100 Days of Creativity 2026

Is 100 days too much of a commitment? … What about if it could potentially lead to my dream job?

Normally I'm staunchly opposed to anyone advocating to "do THIS for X days in a row" to build up a habit because literally half of the population doesn't operate on a 24 hour cycle.

Like, where are the "do X once a month for 18 months in a row" challenges?

No where, because PATRIARCHY!

But back to my question.

Yeah, 100 days is probably too much to commit to something new.

Humans are complicated and it’s never been a matter of picking yourself up by your bootstraps, ignoring your self care, and pushing through no matter what.

That works for some people, but not everyone.

Definitely hasn’t worked for me when it comes to habit building.

And yet.

Somehow I stumbled into a 100 Days of Creativity Challenge hosted by Jessica Swift and it's been pretty good for building my habit of drawing things just for the sake of drawing and not for perfection and selling.

… damn it.

So, how does it work?

From my understanding, the concept is to reignite your relationship with your creativity by doing something – ANYTHING – creative as many times as you can within a 100 day window.

What sets this challenge apart?

Most art "challenges" on social media platforms usually have prompt lists and potentially lots of preparation involved before the challenge even starts if you want to successfully complete that challenge.

(If you’re not sure what I’m talking about, well-known challenges like Inktober - the drawing challenge held in October every year - often involve participants getting ahead or even finishing all of their drawings in advance, so that they can post something new on social media every day for all 31 days. It’s how artists are often able to “complete” the challenge and never skip a day, and why the prompt lists come out earlier than Day 1 of the challenge. They’re not done live, on a day-to-day basis. I remember being surprised and disappointed to learn this.)

This challenge, however, has NO prompts.

And it also came with a pre-warning that we are most likely NOT going to keep up our practice every single day, and that THAT IS OKAY.

The point is the attempt and intention.

You're doing it alongside other people who also want to "see what happens" when we allow ourselves to do creative things in a finite bracket of time.

Very low bar.

That’s what got me to join.

But just in case that's not a low enough bar for you, there's another challenge (that I didn't even know about until I joined the Circle community the challenge is hosted inside of) taking place alongside the main one: the SCRIBBLE challenge.

It goes like this: Literally just scribble every day and that can count if that's all you can manage. And there have been lots of scribbles! And celebrations!

I thought it was a genius to really drive home how low pressure it is to take part in this community activity for the next 3 ish months.

(Note: I’m not personally doing the scribble challenge, but it warms my heart to see other people doing it and feeling their creativity reignited after years of stagnancy)

The low bar I set for myself

My personal prompt for the 100 days is to pencil sketch in my sketchbook every day (most of the days).

It might be doodles, it might be ideas for my next art piece that I obsessively render for a full week.

I made myself a little sticky note for what I want to use the sketches for (hello my forever project manager brain – how to UTILIZE EVERYTHING), but so far I haven't had to refer to it.

There have been plenty of things to draw in the (at the time of this post) last 25 ish days.

Making it meaningful (so that I don’t get bored and drop out)

Why pencil in sketchbook?

I never really jive well with sketching digitally on a screen or a pen tablet.

I have tried all the pen tips and screen covers.

It only feels right when i do it in pencil on paper and then scan that sketch into procreate for cleaner line art and rendering.

Getting more ideas out of my head and onto paper is a great way to start the creative process and have lots of pieces on the art conveyor belt.

When I have more art concepts in front of me, I can come up with more ideas with what to do with the art, and I'm more likely to take the next steps.

A goal I have for myself this year is to get into merch design. But you have to have art to put on merch. And I’m not really interested in making more of the cutesy stuff that’s in my shop right now (though I am still proud of it! But I’m in my character design phase, apparently).

