About four times a year for some years, Schmich and fellow "Tribune" metro columnist Eric Zorn wrote a week of columns that consisted of a back-and-forth exchange of letters. Each December since 1999, Schmich and Zorn have hosted the "Songs of Good Cheer" holiday caroling parties at the Old Town School of Folk Music to raise money for the Tribune Holiday Fund charities. On December 18, 2020, because of the COVID-19 pandemic, Schmich and Zorn held a virtual streaming event that was livecast over YouTube.