EP 306: Finding A New Way To Communicate With Writer Kris Windley | What Works

EP 306: Finding A New Way To Communicate With Writer Kris Windley

Nov 3, 2020 | Creativity, Mindset & Identity, Podcast

In This Episode:

  • How writer Kris Windley learned illustration skills to level up the way she communicates
  • The process she uses to figure out what she’s going to draw and how it’s going to enhance her writing
  • The 3 ways she coaches herself through the hard parts in learning a new skill
  • Where she draws motivation from to continue to learn new things and level up her skills

The very first online course I ever created taught students how to build a WordPress website.

I created the course about 10 years ago before drag & drop page builders were the norm and before premium themes were easily customized.

Back then, building a website was a special kind of skill. If you wanted something custom, you had to know some HTML and some CSS and you had to know where to put it to make it do the things you wanted to do.

The first time I taught the class, the sheer newness of what was involved hit the students like a tsunami. They felt in over their heads and they were quickly drowning among the flotsam & jetsam of page templates and child themes and stylesheets.

I felt horrible.

I wanted to teach them this new skill so badly. I wanted them to feel powerful and in control of their online presences.

But instead, I felt like I had resigned them to the horrible fate of feeling confused and overwhelmed by something that seemed so central to building their businesses.

We worked through it… but I knew I didn’t want a repeat of that.

So the next time I taught the class, instead of diving into the first lesson, I shared a video with them where I explained what was going to happen—not in the class itself, but in their minds.

I asked them to remember back to the last time they were learning something brand new—something that they had no point of reference for. I asked them to remember that it was hard at first but, little by little, it started to make sense and they were able to apply what they were learning.

After I set this expectation, it was a little easier for everyone.

There were still plenty of questions and problems learning the material—but there were far fewer freakouts and panic attacks!

Not only were my students learning to build their websites, I was learning a valuable lesson about what it takes to learn a new, foreign skill as an adult.

This month, we’re exploring how we level up by learning new skills.

We all bring a unique skill set to our businesses. Some of us bring the skills we learned in school or corporate careers that transfer directly into the work we’re doing today. Others bring certifications and licenses from careers that no longer serve us.

Some of us bring skills from our hobbies, personal adventures, or relationships. Others bring skills they had no idea would be useful but have been invaluable to their growth.

The way we leverage our existing skills and learn new ones helps us to creatively solve business problems, invest ourselves in future outcomes, and differentiate our brands.

Over the course of this month, we’ll hear from a number of small business owners who have spent time and energy on learning a new skill so they could level up some aspect of their businesses—or, in one case, start a new one.

You’ll hear from Christianne Squires who committed to leveling up her community-building skills so she could serve her people in a new way.

You’ll hear from Dana Kaye and Felton Kizer about the skills they needed to learn to launch a stock photography business.

You’ll hear from Keina Newell about how she learned to think differently so she could approach sales and pricing with ease—and seriously up her earning power.

And today, I’m talking with Kris Windley, who realized that she could level up her writing business by learning illustration skills.

Kris is a professional writer, certified teacher and curriculum developer, and describes herself as a happily amateur illustrator.

In this conversation, not only will you hear how Kris learned to illustrate and how she uses it in her writing—but you’ll also discover the way she’s learning how her ADHD brain works and how it influences the way she thinks and processes information.

We also talk about why learning new things is hard—and what to do when you feel stuck.

Now, let’s find out what works for Kris Windley!

Kris Windley: Anytime that you're trying to explain something to someone, your brain is trying to reach for something that will connect you to them. So that's what it's really about is finding something, recognizing metaphor helps a lot when there is a missing connection.

Tara McMullin: The very first online course I ever created taught students how to build a WordPress website. I created the course about 10 years ago before drag and drop page builders were the norm And before premium themes were easily customized. Back then building a website was a special kind of skill. If you wanted something custom, you had to know some HTML and some CSS, and you had to know where to put it to make it do the things you wanted it to do.

The first time I taught the class, the sheer newness of what was involved hit the students like a tsunami. They felt in over their heads and they were quickly drowning among the flotsam and jetsam of page templates and child themes and style sheets. And I felt horrible about it. I wanted to teach them this new skills so badly. I wanted them to feel powerful and in control of their online presence.

But instead I felt I had resigned them to the horrible fate of feeling confused and overwhelmed by something that seems so central to building their businesses. We worked through it, but I knew I didn't want to repeat that. So the next time I taught the class, instead of diving into the first lesson, I shared a video with them where I explained what was going to happen, not in the class itself, but in their heads. I asked them to remember back to the last time they were learning something brand new, something that they had no point of reference for. I asked them to remember that it was hard at first, but little by little it started to make sense and they were able to apply what they were learning. Now, after I set this expectation, it was a little easier for everyone. There were still plenty of questions and problems learning the material, but there were far fewer freakouts and panic attacks.

