Rip Van Winkle’s biggest problem was his inability to take responsibility for his own life. He was a man who preferred to escape the burdens of his responsibilities rather than confront them. This led him to neglect his family and work, ultimately causing a rift with his wife, Dame Van Winkle, and leaving him in a state of social and economic disarray.
His inclination to wander into the mountains and avoid his duties illustrates a deeper issue: a lack of ambition and motivation. When he finally wakes up after twenty years, he discovers that not only has the world changed, but so has his own life. His former friends have either moved on or passed away, and his wife is gone. This radical transformation of his reality emphasizes the consequences of his choice to avoid life’s responsibilities.
In essence, Rip’s biggest problem was escaping rather than engaging with life, which ultimately led him to a lonely and uncertain existence in a changed world.