This quote from Mark Twain popped up on Facebook yesterday and that gave me food for thought.

Who hasn’t come to a decision about what to do with one’s life and made a choice that takes your future in a totally different direction? Who hasn’t thought back on what Robert Frost called “the road not taken” and wondered what life would have been like if only one had been more daring and courageous—taken the leap instead of playing it safe?

Who hasn’t wondered whether life would have been less stable and more exciting? Would there have been greater opportunity or less? Would one have accomplished more or been more constrained? Life is choice and we choose every day, creating alternative futures in our minds as we go.

It’s easy to think of that abandoned alternative life as better simply because there are no disappointments, restrictions, bad memories, or unpleasant experiences attached to it. Surely it would have been a better choice, wouldn’t it? Well, maybe not.

A Surprise Fork in the Road

We faced one of those choices early in our marriage. We had gone on vacation from our apartment in Brooklyn to Nantucket for a week to celebrate our first anniversary.  We stayed at the Westmoor Inn, then a bed and breakfast but now the Westmoor Club a private club for the One Percent. (Only the historic house looks like what I remember.)

The Westmoor Inn, now the Westmoor Club

We were talking to the proprietor, Barbara Holdgate, about what we did in New York City and my husband mentioned that he was an English teacher. Mrs. Holdgate was a member of the Nantucket School Committee and she said that the high school had an opening for an English teacher.

The school year was about to open and they must not have had had any candidates in the pipeline because she basically told him that if he applied for the job he would get it.

The kicker was that we would have had to pull up roots in Brooklyn and move to Nantucket in a week. That meant giving up our jobs there, giving up our apartment, finding a place to live on Nantucket, and having our belongings moved. We were kids in our early twenties and that seemed like a huge thing to do in a very short time. (Actually, it still does.)

Mind you, I hated living in New York City and would have loved the move to beautiful, scenic Nantucket. Seth was working in an inner-city middle school where violence visited frequently and “no child left behind” meant kids with severe learning disabilities mainstreamed in a class with regular kids and no aide to help out. Nantucket High School would have been idyllic by comparison.

But making a spur-of-the-moment decision that big and pulling up stakes in one short week was more than we could handle—especially when we had arrived with vacation on the brain.  We came to that surprise fork in the road and we chose not to make the move.  Was that the right thing to do? Was my life better or worse for not taking the leap?

Looking Back at the Road Not Taken

For many years I saw the option of living on Nantucket through the rose-colored glasses of wistful speculation. We visited the island every August for many years, until Nantucket turned into a suburb of New York City and lost its appeal.

Looking back on it now, however, I can see the flaws in the future that might have been.

• Nantucket is a very small island with limited options for full-time, year-round residents. Back then it wasn’t filled with the trophy mansions of millionaires and billionaires as it is now. But the only real industry was the tourist industry and that was really just getting started thanks to Walter Beinecke Jr. Years of the island’s deterioration were finally giving way to a prosperous future but the island wasn’t yet crowded.
  What could I have done to earn money? Even working for Nantucket’s only newspaper, The Inquirer and Mirror, would not have brought in much. There certainly would have been no opportunities like the stock options from start-up companies that helped me into a comfortable retirement.
• I might have met rich and powerful people, especially as the island prospered more number of them arrived year over year. But I would have been working in a service industry, not as an equal.
  During my career in high tech I met a lot of influential people, some of whom had a very positive impact on my life and my personal growth. Sure there were a lot of negative ones, too, and I have written about them at length in this blog. But even those experiences, difficult as they were, generated growth of a different kind.
• Without a career I might have had the time to write fiction but I would not have had the experiences that I put into the two novels that have been published or the two that haven’t. I also wouldn’t have met the person who gave me a recommendation that landed me an agent—critical to getting any fiction published.
• Most importantly, I would not have grown through the kinds of challenges I faced in my life. While I may have hated living and working in New York City, it made me a much more confident, well-rounded and sophisticated person than living on a tiny island would have done.
  And moving up in my high tech career, becoming a manager and then a director, taking advantage of training and meeting the challenges of companies big and small, was critical to developing into the person I am now. Through my career, I have also traveled extensively and seen parts of the world we never could have otherwise afforded.

Should we have done it and made the big leap? Maybe. Had we done so, I certainly could not look back now and even imagine the life I would have missed. Rose-colored glasses aside, I think things have worked out pretty well on the road we did take.