Reflecting On The Paths Less Traveled


If you’ve taken a high school literature class in the past 50 years, you’ll have bumped into Robert Frost’s famous line, “Two roads diverged in a yellow wood.”

Like most popular proverbs, the poem has crystalized into a cliché, stripped of not just its poignancy but most of its meaning.

It’s funny how this happens to wisdom once it’s been packaged in prose.

“Life is a symphony, not a race.”

That initially stopped me in my tracks, but now my eyes often slide over it with the familiarity with which I view my own name — now meaningless with habitual use.

When COVID-19 struck the West, I was on sabbatical from my job at a corporate law firm in London. I’ve spent the lockdown reflecting a lot on paths less traveled.

Take a second to re-explore Frost’s poem and you’ll see it’s conspicuously ambiguous. In fact, the poem’s widely considered to be the most misinterpreted piece of American literature. Frost states that, in reality, the paths he’s talking about had been “worn… really about the same.” The cryptic sigh of the protagonist’s future self suggests an ambivalence as to whether the path taken was even the right choice.

For me, that gets to the heart of the issue. I’ve always derived satisfaction from knowing that I’m on the “right” path. When it comes to life and career decisions, I don’t like feeling lost, and have often impulsively barged down well-worn paths, passing over more adventurous, meandering ones.

Like all insecure overachievers striving for impressive academics or elite job titles ending in “-er” or comfortingly large paychecks, you may find yourself like me—caught up in the packed salmon run of urban white-collar life. Instead of ambitious high achievers gushing out of universities and colleges in myriad varied directions, many of us put our faith in highways to lucrative careers. These roads are comfortingly dependable and well-signposted, unambiguously illustrating the where, when, and how when it comes to progressing our careers and lives. But not the why.

Instead, choosing the less traveled road will bring more loneliness and more uncertainty without the predictably constant signposts documenting your progress and encouraging you onwards. I’m drawn to reconciling the aforementioned concrete, fierce ambition to advance with the more ineffable serendipity of adventure. Will it lead to a more joyful life? I don’t know — I don’t think I’m even close to that supposedly peaceful compromise.

All I can say is that the best experiences of my life haven’t been on the highways. And while the choice not to follow herds of stampeding high achievers down these freeways fills me with a wrenching existential panic, those faithful roads forged by the wise and followed by the sensible are often there for you, should you wish to go back. Although as Frost memorably puts it, “way leads on to way…which leads on to way…which leads on to way” until you may doubt if you “should ever come back”.

If you truly put your faith in the notion that life is more of a musical ramble than a competitive sprint, maybe you’ll find that you’re not constantly reaching for or rushing towards the last note.

“Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.”