Encouraging Risk-Taking and Reflection (Ep. 094)

Ray Yang, AOE’s newest writer, makes his debut on Art Ed Radio to talk to Tim about encouraging risk-taking, appreciating the creative process, and great ways to advocate for your program. Join the guys as they discuss how we create an environment where kids are comfortable failing (5:15), teaching students how to think and reflect (13:00), and how to use extra work as an opportunity to make your program and your school better (18:00). Full episode transcript below.


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Welcome to Art Ed Radio, the podcast for art teachers. This show is produced by the Art of Education, and I’m your host, Tim Bogatz. Today’s guest is someone that is new to the podcast. And, in fact, pretty new to The Art of Ed. But, I’m sure that you are going to love him. It is Ray Yang, the newest writer on the AOE team. Ray had an awesome first month of articles in November, writing about how to enact change with your students, how to teach students to fail spectacularly, and how to use reflection to help students understand and develop their creative process.

People are reading these articles and actually started to bug me. A bunch of emails and a few tweets, “Who’s this Ray Yang? When are you going to have him on the podcast?” Luckily, he was willing to come on to talk about a lot of his ideas. We’ve got a ton to talk about. He’s got some huge, great ideas, and I’m going to bring him on in a quick second. But, I want you to listen for something when we talk here.

Ray is excellent about breaking down both the big picture and the small scale logistics of things. So, when we’re talking about, say, reflection for example. I’m hoping that he can talk about the big picture reasons we need to encourage our students to reflect. But, also, the specific ways in which we can do it in our classroom, and how we can be successful with it. So, we’ll talk reflection and risk taking, and creativity, and even how and why we need to advocate for ourselves as art teachers. I also want to give Ray a chance to talk about all the cool things he’s done throughout his career. So, let me bring him on right now and get the conversation started.

Ray Yang is here with us. Ray, how are you?

Ray: I’m doing good, thanks Tim.

Tim: Good, I’m really excited to have ya on the podcast. I think people have been really excited to read all of your articles, and I know that readers always like to know about whose articles they’re reading. So, can you take a second to just tell us a little bit about yourself? Your career, your teaching, or maybe a little bit about what you like to do outside of school, just let people get to know you a little more?

Ray: Yeah, absolutely. Well, I actually grew up on the East Coast. I’m from New York, originally, Long Island. Always knew I wanted to be doing something in the arts, but wasn’t ever sure what. Wasn’t a real popular thing with my parents they were real excited. I actually double majored. I did a degree in both biology and studio art. Trying to figure out, as a lot of people do after college, what I wanted to do, I went and actually worked for a magazine. Did production work. Did graphic design. Did that for about a year, and really was not excited about it.

So, I went back to school. I went to the Art Institute in Chicago and got my Master’s in Art Education. That really kind of set me on my track for where I am now. I’ve worked in a lot of different types of organizations. I worked for a history museum where I was running their teen programs. I had a group of 15 teens who worked on oral history projects with me. I refer to them as my first kids. They’re all actually in their mid, late 20s now, so that was a while ago. Then I worked for a community arts center, called the Hyde Park Arts Center and ran the outreach programs there for quite a while before going on to work for the district in Chicago.

I worked for Chicago Public Schools in the central office. I worked as an administrator helping to run visual arts program for the whole district. It was a move to help have more impact across district, because there’s about 400,000 kids, about 650 schools in CPS. It was really cool for a couple years, but it’s also really exhausting. It was a job that I think you get a lot of burnout with. I was also teaching grad school classes at the Art Institute at that time. So, after about 15 years in Chicago, my family and I, we decided that we needed a change. So, we moved to Seattle.

We came out here about 2.5 years ago. I was working as a consultant with Seattle Public Schools, helping to do some assessment and curriculum writing. Working as a teaching artist. At that point I realized what I was really missing was working directly with kids. So, I had an opportunity to take a job in classroom, and so I went back into a classroom and I’m an art teacher again, now. It’s exciting and I love doing what I’m doing.

Tim: Yeah. That’s awesome. You have just a ton of experience, which I think is really cool. I love the ideas in your first article. Your debut article was called: How to teach students to fail spectacularly. It talked a lot about getting kids past the idea of their being one right answer. But, can you explain what you do in your classroom to get kids past that mindset?

Ray: Yeah, absolutely. I think what I try to do is really create a space that’s comfortable and safe for them to experiment. I do that through a bunch of different ways. You know, based on just my projects alone, I try to start them off with projects that don’t have right answers.

So I think in the article I mentioned that we’ll do things like blind contour portraits. The goal is, it’s not supposed to necessarily look like the person. Students have this really … It’s funny. When you’re in the project with them, you’re watching them, they all want to look so bad because they all want to get it right. It’s this idea, I think, that’s been really hammered into them throughout school, that there is a right answer that they know. They take tests, and there are right answers. They do homework sheets, and worksheets, and things, and there are correct answers. They get graded and they get the right answer back, and they receive praise for that.

