A little more than four years ago (Labor Day week 2001, to be exact), I started a vacation that led to a career change and a now-pending relocation to the East Coast, from my home of 25 years, Chicago. In my carry-on duffle bag for that week in Provincetown – along with my sunscreen and Speedo (it was Provincetown, after all), I carried a copy of The Outermost House. At this point, I can already hear the groans from old-timers – “Gawd, no, another one – when will they stop selling that book!” But, in that week, while sloshing through the moors-crossing shortcut to Herring Cove Beach, I became entranced by the tidal movement of minnows and gulls, pushed in and pulled out by the current’s flow and ebb. Reading Henry Beston in the dunes (among fauna of an entirely different type – and, if you’ve been to that end of Herring Cove, you know just what I mean) after making that crossing sharpened my appreciation for all that lay around and under Provincetown’s resort-driven hype.

I returned, wistful, to Chicago at the week’s end, and, that Monday, was back at my desk in a business and technology consulting firm that was then experiencing the pinprick that preceded the Internet bubble’s burst. The pop, itself, came the next day, Tuesday, Sept. 11. I was in Chicago, not New York City and not Washington, D.C., but, with planes still in the air, our office’s location on the 27th floor in a building diagonally across from the Sears Tower, our position seemed more than a little precarious. My coworkers and I, along with all the other consultants and traders and accountants and bankers, were evacuated from the Loop, as Mayor Daley’s order fast-forwarded that day’s rush hour from 5 p.m. to 9:30 a.m.

As was the case with a lot of people, that day’s events and the business downturn that followed made me think about what I really wanted to be doing – and where I wanted to do it. Those thoughts kept travelling back to Cape Cod. That Labor Day week trip was far from my first visit – I had spent a little more than 2 years as a kid living in Duxbury, with regular visits over the bridge. And, from the age of 9 to 17, I spent a wonderful four to six weeks with my grandparents in South Dennis, with near-daily seaweed fights with my grandfather in the water off the West Dennis beach.

Initially, my relocation plans were stymied by the absurdity of the Provincetown real-estate market, in which the $340,000 or so I figured my 1,200-sq.-ft. Chicago bungalow might fetch would only be a modest down-payment for anything I might find comparable. Then, accepting that the environment I loved stretched beyond P’town’s gilded borders, I started surfing the real estate ads for places like Brewster, Harwich, Chatham, Eastham and Orleans, and all the sudden, the dream seemed possible.

So, in a couple weeks, I fly out to Brewster, for a long weekend of community and home window shopping. My Chicago realtor is confident my home here will catch a buyer’s eye, and a couple of the Web home listings I’ve seen have me as anxious as a blind-date candidate looking forward to an introductory candle-lit dinner. But, I’m also beginning to get an idea of the culture shock that could accompany this process – from big city to small town, from Midwest to New England – and all the new concepts to master along the way. (For example – I’ve learned a simple two-word phrase that’s guaranteed to turn even the hardest-boiled city dweller squeamish: “septic system.”)

With my friends eyes now glazing over every time I begin describing the perfect little 3-bedroom Cape on a half acre I’ve just seen on realtor.com, I’ve turned to this blog to document this relocation (and the re-education that’s sure to follow). After all, there are millions of blog-surfing strangers who have yet to chime in on the differing personalities of Brewster and Harwich, and, I’m sure, are just itching to do so. So, I look forward to input and correspondence from those who wish to contribute them – and, perhaps, some new friends along the way.