Not only were my students learning to build their websites, I was learning a valuable lesson about what it takes to learn a new foreign skill as an adult. I'm Tara McMullan and this is What Works. The show that takes you behind the scenes to explore how small business owners are building stronger businesses.

This month, we're exploring how we level up by learning new skills. Now, we all bring a unique skill set to our businesses. Some of us bring the skills we learned in school or corporate careers that transfer directly into the work we're doing today. Others bring certifications and licenses from careers that no longer serve them. Some of us bring skills from our hobbies, personal adventures or relationships. Others bring skills they had no idea would be useful, but have been invaluable to their growth. The way we leverage our existing skills and learn new ones helps us to creatively solve business problems, invest ourselves in future outcomes and differentiate our brands. Over the course of this month, we'll hear from a number of small business owners who have spent time and energy on learning a new skill so they could level up some aspect of their businesses or in one case start a brand new one.

You'll hear from Kristianne Squires who committed to leveling up her community building skills so she could serve her people in a new way. You'll hear from Dana K. and Felton Kaiser about the skills they needed to learn to launch a stock photography business. And you'll hear from Keenan Newell about how she learned to think differently so she could approach sales and pricing with ease and seriously up her earning power.

Today I'm talking with Kris Windley who realized that she could level up her writing business by learning illustration skills. Kris is a professional writer, certified teacher, and curriculum developer, and describes herself as a happily amateur illustrator. In this conversation not only will you hear how Kris learned to illustrate and how she uses it in her writing, but you'll also discover the way she's learning how her ADHD brain works and how it influences the way she thinks and processes information. We'll also talk about why learning new things is hard and what to do when you feel stuck. Now, let's find out What Works for Kris Windley. Kris Windley welcome to What Works. Thank you so much for joining me today.

Kris Windley: Thanks for having me. This is great.

Tara McMullin: Absolutely. All right, so let's just start at the very beginning. You are a writer by trade, by business, and you are here today to talk about learning illustration skills. How in the world did you land on deciding that you wanted to learn how to become an illustrator?

Kris Windley: It's kind of the story of the fish learning to fly. It's not something that is innate to me. I was always a reader, I was always the kid that had a story, I had thousands of stories to tell. So writing to me was really natural, it's the way I communicate. But the world and other people don't cater to the way I like to communicate. So there's a lot of people who really require visual pieces to make understanding complete. I tried the whole photography thing and it's just not something that really am good at. I think it's beautiful, I love it, It's so amazing, I wish I could do a good job at it, but it's just not something that I'm great at and I didn't have sort of that initial success that would give me the patience to keep trying.

So I gave up because I'm a bit of a baby if I don't get immediate gratification when I'm learning things. So, illustration it made sense for me because although I could say I'm a visual learner, I have ADHD. So I don't have the ability to actually visualize things. So I can't hold a picture in my head. Maybe that's why photography doesn't work well for me, because it's just something that my brain is like hard no. But I always have when I'm learning things doodle things on paper so that I could better understand them. And because I had a really late diagnosis, usually ladies do, I was 38 when I was diagnosed. I thought that I was a visual learner because I was always drawing little doodles and pictures, turns out opposite even though I'm a certified teacher and I taught for a decade and did curriculum development at a school for people, but with learning disabilities still completely missed my own, which is a bit humbling.

But yeah, so this is not me being a visual learner, it's me trying to compensate for the inability to visualize. So I did it on paper. So I have this kind of doodly ability already. So it gives me that kind of immediate gratification of, yeah, no, you're not absolutely useless at this at the beginning, so there's little wins. And that kind of keeps me going when I get to a place where it's I can't actually make a human face look anything other than a pile of sludge, but I can draw a mean mushroom. So that's what I think I landed on illustration is that I had that initial ability or that tendency to kind of take things and make them visual with really, really simplistic drawings. And it works nicely sort of on the output because I talk a lot about serious things.

And I talk about brain science and I talk about global politics and I talk about feminism and communication online. This is not cheerful stuff all the time. So having really simplistic and cute and fun and almost a caricature of the seriousness of the subject matter, it offsets in an interesting way, that dichotomy is cool. And it also means that you can read a thing that's tough and me telling you no, you have to cite your sources, writers stop being lazy, democratizing journalism is destroying us all. But it's okay, because there's a cute picture of a coffee mug offsets that really heavy stuff, I guess. So it works as far as me being that difficult immediate gratification desiring person, and also it really helps I feel with when I'm trying to communicate difficult things.

