Art Challenge

Why You Should Do an Art Challenge

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Have you ever taken on a month long challenge? Maybe it was to become more fit, drink more water, or participate in Inktober. Challenges are powerful for all realms of life and the same is for art. We are going to share some of our favorite art challenges, share some of the backstory of Inktober, and tell you the benefits of an art challenge and why you should make challenges a part of your life!

Our Current Projects:

Lee: Working on some fun little promos for his agent, and he is getting feedback and having different publishers look at one of his books.

Will: Just submitted the second round of sketches for Bonaparte Falls Apart.

Jake: Super busy with Inktober! Inktober now has several sponsors, which takes a lot of administrative work, looking over contracts, and providing content for them.

Also, he shipped Skyheart, went to New York and talked with editors about working on future projects, and built friendships and connections.

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Drawing Challenges

Have you guys ever done an art challenge?

Will created the Draw 50 Things Challenge, it’s a design challenge where you try and create an illustration that has at least 50 different recognizable objects in it.

Lee once did a 14-week long art challenge, painting a digital landscape every single day, 7 days a week. Which is a TON of painting!

Drawing challenge: you do something daily or you have a project you try to finish in a certain amount of time.

Take something you want to get better at and do it every day, for 30, 50 days.

Jake created Inktober, which is where you create an ink drawing every single day during October.

He also created the Draw 100 Somethings challenge, which is where you draw something and then draw 99 more different somethings, all within narrow constraints, such as 100 different dragons, 100 different pirates, 100 different animals, etc. The key is to not be too broad, the constraints will push your creative muscles!

Why You Should Do an Art Challenge

There are 3 main reasons:

  1. Improve your life, and become more creative.

  2. Improve your habits and develop your craft.

  3. Get attention and exposure.

It is so important that you do it everyday, at first it’s really awkward and it takes time to get in the rhythm, but eventually it becomes second nature. When you first try something, it’s harder and then when you do it again it gets easier.

Repetitive attempts drill it into you. You will become a better and more creative artist by the end of the challenge if you really do it justice.

While in college, Will got let into the illustration program on probation. He had to prove himself during the next semester to stay. He kept asking professors what he needed to work on and ultimately it was design. That’s why he made the Draw 50 Things Challenge, to help push people to sharpen their design and creativity skills.

Lee created the Slowvember art challenge. You create something every day for Inktober and it is really fast paced, then during Slowvember you slow down and spend time every day working to create and polish one amazing piece.

Lee is an advocate for slowing down and doing things right.

So many people can get paintings to 70 or 80 percent of where they need to be but it’s that last 20 percent that really pushes the painting to the next level and its that last 20 percent that takes the longest. Slowvember gives you the opportunity to push something to 100 percent!

Challenging Yourself in Different Ways

Inktober: you should have a vision for it. Think of how you can do it, have a goal.

Don’t do Inktober just do do it, but make it specific and have a goal. Be deliberate.

Don’t just swing at 10,000 golf balls, but have a specific target or goal you are trying to create, then swing for that. That deliberateness will help you learn and improve so much faster!

Maybe you want to do quick 30 minute sketches for Inktober with a goal to get faster at doing quick sketches, then that’s great! Just make sure you have a focused goal and you will get even more out of it.

Fhe vast majority of people who participate in Inktober are hobbyists, people who love creating but aren’t doing it professionally for their career. They come from all walks of life, from middle school to adults, who all like drawing and being creative. Proportionally there aren’t as many professionals. If you fall into that category then for you it doesn’t have to be good it just has to exist. You’re building a habit of drawing and you’re trying to build the creative mindset. It gets you thinking. After 7 days you start to run out of ideas, and you have to push yourself creatively. There is value in just doing it, even if it’s not amazing...yet!

Are You Allowed to Do It Digitally?
Do you think that the guy with the turkey feather guy got mad when the guy with the metal nib pen came and drew next to him?

Will: Art is art, the tools don’t matter. It’s about what you make and how you make the viewer feel.

