What dilemma did the speaker face in the beginning?

At the beginning of the poem, the speaker is faced with the dilemma of choosing which path to take on a diverging road. This is a metaphor for the choices one must make in life, often with limited knowledge of what lies ahead or of how a single choice will affect one's life overall. As one must often do when faced with choices in life, the narrator must decide between the more conventional, expected path, and the less common, less certain path. 

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The speaker is faced with a significant life choice: to take the more conventional (well-traveled) path in life, or to take the one that shows less wear, thus less certainty. He tries to "look" down the road to search for clues to suggest what it might offer, but a distant...

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The speaker is faced with a significant life choice: to take the more conventional (well-traveled) path in life, or to take the one that shows less wear, thus less certainty. He tries to "look" down the road to search for clues to suggest what it might offer, but a distant bend in the road obscures his view. This is a metaphor for life. We all have to make the best decisions we can make with limited information. The future is not certain, and we must take a leap of faith in choosing our direction. This is the conclusion that the speaker ultimately comes to, and he projects himself into the future and thinks optimistically that the less-travelled path will have been more rewarding. He places his faith in a less conventional path and trusts that it will make "all the difference."

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