Tara McMullin: Yeah. I love that. I was going to ask you what are some of the kinds of things that you are adding that visual component into talk about. And so thank you for volunteering that before I got to the actual question, but I'm curious if you could give us an example. Can you talk about maybe a piece that you've written recently or something that you've tried to teach recently and how you incorporated a visual element into that, an illustrated element?

Kris Windley: Sure. Yeah, actually there's something that I did maybe a year or two ago that suddenly the visuals are getting a lot of traction. I think that it was a pin that somebody got into or something and they ended up using it for... There was some kind of a conference or something that was going on and it was about imposter syndrome. It was just a sort of a doodling kind of, I do real simplistic, I'm no Picasso, but it was a side subsection of a face with sections inside, an infographic describing components of imposter syndrome for women. And so tons of people, I've seen it shared recently again on Instagram every now and then I get a little notification that someone else is sharing it. So that's something, again, like imposter syndrome, even talking about it stresses us out and talking about it people respond often by being, yeah, but am I actually good enough to have imposter syndrome?

We don't even that we have imposter syndrome about our imposters syndrome. So it was one of those pieces where I think the cutesy pink and teal picture of a brain might have helped. But recently, I mean, there's something that I'm getting ready to publish this week that is about resistance for writers and this feeling of being unable to start a creative task. And it's something that's even more of an important thing for me to kind of try to muddle through myself since I realized that the feelings that... Because ADHD, one of the things that we have a lack of is tonic dopamine, which is the go-go juice. So it's normal brains, normal is a weird word, but typical brains have a sort of well of dopamine just waiting for you to have something to do. And that ability to visualize the task being done which gives you extra dopamine.

I'm sitting here with this empty well of dopamine and I can't visualize the finished thing, so I don't get that shot. So I need to really figure out a way to give myself shots of dopamine, to do stuff in a healthy way without last minute pressure that's not dopamine, it's the tigers are coming to eat your fear factor. And so, again, it's something that's not ultra-pleasant. The conversation is a little bit tough because a lot of creative people have this feeling of having an empty well, and it's so scary to have something that's so important to who you are. Your creativity is a pillar of your identity and then to show up when you need it and have an empty well is horrifying. So again, little cute mushrooms. I drew because I use them as a visual kind of representation of a thought or a metaphor that I'm using.

And so the mushrooms are there because I'm like you have to look at where your steps are, take small steps, look at where your feet are going, pay attention to the small steps, but don't zoom in on a little mushroom on the forest floor and forget where you're going. So there's a cute little mushroom in that paragraph.

And so it's a thing that lightens it up, but it relates to what I'm talking about too. And then I tend to take those illustrations that are in an article like this and then make Instagram posts for them to refer people back to read the article. So the little mushroom that's going to go on Instagram will have that little piece of, yeah, take care to look at the small steps because if you're just trying to do the whole journey in one leap, you'll not make it, but don't focus too hard on your little mushroom that you forget where you're going. So that's the Instagram sort of bite-sized piece. Go take a look at the whole article if you want to see the rest so to speak.

Tara McMullin: I love it. I want to get to how you actually went about learning the skill at some point, but first I kind of want to hear about your process. So I feel now we have an understanding of how you came to understanding that this would be an important part of how you wanted to communicate, that this would help you share ideas with a world that is largely communicating visually especially on the internet. We have some examples of how you've done that. I would love to hear when you start thinking about putting an article together, putting an idea out there in writing, what kind of method are you using to find the visual that's going to go with it, or the visuals that's going to go with it.

Kris Windley: I love that question. Okay. So I'm slightly obsessed with method and process and-

Tara McMullin: Me too.

Kris Windley: I'm one of those... Oh my gosh, we could talk all day. I have an appointment in two hours. Yeah, I think I'm one of those people who... Forks who see me working or who I talk to about my workflow and stuff like you're so organized and I laugh and it's hilarious because those processes and this really, really serious method that I have built is because of how unorganized my brain is. I need to build a really robust framework or I'm just going to be an amoeba kind of floating around because time doesn't exist. And I can't understand how he does it, it's not real. Yeah, mushroom go and stare at the mushroom for 20 years before you go anywhere.

Right. So, yeah, methods and processes are really important to me and I'm sort of obsessed with it. So when I do this weird kind of hybrid because I use a writing process that's really important. And then I have an illustration process that's also really important, but the creative feeling I need to have, the energy I need to have is different for the two different tasks and it's different for each step of the different tasks.

So I'm going to try not hyper-focus and go for days talking about stuff that's really not important to anybody else's brain, but mine, but basically the way that I start with the article is with a purpose. And with anything I create, I start with purpose. And for writers, your purpose involve knowing your audience, there's an editorial purpose and then there's the reader's purpose.

