iiinova — where your digital self keeps evolving

Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 03/10/2026

I grew up with just a PC and a Game Boy, but I think I turned out alright. Generated using: my9games.net/en

Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 28/09/2026

A tentacled commission from Quest Con Orlando: Lil' Monsta, one of the villains from Blood on the Clocktower. I played the game for the first time at the show. Great premise... but I am not great at social deduction! #bloodontheclocktower #lilmonsta

Black and white illustration of a bunch of tentacles coming out from under a man's bowler hat.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 23/09/2026

A dual commission from Quest Con Orlando: legendary fighters the Sword and the Mountain!

Black and white illustration of two warriors posing with their swords.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 22/09/2026

GAMEHOLE CON COMMISSION PREORDERS NOW OPEN! I'll only be doing a handful of commissions at the show itself, so put your order in early to guarantee a spot (and get a better price)! Message me for more details!

Graphic with details for Gamehole Con Commission Preorders.
Special preorder price: $65
4.5" x 6" b/w character portraits
Order today, pick up at GHC
10 spots available

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 21/09/2026

First commission from Quest Con Orlando: a Grung swamp bard! I miss drawing these wacky little guys.

Black and white drawing of an anthropomorphic frog wearing a cape and tiny bowler hat, playing a one-stringed, banjo-like instrument made of a pan and a board.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 11/09/2026

An Axe-olotl pin I designed for D8 Summit Charities. If you’re at Quest Con Orlando this weekend, pick one up at booth 808!

Photo of an enamel pin on a yellow lanyard. The pin is of a stylized axolotl wearing a helmet and holding a battle axe.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 10/09/2026

All set up for @questconorlando.bsky.social - find me at #709 in the Exhibitor Hall all weekend! I’ve got prints, TTRPG zines, coloring books, and, of course, my commissions are open!

Photo of me at my booth, displaying various books and prints I’ve made.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 04/09/2026

If you're inclined, share your b&w art if you see this post.

Sideview, cutaway illustrations of three train cars. Done for 321RPG's Sunrise Limited.

Isometric map of an extensive network of tunnels populated by goblins up to various shenanigans. Done for Planet X Games' Three Curses for Sister Saren.

Isometric illustration of a building with 31 rooms, each depicting something different. Personal project: Wimmelbildertober2020.

Isometric illustration of a building with 30 rooms, each depicting something different. Personal project: Wimmelbildertober2021.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 28/08/2026

New banner, hot off the presses! See it in person at @questconorlando.bsky.social in a couple weeks!

Photo of me standing next to a retractable banner featuring my name, website, and a drawing of a floating, tentacled eyeball wearing a pork pie hat.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 16/08/2026

Church Doodle Sunday! Featuring this week’s and last week’s two-pager. #churchdoodle

Sketchbook page filled with assorted ballpoint pen drawings.

Sketchbook spread filled with assorted ballpoint pen drawings.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 14/07/2026

A bunch of my game design pals just launched a bunch of great TTRPG projects today in an event called SideQuest, organized by @zacgoins.bsky.social. Check out all the projects here: www.kickstarter.com/discover/adv...

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 02/07/2026

Cover art I did for Sanctum of the Whispering God, a DCC adventure from @mazinga.bsky.social and @rpg-ramblings.bsky.social. Kickstarter live for a few more hours: www.kickstarter.com/projects/1580058713/sanctum-of-the-whispering-god-dcc?ref=3ly0fw

Illustration of a trio of fantasy adventurers secretly peering into a temple in which a group of robed figures are standing before a skeleton in a throne and a mysterious void appearing above an altar.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 22/06/2026

Moved my newsletter over the Substack to try it out. Check out the first issue here: skippinginfinity.substack.com/p/return-of-the-newsletter

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 10/06/2026

Setting sail in July as part of #SideQuestKS: the Gift of the White Elephant, a game of generosity, thievery, and inconvenient relics for Pirate Borg. Follow on Kickstarter: www.kickstarter.com/projects/skippinginfinity/gift-of-the-white-elephant?ref=jvbahu

Cover art for the Gift of the White Elephant: a game of generosity, thievery, and inconvenient relics. It features an illustration of a mammoth skull surrounded by various containers and loose treasure with a iron-banded chest front and center. A tattered cloth waves in the wind behind it all.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 07/06/2026

Something new is coming... what do you think is in the chest?

Black and white illustration of a mammoth skull surrounded by various containers and loose treasure with a iron-banded chest front and center. A tattered cloth waves in the wind behind it all.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 29/05/2026

The Purchakka, peaceful grazing creatures drawn for @darkspacerpg.bsky.social's upcoming Void Echoes 2!

Illustration of a rhino-like creature with six legs, one horn, and thick rolls of protective fat along its back.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 27/05/2026

The Huskborn, crystalline undead creatures, drawn for @darkspacerpg.bsky.social's upcoming Void Echoes 2!

A crystal-covered humanoid with glowing eyes rising up from sitting in a zombie-like fashion.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 21/05/2026

Gon, an enormous crystalline entity drawn for @darkspacerpg.bsky.social’s upcoming Void Echoes 2!

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 19/05/2026

The Chirrax, an insectoid ambush monster drawn for @darkspacerpg.bsky.social's upcoming Void Echoes 2!

Black and white illustration of a cockroach-like alien creature leaping out of the sand.

Linework of the finished illustration, before gray tones were added.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 04/05/2026

Holdo for Star Wars day, by special request from my wife. May the 4th be with you! #starwarsday #maythe4th

Illustration of Holdo from Star Wars, accelerating her ship towards her destiny.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 27/04/2026

I've been hard at work on a number of NDA projects lately, but I finally have something I can share! This is Cosaad Rashin, Togruta bounty hunter. Played by Brian in a #StarWars game.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 14/04/2026

Hey, #PortfolioDay! I'm Matthew, a Chicago-based illustrator working mainly in TTRPGs. I do covers, character/creature design, maps, the works! Portfolio: skippinginfinity.com

Cover illustration for Island of the Whispering God. It features a trio of fantasy adventurers on the deck of a ship as it is attacked by the giant tentacles of a kraken.

Black and white illustration of a large robot floating in space. It is made of several other robots, each based on a different animal. Created for the DarkSpace core rulebook.

Color illustration of an orc barbarian and elf mage looking at a catalog of magic items and pointing out their favorites. Promo image for Magika Nostalgika.

Color illustration of two mutated, humanoid creatures with round robotic heads and a third robotic head floating nearby. Created for Denizens of the Blood Sands.

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 31/03/2026

Commission of #Wolverine I did at #C2E2 for a guy I was on a jury with just a few weeks ago!

Black and white illustration of Wolverine sitting in a jury box, taking notes, mumbling "Yer guilty, Bub."

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Matthew Sargent 🔜 Gamehole Con A16 @skippinginfinity.bsky.social · 30/03/2026

Mega Mawile drawn during #C2E2. I should draw more #Pokémon. So many fun character designs to play around with!

Black and white drawing of the Pokemon Mega Mawile looking over its shoulder at the viewer, two busted halves of a Pokeball on the gound.

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