Drawing Challenges: Grow Your Style, Portfolio, & Community | Bella Boss | Skillshare

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Drawing Challenges: Grow Your Style, Portfolio, & Community

teacher avatar Bella Boss, Illustrator & Animator

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.

      Introduction

      2:07

    • 2.

      Class Project Overview

      2:08

    • 3.

      3 Types Of Drawing Challenges

      2:14

    • 4.

      Defining Your Goals

      0:54

    • 5.

      Picking The Perfect Challenge

      1:15

    • 6.

      Finding the Right Community Challenge

      1:31

    • 7.

      Creating A Personal Challenge

      3:30

    • 8.

      Hosting a Community Drawing Challenge

      5:33

    • 9.

      Helpful Tips & Starting Success Strategies

      4:33

    • 10.

      During The Challenge

      1:50

    • 11.

      After The Challenge

      1:39

    • 12.

      Bonus Lesson: Miscellaneous Challenges

      1:24

    • 13.

      Key Takeaways

      1:25

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About This Class

Discover how to plan, complete, and even host your own drawing challenge with confidence. Over the past five years, I’ve participated in dozens of challenges, hosted many of my own, and even earned the nickname “Queen of Drawing Challenges.” Now, I’m sharing all my best tips and tricks in one place to help you use drawing challenges as a powerful creative tool.

In this actionable class, you’ll learn how to:

  • Choose and plan a drawing challenge that fits your goals and schedule
  • Stay motivated and finish with a full collection of new artwork
  • Build community and confidence along the way

Drawing challenges have completely transformed my own creative journey—helping me connect with other artists, grow my portfolio, and open doors to new opportunities. Whether you’re an experienced artist or just starting out (and even if you have limited time), this class will give you the tools to make drawing challenges work for you again and again.

This class is for:

  • Creatives looking to start a consistent art practice in a busy life
  • Artists who want to gain a greater creative community 
  • Illustrators with an interest in hosting drawing challenges, but unsure where to start
  • Anyone trying to build a collection of work, add to their portfolio, or try a new style

Lessons include:

  • An introduction to drawing challenges
  • Defining your goals
  • Choosing the perfect challenge for you
  • Finding the best community challenges
  • Creating a personal drawing challenge
  • Hosting a community drawing challenge
  • Prep, participation, and post challenge skills
  • Helpful tips and success strategies 
  • Bonus: Miscellaneous Challenges

Materials/Supplies needed:

  • A sketchbook, notebook, or iPad to plan things out
  • Art supplies of your choice (paper, pens, paints, procreate-whatever works for you!)
  • Access to Instagram, Google, and ChatGBT (optional)
  • A creative excitement and desire for growth

By the end of this class, you’ll learn everything you need to know about finding, creating, and hosting drawing challenges to build your portfolio, community, and confidence.

Meet Your Teacher

Teacher Profile Image

Bella Boss

Illustrator & Animator

Teacher

Howdy, I'm Bella!

I'm an illustrator, surface pattern designer, and animator based in Austin, Texas, where I live with my husband and two girls. Inspired by food, travel, and celebration, I started Bee Creates in 2022 to share joy through vibrant, playful art.

Today, my work spans licensing, creative collaborations, and teaching. My mission is to help everyone "Have a Colorful Day" whether that be through joyful illustrations, thoughtful products, playful animation, encouraging classes, or a supportive community.

If you are wanting more in-depth support, check out The Greenhouse. This is my membership community that supports creative entrepreneurs as they grow sustainable, joy-filled businesses.