Why are they coming to me? What do they want from this? What are they going to get from it? Because sometimes those are the same thing. What do I want as a writer to get across, but also as the editor, because I'm both of those things, right. When you're making content through the interwebs. And so understanding all of those different purposes and they're all inside of my general purpose. And then I kind of play around with what ideas would meet those different purposes. And so in this particular one I was talking about resistance. I'm building a writing process or a writing practice kind of curriculum for people. So I want people to be able to build their writing practice and there's certain pieces of it that are problematic. And one of them is dealing with resistance and counter to that is building up a well of different motivations you can tap into.

So we have to address the thing that we're talking about. So I wanted to make a really good article for each of these kind of pieces. And so I'm like, all right, I need to talk about resistance. And then I start letting my brain play around with that idea. And I read a bunch and I do a bunch of research and I keep track of all my different stuff. And I have Trello upon Trello, upon Notion, upon other organizational things to keep all of my stuff stored in. And I have researched articles for years and I'm never going to have to research things again, but I will anyways, because I just love to do it.

Tara McMullin: Totally.

Kris Windley: Right. And so I end up pinpointing one piece and then shaving away the extra extra chapters because I'm not writing a book on resistance, I'm writing an article. And so at one point and then I do an outline that's really, really clear. And the outline is key, it's like a map for me because I'll get lost without it. And in that outline I've got a simple five paragraph essay outline that I would have taught my kids when I taught high school. About my introduction usually it's a story, that's how I roll. And then I've got three pieces that I need to hit in order to get there, to teach the thing, or to express the thing or whatever. And then I have my conclusion with a call to action if there was one. So each of those three important pieces is going to have sub pieces. That's where my research comes in. That's whatever tactic I'm using to express it, it comes in, but each of those will have a visual. So I often use metaphor because I'm a non-fiction writer who's obsessed with fiction.

Tara McMullin: Love it.

Kris Windley: Right. So metaphor everywhere, metaphor for days. My whole how to figure out who you are when you're talking to people online, it's all a Lord of the Rings metaphor that goes far too deep. And it's way too embarrassing for kids. When I'm like, "No, I'm Gandalf and it's fine. Samwise is the best character anyways." And they're like, "Mum." But seriously, so metaphor usually ends up having a visual that's interesting and dichotomous to the message. And that kind of is what I like best is something that's inanimate because they're easier, because I am not a pro. I do it for my work, so I guess theoretically I am pro, but I'm not exceptionally gifted. So I'm a not do a really complicated illustration.

My skills have grown as I use them, but inanimate objects are my comfort zone. So having that, just trigger image of something that I can both draw with my skills such as they are. And that will feel like they go with my overall brand and the message that I'm trying to convey.

So all of those things go together. And so while I'm building my outline for my writer self, I have a list of potential illustrations I can draw for each section for my artists self. So I'm almost building... I don't know, I've lost the word immediately as soon as I was about to say. I'm almost building a job description for the illustrator that works for me. Right. So I'm just like you can draw this, this, this, or this for each of these sections, do What Works. And then when I'm in my kind of writing zone or in my drawing zone, which honestly happens a lot when I'm relaxing in front of Netflix with my older daughter in the evenings sketching and drawing is a lot easier than obviously writing is hard to do when you're watching TV, doesn't really work. So that as whatever ends up working, whatever ends up feeling the best I'm looking the best out of that creative brief I guess is what ends up going into the article.

Tara McMullin: Awesome. Thank you for sharing all of that. That is incredible. And I think it's going to be really helpful for people too. One more point I want to dig a little bit deeper in on your process, which is, you mentioned metaphor everywhere, metaphor for days, I think is how you put it.

This is something that I have given a lot of thought to over the last few years, as I've tried to incorporate more storytelling and more examples into my own writing. And now working with other people... I work with them on podcasting, but a lot of what I do is work with them on writing, right. Because we're working together on scripts. And so it's something that I'm kind of thinking through with other people too. And so I'd love to hear your process for this. When you're coming up with those metaphors, is it a bolt of lightning and it just hits you, "This is the perfect metaphor." Or do you have some sort of set of questions or process for actually identifying, "Oh, this is a good way to communicate that."

Kris Windley: I think that unfortunately it's a bit of the bolt of lightning thing.

Tara McMullin: Okay.

Kris Windley: Sorry.

Tara McMullin: That's okay.

Kris Windley: But I think there's ways to make the bowl happen if that helps, lightning rod. I mean, here we go, metaphor. Right. So part of it is because the way that language is built. Warning, I'm about to go too far into this. The way that language is built is on metaphor as it is. So as you learn studying linguistics and stuff, everything about an expansive library of words, anytime that you have the ability to communicate in a language it's because there are specific and general metaphors that you have grown to understand. So you can learn vocabulary and then you start to gain that cultural knowledge of the way we see this world in language and that's metaphor.

