My First Inktober Adventure

Inktober is a yearly illustration challenge started by Jake Parker in 2009 as a way to inspire himself to do a pen and ink drawing every day in October, no matter what. Since then, #Inktober has taken off across the globe with thousands of professional and hobbyist artists joining in and posting their works online. The rules are simple: make a drawing a day for 31 days, and post it with the hashtags.

Every year, Jake posts a prompt list with one word per day to get your drawing started. I wanted to keep to his prompt list, and except for a couple days where I diverted, pretty much did. I thought Inktober was going to be a challenge, and well, it was.

For some of these I was really inspired with the prompt and had a clear idea what I was going to do. For some others, I was just scrambling to get anything done so I wouldn’t fall behind.

Here’s the whole load of 31 drawings. To see each drawing’s process time lapse video, check out my Instagram page.

Day 1: “Swift”

Taylor Swift on a giant pile of money. I like to think this is what she actually does with her free time. If not, then she’s blowing it.

Day 2: “Divided”

This one was easy. I’ve never felt that our country is more painfully split in how we see each other and what we identify as what makes America “great.” It’s a sad time, and somehow the bozo who’s in the top spot symbolizes everything wrong with this country and manages to make it worse every day. Sigh.

Day 3: “Poison”

I’m not a great inker, it’s a whole skillset unto itself. Crosshatching, feathering, attention to line weight – it’s all business I’ve never really spent much time focusing on until now. Before Inktober started, I signed up for Jake’s “How to Ink” course at his SVS online art school. Picked up a few things which I used a lot over the month. Here I was just getting started applying what I ‘d learned with a good old fashioned tattoo-style skull bottle thing.


Day 4: “Underwater”

Years ago I toyed with a children’s book idea based around a giant whale called a “Tourbellion,” swimming the seas with a whole society that lived on its back. Liked how this one turned out.

Day 5: “Long”

Didn’t have much luck with the prompt on this one, so just went with a big gnarly hair study.

Day 6: “Sword”

At this point, I had to get a solid daily rhythm to keep the output steady. Found that waking up at 6:30am and getting a couple hours drawing time before work did the trick. Music was also key, and after seeing Hamilton in LA the month before, the soundtrack was on endless repeat and made for awesome drawing music. This one was based on a shot of Lin-Manuel Miranda with an especially “man with a mission” look in his eye. If you haven’t seen Hamilton by the way, don’t fail at life and go see that shit, it’s absolutely fantastic.

Day 7: “Shy”

Was starting to fall behind on time at the end of the first week. This is from a shot I found on Shutterstock of a shy-looking Asian school girl.

Day 8: “Crooked”

The Harvey Weinstein scandal was in full fury at this point, and every day his fall came faster and farther. Who knew that this would be the first in a long line of career killing dominoes throughout the whole entertainment industry! From a purely aesthetic standpoint, I was stoked to draw his fat ugly face, there’s a lot of detail in there to mess with. Placed him under the legs from the James Bond “For Your Eyes Only” key art from the 70’s.

Day 9: “Screech”

Some of these prompts I really struggled coming up with something fun to draw. The wife and I had just finished a rewatch of The Shining, so Shelly Duvall’s haunting face in pre-or post scream seemed to fit the bill. Didn’t really get to finish this one as much as I would have liked, think I uploaded right at the midnight mark.

Day 10: “Gigantic”

We have two cats, Popoki and Luna. Luna is a fat little package, and while not gigantic, she’s pretty damn portly. Tried to make her a giant creature in some English-style street. I really need to work on my perspective, I’m such a hack when it comes to accurate buildings, and it takes me a long time to get things somewhat right. The hair took a hell of a long time. I hope she appreciates it.

Day 11: “Run”

We were in the middle of a Stranger Things rewatch in anticipation for Season 2, so Dustin and the crew were top of mind. I’m iffy on this one, I’m not great at cartoon-type characters, he looks kind of like a big baby. On this one I started using greyscale filled areas, which I guess is Inktober “cheating” a little, but I saw lots of artists using Copic markers for this kind of effect, so that’s what I told myself as I cut some corners to finish.

Day 12: “Shattered”

Liked how this one turned out, even if the phone came out a little fat. Took a reference shot of my hand to draw from, and found tons of shots of people’s broken phones. Speaking of which, if your phone looks like this, for God’s sake, get Apple Care and get your life right.

Day 13: “Teeming”

I just couldn’t find a way into this prompt, everything that came to mind conjured up drawing loads of bugs, which I didn’t want to do, yuck. Tried going in reverse by drawing in white over dark grey for a rainy night scene.

Day 14: “Fierce”

Every October, we watch Trick R Treat, my favorite movie for getting in the Halloween spriit. This is Sam, the main character, he’s super cute until he jumps on you and slices your neck open with his cute little lollypop.

Day 15: “Mysterious”

What’s not to love about a good Dia De Los Muertos face? By the way, if you live in LA, you owe it to yourself to go to the LA Day of the Dead festival in the Hollywood Forever Cemetery, it’s wonderful, we try to go every year.

