A portable assistive listening system for enhancing sound for hearing impaired individuals includes a hearing aid and a separate handheld digital signal processing device. The hearing aid includes a microphone, a digital signal processor, a speaker, a power source, an ultra-wide band (UWB) transceiver, and a control system configured and arranged to monitor a status of the power source and a status of the UWB transceiver, to receive an input signal from the microphone, to selectively route the input signal for processing responsive to the status of the power source and of the UWB transceiver, and to deliver an output signal to the speaker. The handheld digital signal processing apparatus includes a UWB transceiver, and a digital audio signal processor configured and arranged to receive the input signal from the earpiece control system, to process the input signal to enhance the input signal and to output the enhanced signal to the hearing aid control system. The hearing aid and the signal processing apparatus communicate through the UWB transceivers.