And that's where you get all kinds of idioms and stuff. And it's gets hard part of learning a language, but once you know that stuff, that's when you're as good as native speaker in that language. So having the understanding of language itself as being just a sea of metaphors that you're bobbing around in helps. Anytime that you're trying to explain something to someone, your brain is trying to reach for something that will connect you to them. And so if I'm trying to explain... So as a teacher I taught in university as well. So I remember a specific lecture where I was discussing a short story of Alice Munro's, feminist story. Okay. I'm a Canadian. And I did CanLit, that was my major or whatever concentration in my literature degree.

So I'm discussing Alice Munro, I'm discussing this particular story of hers. And it's all about growing up as a daughter when the father wanted a son and there's all sorts of symbols in the story that show her being locked into a role. And so I'm trying to describe what these different symbols are like metaphor, metaphor, everything's a metaphor. And I had one of my students in that particular class was a woman who was 63 years old from the Prayers of Canada, which is where this story was said. And another student in the same class, it was a small class. Another student same class, was a 21 year old jock who somehow ended up taking Canadian literature class. And he just could not understand how the fox was a symbol for her being held in a role. He was just like, "It's a fox, I don't understand it."

And the 63 year old woman, I was trying to get there for him. I didn't know what piece could connect us. And this was me 12 or 13 years ago. I might be better to find that connection now. I've grown, I've aged, a little more humble too, all kinds of different things that make me better at finding those connections now than I was then. But the other student in the class, the woman who was 63 years old with that experience, with that understanding was able to find a connection with him. And I don't remember, I wish I did. I don't remember what it was, would be such a better story if I did. I could make it up, but I can't.

So she was able to find something that connected their experiences outside of that place that the connection was missing. There was no way for him to be like, "I get it, 63 year old woman, I felt that way, nope." There was no way for her to be like, I'm a 21 year old jock who's going to university for free because of baseball and don't care about books at all. They just had nothing in that area, but she was able to find a piece that was outside of what they were talking about completely that they connected to. So that's what it's really about is finding something, recognizing metaphor helps a lot when there is a missing connection. And so you can recognize that this thing we're talking about right now, we don't have the language in common to be able to communicate understanding, but this other thing, we have language in common, Lord of the Rings?

We have that in common. So I'm going to use that language to discuss finding your leadership skills, right. I could use all kinds of weird self-helpish language, but that's not going to make the same kind of impact. If you already understand all of the things that go along with this whole pocket of language that goes with the Lord of the Rings, then you're going to understand this way better if I take the pieces of that language, that connect to the idea I know, and then give you the idea I know in this language you already understand.

Tara McMullin: So helpful. Thank you for that. I love that because it's so clearly connected ostensibly what we're here to talk about today, which is how you learnt illustration skills. And it is also so helpful from a writing perspective, from any kind of communication, like you said, it revolves around this shared understanding of the metaphors that we swim in every single day. And it makes so much sense too, as to then how you landed on illustration as a way to become a better communicator even than you already were. So let's get back to that where we can talk about the linguistics and all of that stuff like you said all day long.

We'll hear about the process Kris used to hone her illustrating skills, as well as how she moved forward when she got stuck in just a minute, but first a word from our What Works partners.

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All right, so let's back way up. Once you decided, all right, illustration is something that I really want to explore, something I want to add into my communication toolkit, how did you go about even getting started with that learning process?

Kris Windley: Wow. Okay. So it was a while ago that I started and it was bumpy to get started. I took fine arts classes in university as electives and stuff. But that's a totally different thing from developing digital illustrations. Sketching with pencil is not the same as getting it onto the computer screen. It's just, there's so many pieces in between. And it was long enough ago that the tech stuff has developed unbelievably in the last few years and made it so much easier. The workflow is completely different now from what it was when I began, but I was working with another business owner whose forte was visual stuff. She was a photographer, she did website designs. We ended up working together doing web copy, me, and her doing the web development or design stuff and photography for clients and stuff.

So we had a partnership going and she really wanted to be able to write better. So I was helping to teach her writing skills and helping her to develop an editing and revision workflow. And she was helping me with photography and web design and stuff. So she kind of helped me to feel more comfortable touching the tech piece to get it from my Luddite charcoal on paper version to the computer screen magic. So it was a really awkward kind of process. At first I found Adobe has a capture app that you can use on your phone where you have to line up and kind of take a photo of your line drawing, and then it captures it as a shape. And then you have to upload it to Adobe Illustrator. And it would take me, Tara, hours. I would become obsessed with, because in Illustrator it's all of these little points create a line and the lines create the shapes.

