Some of the most effective random segues involve a song acknowledging the reality of a situation flowing into a tune that gives the listener hope. One iTunes shuffle mode pairing did this for me last month. Billy Joel's "Allentown," about factories being shuttered, segued into GrooveLily's "Weight Of The World," which reminds the listener that no one has to shoulder all the world's burdens at once.
It's comforting to remember during bad times that you can set your burdens down, at least part of the time, and look for silver linings and better days.