by Robert Gillis
Published in The Foxboro Reporter 7/2004 and the Boston City Paper 4/2007

KEYWORDS: Big Dig, Boston, Boston drivers, Boston traffic, City, Dorchester, driving in Boston, Massachusetts, new job, traffic drivers, career change, city drivers

The city of Boston and I have carried on a love/hate relationship for many years. The love began when I was kid and we’d make the annual Christmas shopping trip into the enchanted city. Those trips into Boston remain some of my nicest childhood memories. Even in the 1970s, Boston was magical and exciting.

In the early eighties, I took a job selling papers for the Boston Globe, and for almost two years I was a daily fixture outside Woolworths. As Leonard Nimoy once said about selling papers in Boston during the winter, “That will teach you character.”

In those two years I enjoyed meeting a very interesting variety of people. I got over my shyness talking to girls by working there, and dated some of them. I had many regular customers, many of whom stayed to chat for a while. My favorite customer was Phillip Joe Kelley, who always gave me a 25-cent tip every day, and was one of the most interesting and well-read people I’ve ever met. There were many other very nice people, and of course there were the assorted weirdoes, nut cases, “flamboyant”, and just plane scary people. My personal favorite weirdo was the old woman who would stand on the street corner swearing like a drunk sailor at everyone for hours, then went home. It was an interesting career but I doubt it paid her very well.

I enjoyed the great summer weather and the girls in their summer clothes. We (my sister and friends) often biked from Dorchester to work at the Globe in the summer. I suffered through 1982, one of the coldest winters on record, wearing many lawyers of warm clothes and warmed by a lot of McDonald’s hot chocolate. In 1983, I finally decided I was getting a little too old to be selling newspapers and that I’d need a real job with better money, so I moved on.

As the years passed, I was often in Boston with friends and dates, to go to clubs, movies and just hanging around town, and I really started appreciated how beautiful the city was.

But as we all graduated from college and moved our separate ways, my trips to Boston became much less frequent. In over 16 years across three jobs, I was always in the suburbs — Billerica, Quincy, and Southboro — never working in Boston.

Boston lost a lot of its magic and charm when I started driving through it. It’s one thing to enjoy the relative ease of the T from nearby Dorchester, it’s quite another to be battling 93 north, bad drivers, and insane pedestrians. Sue and I had about thirty million arguments in Boston, and they all revolved around how much I despised driving through the city — the pedestrians were careless and crazy, nobody paid attention to traffic lights, the one ways were confusing even to someone who grew up there … And then things got worse with the Big Dig.

I reached a point with Sue that if she wanted to go into Boston, and we weren’t taking the T, I’d actually start whining in advance of the event — mainly because I knew parking would be awful, driving would be awful, navigating would be awful, and well, that would make the entire evening pretty awful.

I still don’t like driving in Boston. Allow me to clarify: I despise driving in Boston with the preternatural fury of a million exploding suns. Especially with chaos of the Big Dig, I hate driving in Boston. I. Hate. Driving. In. Boston.

But my love of the city itself (sans driving) always remained; and I always regarded it as a beautiful, historic metropolis. It was just the driving part that is awful.

From all this evidence, one might naturally conclude that I would never live in the city, and they would be correct. Too much hustle, too much bustle, too damn expensive, no feeling of community, and all that.

But what surprised me was my recent change of heart about working in the Hub.

Some months back I knew I needed a career change, and since I worked at my last three jobs six years, six years, and five years respectively, you can see that I’m not the type of guy who changes jobs very often. I’d made good friends at my last job and learned a great deal, but I needed a change. And along came the opportunity to work in Boston.

“No way!” I told my recruiter. “I’m not driving into that insane asylum every day!”

But my recruiter was persistent, talking about the company, the excellent opportunity, the company’s success, and how I’d be a good fit, so I relented and agreed to an interview.

On interview day, I deliberately got off a few T stops early to walk down Washington Street and pause for a few moments to stand at my old spot. Woolworths is now a Marshals but the lamppost where I stood is still there and just seeing that familiar view again warmed my heart. By the time I arrived for my interview, I was feeling good.

A few months later, here I am at the new job in Boston. I take the commuter rail in every day — something that has proven to be a very enjoyable experience. I’m reading (rather than listening to) a lot of books, and enjoy not having a 65-mile round trip daily commute. The people at the new job are great and I think I’ll do well here.

But the biggest surprise has been Boston itself. My office affords me a perfect view of Quincy Market. I am minutes from Downtown Crossing and Fanuel Hall. The variety of food and services available is incredible. The tourists, the hubbub, the big buildings, fountains, trolleys, and freedom trail, all of it — well, it’s just amazing.

I go out every day with new friends and co-workers to stop in one of the thousands of local eateries. Sometimes I walk through Quincy Market or Washington Street at lunch. And I find that I really enjoy the brisk walk to and from South Station every day.

At a recent company outing, one of the executives talked about an employee who was relocating to open a new office. “He’s decided to take a life adventure.”

I thought about that and realized that statement applied to me as well — the new job in Boston is very much a life adventure. A leap of faith. While I’m sure I’ll be less enchanted with the Hub during the blizzards and Arctic freeze, I know that I have come to a new appreciation for Boston and all its charms and a detente of sorts toward all its eccentricities, bad drivers and weirdoes.

I still despise driving in the city — my reasons for that are more evident now that I work here and will not change — but I’m not as, well, reluctant to give Boston another chance. In many ways, I feel like just as much a tourists as the families on the trolley tours.

Foxboro will always be my home, Dorchester will always be my old neighborhood, but surprisingly, Boston has turned out to be a very nice place to go to work. Of all the things I’m learning on this latest “life adventure,” this lesson has been the sweetest of all.