You know those moments when a precious dream is shredded by an injection of unwelcome reality? This happened for me when I heard professional journalist Jake Tapper blow an interview on a nationally syndicated radio program where he’d been invited to pimp his new book about a serious issue. It went something like this:
NPR Host: This is indeed a serious issue, and it affects us profoundly as has been shown by recent events...
Jake Tapper: Yes, as I say in my serious and for sale book, some of the many consequential implications of the issue are ...
Small Child: Do you know where Mommy is?
NPR Host: ...
Jake Tapper: …
NPR Host: ... Uhhhh
Jake Tapper: ... I have to go ….
NPR Host: ... We seem to have just lost Jake Tapper …
Funny, right? Not for me.
You see, I live in Gloucester, Massachusetts, a historical seaport about 40 miles north of the Boston/Cambridge brainzone. For years it was a minimum five hours a day spent just getting to and from work downtown, much like those Tibetan monks who have to climb a Himalayan mountain every day to reach their monastery. Just replace “avalanche danger” with “30-minute delay due to wet leaves on tracks” and it’s essentially identical.
During those times, crammed between several hundred fellow commuters on a stalled train, I’d utter an oath to someday quit riding the rails, toiling for other peoples’ bottom lines, and create an independent gig for myself and maybe a few other super-cool, like-minded people. The pinnacle of this imagined life revolved around the perceived bliss of “working from home.”
So when the opportunity to leave corporate serfdom behind finally presented itself, I jumped. As if on cue, my life soon became a Jake Tapperian hellscape.
• • •
Years ago, my wife and I were foolish enough to have bought into that “attachment parenting” thing they were recommending at the time. As a consequence of creating an “unbreakable bond” between us and our children, we found you can never get the little bastards to “leave you alone” for, like, five minutes.
Even when they are slightly older, they still want to take up your precious time by, say, talking to you, asking for advice and wisdom, and showing you endless YouTube videos, some of which are actually hilarious and involve cats and hedgehogs and DID WE JUST SPEND THREE HOURS WATCHING BABY OWLS WEARING HATS HOLY SHIT I’M ON DEADLINE HERE!
Producing anything useful from home was obviously impossible, but I reminded myself I’m a self-directed mobile worker like the people in all those cell-phone commercials except, you know, dorkier. Like them I have a multi-sectioned backpack crammed with expensive wireless technology, and “I’m so all up in the cloud I need to file a flight plan with the FAA before I leave the house” would be a joke I’m trying to make, but I’m not sure if it’s working, really.
Anyway, assuming I could get anything done in the town where I live also turned out to be extremely wrong. Gloucester’s motto could be “cras repellens” (look it up, Latin fans). When my hipster cousins come up from the city and are all, “Wow, you guys really know how to do retro,” I am forced to explain that people here dress in flannel because they actually work outside.
Also, many individuals cycle, not to be cool or healthy, but because our Commonwealth’s court system has determined this is the vehicle they are still permitted to operate through process of elimination.
Overall, Gloucester is assuredly authentic and mostly charming, but if your household income is extracted not from the sea, but instead, the 24-hour, hyper-connected, data-infused global marketplace, working from here can be like trying to conduct laser microsurgery with a butter churn. Made of rocks.
Thus, presented below are all the ways I failed at living the digital life in America’s Oldest Seaport, presented for your infomusement:
The Hipster Coffee Shop
The natural location for the office-free worker, where the java flows nonstop and the vibe says “cool.” In ours, I once saw a patron set up a standing desk with an extensive set of external hard drives and a 27-inch HD monitor. That dude was clearly not from here.
Day to day you’re much less likely to see a fellow creative-class worker than my elderly aunt — it’s a small town — and her book group. She at first tries not to interrupt beyond vigorous waving because of my headphones and knows I’m jamming on my new thing, but initial resistance will be overcome by a need to connect her iPad to the network.
Also, there’s the constant risk of someone on one of my virtual teams messaging, “Let’s jump on a call.”
Taking a work call in the middle of a coffee shop is rude under the best of circumstances, but add the factor the espresso machine in there sounds like a stricken 747 trying to make an emergency landing at a monster truck rally, and you can see why this venue came up short as a long-term solution.
But if it’s all about the joe for you, try these:
The Lone Gull Coffeehouse, Gloucester: The coffee is second-to-none, great baked goods, folks hanging, reading and lap-topping; but it’s tough on the “don’t mind if I hog this table longer than the term of certain Pope’s” crowd.
