A method of operating a headphone configured to be removed from and placed in close proximity to a user's ear can include generating an input signal by an input signal generating device. The method can also include determining whether an insertion event has occurred based on the generated input signal and causing the headphone to operate in 5 a low power mode responsive to an absence of an insertion event determination after a first period of time. The method can also include causing the headphone to operate in an ultra-low power mode responsive to the absence of an insertion event determination after a second period of time that occurs after the first period of time, the ultra-low power mode having a lower power consumption than the low power mode.