All Hallows' Eve and the Four Last Things
The Last Judgment by Michelangelo As we observe Halloween (really a Catholic holiday that got "co-opted" by the secularists) and move into the month of November, where we traditionally remember to pray for the dead, here's an article from the National Catholic Register that explains a bit about where Halloween came from and why the tradition of the Church has always reminded us that it is spiritually helpful to contemplate our own death. More generally, thinking and praying about death, judgment, (purgatory leading to) heaven and hell (collectively called the Four Last Things should be a very frequent practice in the life of every Christian. Here's the section from the Catechism of the Catholic Church that addresses those important topics. The "Reader's Digest" version of that from EWTN is here.