Stephen Colbert hit an unforeseen career roadblock when CBS canceled "The Late Show" in 2025 after 11 years on the air. At least publicly, the late-night host has seemed to take his career pivot in stride, a tack that's in line with some advice he gave recent college graduates in 2011. After working on comedy shows like "The Dana Carvey Show" and HBO's "Exit 57" in the 1990s, Colbert's career morphed into something unique in 1997 when he landed a role as a bumbling correspondent on "The Daily Show." After eight years, he left the Comedy Central series in 2005 to star in something of a spiritual spinoff, "The Colbert Report," playing an exaggerated, conservative version of himself. In fact, this next phase of Colbert's life perfectly symbolizes his advice about dreams.