When extending the leader or tape from a traditional tape measure over a large distance, a user situated away from the body of the tape measure is unable to determine the length that has been extended at the leading edge. Presented herein is a retractable measuring device in which the body of the measuring device is configured to compute and broadcast the amount of tape that has been withdrawn from the body to a receiver. The receiver may be located at the leading edge of the tape or comprise a secondary device such as a smartphone. Alternatively, the broadcast may include tactile, audible, or visual feedback relating to the distance that may be received directly by the user. Additionally, the retractable device may include an interface for setting a desired length and provide either the user or receiver with feedback when the desired length has been reached.