Can I share a secret with ya? (It’s not a secret, but I haven’t told many people because it still feels too big, which is unusual for me, miss “I HAVE A GOAL, WATCH ME PLAN THE STEPS AND TRAMPLE EVERYTHING ON MY WAY TO IT”)

A secret dream of mine

My pie in the sky goal is to be an illustrator and merch designer for Dropout.TV. Dropout (and specifically Brennan Lee Mulligan’s GMing on their D&D show, Dimension 20) is what got me through a lot of dark moments in the last couple of years of depression.

A skit on their improv show “Make Some Noise” made me go down the rabbit hole of what a Nat 20 Charisma means. I was in a deep depression around 2023 and found comfort for my loneliness in the balance of humor and deep topics from their actual play shows.

Then my brother died and my life felt like its own dramatic fictional show with a dreadful storyline I wasn’t allowed to stop watching.

But then! To cope with my life being ripped apart, I let myself start doing all the things I’ve ever wanted to do. I started playing D&D with strangers on the internet (and eventually in-person) and I learned why role play has been so life-changing (and life saving?) for me.

And now my whole personality is wrapped up in the TTRPG world.

But back to that pie in the sky dream:

To become a contracted artist for Dropout I’ll need to make some merch and art and get myself out there and hopefully make the right connections to get introduced to the right people.

The re-awakened strategist in me thinks it can happen.

But I gotta get past where I am now, sketching random ideas in a sketchbook, and start making things I feel proud to ask my friends to share.

That means I need a portfolio of examples of merch, showcasing what I can do for the company I want to work for.

Time for fanart plus original IP, and probably repeating patterns that bring a cohesive collection together.

I'm way more likely to (refers to sticky note) design a repeating pattern if I have little doodles and motifs to flip through, nudging me to take to the next step.

Also, one of my ttrpg characters is morphing into what I think will be some kind of short-form graphic novel series of illustrations (read: I think i am overwhelming both myself and my table with how in depth I'm taking his backstory and maybe the ttrpg format isn't the right place for me to pull this story out of myself. more details to come, but I have often been “too much” so I’m not too surprised at my predicament).

But, you know. It all starts with sketches!

So, ~100 sketches it is!

Putting up childproof gates (so I don’t get bored and drop out)

I learned something about myself from “daily sketching” challenges in Skillshare courses: If I don’t have a designated place to do my drawings, they will end up on random scraps of paper and napkins.

Those still count as being creative, and are valuable. And a nice way to showcase that creative ideas can strike at any moment, and the medium doesn’t matter, as long as you acknowledge the sparks.

But!

I’ll have the best of intentions to keep them organized, but I will LOSE at least some and I will also get overwhelmed because I won’t have a clean path of progress to look back on. Because of that, I will lose some of my motivation to continue.

So instead, I’m using a sketchbook. It’s gonna be filled by the time this challenge is done!

The Super Awesome Sketchbook by AnthonyWheelerArt

I got this particular sketchbook from Anthony Wheeler and to be honest, I'm not really doing it justice because this paper is NICE and meant for inking and markers. I have some guilt over that, for no reason.

Because it's my frickin' sketchbook and also Wheeler wouldn't approve of me feeling guilty over any of my art decisions.

But anyway.

The size of these pages is overwhelming for me.

I have the maximalist need to fill in all the space.

A "finish all the food on your plate," mentality, if you will.

So to get around all of that, I’m prepping each page with a label of what day it'll be for, plus I put a piece of washi tape down the center to split each page in half. That way I don't have much space to fill each day.

And hey, it's been working well for me! I counted out the rest of the pages and I think i have enough room in this sketchbook for 80 days of sketches. After that I'll either start my next sketchbook or go back and fill in the gaps.

(Because I must fill in the gaps.)

Wanna see more of my sketches?

This blog post will be updated (let’s face it — sporadically) throughout the challenge, which runs through the beginning of June, 2026.

[from Artist & Writer Rochelle Sanchez]

Thoughtful reminders emailed twice a month (on the 5th and 20th) about running your business in a way that actually fits your life. Plus behind-the-scenes stories, art drops, and the occasional rant, because have you SEEN the state of the world right now? Yeah, you get it.

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