🎄 Episode 102 – Christmas Detours, Seasonal Turns & One Very Bad Idea

Episode 102 is our official Christmas episode, which—naturally—means we don’t start with a Christmas song at all. Jonathan opens with a polished, radio-era track from Steve Winwood’s Back in the High Life period, proving once again that this show cannot go straight from point A to point B.Curtis then officially flips the seasonal switch with a thoughtful, modern Christmas selection from Andrew Peterson, setting a reflective tone before things inevitably get weird.In the category songs, Jonathan leans fully into ’Tis The Season with a beautifully restrained holiday pick from Shawn Colvin, while Curtis closes the episode by lighting a match and walking away—bringing what he argues may be the Worst of Christmas, courtesy of an unforgettable collaboration between Bing Crosby and David Bowie.It’s reverent, irreverent, sincere, and completely on brand—holiday music filtered through deep cuts, strong opinions, and just enough chaos to feel festive.Curtis Gross is a self-employed video editor.Jonathan Workman is an adult learning consultant based in Wichita, KS.---Make sure you are subscribed to Why Is This So Hard For You. Type Why Is This So Hard For You in your podcast provider, hit that subscription button, and leave us a five-star review. This will make it easier for other podcast listeners to find the podcast.---The intro music is the first 30 seconds of the Ornette Coleman tune "Song X" fed into AI software that attempts to output the song to a solo piano transcription. The outro music is the first 30 seconds of Sonny Rollins' version of the tune "St. Thomas" fed into the same software.