I also love sharing my latest work, process videos, and art ... See full profile

Level: All Levels

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Transcripts

1. Introduction: What do all of these pieces of art have in common? I made them all as part of drawing challenges. Hi, I'm Bella, an illustrator and pattern designer making art in the margins of motherhood. I've had the opportunity to partner with amazing brands like Adobe and earn thousands of dollars licensing my artwork. All we being a stay at home mom of toddlers. I know what it's like to have artistic goals and dreams, but also balancing limited time. When I was first starting out in my illustration journey, I participated in a few community drawing challenges and a personal 100 day illustration project. Each of these was super impactful for my growth as an artist. In the past five years, I have joined dozens more challenges and hosted a variety of my own. I credit these challenges with developing my style, building a supportive and inspiring community, and giving me confidence as an illustrator. Throughout challenge hosting and participation, I have learned a ton. In this class, I'm sharing it all with you. The class project will be completing your varied on drawing challenge. Lessons will cover everything from choosing the right challenge based on your goals to hosting your own creative challenge to tips for participation to examples of success. I created these lessons to be perfect for beginners. This class is specifically for creatives looking to start a consistent art practice in a busy life. Artists who want to gain a greater creative community, illustrators with an interest in hosting drawing challenges, but unsure where to start, or anyone trying to build a collection of work, add to their portfolio or try a new style. Whether you were hosting your own drawing challenge, participating in a community challenge, or completing a personal challenge, this class will help you find success in building your portfolio, community, and confidence. Join me in the next lesson, where I break down the class project into more in depth. 2. Class Project Overview: I'm so glad you decided to jump in and join my class. Throughout each lesson, we will take steps to complete your very own drawing challenge and create a brand new collection of artwork. I chose this subject for a few reasons. Mainly, utilizing drawing challenges can help you reach so many creative goals. It's such a powerful tool and I want to share that. Additionally, friends have called me the Queen of art challenges, and with all my experience in participation and hosting, I find myself uniquely poised to teach about the subject. Lastly, I have yet to see a class specifically on drawing challenges. Lessons will cover the different types of drawing challenges. Choosing a challenge that will help you reach your goals, joining, creating, hosting, and participating in challenges, tips and examples for success, and a bonus lesson on miscellaneous challenges. The supplies for this class are simple. You will need a sketchbook, notebook, or iPad to plan things out. Whatever art supplies you want to create with, this can be paper, pens, paints, procreate, whatever works for you, and this is optional based on what challenge you decide to complete. You might need Instagram, Google, or chat GPT. Most importantly, you will need a creative excitement and desire for growth. I have provided many downloads for this class, including a list of my favorite drawing challenges, a list of themes for drawing challenges, a checklist for hosting a drawing challenge, and tips for challenge participation. My biggest tip for success is to be kind to yourself. Art challenges can be challenging. The goal is not perfection. It's growth, growing your artistic skill, growing your portfolio, and growing your creative community. I hope you're feeling inspired because next up, I'll give you a brief rundown on the different types of drawing challenges. 3. 3 Types Of Drawing Challenges: In this lesson, we'll learn about different types of drawing challenges and why you should participate in them. If you decided to take this class, you'll likely know what a drawing challenge is. But if not, it's essentially a list of prompts to interpret and create in your own style. They're often to be finished over a certain period of time, such as a month or 100 days. Usually, they push artists out of their comfort zone by focusing on a certain, perhaps unfamiliar medium or by creating many pieces in a short time. In this class, we'll be talking about three types of drawing challenges, community challenges hosted on Instagram, personal challenges such as a 100 J project, or hosting and creating your own drawing challenge. Each challenge has specific benefits. But generally speaking, drawing challenges help you work towards your creative goals by giving you specific deadlines and parameters. The very first challenge I participated in was the pattern challenge by Mel. It was also her very first edition, hosting it. I had just barely gotten an iPad with Procreate and started Instagram for my extremely novice illustrations. It felt awfully ambitious to draw every day for a whole month, but with the accountability of posting on Instagram, I did it. And after that 30 days, my skills were better. I also made great Instagram friends from commenting on their challenge entries and them seeing mine. Mel even turned some of her favorite community patterns into a fun newspaper that I got to be part of. All this to say, a drawing challenge was the beginning of my own Illustration journey, and I'm so glad I did it. One more note. There are a few assorted challenges that don't fit into this specific mold or format. They can still be fun to join in, but you get a one off piece of art. I have added a bonus lesson in case you want more information on these miscellaneous challenges. Now you have a basic idea of what drawing challenges are. In the next lesson, you'll define your goals, so you can pick a challenge that's right for you. 4. Defining Your Goals: Now that we have a basic idea of different types of drawing challenges, we're going to define our goals. By the end of this class, you'll have a better idea for what