They don’t get praise for screwing up and then fixing it. You know? And then actually kind of pushing through challenges. They don’t get praise, or they don’t get reinforcement around, “Wow! That’s a really difficult thing and it didn’t work. Now, let’s take a look at that and figure out how we can make it work.” So, I think it’s about creating a space where they’re going to feel comfortable.

I try to really get to know the kids too, and really start what understand what I can push with them, and what I can’t. Because I think some kids are ready. They’ve been waiting for this class, so they’ll be able to open the floodgates and just try and experiment. Other kids, it’s a real challenge, and so you kind of have to move, I think, a little more slowly with them. Through repetition, through lots of opportunities where you show them that if it doesn’t work out, that it’s okay.

I was just having a conversation with a student about this. She was really tentative with her paint. She was working with paint for the first time. She has really strong drawing skills. It was like, she would just do a little bit and ask me to come over, and take a look and ask me, “How does this look?”

Eventually, we got to the point in this conversation I was like, “What’s the worst thing that happens if this doesn’t go well? If you feel like it’s now working?”

She’s like, “I don’t know?”

It’s like, “Start again.”

And she kind of had this like, “That’s okay?” You know, like, “That’s all right?”

I was like, “yeah. We’ll start again. You’ve done thousands of drawing in your life, and not all of them have always gone well, but you were able to start again. We’ll do that with this.”

I think it was kind of freeing for her to be able to say, “I can start over if it doesn’t work.”

So, I think it’s really about creating a space where they’re going to be comfortable and building in that culture of, “It’s all right to mess up, and we’ll keep going.”

Tim: Yeah, and I think that transitions really well into something else I wanted to ask you. Because you also give some specific suggestions for encouraging risk-taking in your classroom, including what you said, “Creating a culture of yes, and having an ongoing dialogue with kids as they work.” Which is something you just gave a great example of right there. But, can you also talk a little bit about other ways you empower kids in your classroom?

Ray: Sure. I try not to be too hands-on with them. I think one of the things I’ve learned in my teaching career is that as I’ve gotten more experience, I’ve become more comfortable with stepping away and letting them figure things out. I was joking to someone else in my department that I feel like, “If you look at my teaching now versus when I first started as a teaching artist and the classroom stuff, you feel like I’m probably lazier now.” Because it looks like I’m doing nothing. I used to be like this ball of energy, running around, making sure everyone’s on top of things. Now, I really start to step further and further away, because I think I try to set things up on the front end with the projects, and reflection questions and other things that are built into the project. So, I try to not be too didactic with things.

So, as they’re working through a challenge or a project, I’ll talk with them, but my goal is not to give them the answer. Right? Like I might know what technique will work in this specific instance to solve the issue they’re working with. I might know what material, or what they need to do as they’re talking about how trying to figure out they want to approach a question, or I like to frame it as a visual problem, or a visual challenge for them. But, I don’t want to give it to them, and I want them to feel like they have ownership over that and that they’re figuring this out. So, I really try to step away.

You mentioned this idea of the culture of yes, and so along those lines, I try not to say no to a lot of things. We were just doing a project where we were working on value in color. We were using torn paper to create this portrait. There’s a lot of construction paper out on the table. That was what I was providing them and letting them to use. A kid came to me and said, “Can I try these different kinds of things.” They had gone to the closet and found all sorts of different types of paper. I’d laid out something but they were like, “I found this other material.” They actually found some aluminum foil and stuff they wanted to use, too.

I feel like I would have had an instinct in the past to say, “No, we’re going to use the paper that’s out here.” But instead, now I try to say to them, “Well, tell me why you want to use this. Explain to me what you’re thinking.” And they did. They were really thinking about light and reflecting off of that shiny surface of the aluminum foil. “All right. Let’s give it a try.” So, I’m really trying to give them that ownership to not say no too often. Because I think they probably get that a lot in a lot of other classes, too.

You know, coming up to a teacher and saying, “I want to try something different,” or, “I want to do something else,” which is often, “No,” and for really good reasons, I think, in some classrooms. In the science lab, maybe, “You can’t do that with other chemicals. ” Or like, “No, you can’t flip the Bunsen burner upside …” Whatever it might be, there are really good reasons for that. But, I think in my space, we can experiment a little more. So, trying to say no less often.

Tim: Yeah, I think that’s really good. And I think, giving kids that ability to try something out, something different with the process, is huge, when we’re talking creativity and when we’re talking about getting them to appreciate the process. Actually, that takes me into my next question, too. You wrote a great article on reflection and the creative process. Can you talk a little bit about how you build reflection time into your classroom? What that looks like in your classroom? And what you want kids to get out of, I guess, that focus on the process?

