Why workcations don’t “work”

Block Island is a quaint and picturesque beach town off the Long Island Sound.

It doesn’t garner the attention of its neighboring hot spots (Montauk for the Panerai-flexing bankers; Martha’s Vineyards for the salmon colored pants and sock-less loafers). But it’s a tiny slice of heaven.

A short bike ride around the island will span its spectacular bluffs and two historic lighthouses. At the Sachem pond you’ll encounter gulls, swallows and other migratory birds.

Once back in town, you can grab a lobster roll (freshly caught!) and wash it down with cold 16 oz Narragansett tall boy.

The entire island feels like a time capsule. There’s a surfeit of tchotchke stores selling Block Island hats, mugs, hoodies and swag.

The rental houses all come equipped include DVDs, VCRs and CD players.

There’s no golf course. (Gasp!)

There’s no Starbucks. (Double Gasp!)

And there’s also no high-speed Wifi.

Yup, an entire island where it’s impossible to make a video Zoom call. (Like I said, a little slice of heaven.)

Which leads to some very strange behaviors from knowledge-workers-who-can’t-seem-to-disconnect.

They all congregate to a not-so-secret hot spot: The Block Island Public Library.

You see, the Public Library has “fast” WiFi. (Fast = I can access my Google Drive.)

It’s the only place where you have a shot at seeing your boss’ familiar digital face.

Ant this turns the library into a Hunger Games arena.

There are bankers circling the parking lot, hoping to hit F9 on their financial model from the comfort of their air conditioned Cayennes.

There are entrepreneurs scrambling to upload a blog post, while snagging a spot under a tree to avoid the pounding rays of high noon.

And while the competition for bandwith is fierce, these WiFi hogs are united by a common goal: To be done by 5pm.

Yup, at 5 PM the library staff literally pulls the plug on the WiFi.

Our week in Block Island is a good metaphor for the 2 month break I took from writing a weekly newsletter. And here are three lessons I took from this long-needed break.

The Zeigarnik Effect is real

It usually takes 3-5 hours each week to compile, write, edit and distribute the newsletter. And while it’s become second nature over the past 307 weeks, it turned out that this time estimate was grossly inaccurate. Why?

The Zeigarnik effect.

In the article Hundreds of Ways to Get S#!+ Done—and We Still Don’t Wired’s Clive Thompson describes this psychological effect as follows:

When a task is unfinished, we can’t seem to stop thinking about it. We perseverate. Psychologists still argue about why; possibly it’s a kind of constant refresh to keep whatever’s pending from vanishing from our short-term memory, like putting something by the front door at night so you don’t forget to take it with you the next morning.

It’s the difference between holding tasks in RAM (short-term memory) and on a hard drive (long term memory).

The recurring and repetitive nature of the weekly newsletter had crept into my RAM and was consuming mindspace far beyond the nature of the task.

Only a break could help me understand the true cognitive cost of this weekly activity.

Atelic reading is the bomb

The two month break also revealed another hidden externality: my reading list.

Once again, for six straight years I’ve been on a treasure hunt for Internet gems on how to lead a productive, examined and joyful life. The best five gems make it into an email that’s shared with our 30,000+ global community.

And that is just a rad honor that I take quite seriously.

But a two month break revealed that my reading list has been subconsciously guided by the responsibility of curation. My reading had become purposeful and outcome-oriented.

Herein lies a quixotic trade-off.

Does one read purely for joy? Without the pressures of learning, note-taking, repurposing and curation.

As a community of high-performers, it’s easy to forget that atelic (or non-outcome activities) are a rich part of life.

During the break, I read some juicy, moving and deeply reflective prose. I didn’t take notes. I won’t blog about it. Dang, I won’t even share the names of the books.

And boy, was that special.

Soft boundaries are problematic

The hardest part about the workcation was that I never set clear boundaries. (Actually, that’s the hardest part about entrepreneurship more broadly.)

While we were on the road for nearly 6 weeks, I’m certainly not in a position to take 6 weeks off from work.

So every day turned into a half work-day, half family-day – usually dictated by the constraints of du jour.

If we were on a flight, then I’d be wrangling our 4 year old.

When the kids were with grandparents, I ran around NYC doing meetings.

But one constraint put everything into perspective. No working WiFi.

And when I threw in the towel on the Library WiFi Hunger Games, something else emerged.

I finally gave myself permission to step away from the workcation.

And take a true vacation.

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