Later on, reading water and being real about one's abilities takes years to develop. If there had been a standardized rolling format when I learned, I may have missed out on the last 20 swims in my novice phase. A person either has it in some form and develops it, or else they don't. You can see its presence immediately, but it takes years to nurture it into a style. Paddling instruction has been honed, almost to a science, by the strong schools and clubs we have around the country.
Many schools discuss the psychological aspects of learning, as well.
Whether you start with a club, school, or private instruction, you are limited only by the expertise and ability to coach of those with whom you paddle. I am happiest when I paddle in groups that have at least one person whose skill far exceed mine. I have stalled my learning when I quit doing this for a period. If you read books and the Internet, watch videos and are out with any frequency, you can become an advanced intermediate quickly.