So the simple, beautiful, easy looking cartoon line of my illustration was thousands and thousands of little points that I had to move and become obsessively hyper-focused with. And days later, my cramped little neck would come up from the computer screen and it'd be like that's a good circle you made, hours and hours later. So that was the initial process. It sucked, but it was cool because it was new. And once I get that little piece of the initial immediate gratification of you had a win, you did a thing, and it wasn't terrible that gives me the boost to keep on going. And I get obsessively learn about the thing. So I did that for a while and it got to the place where the newness was gone. So the headache of the workflow started to become a bigger problem.

And at that time, Procreate started to become a thing, which is a piece of software that if any listeners don't know what it is, it's 2020, it's everywhere guys. But it's something that you can use on your iPad with an Apple pencil. And you can draw basically on the tablet and it's like, it's digital. It happened already. So there's little pieces with that. It's not the same quality, whatever, but for the illustrations that go into my articles and that go on to Instagram, it's amazing. And that's something that I just started doing this year is using that. So the biggest learning curve thing for me has been the workflow so far. Now that the workflow, the practice piece of it is starting to become smoother, it's starting to make more sense to me, it's starting to become almost habitual or second nature.

Now, I'm starting to look at, okay, skill development. It's the same process as learning writing. The practice piece is your first piece, get your resources, get your workflow, get your materials in place. And then you can start to say, all right, here's a skill vacuum you need to fill. Perhaps you should take a Skillshare class on how to draw a face instead of crying about it all the time. And get over the fact that it's not easy, everything isn't always easy for you, Kris. Sometimes things are hard and it's going to be fine. Just do the work, it will get easier. So that's where I am right now. I'm past the workflow hiccups a little bit, I'm looking at it okay. So skill development time and it's cool, it's interesting, it's humbling.

Tara McMullin: Yeah. Well, I'm curious about that piece because I think for so many people when things get hard... Well, they're hard at the beginning and then they get easier and then they get hard again. Right. And anytime things are hard, we have a hard time especially as adults moving through them. Right.

You've mentioned you're ADHD and I think that for different people with all different kinds of brain chemistries and makeups and thought patterns, we all approach that a little bit differently, but I'd love to hear from your perspective, what are you doing? What's going on in your head? What are you telling yourself to move through those places where you would rather sit there crying that you can't draw a face. What's going on in your head as you kind of move yourself through those periods?

Kris Windley: Okay. I think three things, I'm going to probably forget the third one by the time I get back to it. But three things thing [crosstalk 00:36:22].

Tara McMullin: Totally understand that.

Kris Windley: Thing one is my oldest daughter should be 21 in January, which strikes me as impossible, but it's the way that it is. She has cerebral palsy and has had significant difficulties with all kinds of stuff that most people take for granted. And she also has the type of personality that tends to ward just being thrilled with the world around her, which is wildly endearing. It's weird for a mom to be why in the hell are you so happy? I am really mad about this on your behalf and you should always be mad. But things are more difficult for her than for me in a lot of areas. Some things are easier for her than me all the time with the smiling.

But one of the things that we have gotten accustomed to the 21 years that she's been my sidekick, we've become accustomed to saying is, I know it's really hard luckily you can do hard things. And she can, she's one of those really cool people who's like, her MRIs we'd roll into a doctor's office when she was five or six and they would look at their charts then they'd look at her and they'd look at their charts again and be like this brain shouldn't be walking. And she was in a tutu doing a pirouette. You know what I mean? A clumsy one, but with a giant grant and all the sparkles.

So she's one of those people whose brain is just the Alaska City in there. It's just so tremendous that she proves it over and over again. Which is both motivating for those of us watching and kind of following along and slightly demotivating because it's sometimes I do want to cry, but space being hard to draw. That's important too, please. So that's one of the pieces is this just mindset of being this is hard and it sucks, but at the same time that that truth exists, the truth exists that I can do hard things and that's really helpful, so that's thing one.

Thing two is that there's ceilings of ease and difficulty. Okay, there's metaphor brewing, it's happening in real time. So we're in an apartment building and we're trying to go up to the top. The top is peak, professional, amazing capabilities, right. And to get from one floor to the next is hard. And when we get to the next floor, it's difficult being there for a while. You have to get used to it, you're still working on it. It's not easy, but then you get there and you're comfortable and you kind of want to hang out for a bit, but it gets boring and you want to move on.

So we just keep doing this movement upwards or whatever, and it's okay for you to stay in on one floor for a while. If that serves you, if you're getting everything you need from it, cool, hang out, you don't need to go anywhere right now. But if you realize that there is something you need on floor 19, and you're on floor 17, and you need to get there, then you have a reason to go through the hard where it's not going to make it easier, but it's going to make it worth it.

