I am no stranger to monthly challenges to get me making something. Nanowrimo, Inktober, even Figuary. I'm surprised I haven't attempted Jamuary, yet, to be honest.

These themed months are a fantastic way to take your rear and put it in gear. Want to finally write that novel? NaNoWriMo challenges you write 50,000 words in one month. Want to draw more? Put pen to paper with Inktober, and draw something each day based on a prompt.

I've done both of these challenges, multiple times. I have nothing bad to say about either of them. After having completed a few of these I've gotten to thinking about how they work conceptually, the challenges brought by constraints, deadlines, streaks, community and discipline.


When looking at what I've done, constraints have nearly always helped me make things faster and better. I've punched this clock too many times in earlier writing, so I won't make it ring too much more. Our tools offer us infinite capacity (well, up to our computer's memory limits), and we are finite beings with limited capacity. You can have as many layers in photoshop as your computer can handle (more than your mind can handle, likely). Your digital audio workstation (DAW) can have hundreds of audio and midi tracks. You can undo and redo, anything, forever.

If you're someone like me, those infinite capacities can incapacitate you. Sometimes you need a little help drawing the line. For me, Something has to fence me in from time to time, otherwise I'll just keep roaming.


What thrills me about things like NaNoWrimo and Inktober (and other challenges) is that they bring people together toward a common goals that still remains personal and individual. You can cheer your friend on, who may even be drawing today's inktober prompt next to you, or you can browse the #inktober hashtag to see what the world is coming up with.

What's more, I think being part of an internet community striving toward the same, individual goals can help you get out of the unhelpful tortured/isolated/genius mindset. In these cases, it's hard to ignore other people with the same intentions. That can bring a certain humbleness and friendliness, rather than thinking it's you and your creative darling against the world.

Curiousity on Discipline

Completing a monthly challenge, or even just attempting it and making it part way can be a spring board to asking questions like: what if I took two months to do X? Four? What could I get done in a year? What would happen if I set a deadline for myself?

I'm going to try X for Y Time

Sometimes, when taking on a new habit or hobby, I can feel like I have to keep doing it for the rest of my life (especially if it's something that has been deemed by the external world—meditation, walking, better posture, journaling, whatever). Monthly challenges can help subvert those expectations we place on ourselves.

Previously, I've found it freeing to ask myself to try things for a week, or a month. I'm going to run an experiment and try meditating every day this week. Lots of people throw around things like meditation as a thing to do, but there's really no need to get started on the years long path to a healthy meditation habit. Why not try a week and see how I feel?

Monthly challenges do this to some extend, while, I think, remaining playful enough to be encouraging. I think they exist to be an antidote to grandiose expectations.

Graduating beyond the month

What happens when you complete your monthly challenge? You've written 50,000 words, or you've drawn an ink sketch everyday? I think this warrants a) a little celebration and b) some reflection. It's no small feat to dedicate yourself to your craft, whatever it may be, a little bit every day.

With reflection you can try to answer some possible questions such as:

  • Would I do this again?
  • Do I work well with a deadline?
  • What would I be capable of doing in 2 months? 4 Months? A year?
  • Does doing X task everyday make my life more or less stressful, or the same?
  • Did I enjoy doing my craft alongside other people (even if they are spread around the world)?

Don't just wait for the month

For me, after completing two NaNoWriMo's, someone asked me if I would just write a novel (as in, regardless of it being November). At the time, I couldn't really answer yes, as much as I might have liked to. The reality was, that I needed some kind of challenge and constraints to make writing a novel happen, no matter how rushed or glued together it came out. At the time, the world was too big, my mind too busy, and my ideas to scattered that actually making a novel outside of the boundaries of something like NaNoWriMo was not easily conceivable.

Some of the above feelings are starting to change; I think without having done a challenge like NaNoWriMo, I might not have seen the possibility to think bigger.