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Yeah, I was afraid that would happen. I didn't want to just tell the player exactly what I wanted them to do, so that it felt like they figured out what to do—or even better, like they were rebelling against the orders of their boss.

I'd planned to have some friends playtest it so I could figure out whether I was giving players enough guidance, but stuff came up and none of them were actually able to help. I ended up just guessing and hoping.

Lessons for next game jam: Don't design for an experience centered around players figuring out what they're supposed to do unless you KNOW you can get playtesters before the end of the jam.

Yeah I think playtesters are important for exactly that, since you know your game, so you don't need to figure out what to do. Playtesters help to point it out. Good job still and it's nice you learned something out of it.