iiinova — where your digital self keeps evolving

Olivia When @oliviawhen.com · 25/09/2026

Very happy with this joke lol.

Signs on a cardboard box: A yellow dog licking their lips looking at a cheese labeled ART under a box and stick trap. Under that is a few blue flowers.

Olivia When @oliviawhen.com · 25/09/2026

If you're in the Bay Area come check out IlloMart this weekend! TBH I may only doing these events so I can make fun signs.

Painted signs on a flattened box on a floral rug. The signs are an easel with "Olivia When" on a white sign and a seal holding a big pencil on their head.

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Olivia When @oliviawhen.com · 21/09/2026

Super cool event where they just put out pianos and let anyone come play. Very wholesome!

Several peach and blue marker sketches of a poodle with the hair on the top of their head tied up in a ponytail. A tea and a latte for here. And an ensemble group of teens playing the piano in the New Zealand area of the park. One person is playing sax, one is playing piano, another playing drums while sitting on the bench too.

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Olivia When @oliviawhen.com · 21/09/2026

Rainy flower piano weekend at the sf botanical garden! Feat @fivepaninis.bsky.social! 🌸

Marker sketch in blue, green, and peach with some pencil on top. A big conifer sitting behind a grand piano with an outdoor umbrella protecting it from the rain. A person with round glasses in a hooded jacket is playing Ready to love by Seventeen!!

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Olivia When @oliviawhen.com · 05/09/2026

The fountain pen inks mainly used this month were Sailor Manyou Hinoki and Rohrer & Klingner Helianthus. ☀️

Several ink swatch squares, rectangles, and shooting stars showing off the yellow and blue inks alone and blended together. A yellow and blue brush pen are to the right. Below is a little painting of a dog leaping with many shooting stars above them.

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Olivia When @oliviawhen.com · 01/09/2026

Plus an extra lost star dog. 💫

A floppy-eared dog with lighter nose and paws in shallow water with many wiggly stars or star reflections around them. They are happily wagging their tail at this phenomenon.

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Olivia When @oliviawhen.com · 01/09/2026

Doggust day 31: Carin Terrier 💐 Came back around to the prompts for the last day! A tiny terrier.

A vase of blue-purple hydrangeas. The water is blurry from wet on wet painting, and a tiny carin terrier (a pointy-eared scruffy orange dog) is peeking out from the right side of it.

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Olivia When @oliviawhen.com · 31/08/2026

And the 2016 version! Same medium, but with brush pen and white gel pen for the outlines.

A little floppy-eared dog wearing a backpack looks through a big telescope from under an ivy colored bridge. The are stairs to the left, and a plaque on the right that says "canis major". The sky has many dots of stars and a few small white shooting stars. The main colors are dark purple, maroon, grey, and a dark blue. There are thick black lines inked with a brush pen.

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Olivia When @oliviawhen.com · 31/08/2026

Time passes so fast, but every August I remind myself that there are lots of hours in a day to improve at anything I want to. If you're hesitating to try something, or get back into something ,just remember you could've already drawn a dog in the time you were thinking about it!

A dark arched doorway with many shooting yellow, orange, and purple stars filling the top half. A little floppy-eared dog with a backpack is looking through a telescope at them. The main colors are teal, blue, white, and yellow from two inks.

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Olivia When @oliviawhen.com · 31/08/2026

Doggust day 30: Canis Major 🔭🐕 This year is 10 years since what I consider to be my first Doggust, so I decided to revisit one of the pieces that was star themed since it kind of fit with this year.

A little floppy-eared dog looking through a telescope at many shooting stars from under a bridge. The bridge is covered in ivy, and the yellow and white stars are huge and flying down in front of the bridge. The main colors are teal, blue, and yellow from two inks.

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Olivia When @oliviawhen.com · 29/08/2026

Doggust day 29: Pâtisserie 🥐 I was on the fence about dachsbun until I saw one in pokopia and now I've seen the light.

A dachsbun is sleeping curled up on an orange cafe chair next to an orange cafe table. There's a white cup on a saucer on the table, and a tall rectangular planter with some monkey grass in it behind.

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Olivia When @oliviawhen.com · 29/08/2026

One more, with my fav big dog lycanroc.

A lycanroc sleeping in a muni bus shelter with two bags of groceries on the ground in front. The shelter has a wavy yellow orange roof. A herdier is looking off screen waiting for the bus.

