As school systems struggle to recover from years of disruption, new programs, policies, and nontraditional organizations that support innovation in the teaching role will need to grow to support all students' learning. But what is it like to teach in new ways? What are the advantages and drawbacks? What brought educators to these unconventional roles and what might help them stay? This report addresses these questions through interviews with teachers who are serving in unconventional roles. Key findings include: (1) Across different contexts and instructional approaches, educators liked these unconventional roles; (2) The appeal came from increased autonomy and deeper personal connections, which cultivated a sense of ownership and investment; (3) There were downsides: autonomy could be isolating, collaboration could be tricky to get right, and innovation often meant more responsibility and less guidance from leadership; and (4) Educators expressed uncertainty about the sustainability of their unconventional roles, and many did not see themselves staying in the role for more than a few years.