An illustration of Mollymauk Teafleaf from "Critical Role".

Death (Reversed) — Something that should have ended but did not. 
Fool — New beginnings, a fresh start, optimism 
Wheel of Fortune — Destiny, meeting people due to destiny leading them to you
Lovers — Being with the people we love, who love us, and who make us whole
Star — Joy, hope, a bright future
World — A cycle is complete