challenge you want to participate in. There's likely a reason you want to participate in a drawing challenge. So think about it and be honest with yourself. What are your goals? Portfolio building, confidence, improving illustration in a specific subject matter, building community, experimenting with a new medium or style. Write down your top two or three goals and keep them in mind. Then join me in the next lesson where we discuss benefits of different challenges and you pick a direction to go in. 5. Picking The Perfect Challenge: Now that you have defined your goals, I'm going to tell you about the benefits of each type of drawing challenge. By the end of this lesson, you'll know exactly what challenge to participate in. Joining community drawing challenges, builds community, gets your work seen, helps with accountability. Prompts are already created for you. Creating personal drawing challenges, can personalize to your own specific prompts, can work at your own pace. Great for experimenting with a new medium or style. Hosting a new drawing challenge. Can create your own prompts. Builds community. Gets your work seen. Helps with accountability. With all of this in mind, you should pick the challenge that aligns with your goals. The next three lessons, I'll go into more depth on each challenge. And you can watch all these videos for future reference, or you can just pick the one that aligns with your goals. 6. Finding the Right Community Challenge: In our last lesson, you chose a challenge type based on your creative goals. By the end of this lesson, you'll find a community challenge you want to participate in. Artists are always posting various prompt lists on Instagram for you to join in on. Some take place annually or are seasonally themed. In October and Peach tober both happen every year in October. 36 days of type nearly always happens in the spring. There are often ample prompt lists released around Christmas time. My best tip for finding challenges to join in on is following your favorite artists on Instagram or subscribing to their newsletter. Oftentimes, artists will share the prompt list early or give bonus prompts in their email. Another way to find challenges is by searching simple hash tags like hashtag drawing Challenge or hashtag art Challenge. I have created a list of some of my favorite drawing challenges. Who hosts them and when they take place? You can download it below. Choose a drawing challenge that aligns with the subject matter and timeline you're interested in. Now that you know how to find challenges, give it a shot. Choose a challenge to participate in and share it in the class project section, so other students can find it too. Then join me in the next lesson where I talk about creating your own custom challenge. 7. Creating A Personal Challenge: If the idea of participating in a community drawing challenge doesn't appeal to you, then you can always create your own challenge. By the end of this lesson, you'll know just how to do that. About a year into my illustration journey, I desperately wanted to find my style. I wasn't sure if I wanted to keep making art digitally or move into color pencils. I decided I needed a lot more practice drawing random mundane items. So I made a list of 100 items to draw in 100 days. Man was at a lot of work, but I learned so much. I gravitated more towards digital art and certain patterns of my work began to shine through. Obviously style development is never complete as an artist, but I credit this challenge with finding my style. Since then, I have simply been tweaking and improving. I didn't end up with 100 great pieces of work, but I made some great pieces that are still in my portfolio today. If you are hoping to develop your style, improve in a specific medium or subject or create a new collection of work, creating your own personal challenge will help you with these goals. Keep your artistic goals in mind as you're deciding on parameters. Here's steps for creating a challenge. First, come up with a theme. You can choose something as general as florals or as specific as woodland creatures wearing hats. I have a whole list of themes you can download in the notes of this lesson. After that, you'll come up with a duration and frequency. Having a plan from the beginning helps you stay consistent. You can do a month long challenge, a 100 day project, a yearly project. You can do every day, only weekdays, once a week, anything. Be realistic, but also push yourself. This is a challenge after all. The next step is to come up with prompts. I find, at least for me, that the more specific you are, the better. Then each time you sit down to create, you aren't spending time thinking of what to make. You can get right to it. One trick for coming up with prompts is to simply Google list of spring flowers or list of school supplies. This is a great way to get started if you're lacking ideas. You can also use chat GPT. Here's an example of what I would say. I am a describe the type of artist you are, and I'm working on a drawing challenge too. Grow my portfolio, get better at using colored pencils, et cetera. The theme of this challenge is describe your theme. Please give me 20 or however many prompts reflecting this theme. I also keep a running list on my phone and in my notebook of things I want to draw, so I am ready with inspiration. Now, put this into action. Follow these steps and create your very own drawing challenge and share it in the class projects page. Then join me in the next lesson where I talk about hosting your very own community drawing challenge. 