Beautiful Landscapes, Idly Painted

Is Inktober for me?

October’s coming up, and once again, I need to decide whether to do Inktober. 

For the uninitiated, Inktober is a popular ink drawing challenge started by animator Jake Parker in 2009, initially as a self-challenge to improve his own inking skills. It took off in a big way on social media (I credit the extremely good portmanteau). Parker also releases a daily list of prompts. Many of the artists that I know personally or follow online participate, in part of in full, with a variety of definitions of “ink”: anywhere from classic fountain or dip pen, to felt tip pen, to watercolor, to digital art and other media. 

I’ve started Inktober in various years (and never finished it). I’ve also bailed on many other “thing-a-day” challenges. It always feels like a failing, somehow, but I’m not sure that it needs to! 

What “thing-a-day” challenges are good for

I find thing-a-day challenges useful in specific circumstances.

Establishing Routines

A daily challenge can be helpful as a short-term “boot camp” to establish a habit or improve a skill, such as in Parker’s original use case. An example that I personally enjoyed was Kolbie Blume’s 10 Day Painting the Wilderness challenge. I found distinct benefits from painting daily. Daily practice discourages perfectionism via time-blocking and frequent clean slates; it reveals patterns through repetition; and it forces you to establish simple routines to integrate art into your daily life. Also, at the time I did the challenge, I was extremely motivated to learn new watercolor techniques through tutorials, so it was a great match.

Providing Structure

If I’m feeling unmotivated, lacking inspiration, or spend a lot of time each day wondering what to create, the structure of the daily challenges/prompts can be a relief.

Creating Momentum

Casual resolutions are easy to ignore, but the formality of a challenge – with defined rules, prompts, and social accountability – can create a momentum of its own that pushes me to work harder and maintain consistency. (And it helps if there’s a catchy name.) 

Community Cheerleading/Accountability

Popular challenges held at specific times can also have the benefit of a sense of community. By participating in the same project that others are undertaking at the same time, you can feel as though you are a part of something bigger. If people in your particular circle are participating, you can cheer each other on.

Why “thing-a-day” challenges fall flat

So if there are all these benefits, why don’t I do them more often?

Motivation Mismatch

A daily challenge for an entire month is a big undertaking. For something so large-scale, I need my own motivation, not someone else’s. Parker was following his own interests and desires when he invented Inktober, but I’d just be following the herd. It would be different if ink were a particular focus of mine at the moment, but at the present season of my life, I’m more interested in color. 

Opportunity Cost

Whenever you’re doing something, you’re not doing something else. Thing-a-day challenges tend to soak up all of my art time, meaning I can’t work on my own projects for an entire month! This is particularly painful in October, a month when I typically want to spend all of my time painting foliage.

Unmanageable amount of daily work

This is not usually the fault of the challenge, which is often designed to scale to fit various amounts of daily time commitment, but I personally find it difficult to scale the “projects” I take on to a reasonable size that can be completed in the time available. I tend to bite off more than I can chew, especially on a workday. 

Unmanageable duration

As a person with some level of time blindness, I can keep about a week, maybe two in my personal buffer, but a month might as well be “forever.” 

Following isn’t connection

I haven’t found challenges to be a useful way to make friends. The fact that another artist and I made art for the same hashtag does not connect us. I tend to make more genuine connections by following my own idiosyncratic path and running into others along the way, rather than forcing myself onto the popular highway.

Conclusion

Daily challenges work for me when:

  • Matched motivation: The daily activity matches my current motivation or I am not particularly motivated at the moment.
  • Low opportunity cost: I do not presently have other things I would rather be working on or that I would have to put aside for this challenge. 
  • Manageable workload: For me, this means that the daily project can scale to various levels of available time, with the smallest unit being extremely bite-sized. Also, the duration of the time period doesn’t feel like forever (forever = any more than 2 weeks).

Because these aren’t presently true for me for Inktober, I’m unlikely to participate this year – although I may occasionally do a challenge or two, especially in a social situation. What I will almost certainly focus on is my annual motivation: LEAVES.

Comments

3 responses to “Is Inktober for me?”

  1. Veronica Avatar
    Veronica

    Leaftober
    Day 1: Leaf
    Day 2: Leaf
    Day 3-30: Leaf
    Day 31: Spooky Leaf

    1. Sarah Avatar
      Sarah

      Yes. Aspen, maple, birch….

  2. Lynne Avatar

    Matched motivation for the win. The one success I have had out of many attempts to complete a challenge was the June 2025 30×30 Direct Watercolor challenge and it worked for me for two reasons:

    1. I was very interested in improving my ability to paint without first drawing even a light sketch. This got me started, but I’m not sure it would have gotten me through the month without #2.

    2. As the days passed, I could see my learning; my skills, namely my ability to see and create shapes in my painting, increased enormously. I’m not sure I would have completed the challenge otherwise. The motivation that came from seeing the “daily” practice actually work was incredible. Disclaimer: there were a few spells when I missed a couple of days and had to catch up, but I did!

    As a follow up, I have noticed that I continue to apply what I learned whether doing direct watercolor or sketching first. I do think the intensity created by the challenge had a greater impact on me than simply practicing the skill randomly. As a result it’s changed my perspective about and willingness to take on one of these challenges. Though a skill or technique may be the best fit for me. I’m not sure I’ll ever be able to stick with prescribed prompts. But I think I can do Inktober…I’ve been wanting to take a deep dive into a recently acquired fude pen…