Pleasant Street Tea Company, Gloucester: Yep, it’s a “tea company” but don’t let that fool you. There’s plenty of coffee. Good coffee. And the “monster” chicken pesto sandwich is not to be trifled with. The wifi’s good and if you’re inclined to recline, there’s a comfy leather sofa in the back. And, if you’re early enough, it’s yours all day.
Studio Crepe, Rockport: You wouldn’t necessarily go there for the coffee, but the room is the best on Cape Ann. The closest thing to a hipster coworking space we’ve got, and they encourage you to come and drain their wifi. Seriously. (They also found my wallet once when I lost it there, so I owe them a plug just for saving me having to cancel one zillion cards and get a new license.)
Dunkin’ Donuts, Everywhere: They’re ubiquitous, clean, and nothing says “I’m displaced” like sitting on one of the molded plastic chairs in the color of your favorite cake frosting for three hours. Fine for a late night “need to get the hell out” quickie, but long-term working from a Dunkies feels like you’re in a doctor’s office waiting room you can never escape.
• • •
Shhhhh. (The Library)
“You should go to the library!” a friend suggested. “They have free wireless and cubbies and it’s a purpose-built studious environment.”
Yes! The library is a great public service! We support our local library! But the problem is, again, the still-critical need for impromptu voice communication. At least at the coffee shop you could have a quick update with friendly team members who are bemused when your aunt breaks in with, “does it matter if I use capital letters?” No such luck at the library. Slightly worse places to take calls than the library are: 1) A wake, 2) Lined up for inspection by the senior drill sergeant, and 3) While the judge is speaking at your sentencing.
All four towns on Cape Ann have libraries. If you’re the “quiet type” try them all. Each is housed in a beautiful historic building. Just come to terms with the fact that, other than the staff, you’re likely to be the youngest — perhaps by decades — person in the building.
The Sawyer Free Library, Gloucester: Great location. Cool building. Plenty of parking.
Manchester-by-the-Sea Public Library, Manchester: More museum than library — though there are books — with a few cozy spots to set up shop. Plus, it must be by the sea ... it says so in the name. Free wifi.
Thomas Oliver Hazard Perry Burnham Library, Essex: First, why did Mr. Burnham need so many names? Second, it’s on the National Register of Historic Places, so there’s that.
Rockport Public Library, Rockport: All-in-all, a nice, clean building with a few nice workspaces and all-you-can-eat wifi. Not a bad thing that it’s kitty-corner to the Rockport House of Pizza. Not a bad thing at all.
• • •
Your Local (“Of course I didn’t spend my entire day at a bar, Honey!”) Bar
Feel free to go with your first assumption as to why this was a poor life choice, suffice to say: You know how you think you’re way funnier than you actually are after a couple of drinks? It turns out your “edgy” emails to clients challenging their outdated norms are much, much less clever also.
But if the 3-martini late breakfast/lunch/tea-time is your thing, try these:
Stones Pub (our top choice), Gloucester: There’s a booth in the back for impromptu meetings with local collaborators, the front feels actually pub-ish not like a restaurant where you have to be on display.
Magnolia 525, Gloucester: For our money, the truest “neighborhood bar” in the West Gloucester neighborhood. That means that everybody in there is working hard (not hardly working). They understand that you’ve got a job to do, and that you might actually do it better with a double Gin & Hate. They understand the working man.
Cala’s, Manchester: I once had a “lunch meeting” there. Closed the deal. Any questions?
Riversbend, Essex: Honestly, I haven’t been there. Yet. But I can totally see myself sitting by the window [enjoying an ice cold Bad Martha Flagship Ale and a platter of Wellfleets while I watch the sun set over the Essex River ] wrestling with tomorrow’s PowerPoint presentation.
• • •
Ah, The Park
One of the reasons my (remaining) clients tend to like me is I’m an “out-of-the-box” thinker. So, I thought I’d get out of the box. Literally.
On a nice day I pack up my long-duration Chromebook, phone, and a lunch and head into the great outdoors. I select a bench overlooking the harbor under a tree and get cracking. It’s then I learn the homeless are fond of chit-chat, which makes sense if you’re socially isolated and without anything pressing to do.
Folks keep coming over and, in nothing but the most well-intentioned way, ask me about my computer and what I’m up to. Considering I’m sort of on their turf, it feels impolite to try and brush off with, “Hey, I’m working here, m’kay?”
I roll with the distractions as best I can. At one point a guy comes over and starts slurring unintelligibly, so I smile and point to my headset. He thinks I mean a spot over my head rather than my ear. He looks up to see what he thinks I’m pointing at, but his extreme level of shitfacedness causes him to fall backward, trundling down the grassy slope losing his hat, one of his shoes, and the contents of his backpack.