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Olivia When @oliviawhen.com · 29/08/2026

Doggust day 28: Take the bus! 🚌🐕 Some dog pokemon to celebrate Pokemon Worlds being in town! Kinda biased, but all the dog pokemon are very very good and almost never miss.

A yamper is hopping off a muni bus. A little rockruff and riolu are looking out the window with their paws pressed against it.

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Olivia When @oliviawhen.com · 27/08/2026

Something I drew very early in the month about how seeing a dog feels. Thanks people walking and sharing your dogs!

6 panels in marker and messy pencil expanding on the previous 2 panels. A mix of different compositions, and alts with the artist as a skeleton yelling and the dog entirely yellow on yellow.

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Olivia When @oliviawhen.com · 23/08/2026

After looking at this community, random posts started to appear in my feed, and I really enjoy the out of context confusion it's added.

A post from the Pretend to be ants in a colony community.

Title: Ant 7546
Post text: guys I found this HUGE sandwich it could feed us all for days help me bring it back
3 comments, 12 ant emoji reactions, 13 weightlifting emoji reactions.

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Olivia When @oliviawhen.com · 23/08/2026

There are constant debates about bluesky vs twitter vs threads, meanwhile on tumblr 36,000 people are pretending to be ants in a colony.

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Olivia When @oliviawhen.com · 21/08/2026

I think we can go back, and I won’t have to be so nostalgic, but in the meantime I just wanted to say the time spent not using AI tools isn’t wasted, it’s remembered fondly by me. Ok thanks for reading! 💐

Many dogs are running or standing around, catching their tail , chasing a frisbee, carrying a flower, all tangled up together by their long winding leashes.

Text reads: "I enjoyed all the imperfect, inefficient time we spent together."

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Olivia When @oliviawhen.com · 21/08/2026

I feel sad I can’t make other people understand what I find endearing about unpolished things and human fumbling. I feel like people gave up so much it can’t even be properly accounted for, and for what?

A yellow dog is resting their head on a table peeking over at many rough drawings. There are lots of little dogs, some doing magic, some with health bars, one with a sword. There's a big sun, clouds, and grass to denote the environment.

Text reads: "I like every placeholder drawing even if you hate it."

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Olivia When @oliviawhen.com · 21/08/2026

When I think about AI (all the time everyday), I mostly feel extreme anger and buried under that, extreme sadness. I don’t think I have anything particularly new to say on this topic, I just wanted to try to reframe it for myself.

A white dog is curled into a donut shape sleeping. There's a yellow sticky note with donut drawn on it stuck to the dog. Below that is a yellow sticky note with an arrow pointing to the dog, just to emphasize we're talking about. Several more sticky notes are in the bg, probably past pranks.

Text reads: "I like the joke you spent 20 minutes crafting."

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Olivia When @oliviawhen.com · 21/08/2026

Doggust day 20: Some things lost to AI. 📝 #doggust2026

A yellow dog is amazed looking at a poster on a pillar that says "graphic design". Below is a close up of the poster. There's a yellow dog on it at an old computer an the text above says either "graphic design is my passion" or "graphic design my is passion." It's unclear, due to the graphic design. There are several pull tabs below that just say "help."

Text reads: "I like every weird handmade poster."

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Olivia When @oliviawhen.com · 20/08/2026

Why do they become max comfy 5 sec before you need to relocate them??

A siamese cat sleeping in donut shape on a fluffy blanket in a desk chair, sadly not doing my job.

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Olivia When @oliviawhen.com · 18/08/2026

Last two!! I think that's all of them!! These dogs belong to @shesaidsarcasticly.bsky.social and @kvrapcu.bsky.social!

A pale yellow, orange, and brown dog is sleeping somewhat folded up with legs by chest, smiling while sleeping. Their tail curls around below them.

A blue spotted curly haired dog is sleeping so cushioned on every side that they look a bit like a rectangle, or a bowling pin. Their look very happy about this.

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Olivia When @oliviawhen.com · 18/08/2026

And @mac-b5.stickimporters.com's Lumi! A last little meteor flying by.

A teal and purple finnish lapphund sleeping happily on a white bg with orange and blue stars streaking down overhead.

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Olivia When @oliviawhen.com · 17/08/2026

Two more! These are @darthziggy.bsky.social and @whelmedbunny.bsky.social's dogs!

