Jenna Shapiro woke up miserable the day after Donald J. Trump’s election in 2016. The daughter of Democratic activists, Shapiro had canvassed for Hillary Clinton in New Hampshire and worked on phone banks at Wesleyan, where she was a senior contemplating a career in teaching. “I felt like I hadn’t done enough, not nearly enough,” Shapiro said. “I never want to wake up after another election believing I hadn’t done everything I could for a candidate I believed in.” She woke up happy this year, having put off teaching to help run the Democratic GOTV campaign in Connecticut.