8. Hosting a Community Drawing Challenge: In our last video, we learned about creating our own personal challenge. But if more community and involvement is appealing to you, then you might want to host your own drawing challenge. This can be a super fun way to get involved with other artists. You can gain inspiration from others and expose more people to your work. By the end of this lesson, you will know how to successfully host your own Instagram challenge. Here's some chronological notes on how to host an Instagram drawing challenge. If you host a challenge, an initial consideration is whether or not you want any co hosts. I love hosting with others, as we can brainstorm proms together, and it usually draws in more people. If you are interested in finding a co host, simply DM an artist on Instagram. Tell them your rough idea for the challenge you want to create and ask if they want to participate. It might be nerve wracking at first, but I have done this dozens of times and people have always been nice. Feel free to ask a few different people to create a small group. I think the ideal number of hosts is three to eight. Once you have your group, you can create an Instagram chat, email thread, WhatsApp message, or whatever to share information and plan out details. Odds are, if you want to host a challenge, you have a theme in mind. If not, decide as a group. I have provided a list of theme ideas below if you need some inspiration. After you decide on a theme, pick out when and how often you want the challenge to run. Typically challenges last a month and are anywhere from once a week to every day. Now you know how many prompts you need, and you can start brainstorming. Coming up with fun and creative prompts is so important, as it inspires people to join your challenge. Prompts can range from specific to open ended. I personally like to do a bit of a mix. The goal is for people to have fun and get creative, but not be so open ended that people don't know what to draw. Alliteration or clever puns can help create engaging prompts. Similar to creating a personal challenge, I have a couple go to strategies for creating prompts. Good old fashioned brainstorming. Write down everything that comes to mind on paper and good ideas will surface. Use the help of Google. For example, you can search list of seeing animals or fun movie quotes and my personal favorite strategy, you chat GPT. Here's an example of what to ask Chat GBT. I am a describe the type of artist you are, and I am hosting a drawing challenge during describe your time period. The theme of this challenge is describe your theme. Please give me 20 or however many prompts reflecting this theme. To determine prompts, each host can come up with abortion. You can all make a big list and vote on favorites, or you can just talk it out. Be willing to compromise and have fun. Then you'll choose a hash tag. Make sure it is unique enough that it will only be used for challenge entries. Next, you'll need to make a post sharing the prompt list. Here's some examples of challenge graphics I have used in the past. You can do a static post or a arausel. Make sure all the info is easy to read. Things to include in your challenge post are title, hash tag, prompts, dates, hosts, and any other information or rules you feel relevant. For example, you can provide a color palette to be used for the challenge, specify a certain medium or have an emphasis on surface patterns. Once you've done this, share about your challenge far and wide. Post on Instagram a week or so before the challenge starts. Share about it in your newsletter. Whatever you can think of, make sure to spread the word and give people enough time to prepare. Also, prepare yourself for the challenge. As a host, you'll often share your own interpretation of each prompt. Plan, sketch, and perhaps even complete your artwork ahead of time so you can be a participant in your own challenge. Lastly, remember to have fun. You might have other goals, but fun really is the whole point of a community drawing challenge. This might seem like a lot. So I shared a downloadable hosting challenge checklist below. Now that you have the know how, plan and create your very own community drawing challenge. Share the challenge graphic on socials and post it in the project section as well. Then join me in the next lesson where I talk about how you can be successful before the challenge starts. 9. Helpful Tips & Starting Success Strategies: By this point, you have chosen and created a challenge. Now I'm going to give you some tips on how you can set yourself up for success and keep a positive mindset throughout this process. Also, I created a list of all of these tips available to download so you don't need to worry about taking notes. Find the link below. Now, whether you were joining another challenge, completing a personal challenge or hosting your own, here's some tips to help you participate with the greatest success. While creating, be consistent with your time. Give yourself a time limit for how long you'll create. Do it at the same time every day, set a timer if you need to. This is particularly helpful for a challenge where you're drawing every day, such as 100 day project. You can also pair this activity with a habit you already have in your everyday life. So you can draw while you're drinking your morning coffee or give 5 minutes to create after you brush your teeth every night. Give yourself parameters. Choose a certain medium and stick with it. Pick a color palette. Will you only draw in patterns? Will you fill one page of a sketchbook? This will help you enhance your skills in that certain medium or particular subject matter. Be accountable. This is a really important one for me. Whether it's posting on Instagram or texting a photo of your work to a partner or even just checking a box on your to do list, make sure you have an accountability plan. Do some prep. Sometimes your goal will be to draw every day, but let me let you in on a little secret. Most people that participate in Instagram challenges have their pieces sketched out or already completed before the challenge even starts. So do yourself a favor and sketch things out ahead of time. This can make it so that when you sit down to create, you're not thinking of what to draw and you're ready to just get started. Be realistic. It can be fun to say, I'm going to draw for an hour every day for 100 days. But also, that's a lot. Pick a practice that fits in with your life and start out small. Creating a mindset that is flexible and understanding can help you avoid burnout. I failed or dropped out of challenges when the commitment was too big or I had too much going on in my personal life. I often use drawing challenges to create collections. If you do this, I highly recommend sketching out your ideas beforehand. This makes sure that the collection is cohesive and you can include all of the