This line comes from a poem titled, “The Road Not Taken,” by the American poet, Robert Frost (1874-1963). From it originates the English expression, “to take the road less traveled,” which is often used as a means of celebrating individualism.  

This, however, is a misinterpretation of the poem’s meaning in its original context, which primarily deals with ideas of emotional unrest associated with decision-making.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.
(The Road Not Taken, 16-20)

Frost wrote the poem in 1915, intended as a joke for his English friend, Edward Thomas. According to an exchange of letters between the two, the poem refers to frequent walks they would take through wooded paths while Frost lived in England for a time. When they came to forks in the trails, they’d choose one path and afterward Thomas would invariably lament not having taken the other, expressing that it could have been the more beautiful of the two. 

In his letter, Frost wrote with friendly banter, “No matter which road you take, you’ll always sigh, and wish you’d taken another.”

In the poem, the two paths are ultimately described as equally desirable options. In this sense, Frost explores and satirizes the notion of regret surrounding the unanswerable (and arguably unnecessary) question, “what if?”. Because who can know with certainty whether one way will turn out better than the other? So why dwell in the what-ifs and why not dwell in the beauty of the here and now?