A system is provided to exchange information between a computer and a programmable portable information device (PID) using a standard memory drive, such as a 3.5" disk drive or a PCMCIA port. The PID has a protective encasing with a form factor that is physically compatible with the computer memory drive. In one embodiment, the portable information device has the form factor of a 3.5" memory diskette, while in another embodiment, the portable information device has a form factor of a PCMCIA card. The portable information device includes a keypad and a flat panel display provided on the exterior of the protective encasing, but within the form factor so as not to interrupt the insertion of the portable information device into the memory drive. The uniquely configured portable information device can be inserted into or removed from a standard computer memory drive. When inserted, communication between the portable information device and computer is automatically initiated. The PID receives executable instructions and/or data from the computer via the computer memory drive and transfers other data back to the computer in the same way. This permits the computer and PID to simultaneously update each other's data with the most recent scheduling information. When removed, the PID has its own power supply and is operable to organize tasks, remind the user of important dates, and perform any other functions of a personal organizer. The user can enter information using the keypad, or read scheduling information on the flat panel display.