think about it. You love it. You're like, this is inspiring. This is making me want to do something. Great. You dig in and, no, this isn't there yet. But you ruminate on how you want to do it and then while you're ruminating and while you're sitting there and while you're thinking about and thinking about. You lose all that creative time and then it's time to go back to your office job that you hate. You hate your boss because your boss won't let you text when you go to the bathroom. How many times you're like, Okay, I've got the creative drive? I've got this, I want to do it. I know all these projects I've seen on Pinterest that I want to do, I'm going to go to the one of those pins. Only you don't, you just start pinning new things. Then three hours goes by and you just in pinning, and then it's like, I got to go to bed. The learning trap is a vicious cycle. Everybody sucks. You have to learn to like to suck because these are all things that you can learn from and grow from. If you don't suck it first, how are you ever going to be good? Like nobody starts good. The same thing as when I teach and that little thing snaps and I see it in somebody's head, I'm like, Okay. They got this. That excitement. You should do that for yourself and celebrate those little victories of things when you understand them because it's steps. If you start off wonderfully, you're not going to have the appreciation for your work. Learning and practice. This is something that you have to do, but then what happens is you start comparing yourself to people. Nobody, no matter how similar your style is to somebody else's. I've had people that have come in to me about this and they learn from me, which is great and I love that. Their style does look a lot like mine and they worry about that and they're like, hey, I learned from you but I'm noticing that my style has organically grown into what yours looks like. That's fine because you look at us next to each other and there's so much that she can do that I can't do and vice versa. Nobody can be uniquely you and whatever your style organically falls into, that's just what happens. Comparison, you might want to be a lot like this when I started calligraphy, I want to do those long whiskey beautiful wedding stuff and that's not what I turned out to be. I can do it, but a lot of thought goes into it because I have my natural what I settled into, and it's just what happens. In the learning process and the more you create muscle memory, I don't if all you guys are into art stuff. Basically what I'm saying is it will happen. Anyway, from comparison comes disappointment, and then you sit, and then you ruminate, and then it resets because you get inspiration again. Community is amazing, if you use this and you, build community, there's nothing like that support and just an amazing world of brilliant minds. You get to connect with these people and it's incredible. Then you can network with people and you can collaborate with people and you can come up with new ideas and things that you never really thought your business or branch into. Whatever that means and then exposure, obviously that's really helpful. That's the reason why I have a brand as Instagram. It shouldn't be about numbers. First, before I get into cons, I want to say that there are so many people that are very successful artists or you name whatever it is that they do and they don't even have an account. This isn't about social media exposure. It is beneficial, for sure, millennial world that we live in, but it's not something that's necessary. It's not a numbers game. When you are posting something that you sat on forever because you want it to be the perfect timing and it doesn't get nearly as much engagement as this one that you're like, I threw that together in five seconds. You can't sit on that. It does feel personal, it's algorithm. Don't let what made you once feel so passionate about your creativity turn into a popularity contest. Imposter syndrome is something that a lot of us feel. It says internalize, but even externalize, you don't have that confidence behind what you're doing. It's been discussed as one of the main culprits to things like perfectionism, which is why we sit there and go over and over, how can I make this better? This isn't good enough. I don't deserve this. Exhausting yourself by putting too much energy and working excessive hours. This can be just an office job too. If you have this personality you go in at 5:00 AM, you're there until 9:00 PM because you're just, like, I'll just finish this project. I'm one of these people. Not going to lie. I pretend that I don't have Imposter syndrome, but don't we all? Everyone at the bottom somewhere in their brain is like, I have no idea what I'm doing. I don't know. Then you think, why would they choose me to do this? I'm not at this level, but there's a reason why you are who you are, so own your confidence. It's funny how this is linked to Imposter syndrome, but I'm the epitome of superhero complex. I don't like asking for help. I don't like when help comes at me, I'm just like no. If I want to learn it, I'm going to learn it and I research and most of my job is research because I'm learning. I love learning, but this will stifle you and you will go stagnate at some point, which I did. I have an agent now. She reached out to me and in conversation over several months, she convinced me and sold me to have her as an agent. I'm just like, no, even though we were talking. I have an assistant now, that's huge. I have freed up so much time. Delegate what you need to do. You can not do it all. There are people in industries that do what they do for a reason. They specialize in that thing. I specialize in stuff but you might ask me to do this random off thing and I'm like, yeah, totally I can do that. You have no idea and then you have to learn it really fast. Then, I did that special effects make up one time. Just so you know, it was really good. Bat bites, swollen. It was good. Why do we take these things on? It's really powerful. It's one of the most powerful driving forces. Fear and love. These are things that dictate what we do. It works in two ways: it can either be a motivating drive or it can be completely crippling. The effect is not good. A lot of instances where people that are really driven, really motivated, trigger happy, feel like they have to get there. Motivating drive, this is great. It could be dangerous because it could go into that you're overworked, or it could completely freeze. You just can't do anything because you're afraid of taking that leap. Motivating drive propels you forward, helps you discover new opportunities, because you're putting a lot of effort in. The crippling effect can make you lose your confidence because you're sitting there thinking about it, and thinking about it, and then thinking, I can't do it, there's no way this is going to work. Confidence is the battle. I don't want to hear confidence is half the battle ever again. It is the battle. Fake it until you make it. This