April and I rocking our Grady Twins from The Shining costumes at La Day of the Dead

Day 16: #MeToo

The “fat” prompt was wasn’t working for me so I went off script for this one. Since Alyssa Milano’s #MeToo hashtag showed up a day or two before, my social feeds were a painful and non-stop stream of friends and family who all had the courage to speak up about sexual harassment. One of the most powerful and effective uses of a hashtag I’ve ever seen, though I wish there wasn’t a need for it.

Day 17: “Graceful”

I just love jellyfish, and once I tried to draw one, found out they are a bitch and half to get right. Was running out of time on this day, so I did the light lines on grey approach again.

Day 18: “Filthy”

Early on, I found that early morning drawing sessions wouldn’t be enough to keep up, so I ended up doing a lot of drawing after work as well. This meant that April watched a lot of TV without me. She started watching The Walking Dead beginning to end, so as a soundtrack to a lot of these drawings I heard about a thousand knives splurtching into zombie skulls and about the same amount of inspirational Rick Grimes speeches.

Day 19: “Cloud”

This one started off as the atom bomb from Twin Peaks: The Return, but I started to hate it, and deleted it and drew this little guy. On my Instagram post time lapse video (click to the second frame in the album) you can see the first version’s aborted attempt.

Day 20: “Deep”

This was one of my favorites. A buddy on Facebook said that he’d totally get a shirt of this, so I started looking into making my own DTG (Direct to Garment) product page. I’ll need to redraw some of these at a higher print resolution for that to be ready, stay tuned.

Day 21: “Furious”

Another one of my favorites is Chernabog, the demon from the final sequence in Fantasia. Pretty happy with how this came out compositionally, but didn’t really nail the lighting and could definitely have upped the drama with a little more time.

Day 22: “Trail”

The final week. Home stretch. Wasn’t super stoked on this one, I’m nuts about Halloween, and overall this Haunted House scene doesn’t have any dramatic lighting or feeling of night time. I’ve found that effectively doing skies and big shaded areas in pen and ink style is really hard and time consuming. Did a lot of attempts on the sky to try to get the vibe right, but nothing worked so I kept it white.

Day 23: “Juicy”

I wanted to get my lovely wife April in here somewhere, so I used a reference photo I had of her after a visit to the smoothie shop. Of course, she wasn’t happy with the shot I picked ;)

Day 24: “Blind”

The pic should say it all. If you are visiting this page from another country, let me say that NO ONE I KNOW LIKES WHAT IS HAPPENING IN OUR COUNTRY, NO ONE VOTED FOR THIS LOSER, AND WE’RE ALL SO VERY SORRY.

Day 25: “Ship”

I like this one a lot. You can see the issue I was just talking about with the difficulty of getting cool looking skies rendered with crosshatching, can’t say I love the sky here — feels kind of Van Gogh-y out of trial and error, not some cool artistic choice, but still like how the composition came out.

Day 26: “Squeak”

Another prompt I had a hard time with. Can’t say I love Jake’s 2017 prompt list, but it is what it is. So here’s a black metal Mickey Mouse.

Day 27: “Climb”

Another Stranger Things inspired piece, this was on Season 2’s release day on Netflix, and we were getting ready for a binge. Poor Barb.

Day 28: “Fall”

As I was learning a ton in my daily exercise, I found that I just love the scratchboard illustration style. This is a pretty simple execution of a leaf, but I really want to learn more and get good at this style. Some illustrators do fantastic portrait renderings and I really want to get a better handle on this look in the future.

Day 29: “United”

The only regret I have on this one would be to have Freddie Mercury on lead vocals/piano. Should have swapped him for Tom Petty, but Tom had just passed, so he got a …pass.

Day 30: “Found”

The final days of Inktober collided with the weekend before Halloween, so free time was tight. Said screw it to the prompt, and went with a jack o’ lantern. Feel pretty meh about this one.

Day 31: “Mask”

I’d waited all month to do this one, did the undersketch as one of the first drawings in preparation for Inktober, and finally got to finish it on the final day. One of my favorite illustrators is R. Kikuo Johnson, who does amazing New Yorker covers. He combines a deceptively simple comic book style with astute narrative and storytelling, I think he’s just a master. This was me trying to do my best Kikuo.

Well, after hours and hours of hunching over my iPad, I made it! So happy I did, and I plan on jumping in again next year. Here’s the stuff I used to make it happen:

  • iPad Pro, 2nd generation 2017 model

  • Apple Pencil

  • Procreate App: A must for anyone making art on the iPad

  • Elevation Labs DraftTable: I LOVE this — an adjustable stand so the iPad sits perfectly solid. Dig it so much I bought two, one for home, one for the office.

  • Two-fingered drawing glove: The iPad has perfect wrist-rejection, but this glove makes drawing super smooth and keeps the screen from getting smudgy.

Thanks for reading, and thanks to Jake Parker for starting this amazing movement, and to all the artists all over the world who inspired me every day.

Steve Isaacs