When I graduated from college, my parents gave me an emerald green Moleskine and a luggage tag decorated with an old map. The objects were a message. This blank book would hold my ramblings, my to do lists, and my ideas, as I set off into the wider world like so many before me. Writing in it, I felt connected to the travelers and thinkers of old, whose scribblings in notebooks just like mine, shaped my own understanding of the world.

Which is to say: I bought entirely into the Moleskine brand and its offer of the authentic, pen-to-paper literary experience.

The company, born in 1997, was inspired by the travel writings of Bruce Chatwin, who wrote gushingly in his 1987 book The Songlines about the black oilcloth-bound notebooks he would pick up at a boutique French papeterie: “To lose a passport was the least of one’s worries: to lose a notebook was a catastrophe.” He thought of these paper “moleskines” as the home for “the ideas, quotations, and encounters which had amused and obsessed me”—a conception that would be co-opted by the savvy marketers over at Moleskine. The brand claims Chatwin, along with Hemingway, Picasso, and Van Gogh, as part of its prestigious lineage of users, in spirit if not in reality. And it’s been hugely successful in convincing the creative class, from writers to startup founders, that its product—a blank, bound book made of thick creamy paper and a smooth, durable cover—is worth the expensive price tag.

“It’s a masterful bit of excavation of the human psyche,” the design critic Stephen Bayley told The Guardian in 2012 to explain the plain notebooks’ immense popularity. “The stuff you’re writing in it could be the most brainless trivia, but it makes you feel connected to Hemingway ... there aren’t many things you can buy for £10 that are the best of their kind. I buy them compulsively. It makes you think you are just about to write, for once, something brilliant.”

But Moleskine, a company whose ethos is so connected to the tactile, physical engagement with pen and page, has shifted its gaze toward the digital world. This week, Moleskine took a significant step toward that goal with the release of the “Smart Writing Set,” made of an aptly named “Paper Tablet,” smart pen, and app, which promises to preserve the hallowed communion between mind and paper while also providing the ease of online tools. Equipped with bluetooth technology and an infrared camera that tracks your every word, the “Pen+” transfers your scribblings from the specialized notebook’s grid in real time over to your smart device, where you can transcribe into typed text (depending on how neatly you write), edit, organize, and share your doodles and notes.

I recently got my hands on a test version of the “Smart Writing Set” and began using it for lecture notes and to-do lists. Watching my real life chicken scratch materialize magically on the screen of my phone was exciting, but the pen's girth is wider than I'm used to, and made my hand ache after a while. My paper notebooks—annoyingly unsearchable—often remain closed when I am done with them, but now I could find the Zadie Smith quotes I’d reverently inscribed with a few taps and a little bit of patience (it takes a while for the app to transcribe and search through everything you’ve written).

A screenshot of my handwriting in the Moleskine Smart Writing Set’s app

Not that the product itself is particularly new. More than six years ago, my colleague Jim Fallows wrote glowingly about Livescribe’s Pulse pen, which “registers exactly what sound you were hearing at exactly the moment you are writing a certain word, letter, or doodle,” as his “new favorite gadget.” Today, there are a whole host of smart pens out there, many of which require special notebook paper, use bluetooth, and record audio, just like the “Smart Writing Set.”

Over the last few years, Moleskine has gotten into the digital game in incremental steps, forming partnerships with tech companies that paired its notebooks with their products. The partnerships have allowed Moleskine customers to upload transcribable images of their notes to Evernote, take pictures of drawings that can then be edited in Adobe, print sketches that began online into a physical notebook, and use the Livescribe smartpens to instantly digitize notes. This update moves beyond that, creating an entire system that syncs effortlessly. The biggest thing the set has going for it is that it can pretend to be just another Moleskine™ notebook, maintaining the cultural cachet of pre-digital creativity—and the pretension that goes with it.

It’s easy to wax philosophical about the role paper can play in creativity, regardless of its veracity. But the physical notebook does offer an immediacy that an online word processor lacks: It’s organically distraction-free, an open space where your thoughts can roam. But Moleskine, which espouses the research-backed cognitive benefits of doodling and handwriting alike, isn’t trying to ignore the digital world. Instead, the company wants its customers to be able have their paper-and-ink cake and eat it too.  

“We want to stay in the warm side, the human side of technology. We strongly believe in the strength and in the power of physical gestures,” says Maria Sebregondi, the co-founder of Moleskine who currently oversees the company’s brand development.

But Moleskine’s true appeal has nothing to do with technology. Its notebooks tap into personal identity. To carry a Moleskine is to declare your values, that you are a person who believes in ideas, a conception fantastically lampooned in the satirical blog Stuff White People Like: “Since all white people consider themselves to be ‘creative,’ they are constantly in need of products and accessories that will allow them to capture their thoughts … [the Moleskine] serves as a signal to the other white people in the shop that the owner of both instruments is truly creative.”  

When you pull out the “Paper Tablet” in a coffee shop in order to jot down something creative, you signal your old-school, analog seriousness to everyone else around you, and conveniently reinforce the literary lineage the brand so proudly claims—all while keeping the new tech conveniently hidden from view.

Will I purchase a Smart Writing Set for myself? Its $199 price tag makes it an indulgence for careful identity crafters with a pocket book much larger than mine. For now, I’ll stick with my emerald green Moleskine, and think of Hemingway.