elements you want. Give yourself grace, commit to staying consistent, but also recognize that life happens. You're not perfect, so don't be yourself up over it. If you miss a day or two, don't let that derail your whole challenge. Also, you aren't going to like everything. That's not the goal anyway. Just know that some pieces will turn out better than you imagined and some will flop. That's all part of the process. Remember your why. Was your original goal to get into the habit of creating every day? If yes, then a quick five minute sketch will help you achieve that? What's your goal to get better at a new medium? If yes, then even if you miss a day, you're still improving. Remember that even if you're not perfect, you can still be reaching your goals. And perhaps most importantly, have fun. This one is easy to forget. We can get so caught up in being perfect and checking things off the list that we forget the whole point. So keep things light and remember to enjoy the process. Now write down your parameters, decide how you'll be accountable and plan out your challenge pieces. Sometime later. Now you have planned and prepped and are ready to make some art. Join me in the next lesson where I shared some tips on how to remain consistent throughout the challenge. 10. During The Challenge: In our last lesson, you set yourself up for success. Now, I'm going to tell you all my tips for remaining consistent throughout the challenge. Throughout the challenge, make sure to share your work. Text it to a friend, share it on socials, send it in a newsletter. And if you're participating in a community challenge, don't forget to use the hash tag and tag all the hosts. Keep going. If you skip today, pick it back up. Challenges are challenging, but also you totally got this. If you are participating in a community challenge, actively build your community. Look at other artists' work, give them compliments or feedback. If you find a new artist that you like, give them a follow and maybe even send them a message. Building community as an artist is so valuable and it's really helpful to get and receive feedback. If you're hosting a challenge, consider sharing your favorite entries. I often do this by sharing them in my stories. Also, I try really hard to leave a comment on everyone's entry or at the very least like them. You can see all the entries by looking at tags and mentions under your notification section and Instagram. But also algorithms are always changing, so just try your hardest and honestly, best of block. Now that you've completed the challenge, you should be so proud of yourself. Join me in the next lesson where I share with you all the things I do once I've completed a challenge. H. 11. After The Challenge: In the last lesson, you completed your drawing challenge. Yeah. Now I'm going to share with you a few things I do at the end of every challenge. First things first, celebrate. Drawing challenges are indeed a challenge, and you should be proud of yourself. Get yourself a little treat, do something fun, or even buy yourself some new art supplies. It's important to take a minute and celebrate before you start the next thing. Reflect. What about this challenge was successful? Where did you struggle? What could you do better on next time? Did you like the work you produced? Share your work. Hopefully you at least end up with a few pieces you like. Put them on your portfolio, share them on an Instagram recap, or send them out in your newsletter. You can also let people know that your art is available for licensing or post it on a POD site, so people can buy your art on products or prints. If you are hosting a challenge, also consider posting a recap of your favorite entries. This can be an Instagram carousel or a newsletter feature. Now that you've celebrated, reflected, and shared, upload some of your favorite pieces to the class project section, and join me in the next lesson where I wrap things up. 12. Bonus Lesson: Miscellaneous Challenges: The typical challenge format includes a list of prompts and dates. But there are also a few challenges that do not fit this format. One example of this is a challenge called Draw This in your style or DTIYS. This is a single piece created by an artist with an invitation for you to recreate it in your very own way. Here are some examples. You can find these by simply searching Hashtag draw This in your style or hashtag DT IYS. There are also ongoing challenges in which prompts are posted every so often. Some examples of this are still Here Still Life and Room Portrait Club. Some challenges are more open to your own interpretation. The point of reflect and grow challenge is to revisit and update past work. Artist Book Club encourages you to make book covers, letter quotes or create art from any books that you read. These are all examples of other drawing challenges that don't necessarily accomplish the same goals but can still be fun to join. Also, these can spark ideas for your own unique challenges in the future. Now that you know about some of these other challenges, you can pick back up where you left off. 13. Key Takeaways: You did it. Congratulations on completing your very own drawing challenge. Whether you joined in a community challenge, created a personal challenge or hosted your very own. It takes bravery and dedication, and you should be very proud of yourself. I hope this class broke down the process of drawing challenges and gave you confidence for many more in the future. Throughout the lessons, you learn to define your goals, decide which challenges are right for you, and how to successfully participate from start to finish. You should feel confident in your creative practice. Moving forward, you can now use drawing challenges to continue developing your style, building your community, and enhancing your portfolio. I would love to see the results of your own drawing challenge and give you feedback on your project. Upload your creations to the class page. You can also tag me on Instagram at BEE Underscore Creates or Follow Long for more challenges. One last thing. If you like this class, please share it. Write a review, post about it on social media, or send it to a friend. Thank you so much for being here. Have a colorful day.