So you are trying of dragging your cooler behind you by hand? Why not make an autonomous one that can follow you everywhere you go. Hacker House has shared a video that shows you how to do just that. Their Arduino Uno powered autonomous follow me cooler connects to your phone via Bluetooth and receives GPS coordinates to follow you.
The electronics are in the base, so you can carry your things with peace of mind. You are going to need a cooler, 6 inch wheels, 2 DC motors, and a few other components to complete this.