It is doubtful that A.A. Milne had read the Transcendental writing of Henry David Thoreau when he wrote and published Winnie-the-Pooh. Thoreau, like Pooh, lived alone in the woods with friends near to him but not overwhelmingly close. Thoreau lived frugally : eating what he gained by his own hand, building his own shelter, and walking about in nature studying the patterns of life and gaining insight.
Pooh also simply lives by simple means and simple rules, but Pooh is complex and often misunderstood. His naive, simplistic life is not one easily achieved nor easily enjoyed by just any inhabitant of the Hundred acre Wood. Pooh's life is without the worry of planting a garden and gaining materialistic success (Rabbit), the endless pursuit of useless knowledge to confuse everyone else (Owl),
the constant pessimism and depression that comes from to much interaction with unimportant worldly (Eeyore), and the nervous insecurity that is a result of an unsure character without a grasp on his true self (Piglet), Pooh is in fact a Transcendentalist, and a perfect model for children and adults who want a happy peaceful life in harmony with both themselves and nature, free of strife and materialistic worries.