The problem with digital is when you don’t understand the traditional medium and the look that you are going for. When you know how to do it traditionally, then you can recreate that feeling and look digitally.

Lee’s Challenge to Digital: Do half digital, and half traditional. That way you will get pushed and those two halves will begin to complement one another.

Jake was blindsided last year by Inktober controversy over digital vs. traditional. Jake lives in both the traditional and digital world. He sees digital as valuable and the best thing that has happened to art; and that tradition is valuable and the best thing that has happened to art, there wouldn’t be any digital without it.

Inktober was created to focus on linework, without the extra pressure of worrying about color. You can still do that challenge with a stylus, you can still make it simple and beautiful digitally.

There are certain lines you can’t do digitally that are easier to do traditionally, learning to create those lines digitally is a skill in and of itself. There is value in doing the Inktober challenge digitally. It’s a different skill.

However, there still are things to learn from stepping away from digital and doing traditional.

Jake did a post encouraging digital artists to do traditional, that offended some people. People took it as him saying that they wouldn’t be getting the full experience. However, there is value to both digital and traditional, they both have their virtues. Jake didn’t mean to invalidate people.

Jake took Inktober on as a personal challenge.

Lately Jake has tried to ink digitally more with the iPad and Cintiq, and saw how there is something special to digital, both traditional and digital are so useful.

Still, the drawings should be simple with just line work and maybe a splash of color, not full color paintings.

If you normally work digitally, try it traditionally!

Inktober, all about doing it daily and improving as an artist.

Be Creative

Will: Don’t worry about what others say Inktober has to be. You can try to be different. There is no Inktober police.

When people are saying you’re doing something wrong then you are on to something.

After Picasso got others to start doing Cubism, a Cubism group quickly emerged and they kicked him out, however now he is the only one that is well recognized.

You don’t want to be an “if only” artist. You don’t want to be an artist who can draw “if only” they have the right gear with them. You want to be able to draw with anything. You don’t need all this stuff.

Inktober for writers: There was a writer who writes a little story to go with each daily prompt, and there is a group of writers that have gotten together to share their Inktober stories. That’s great!

Well if Inktober means that you can just do anything, then it doesn’t mean anything. There is a reason for it, but you can be creative and do what you need to do.


Zebra, Adobe, Pentel, Blick, and Kingart are all doing Inktober contests.

There are contests. It could be that they are looking for traditional instead of digital or a dash of color.

If you are going to enter contests, be careful that they don’t own your work.

Pentel did a contest, they said that they own your artwork. They said that you could use it for anything they want to use it for. People were upset with it. Their lawyer looked at it and Inktober’s lawyer looked at it, and it has specific wording to be able to use that work to post it and share it on their channels, not to use to advertise on their products. They went in and adjusted some wording. Really be aware of what the contest rules are, just be aware.

If the contest is worth it, then maybe do artwork specifically for the contest for exposure.

Instagram, Facebook, Twitter has similar wording to these contests. There are some risks and things that you just have to deal with, that’s just apart of being an online artist.

The Power of Inktober

Jake never would have imagined that Inktober would have turned into what it is today.

He started the challenge to have:

  • Constraints,

  • Accountability, he tries to be a person who does what he says he’s going to do.

  • Wanted a way to get more exposure as an artist, and a reason for people to come to his art blog.

Inktober is still all about getting better at art, and getting people to want to come look at your work.

Inktober has changed a lot of people's lives, got them in the habit of drawing, and boosted their followers.

Inktober is like New Year’s, it’s a time when people say, “I’m gonna do it, I’m gonna make it happen.” It’s a line in the sand. Happy drawing!

Thank so much for listening!


Jake Parker: Instagram: @jakeparker, Youtube: JakeParker44

Will Terry: Instagram: @willterryart, Youtube: WillTerryArt

Lee White: Instagram: @leewhiteillo

Tanner Garlick: Instagram: @tannergarlick

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