Right. So that's thing two. Holy crap, I remember thing three, this is amazing. So thing three is that you decide to go to the place where it's hard. You find the flight of stairs, you go to the elevator, whatever, we'll find the metaphor piece that works for it. You get to the floor where it's difficult for you to exist. You start to learn the things that make it easier for you. And you can hang out there long enough to understand how you got there and sort of turn around and hand that off to someone else, which makes it easier for you to keep moving upward.

It's a thing that happens with teaching. I'm a teacher, so there's reasons, teachers are amazing people. My parents are both teachers. My sister's a teacher. Teachers in general, phenomenal human beings. I don't say this as being I'm an amazing person because I'm a teacher. No, I'm not a classroom teacher anymore because also it's impossible. It's the hardest thing in the world. So teachers are really cool. They do a lot of stuff because it's good for the world.

But also there's a really cool feedback loop. And one of the things that happens in that when you're teaching someone, is that it becomes clearer for you. And in figuring that connection, finding that metaphor, finding that way to connect to this idea to someone else, you find it for yourself too. So if you're struggling to get up those stairs and you're looking around and there's somebody else who's also struggling to get there and you're, "Hey, this is a thing I figured out, oh, I did figure that out." You almost didn't know you knew it until you tried to explain it to somebody else. So I find that is a really helpful piece, sort of stuff that goes together is that mindset of being this is going to be hard, but I can do hard things, so that's okay.

And then the other piece being, yeah, but maybe it doesn't need to be hard yet, you don't actually need to do the hard thing right now, so don't, relax. Don't try to get to the top because the top is somehow better than not top, that's not true. The top is better if what you need is there. And then this other piece of being the learning process is also the teaching process and let it be something that's not just about yourself.

It takes the stakes away somehow. It makes them lower stakes. And then you're not sitting there with that feeling of tigers are going to eat me, fight or flight about needing to learn this thing. You're looking across the campfire or whatever and you're like, "Hey guys, all of us should be aware of tigers exist. Let's work together on making it easy to not get eaten by them." And becomes less, the stakes are lower and that makes it just easier to learn. It's easy to learn when you're not afraid, that's brain science. That's the truth. So do what you can to not be afraid of the thing that you don't know how to do.

Tara McMullin: Gold, just gold. I do have a couple more questions. I'm tempted to just be like, no, we're going to leave it there, that was brilliant.

Kris Windley: Thank you Tara.

Tara McMullin: But I have a couple of other nuts and bolts questions. One of which is simply what do you do to practice? So as you're kind of leveling up, as you're working on skills, as you're learning how to draw a face, what is your process for practicing?

Kris Windley: So the face I'm not doing that. That's three floors up. I'm not there yet. It's okay. I don't need it yet, I will. I will just not today. So one of the things that I do honestly is that I piggyback it with something that I'm good at, right? This is why it works really nicely for me and my process is that writing is innately easy for me, as you can tell a little for both, got words golore, they just come out.

So I connect it to something that already makes sense to me. And every time that I want to publish an article, I want to draw some stuff for it. So it's just something that I do regularly when I'm trying to share stuff with the world. A lot of my motivation to do my work comes from people receiving it. That's where most of my motivation comes from. I get after the fact when people are like, "Oh, I loved the way you said that." I'm just like, "Eat it, eat it, eat it for lunch."

And that was all I live off of. So knowing that sharing things visually, especially on Instagram the more people will be able to receive it and they'll get it. It just drives me to do the thing. So that's really the key thing is just for projects I'm doing. I would get better faster if I were drawing every day. I know this for a fact because that's how learning works, right? Practice is better if you just do it all the time.

But I write every day and that's my number one skill that I'm developing. So illustration it's that stakes thing, like I said, the stakes for illustration are not as high. I don't need to illustrate an entire book. I need to write one. So that's the thing that I'm working on day in and day out. And I can hold, this is the thing that's hard at the beginning of learning a new skill. For those of us who have a skill that is highly developed. And I can say that because I'm 40 years old, I went to school for a million years. I still owed money on it will forever. I know that my writing voice is mature. I know that those skills are far higher than the average bear. I know that I can teach people how to do it really well. I know this and I'm confident in it and it can exist in a world where my illustration skills are not the best and that's okay.

It's real hard for some of us. If you're accustomed to being the best in the room at something it's really hard to go into a different room where you're not, and you're not ever going to be on the best illustration in a very small room. Right. And most of the people in that room don't even draw anything. They're just like, "That's neat that you can do that." I'm like, "I can't do it really well, but thanks."

