The Real Meaning of "The Road Not Taken"
It's not about rugged individualism
It’s graduation season, that special time of year when young people wear robes while booing mentions of AI, and when I get to hear Robert Frost’s poem “The Road Not Taken” cited regularly — and almost always erroneously.
Here is the famous snippet that shows up at commencement:
“Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”
It is invoked as an ode to rugged individualism. You can picture the narrator, standing in the forest, staring at two possible paths. One is well trodden, filled with sunlight, leading to an obvious destination. The other is dark, bounded by gnarled trees. Where does it go? Only one way to find out.
The pep-talk implication is that the traveler decides to choose the riskier, less certain path, and that courage to diverge from the norm leads to success.
It’s a nice image, and often a good point in speeches—that young people should be willing to take risk rather than rushing to a known destination. It’s also not what Robert Frost had in mind, and I think his real point is even more timely.
If you read the poem carefully, you will see that there is actually no discernible difference between the two roads.
One road is “just as fair” as the other; travelers had “worn them really about the same.” Both roads “that morning equally lay / In leaves no step had trodden black.” There is no road less traveled. They’re the same!
The end of the poem does not actually depict the narrator looking back at a bold decision with pride. Rather, the narrator is projecting to a future in which they will tell the story of this choice as if it mattered, when really it made no difference.
The poem is about agonizing over meaningless decisions. Frost wrote it for a friend of his, Edward Thomas, who dithered over which path to take when they went on walks together, and then would later regret that they hadn’t gone a different way.1
Thomas was falling prey to Fredkin’s paradox: the more similar our options, the less choosing between them matters, but the harder choosing between them is. Thus, we’re liable to spend the most energy on the least important decisions.
Frost's poem dovetails with the work of the Nobel laureate Herbert Simon, who coined the term "satisficing" — a portmanteau of satisfy and suffice — to describe how, in real decision making, we can't actually optimize. We are not equipped to accurately evaluate all our options. We must settle for good enough. And, Simon, thought, we should be eager to settle for good enough.
Simon referred to himself as an ‘incorrigible satisficer.’ He bought the same beret from the same store, wore one kind of socks, ate the same breakfast every day, and lived in the same house for 46 years. He told his daughter Katherine that a person needs only three sets of clothing: “one on one’s body, one in the wash and one in the closet ready to wear.” As Katherine later wrote: “My father simplified his life in terms of his daily habits, thus eliminating the need to make little decisions about everything.”
Psychologists like Barry Schwartz, who extended some of Simon’s thinking, created a scale to measure how much of a satisficer or “maximizer” one is. (Today we might say “optimizer.”) If you have trouble making decisions because you’re worried that you might not be getting the best, you might be a maximizer. Robert Frost’s friend Edward Thomas seems to have been a maximizer, at least when it came to trail selection.2 He agonized over every decision and then regretted it no matter what he chose. The work by Schwartz and colleagues found that, when it comes to contentment, it is usually bad to be a maximizer.
Maximizers tend to be less happy with their decisions, and their lives, and more prone to regret and to comparing themselves to others. There are some signs that behaviors related to maximizing are on the rise, at least in some parts of the world. As I write in Inside the Box:
“…a study of more than forty thousand students in the US, Canada, and the UK documented a dramatic increase in recent years in perfectionist tendencies. The biggest increase was in ‘socially prescribed perfectionism,’ the feeling that you must be flawless to earn others’ approval. Combine the ability to compare oneself to the entire internet with a massive increase in choice, and it’s a recipe for dissatisfaction. If, that is, we don’t behave like Simon, and choose when to choose.”
In the abstract, having more choice so that you can find the best of everything seems obviously good. In reality, it’s often not the case. Let’s call it the Edward Thomas effect. Again, from Inside the Box:
“When it comes to entertainment, it feels like more options should always be better, yet research shows that giving viewers many videos that they can flip between actually makes them more bored than if they simply focus on one. The mere notion that something better might be out there can spoil the experience of the moment itself. Perhaps unsurprisingly, large surveys in the U.S. and China show that young people have become increasingly bored since about 2010.”
The maximizer’s tragedy always reminds me of a short story by the Japanese novelist Haruki Murakami. In the story, a lonely young boy and girl meet on a street corner and immediately recognize that they are perfect for one another. It’s a miracle. They walk to a park bench, hold hands, and talk and talk for hours. “As they sat and talked, however, a tiny, tiny sliver of doubt took root in their hearts: Was it really all right for one’s dreams to come true so easily?” They come up with a test. If they really are perfect for one another, they can walk away and they’ll inevitably meet again. Then they can be absolutely sure that they’re the 100 percent perfect match, and will get married then and there. The boy walks off west, and the girl east. They really were perfect for each other, but, sadly, they never meet again.
In a world of endless swiping, I think this actually might be the more powerful commencement message.
Thank you for reading. If you’re interested in this topic, there’s a lot more detail in the last chapter of Inside the Box: How Constraints Make Us Better. It is now a New York Times best seller.
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Until next time…
David
David Orr wrote a book on this if you’re interested in a complete history.
Maximizing is a spectrum, and no one is a maximizer in all things.
Totally disagree with you here. You need to go deeper. It is about rugged individualism. There is a third deeper layer to interpreting the poem that scholars miss. The first layer is the superficial inspirational layer, as you point out. This is the sickly sweet high school graduation layer.
The second layer is regret disguised as triumph. Our need to confabulate and exaggerate the symbolism of our choices after the fact. Ok, hat tip to the psychologists.
But the third deeper layers says, but wait, everyone agrees that the unconventional path would in fact lead to a richer, more authentic life. Just because the speaker makes that up about his own past choice does not diminish the moral force of taking unconventional paths. And so the tragedy of the speaker's life isn't so much that he later confabulates, but that he regrets putting himself into a meaningless fork where both choices are the same. The convention wasn't in the choice. It was in the meaningless fork. And he could have done a better job hunting down truly unconventional paths.
The third layer introduces a meta-tragedy: not just the speaker's confabulation, but the missed opportunity to escape convention altogether by seeking out forks that aren't illusory or equivalent. The poem is lamenting a life where true divergence—and thus authentic growth—requires more aggressive pursuit of the unconventional. The "yellow wood" becomes a symbol not just of decision points, but of a tame, undifferentiated landscape that the speaker passively accepts.
Like all great American rugged individualists, Frost is a challenging one.
Fredkin's paradox is closely related to the concept of "regret minimization" in Bandit theory, which falls under Reinforcement Learning. As delta -- the gap between a given choice and the optimal choice -- gets smaller, the decision becomes harder and an agent may end up exploring more with marginally diminishing returns.