A dog with dark ears is folded up in half sleeping happily. There are lots of purple paint splatters to represent their speckles. Painted in blue ink on white bg.

A little floppy-eared dog is resting their head on the arm of an outdoor chair in the sun. One paw overflows off the side under them. They have a serene smile on. Painted in blue ink on white bg.

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Olivia When @oliviawhen.com · 17/08/2026

Doggust day 16: Zzz. ☀️🌑 These are @infromthesnow.bsky.social & @bitingnclawing.bsky.social's dogs and cat! #doggust2026

A jindo-husky curled into a donut. Originally white, here she's painted orange where the sun is toasting her, and blue in the cool shadows.

A tabby in a harness giving a smooch on the head to a sleeping husky. They're painted with a dual shading teal-purple ink, and have lots of thin lines to show off their stripes and floof.

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Olivia When @oliviawhen.com · 14/08/2026

Just something silly off the sketches I accumulated over the week. Sleep well! Eat breakfast!! 💫🍽️

A blue dog waiting with open mouth about to eat a shooting star, and below, another white dog leaping in with open mouth to eat another shooting star.

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Olivia When @oliviawhen.com · 14/08/2026

Doggust day 13: Perseids 4. ☆₊˚. Catch! #doggust2026

A blue beagle-esque hound with their arms and legs stretched out jumping over a patch of green grass. They're trying to catch a yellow tennis ball, among many arches of shooting stars above.

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Olivia When @oliviawhen.com · 13/08/2026

And @eoulla.bsky.social's Koda. Immune to meteors. 💫

A floofy teal-purple dog is sleeping with his paws and tail all jumbled. Shooting stars are falling down and bouncing off him.

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Olivia When @oliviawhen.com · 13/08/2026

Some dogs with interesting sleep poses for today! @carinacraftblog.bsky.social's Blake on a quilt. 📐

A light blue dog with dark brown ears is sleeping at a right angle in the bottom right corner. A quilt is behind him, and many big shooting star shapes are going across it and him. Despite the L shaped pose, he is smiling happily in his sleep.

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Olivia When @oliviawhen.com · 13/08/2026

Doggust day 12: Perseids 3, starbeam. 🌟 With @sarahmills.bsky.social's Leo! #doggust2026

A boston terrier with a white face is sleeping tucked into a bed with his paw around a human-shaped plush toy. A beam of light filled with yelow and orange stars is falling on him. All the shadows are blue.

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Olivia When @oliviawhen.com · 12/08/2026

And @finnichang.bsky.social's perfect loaf Pixel! 🔭

A little pointy-eared pomsky curled up in a ball, nosed tucked under tail. Green, yellow, and blue shooting stars are curving above, crashing, and shooting across below. Ink on a a white bg.
Photo sent in by hype man @daysofcolor

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Olivia When @oliviawhen.com · 12/08/2026

@elizastein.bsky.social's Barney, who looks a bit like the earth. 🌟

A hound dog curled up in a ball sleeping, with blue, purple, and yellow shooting stars curling above them. The dog is painted in a light yellow, purple, and teal. Ink on a a white bg.

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Olivia When @oliviawhen.com · 12/08/2026

Doggust day 10: Perseids 2. 💫 With @umbellule.bsky.social's Pepper! #doggust2026

A blue-toned toy poodle sleeping with their head on a window ledge. Their sleepy face is reflected. In the dark windows are many big bright yellow shooting stars.

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Olivia When @oliviawhen.com · 11/08/2026

The first is based off an old sketch, and this one is @suzannedubpup.bsky.social's Dublin! 💫

A black lab mix with white face snoozing on a white bg with his legs straight and all the beans piled up together. Stylized yellow orange stars with trails are falling from right to left.

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Olivia When @oliviawhen.com · 11/08/2026

Doggust day 10: Perseids. 🔭🐶 Decided to do some dogs sleeping under meteors this week. #doggust2026

A peach and sky blue colored greyhound, sleeping in a position reminiscent of a folded up lawn chair.

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Olivia When @oliviawhen.com · 09/08/2026

Doggust day 8: Mail! I've been wanting to make something silly for my contact page for awhile. The frames were sketched digitally, painted traditionally. #doggust2026

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Olivia When @oliviawhen.com · 08/08/2026