So it's okay that I don't practice it every day. I know it would be better. I know I'd be drawing faces like crazy. I know that I would have so much more freedom with it because I have ideas of things I'd love to create visually, but I just don't have the skill to get there yet. But I don't need to rely on that as my number one skill. It's my back pocket skill and it's doing well. It's great at it's job. And I can let it not be the most important thing in my sort of tool belt or whatever. I don't know if that helps. It's practice every day, but except don't.

Tara McMullin: No, I think that helps a lot. I think what you said about kind of coping with having both a very highly developed skill, something that you have a lot of ease and facility with at the same time that you are working through something that feels a lot thicker stickier is I think a lot of people can relate to that and I am very much in awe of people who do that gracefully. So whether you feel you do a gracefully or not, you have represented it to us very gracefully, and for that, I am very, very grateful.

Kris Windley: Am not called graceful often, I'll take it.

Tara McMullin: So as we do start to wrap up here I'm curious what are your future plans for the skill? You've mentioned that there's things you'd like to be able to do. Do you have a particular project or a particular idea that you are working toward right now with the skill?

Kris Windley: Yeah, actually because what I do in my business, my day job is teach and support people who are also writing. So I write a lot, but I also do this thing where I teach and support people who are writing. There's something about when you work in theories and you'll understand this because you do this too. When you work in a world of thought everything feels sort of a cereal and it's like you can't really touch any of the stuff that you make. And it's hard sometimes to really understand that it exists. So you do all of this work and it just kind of exists in people's heads all over the place, which is very cool, but also really hard to put your finger on. And sometimes you need to be able to do that. And so I've wanted to for years have some physical products to offer to people mostly so that I could have something in my hands and be like I made this thing, it exists now, and it didn't yesterday. Because that feels good when generally you're manufacturing the stuff that doesn't really exist.

So I'm doing some posters and some basically learning aid stuff to start by helping folks who are my writer people, my adore, and whose voices are necessary to feel the kind of happy joy pieces of it. Because like I said, that's what the illustrations tend to be cute and fun and live in a world of simplicity where people who were learning how to share their voices, particularly ladies because I work with women identifying writers generally, it's complicated. It's not simple. It's really hard. And it's dark. It's not bright red and teal and cute typewriters and poke it out and mugs and stuff. It's hard and it's not pleasant. So I want to create things for us to have around ourselves that are cute, pleasant, just because fun is a good enough reason. So I'm doing that and it's weird because of this stuff of the imposter syndrome stuff.

And it's weird to create something using your back pocket skill when you've been creating something with your front pocket, it's coming on with that metaphor fell, they're not all winners, but it's weird to be having used a skill that you're really confident with for two decades to now be creating something almost solely with something that you're not as strong at, it's tough, but exciting. So that's kind of what I'm working on. I'm making journals and I have prompts that people use to develop their writing practice. So I'm going to have sticker versions of those prompts for people to put in their notebooks and everything because it's hard, learning things is art. So I want it to be fun and also I want to make fun things. So that's what I'm doing with it.

Tara McMullin: That's awesome. Well, you may have already just answered this question, but the last question I always ask everyone is what are you excited about right now?

Kris Windley: I think that, yeah, I'm excited making some real life things that I can clutter my physical life with a little bit, because it's really cool to do theoretical work. It's what I'm made for. But yeah, I want to be able to touch something. I want to be able to hold something in my hand and know that I made it happen. So yeah, I'm excited about that right now I think.

Tara McMullin: Incredible. Kris Windley, thank you so much for giving us a look inside your learning process, inside your writing, and drawing practice. I'm just so grateful for everything that you've shared with us.

Kris Windley: Oh, thanks for having me. It was a blast. Anytime I'd love to come back and chat some more, some other time.

Tara McMullin: Is there a skill you've been wanting to learn, but you're afraid it's going to be hard. Look learning a new skill can be overwhelming and humbling. I love what Kris shared about reminding herself and her daughter that we can do hard things, that we can push through the times we feel stuck by focusing on why we want to get better and that we can make it easier on ourselves by teaching others what we've learned. If there's something you want to learn, I know you can do it. How could you take a baby step in that direction today? Find out more about Kris Windley at withakwriting.com. Next week, I talk with Christianne Squires about how she learned to become a better community builder and how that skill has transformed her business.

What Works is produced by Yellow House Media, our production coordinator is Sean McMullan. This episode was edited by Marty Seefeldt and our production assistants are Kristen Runvik and Lou Glazer. What Works is recorded in what is now known as Lititz Pennsylvania, which is on the homeland of Susquehannock people. The Yellow House is located in what is now known as the Flathead Valley of Montana on the homeland of the ktunaxa nation.

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Tara is a podcaster, small business community leader, strategist, and speaker. She’s been helping small business owners build stronger businesses for over a decade.  

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