Answer:
Yes, if you present it as a job, a dog can learn that tasks such as cart- and sled-pulling and even rollerblading means it is time to work. There are no happier dogs than those that are given jobs. Most breeds were originally bred as working dogs and they still love having a task to this day. When rollerblading, it is best if the handler can get the dog to run beside them.
During specific times the handler can allow the dog to pull them, for example, up a hill. However the handler must be able to get the dog to fall back beside them on command. It is important that the handler is in complete control. The human needs to show the dog leadership before, during, and after the signal is given to pull, showing an air of authority. The dog will see it as a job. When they are finished the task the dog needs to go right back into the heeling mode and the handler should enter any yards and or gates before them.