The Boston Auto Tour: First Post

Boston, From Mt. Bowdoin (Dorchester)

Boston, From Mt. Bowdoin (Dorchester)

Hello World!

You’ve heard about the Boston Post Road, that colonial-era highway that forever changed the American landscape? Well, this is the first post for the Boston Auto Tour a new blog about shuttling around Boston as an Uber driver these past few years. The Wall Street Journal reported that Boston has the most congested roads in America.

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Of course, Bostonians don’t need to be told this. It is well known. Yet driving throughout the Boston area for years as a rideshare driver offers untold rewards in the form of spectacular panoramas and a plethora of heritage and historical sites almost at every turn.

There is a dual purpose to this blog.  First, it will detail my experiences driving for Uber and Lyft throughout Greater Boston the past four years.  Next, it will lay out the foundation for the Boston Auto Tour, an update and expansion of the classic and historic Boston-by-foot or Boston-by-trolley tours.  It will also be salve and salvation to harried Bostonians trying to tame the off-the-wall road patterns that exist in the city and suburbs.

It was relatively easy in 1775 for Paul Revere and his compatriots to ride their horses throughout the area, a time when redcoats were more fearsome than red lights or Red Sox.

The British of the colonial era would certainly have been stymied if confronted with today’s Boston traffic map with its notoriously winding roads and convoluted rotaries. Downtown Boston is a gridless maze of one-way streets that even the most seasoned cab drivers have trouble understanding.  This is perhaps why there are many public transportation options (bus, subway, commuter rail and now a large advanced network of publicly available bicycles and bike lanes).  Tourists from grid-friendly cities like Chicago, Los Angeles, or New York feel they are leaping from the griddle into the fire when they visit Beantown.

My years as an Uber and Lyft driver in and among these crazy streets have convinced me that it’s time consider a new tour, a blog and potentially a book to help to ease the pain of deciphering the gridlock that is Boston. Such a tour could be targeted toward students, tourists, business travelers, as well as new residents and seasoned locals. The sophistication of GPS systems now allows for auto drivers to understand greater Boston in the same way Paul Revere did with his horse using eighteenth-century road markers as his GPS.

In November 2013 I did something new.  I responded to an ad on Facebook titled, “Drive For Uber, Make $25/hr.” This seemed kind of interesting.   Not such bad pay for a part-time job.  At the same time, I had apprehensions about driving a cab.  I feared this would be a dead-end job for me.  It seemed kind of disconcerting to become a cab driver after plunking down X thousands of dollars and four years of life pursuing an undergrad degree.  In hindsight, this was smug thinking.  I decided to go for it.

How wrong I was.  For the past four years, I’ve come to achieve the impossible: the mastery of the difficult, rotary- filled roads, the same ones that have made aggressive drivers out of the most milquetoasty of Brahmins.

With this blog, I hope to share so that others can appreciate the incredible things I’ve seen and done.  It would (and will) make for a great book.  But there is so much to discuss, on so many different fronts, I thought the best way to lay it out would be simply to start blogging.  It seems the only way to pull all this together in a meaningful and organized way.

I began in February, 2014.  It took me a few months from seeing the FB ad to get registered and summon the courage to go out and give my first ride.  I’ll explain why in another post.  For the first three years, I drove sporadically.  I’d go out for a month, then I wouldn’t work for a year.  Then another couple months.  Then a few months off.

In April 2017 things changed.  I began working full-time.  And by that I mean driving seven days  week, roughly twelve hours a day on average.  I have worked about 80 percent of the past two years with this schedule.  Not to worry though, I take lots of breaks.  You can take a break whenever you want.  You can even work for 10 minutes in one day and then go home.  Total flexibility.

These days, I’ll go out to work around noon, then come home in the later afternoon and try to rest or take a nap.  Then I’ll head out again for the late-night shift.  It also helps that there really is no supervisor.  As drivers, we never really deal directly with Uber and Lyft HQ unless we need tech support.  It’s the strangest thing.  The companies are making billions but they never talk to their employees.  Great business model!    The riders are actually the supervisors. 

Needless to say, once you start doing this much work every day you get used to it and it becomes easier to handle.  You also learn that you can make decent money.  You just have to work long and hard for it. I know there has been mixed reporting about what ride-share drivers are actually making.  But if you work hard and work smart you can do okay. 

As a side note, when I first signed up for Lyft, which I began back in 2016, I was interviewed by a Lyft driver.  I'm not sure if Lyft still does this but they have an experienced driver come out to visit you when you sign up, to take your photo and inspect your car.  You can also have a little chit chat with the driver to help put you at ease about what it is you are about to do.  It is sort of like a mentoring program.  When I asked this person how much he made a week, he casually showed me his phone where his weekly tally to that point was listed.  It read over $2,000.  I was stunned.   In fact, it took me a lot of rides from 2014 through 2017 to finally think that I myself could attempt to try for a sizable number like this. But this was another reason I was compelled to think I could try driving full time, seven days/week and try to shoot for larger earnings.

Another thing happened in April 2017. I started taking notes.  Suffice it to say, I’ve compiled an enormous volume of yet-to-be-published urban observations. And not just ordinary stories.  But hundreds of interesting, out-of-the box stories from a wide variety of riders, locals and visitors alike, people from all over the world.

I’ve also compiled a long list of interesting seldom seen, road-related information.  Bad intersections, bad rotaries, hundreds of restaurant picks people have given me, a  huge list of secret and beautiful neighborhoods I’ve seen throughout the area.  And over a hundred spots around the area where you can see panoramic views of Boston, each one unique.

Geologically, Boston is in a basin surrounded by hills on all sides.  This is something I wasn’t aware of until I started driving all around it.   I’ve seen lots of interesting historical sites, downtown and in the suburbs, quirky and interesting sites and businesses. And I’ve seen so many funny, snarky and angry bumper stickers, I’m bursting out of my seat to share the photos. Boston is a town of messages. And not just paid advertisement messages.

I’m going to try to lay it all out here over time.  But you’ll have to bear with me, this will take a while. Welcome to the ride!