The article explores how intentional instability may be defined as a quality of a learning environment, thus aiming to contribute to the discussion concerning the complex question of what constitutes a creative learning environment. The study uses interviews and observations from three different art academies’ learning environments as a point of departure. Five variations of intentional instability are discerned and discussed, and intentional instability defined as follows: By intentionally twisting what we experience as familiar a bit, thus adding some instability, we are forced to shift positions and experience the familiar in new ways, and it is in this gap created in the discrepancy between balance and off balance that new insights may be articulated.