After a few minutes of him all splayed out and not moving at the bottom of the hill I start to worry. But he’s snoring happily when I go check if he’s OK, so I head back to the bench and start packing my stuff.
The park = no good.
However, as Thoreau always said, a man needs fresh air (or something). If the great out-of-doors is for you:
Stage Fort Park, Gloucester: Grass, a gazebo, expansive ocean views.
Millbrook Meadow, Rockport: Because it’s there. (We’ve seen it).
Ravenswood Park, Gloucester: Just dirt paths and swamps, so not a great place to work unless you want to set up a makeshift hut and do it hermit-style. I recommend a squirrel pelt vest and a beard with twigs in it. It adds to the look.
• • •
Eventually I find myself on a woodsy dead-end, desperate for a quiet place to give a virtual presentation. Of course the police, well-attuned to any variations in the normal comings and goings of their patrol area, pull up alongside and I have to go on mute and explain what I’m doing and how I’m not there for anything drug related or to dump a body, ha ha. No sir, not at all.
The cop just rolled his eyes in the middle of my stammering plea of innocence, affirming I’m nowhere near cool enough to be a suspected criminal.
“You need an office, buddy,” he cracks, pulling off to go find an offender less fundamentally lame.
• • •
Hey, What About an Office?
Explaining to my wife I was risking prison to justify the expense, eventually I give up and rent a tiny office in a rambling historical building downtown.
This was great, for a while. I had my own space, could take calls, naps, and even hung some shower-liner panels on the walls to act as improvised whiteboards. But over time the physical surroundings of my new world headquarters began to deteriorate.
Water damage from a storm was never quite repaired. Removed hallway carpet went unreplaced. Heat refused to come on or go off with the seasons. The crack in the glass of the front door spread into a spiderweb pattern and eventually an official-looking “do not use” sticker was plastered over the elevator. A banister fell off the stairs and was kicked to the side. Mail and packages stopped being delivered.
Each week, more and more (and more), it came to resemble that building in Blade Runner where Harrison Ford’s character lived. I would hardly have been surprised to find Rutger Hauer sitting on a pile of junk in one of the empty rooms going on about “attack ships on fire off the shoulder of Orion.” The entire arrangement has a strong sense of temporality.
So where next, assuming I don’t wind up at a desk back in Cambridge on some kind of futuristic hover-blimp full of Virtual Reality setups and free, all-you-can-drink Kombucha? The new dream that’s supplanted my “work-from-home” vision has become one a group in Gloucester is actively trying to start: A coworking space.
If you haven’t experienced co-working before you really must try it. The idea is simple: shared open workspace, conference rooms, a few cozy offices, and separate areas for calls and meetings alongside essentials like wifi, a kitchen, and a semi-industrial caffeine setup.
The whole thing is set up for work. It’s like a cool startup office but everyone is from a different company and without the constant threat of layoffs.
The ones I’ve been to are chill in vibe and high in design, where most of the inhabitants are solo or in small teams (like so many of us these days). You find startups mixed in with folks who just need a place to work that doesn’t have the pressing demands of Lego and laundry pick-up, and others who need somewhere to give presentations and hold seminars. For the remote worker, it forces you to bathe and put on pants, reforging your relationship with the human race after living like a particularly filthy hermit with only houseplants and pets as companions.
If we had a coworking space here, I could work there a couple of days a week and spend the rest at my clients’ sites as needed, without my fledgling enterprise having to bear the major expense of a full-scale office. I could chit-chat with real people during lunch rather than scan the semi-racist Facebook posts of people I went to high school with.
It’s even more ideal than my work-from-home fantasy because it’s somewhere I will have no responsibility to vacuum, stock with paper towels, or wait for the cable guy to come sometime between 2 p.m. Thursday and when our sun exhausts its hydrogen fuel and expands into a red-giant, engulfing the inner planets. My aunt could even have her book group there.
I’m even willing to help set up the IT systems. The wifi password will be: “jaketapper” all lowercase, no space.
Alas, our coworking cupboard is bare, but there are a few, well, one, CAA (Cape Ann Adjacent) option:
Workbar @ Staples, Danvers: I’m not typically down with chain-anything, but these places popping up in major metros can be useful. If I have a lunch or later meeting in Cambostown sometimes I stop there, do an hour or two of work, print out some documents at the printer center at the Staples then head in after the traffic.