Wherever you are in the world, being in government is hard. Still, all sorts of progressives and radicals pursue high office. This century started with new people in groups winning state power in countries like Bolivia, where Evo Morales became the first indigenous president backed by a popular movement, Vivir Bien. In 2015, Greeks selected the progressive left block’s Syriza for the first time. This spring, I had a chance to talk with men who served in those administrations about their expectations, experiences, and what they learned about doing governance differently. Andreas Karitzis served with Syriza, Pablo Solón with President Morales.