is a thing. It's very true. But, the thing that happens with that is, I come across like I have a ton of confidence, so I hear. This is something that has been told to me so many times. They're like, "When you walk into a room, you just demand presence." My mouth is so dry right now, but I'm scared to take a moment and take a drink of water. Because it's like, oh gosh, if I'm even a second of silence, everyone's going to die. I am going to be completely humiliated, because there was a moment of silence. Anyway, no, confidence is the battle. But what happens is, once you start expressing, you start pushing yourself, it's baby steps, do one thing out of your comfort zone, you will build that up, and then it will come naturally. Then all of a sudden, whatever it is that you want to do, it's like you're building muscle memory for your brain. It is the battle. How can I build confidence when I'm not good enough? That's problematic thinking. Make it go away. Anytime it comes up, it's a wall. You're not trying to work yourself through that situation. It's a wall. Just make it go away. It's not a question. Sorry. It's learning, it's honing your craft, whatever it is that you're doing. Your skill set, craft doesn't have to be a craft, you get it. It's a word that you use. But, practice, they say practice makes progress. It never makes perfect, makes progress. I feel very strongly about this, that nothing, will help you build your confidence like owning your journey. I know this is cheesy and it's a blanket statement, but I want it to resonate because, if you can think of your truth, of why you want to do what you do, or what you want to do, whatever it is. Why you want to do what you want to do, or why you want to do what you do, or why you do what you do, or why you're thinking about doing something and not doing it. This is all part of your journey. Fear can be there. You can accept fear, but just don't let it drive your action. The worst-case scenario that's going to happen from this, is that, either it didn't work and you failed. First attempt in learning. Someone's going to say no to you, it will happen. I reached out to probably, two dozen publishers about my book idea, and I came back with, ''We like this idea, but what if we did this?'' It's like, well, I'm working on my book or it was just no. I published my book, it became the best seller, all these publishers came back. They were like, ''Hey, we'd love to publish this and get you better distribution, '' I'm like, ''Is that because you are seeing numbers right now?'' question mark. If you take ownership of that, then you are resourceful. I'm like, ''I'm just going to self-publish, and see how it goes.'' Then I networked, and I reached out to some people that I have met over time, and who also have a presence. But this is networking. You're building up these relationships, and then all of a sudden, you have this success that's happening. Because, it's a community. Full circle. But discovering your style, what makes what you do unique to you? Or, whatever it maybe. This is something that is difficult, in comparison. With comparison things. When I wanted to get into painting and drawing, I can't draw. I stand here today, in front of you to tell you that I can't draw, and I believe this. Until your mind is trained, and you switch that part off, switch this part on, and you're like, I'm looking at things and shapes, and lines and all these weird things, and it looks horrible as I'm building it, but then the finished product is amazing. When I was like 18, 19 around my fire dancing years, maybe I was 21. I forced my friends to stay up until four or five in the morning with me on the back porch, and we did paint parties with acrylic paint. This is so embarrassing, but I want to admit it openly. At that time, I loved doing it. I couldn't draw, I couldn't look at something and draw it to save my life, unless it was already art. I just reproduced everything that I saw. I'm like, I like this, I'm going to paint it. This was a secret. Nobody knew that. They were only plastered in my walls at home, but was it from me? No. This is something I was inspired by and, I didn't change it at all. At all. It was because I was scared to try. I didn't think I could do it. The more that you practice, and the more that you build muscle memory, this could be something that's not just art, but the more it will come naturally, and the more you will start to naturally evolve into your own style. Learning this one, this one, this one, this one. I was still doing a practice. I was still getting familiar, and getting my hands dirty, and understanding texture of acrylic paint. I was still understanding how these things are mixing, and what not. Which helped me later down the line, when I was like, maybe I could try. You're always learning, and you're always building muscle memory. What is your why? I actually went through a process of learning to be mindful in a different way. It was just to be present, and to take ownership of my journey. But, to really feel what I was feeling and really go through the emotions. When I talked about, the rejection that I hit and then I tried to channel it in a different way, which was when I discovered Skillshare. It allowed me to cope differently. Suddenly, I was a lot healthier. I started getting happier naturally. Because I was doing something I love to do, instead of being completely demolishing to everything in myself, and around me. I wasn't going to ruin my life before it ruined me. I was taking ownership, and I was doing something that I loved. Which touches on curiosity, and touches on self-empowerment. All that nervous energy that we probably all have, your channeling that into something. Then you can be so proud, of what you did with your hands, whether it's in the very beginning stages, and you're appreciating the suck that came out of you. Or it's amazing. Mental health is so big and there's such a stigma, and I think that now it's calming a little bit, because people are understanding they're like, ''Hey, human beings really need better coping mechanisms, like really well.'' This is a really, really easy avenue and good door to open to do it. You're also constantly learning while you're creating. That's always really good for your brain. I love this. But maybe the journey isn't so much about becoming anything. Maybe it's about unbecoming everything that isn't really you, so that you can be who you were meant to be in the first place. Isn't that good? When I read that, even now, goosebumps and tears in the back of my eyes, and I'm just like yes, you're speaking to my soul. But yeah, so it's not about having the best stop. It's about, passion and substance, and the you behind what you do. Bringing that in, back to this question from me to you, is, there's an art to art. What is the art in art? Anyone? Anyone? There's no prizes involved. There you go. I would drop my mic, but it's attached to me. That is all I have for you, and I hope that resonates, and I hope that it speaks to some of you.