Artober: The What, How, and What Happened
Table of Contents
I"m always excited by the arrival of October. Autumn is my favorite season; the cooling temperatures, the changing colors of nature, that feeling of the world slowing down, plus spooky season/witchy season, sweater weather and jackets… I love it! Where I live we get about two good weeks of real fall weather, and then it snows. Snow season is October to May, and I love the snow, but that short window of time forces me to be present for the season and take it all in.
October is also the month of art challenges! Inktober, Drawtober, Peachtober, inset-a-name-tober, there are so many different and uniques challenges created by talent artists all over social media. It can be a little daunting and overwhelming, so I thought I’d share the way I manages all the options and prompts this year.
The What #
What is Artober? #
I saw a stationary site use this phrase to describe the multitude of art challenges that occur during October and have adopted it, though some may just call it Inktober. Inktober, however, is a specific challenge with a specific list of prompts, so I didn’t want to use that title to describe the whole concept.
So, Artober describes the month of art challenges held by various groups and individual artists on social media. THe rules and specifications of the challenges vary; some are daily drawing prompts, some limit to a specific medium, and some are week long prompts that anticipate more detailed and finished artwork by the end of the time limit.
Inktober, created by artist Jake Parker, is credited with staring the tradition, the same way #mermay started the tradition of drawing mermaids in May. At the beginning of the month, a prompt list is shared on Instagram with the goal of doing one artwork a day inspired by the word in the list for that day. Intially, the challenge was to use ink only, but there is no rule that says you can’t use another medium now, and many artists with use multiple mediums (like me).
After Inktober became popular, other artists statted creating their own “-tober” prompt lists. The number of lists available to follow is overwhelming. Almost every artist with a community following will do their own prompt lists, and I think it’s great. It’s the reason I find it so difficult to choose just one list to do each year.
It is meant to be practice. It is meant to be fun.
But it can also be a lot.
The How #
How to Choose a List #
Since there are soooooo many prompts out there, it can be hard to choose just one. Some people like to stick with the original, or feel a pull to a specific artists prompt list, and that’s great. I wish I had that dedication and motivation, but I like variety. Personally, I find the official Inktober prompts don’t always inspire me the way I want it to, so I pick a few lists to have options to choose from.
This year, I chose these four;
- The official Inktober list
- Linktober, and Legend of Zelda themed prompt list
- Drawtober, a weekly whimsical fantasy list
- And the prompt list by artist @Drakofey.Studios on tiktok and Youtube
There are plenty of critics out there (or in our own minds) that will say trying to follow more than one list defeats the purpose of the challenges. I have seen and heard people who think week long prompts are also “not right” and not the purpose of the Artober concept.
To those people I say; Cool. You do you. Pick one list and have at it.
But if you’re anything like me, the idea of sticking to one list or one medium is both boring and daunting, and art is not meant to be either of those things. I understand the idea of pushing creative boundaries, but as a “pants-er” type artist, if I’m not inspired to create then I can’t do the work. The point of the Artober challenges is to “develop positive drawing habits”, like drawing everyday (quoted from the official Inktober website). So, I think; it doesn’t matter which list or lists you decide to use, if you are inspired and motivated to do even a little art everyday, then whatever you choose is perfect.
Setting a Goal #
Regardless of how many prompt lists you use, or whether or not you do daily drawings or weekly illustrations, or even if you stick to one medium or many, it is important to know what the goal of the challenge is for you, maybe in addition to trying to draw everyday.
Here’s a quick list of goals that might enhance the daily challenge:
- Study and improve skills by drawing a specific thing for each prompt (like anatomy, line work, composition, etc.)
- Only draw things outside your comfort zone
- Try or add a medium you’ve always wanted to experiment with
- Stick to a scheduled time or time limit for each day
- Post artwork everyday to social media, regardless of how good you think it is
My goal this October (2025) was to balance daily prompts in digital art with weekly prompts in paper art. I wanted to push myself to think less about the quality of the artwork and try for quantity, in the hopes of getting over perfectionism. I decided to stick to a specific schedule to accomplish that goal, which is difficult for me most of the time, because I find most deadlines to be arbitary. The challenge wasn’t so much in the inspirtation or motivation, but not letting myself get carried away in the details of any one particular artwork and sticking to the plan.
