Jim Wilson practiced law with the Legal Aid Society in Louisville, KY and Ann Arbor, MI before entering academia to teach law for more than 35 years. Among other subjects, he taught constitutional law, poverty law, legal history, and legal philosophy. He also led meditation sessions that were open to students, faculty, and staff. He started his newsletter, Hope But No Expectations, on Substack.com in 2021, initially writing about political and cultural matters. After he was diagnosed in 2022 with brain cancer (glioblastoma) and was recovering from surgery, he launched a new series, Cancer, Be Not Proud.