Well, not so much the poem itself, but the concept of taking the road less traveled.

Seems “Two roads diverged in a wood, and I—I took the one less traveled by” was a big hit in Scarsdale NY in 1983. Lot of students in my graduating class used it as their yearbook quote.

Which is laughable, because Scarsdale was not known for producing divergent thinkers.

Scarsdale is a lovely, leafy suburb of New York City with one of the top public school systems in the country. And the property taxes rates to prove it. Scarsdale has a reputation for academic excellence, which could get your kids into the best colleges in the country. About 25% of my graduating class applied to Harvard (myself included) – and we all could have gotten in on our academic merit … if Harvard hadn’t been adverse to filling so many spots from just one town. They wanted geographic, athletic, ethnic diversity.

Frost’s poem became a way our graduating class of (largely) conformists (myself included), expressed their wish — in some small way — to have the courage to really take that road less traveled.

Which we often didn’t.

Like me, many went to good colleges, got good grades, made good friends, and pursued the safe kinds of careers and lives that made their parents proud.

[ASIDE: My yearbook quotes were Don’t we pay for all the things we do. (Ernest Hemingway, The Sun Also Rises) and It’s what you do with it now. (William Faulkner, Light in August). How wonderfully world-weary I was at 17!]

Fast-forward 40 years. I’m choosing to step away from a successful legal career. To retire from private practice at age 57, instead of sticking it out to 65. To stop chasing status and material accumulation as validation of my worth. Not the sort of thing that makes Mom and Dad proud. (Though they’re now dead).

The theme of taking the road less traveled came back to me, so I looked it up and re-read the poem. Really sat with it.

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

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
Robert Frost – 1874-1963

And started to cry.

I now saw myself at Frost’s crossroads. Wished I could see into the future which path would be the “better” one. Sorry that I couldn’t travel both. (As they say in Yiddish, “With one tuchis, you can’t dance at two weddings.”)

Sure, I could continue to slog away at the solo law firm thing. But a different way of life calls. While I’ve left the door open to come back (I’m keeping my NY law license active for now), I have doubts I’ll return to private law practice.

It’s taking a huge leap of faith. Right now, it’s scary and unknown and riddled with anxiety. But I have a sneaking suspicion that years from now, this transition will be a great personal “war story.”

It will make all the difference.

First posted February 3, 2023