Ray: Yeah, absolutely. I think that’s a, for me, that’s huge. I have started to … I think part of my job is always about teaching students about materials and techniques, and learning different things that they haven’t tried before. But, I also think a big part of every art teacher’s job is actually teaching students how to think and how to reflect, and how to engage with the creative process. It’s something that carries over, I think, into every single subject area, into all part of life, being able to reflect and think about how you’re impacting, changing, shifting things. So, it’s vital and it’s so important to me.

In the classroom, it’s hard though, right? Because we have so much we want to get done, there’s so many projects that we want to do. I definitely recognize, I’m super privileged in terms of my classroom and my school. Where, I don’t have a ton of oversight telling me like, “these are the things you have to do,” or, “these are the projects you do.” I work at an independent school, that’s pretty well resourced. I’ve worked with a ton of public school teachers, when I was working as an administrator for central office in Chicago. So, I know how many demands are put on them, and also how little time they get with kids.

So, how do you build in time to be able to reflect, when it feels like you’re just trying to get the projects done? Different things. Some stuff that I mentioned in the article. Stuff like exit slips, right? Just short, two question prompts that get them to think about it. Think about what they’ve just done that day. I usually just do them weekly with them, and the questions are, most frequently it’s something like, “What was something you were successful at today?” Or I’ll say, “What is something you are awesome at today?” And the other one being, “What was something that you had a challenge with?” Or “What was something that was an obstacle for you in class today?”

I think it’s really great. The more you do it, you see that kids really start to embrace this in the moment to be able to have some say in what’s happening in class. Or, they’ll tell me, “I felt super rushed today. I’m not just getting this project done and I need more time.” That helps me too, in terms of managing the class.

I try to build in reflection and thinking about the process right from the very start. So the first thing I do with all my projects now is I have kids start to think about those questions. We spend about ten minutes or so talking about that at the start. And, it’s like, “These are questions I want you to consider all the way through this project.”

And at the end, for my class, they’ll always do a short reflection as well. So, you know, like writing a short paragraph. I’ll have a series of prompts specific to the project, asking them to let me know, “What did you think of this?” Like, “How did you change your piece, based on whatever it is?” That’s another moment.

It’s really, I think, that relationship you build with the student during the class. Encouraging them to step back from the work. I think that helps them to also see the process. They get really tunnel vision sometimes, on working on what’s right in front of them, that we don’t take breaks and moments, and literally, it’s like, “Everyone, take a step back. Take a look at what you’re working on right now. Take a walk around. See what other people are doing.”

My school, kids have iPads, and so I take full advantage of that. We don’t take pictures of their work just at the end. They’re taking pictures of the work throughout, so they can see how it’s progressed, and where it changed. Then I always ask them to look back on their work too, and we’ll look at it together, like, “Do you see how you worked on this one section of this drawing and you were really able to develop all of the value and it’s so much stronger now? And do you remember how you felt? You were really down about it at that moment.” So, I try to build it in all over the place. Some of it works better than others, some of the approaches. But, I think it’s so important that I really want my students to be thinking about that all the time.

Tim: Yeah. And, I think that’s a good big picture view for the kids and for you as well. I would encourage everybody to reflect on that and think about how we are teaching kids about our process. Then, just a couple last question for ya. First, yesterday’s article was all about how we aren’t here as teachers to make posters and make bulletin boards. I think Andrew and I recorded an entire episode about how to say no, before. And this whole idea of what we should be doing and what we should stand up for as art teacher, is something that people are passionate about. But, can you explain why you wanted to write this article and give us a quick rundown of what’s in it?

Ray: Yeah, sure. I think every teacher, not just art teachers, we’re constantly being asked to do extra things. Things that come under the “other duties as needed.” Right?

Tim: Yes. Yes.

Ray: I think teachers, especially, it’s not just about the teaching. A lot of people talk about their job and it’s just this. But, it’s also about like, for us, we have our own professional development we’re trying to maintain. We are lesson planning, doing assessments. There’s maybe curriculum writing. We’re probably on a couple committees at the school. Maybe a committee about taking care of the environment of the school. Maybe it’s something about social justice. There’s always additional work that needs to be done, because I think we all also care about the school. And, so how do you balance all those things?

And also, recognize that art teachers are often looked to to do just one level of stuff. It’s like, “Hey, the school, we have open house coming up. Can you whip together something for the bulletin board, to make it look real great? Can you put some kids’ work up?” That’s when we get asks.

