Hey! Thank you so much for sharing your thoughts about the game. I'm glad you enjoyed it and could picture yourself in the vibe.
Yes, running out of icons to cross out ends the game. The approach I was going for is to choose WASTE or WORK depending on how much coffee icons or boss icons you have left. So if you're running out of coffee (because you had to reroll a lot during WORK), it's better to go for the die representing WASTE (risking crossing off boss icons instead of coffee icons if you have to keep rerolling).
Anyway, thank you for giving such focused feedback because that means I didn't explain the concepts properly or there should be more icons preventing the game from ending early. Have fun during your next session!