This is one of the cool things about roleplaying. You get to make plans that no sane person would even contemplate, and have the expectation that they just might work. That alone is worth the entry into the world of tabletop gaming.

Transcript

Han: Right, here's the crazy plan.
Luke: Okay...
Han: I get hurled into the Sarlacc's maw.
Luke: Yeeess...
Han: It slices up my brain.
Luke: Um...
Han: And I die. Heroically.
Luke: Er...
Han: Luke, use the distraction to Force Jump off into the sand.
Han: Go for reinforcements and save the others.
R2-D2: That's beautiful, noble, and heroic. There's just one problem.
[SFX]: < eedoo eezoo eebloo bidoot >
Han: It's okay. I'll reroll as one of the reinforcements!
R2-D2: They're pushing Luke in first. Remember?
[SFX]: < doing ting doip-ding-spip zik-pik-jang bizz >
Han: Oh, yeah. I told you it was crazy.