We don’t necessarily get asked to weigh in on something in terms of the reading curriculum, or the math curriculum, even though I think it’s so important that art teachers just know the kids better I think, oftentimes. Or not, the kids, but know the whole school, because we’ll see more of the kids then, especially at the elementary level. They’ll see one grade level. Or, in the middle school and upper school, they’ll see one group of kids. I teach across all the grades. So, we have this other perspective, this larger perspective that I don’t think gets valued.

Anyway, but we get asked these very time intensive things that are very aesthetically based. That’s sort of where our value is placed. That’s what people assume we do, so in my article I talked about, “You know, that’s great and it’s important to do that. But, you need to also lay down some boundaries for people around being really clear, transparent and letting them know ahead of time, ‘If you talk to me an hour before, it’s going to be really tough for me to help you out with this. If you talk with me a couple weeks before, I’m probably going to be able to do it, and I probably will be excited to do it.'”

But, how do you start having those conversations and laying some of those boundaries down sooner than later, so that people can understand. I don’t think they’re ever necessarily knowingly trying to take advantage of an art teacher, but that assumption, and by being clear with your expectations, you kind of get to head that off. You know, you’re proactive around it, so I think you make your own life easier, then.

Tim: Yeah, I think that’s a good point and I think that’s some really good advice. So, if guys haven’t read that article, I’m going to encourage you to go check that out. One last question, just kind of big picture view, what can we expect from ya in the future? What do you have coming later this month, and what do you have coming over the next few months? What ideas are you passionate about and what are you going to be writing about in the near future, here?

Ray: There’s actually a range of stuff that I’m starting. I like to look back and think about how I’ve had such a varied career. I think my route to being a classroom art teacher is really different than a lot of other folks. So, I’ll be looking at some other careers outside of the classroom, or opportunities how you can connect maybe, or do some work that’s a variation than maybe just the classroom teaching.

You know, I’ve worked a lot with teens. I’ve started a couple different teen programs. Those happened primarily in Chicago. I’ve worked with some teen groups here in Seattle. I don’t think anyone can say they understand teens, but I think I’ve got a good handle on different approaches and ways. So, one of my upcoming articles will be around offering some tips with working with teens.

I’ll also be thinking about how art teachers can better connect with the creative community that’s around them. I think that’s so important, that we as art teachers can oftentimes end up in our classroom and stuck there, almost. Like, you know, we’re working so much out of the classroom that we forget that there’s this amazing community that’s out there. Whether that’s, you’re in an urban environment, or in a city, there are tons of resources. But, whether you’re in a rural climate too, there are lots of creative folks out there who, it’s great if you’re able to get out and work with them. Whether that’s as an artist or as an educator or bringing them into your classroom. There are just so many ways to connect. So, I think that helps just … it’s important to keep restoring ourselves, I think, in that way, with that creativity that’s outside of our classroom.

Because, our kids are great, but also, working with the students the other day, it’s a grind sometimes. Especially when you hit, I think, sometimes, this point of year. As your right smack in the middle of the school year, and every art teacher feels that, “I’m just trying to get to that next break as a teacher,” right? You’re just trying to get through things. It’s hard. It’s a grind. But, if you’ve got some of those outside connections, it helps, I think to restore you, and fuels you through the year.

Tim: Yeah, that sounds really cool, and I think that’s a lot of good stuff to look forward too. But, we’ll go ahead and wrap it up there. Ray, thank you very much for coming on. It was awesome to hear from you, and I really appreciate you making some time.

Ray: Yeah, no. Absolutely. It was great talking with you too. Thanks so much.

Tim: That conversation went a little long, but I think there was so much great advice that Ray had there. I really love what he said about reflection and about creativity, and teaching kids to appreciate the art making process. I really want you to take a look at his article from yesterday, it is spectacular, about how we aren’t just here to make poster and bulletin boards. Ray has so many great things to say. This was an awesome conversation, and it might actually be an episode that’s worth listening to twice. If nothing else, we’ll have to have Ray back on again. I think I will leave you with one of my favorite things that he said in this episode.

“It’s about creating a space where kids are comfortable, where kids can experiment. We give them opportunities to try things. And, if it doesn’t work out, that’s okay.” That one quote doesn’t encapsulate everything that we talked about today, or everything that we covered, but it’s a great thought to leave you with. If things don’t work out every time, that’s okay.

Art Ed Radio is produced by the Art of Education with audio engineering from Michael Crocker. Remember that you can sign up for our email list at And one last thing, if you haven’t done so yet, please go sign up for your 30 day free trial of Pro, at It is spectacular professional development and I really can’t tell ya how great it is. It’s something you need to see for yourself, if you have not done so already. So again, go check out Art Ed PRO, at the Thanks for listening.


Magazine articles and podcasts are opinions of professional education contributors and do not necessarily represent the position of the Art of Education University (AOEU) or its academic offerings. Contributors use terms in the way they are most often talked about in the scope of their educational experiences.