Choosing Prompts #
Once I had my goals and lists chosen, I had to get organized. I made myself a calendar to have a clear visual of all the available prompts and to track my progress throughout the month. You can see it above. Between the four lists I chose this year, I had near 100 total prompts to choose from! There was absolutely zero plan to do them all, so each day I chose the prompt that inspired me the most. (They’re highlighted on the calendar.)
After setting up the the calendar, I picked my prompts and spent a day doing sketches. Coming up with the ideas is the most tedious part of the process, so doing this helped to take away the anxiety and pressure of doing it everyday, so I could focus on the art part for the rest of the month.
What Happened #
An Example Day #
For October 14th:
- The Inktober prompt was TRUNK
- THe Linktober prompt was STATUE
- Drakofey’s prompt was GARLAND
- And the Drawtober prompt was day 4/5 for MUSHROOM FAIRY
Honestly, TRUNK wasn’t doing anything for me. Sure, I have ideas in mind for it, but I had zero desire to draw any of them. STATUE, on the other hand, was easy. The other option was GARLAND, so I decided I would combine the prompts and do one simple illustration. The result was the Goddess Statue from BOTW/TOTK with a garland around her head.
The reason I chose the easy option that day is because I was also working on MUSHROOM FAIRY as a paper art doll. I was so excited for this prompt since I had decided to try something new. I never made a paper doll before, with poseable arms and legs, so figuring that out was so much fun. The process wasn’t too far from my usual, just a small change to how and when the pieces came together. Since I didn’t need to think about a background, I found myself really enjoying the process.
I liked it so much that I have plans to make more for the holidays! I’m still working on the design concepts and ideas, but I’m thinking Nutcracker inspired! Sugar Plum fairies and ballerinas, which are both concepts I’ve wanted to try for years.
Hiccups #
I’d love to end this blog showing off all 25ish peices of digital and traditional art I created this month, but that’s not what happened. As they say, “Life happens when you’re busy making other plans” and that was so true this month. I set my goals, made my plans, and then health (both physical and mental) had other plans for me, along with some other hiccups.
I wasn’t able to stick to my schedule. I wasn’t able to draw everyday. I didn’t accomplish my goal.
Am I upset about it?
No.
I mentioned before that I struggle to stick to a schedule for creating art, and that’s mostly because I am the type of person that needs to feel my art in order to make it. I do things when I feel the most motivated. I could force myself to draw anything for any prompt, but it’s not going to be good if my hearts not in it. I know it’s not about making good art all the time, but to me, if it’s not good enough, then it’s not worth my time to do it. If I try, then get caught up in how not good it is, I’ll fall into artblock, which is worse in the long run.
That’s not to say I don’t try new things or make crappy art, because I do. A lot of it. I just do it within a space of comfort to not trigger the imposter syndrome.
My bigger goal, beyond the scope of Artober, is to keep myself motivated and consistently creative, which means breaking the rules sometimes. It’s unfortunate that I have to consider my health as well, which always throws curves at me, but it’s the reason why I have this particular goal, because it’s too easy to fall apart or give up when something isn’t going the way I expected it to.
At the beginning of the month, I was so excited and motivated for the challenge. I had the energy, I had the plan, and I was determined to push myself to finish a drawing almost everyday. I knew I wasn’t going to do it everyday, but if I could do it 5-6 days a week, I would be satisfied. However, without sharing all the personal details, a week after starting my grand plans I had to take a break and it threw off the rest of the month.
Even while I was struggling day to day, I kept drawing, but I couldn’t get past the messy sketch stage. I missed prompts I was most excited for and tried to catch up, but wasn’t able to. I tried to focus just on Drawtober (the weekly prompts) to remove the pressure of daily drawing, to give myself focus, but that failed, too. On top of the health stuff and usual distractions, I had to replace my iPad, which also caused a delay (even if it was a good one).
Mushroom Fairy was the last prompt I completed in October, and I made a total of 9 and a half artworks.
Reflections #
Now, that’s not nothing. 9 and half is more than I’ve done any other month this year, so it’s still a success. It also doesn’t count the dozens of sketches I did throughout the month. While the energy to complete the artwork was hard to generate, it did not stop me from wanting to draw and create, and I think that is an important result to recognize.
I kept myself consistently motivated to create through the hard days and the hiccups. Even if none of that art is ready to be shared, it was still made, and that is success.
I may not have been able to complete all the prompts I wanted to, but I did make art, improved in skill, and discovered a new concept to explore more.
That all sounds like a win.