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Review: Moleskine's Smart Planner doesn't quite merge smartphone, paper calendars

Aaron Aupperlee
| Tuesday, Oct. 31, 2017, 2:36 p.m.

When it comes to keeping track of where I'm supposed to be and what I'm supposed to be doing, I'm stuck in two worlds, the digital and the analog.

On the one hand, nothing beats the convenience of keeping appointments, meetings and events in a calendar app on my phone. It's always with me, and more times than not, the buzz of the reminder notification has been a life saver.

On the other, I also use a pen and paper planner. Writing, physically writing, something down helps me remember it.

Often times, however, what's in my phone's calendar doesn't make it to my planner and vice-versa, leaving me to check both before I can tell you if I'm free Thursday afternoon.

Moleskine's newly released Smart Planner aims to bridge the digital-analog divide, and it caught my eye.

The Smart Planner automatically syncs with the iCal, Google and Outlook calendar apps through the Moleskine Notes app available for both Apple and Android phones. It offers the potential to transfer handwritten entries from pen and paper world to the world of the smartphone.

"We believe that this is the most natural and seamless way for consumers to connect their trusted paper planner with their digital calendar — being digital-savvy, while still enjoying the physical sense of the pen and paper," Peter Jensen, Moleskine's chief digital officer, wrote in an email to the Tribune-Review.

Moleskine sent me a 2018 Smart Planner and its Smart Writing Set, which included the company's Paper Tablet and Pen+ smartpen, to try out.

When properly synced, the smartpen, planner and phone communicate in near real-time, copying my handwriting from planner to phone.

But the technology had a hard time deciphering my handwriting at times, creating nonsensical entries at incorrect times. I didn't feel confident that it would transfer important meetings reliably from paper to smartphone.

The pen and calendar combo works well if you're writing very short entries. For example, writing "First spin class of 2018 @ 6 pm" on Jan. 4 resulted in five different calendar entries, all nonsense and without the correct time. Writing "Spin 6 pm," however, put one entry, titled "Spin," in my Google calendar with the correct time.

It took me a few attempts to schedule my first spin class of 2018.

Moleskine's Smart Planner and smartpen combo is a good step in bridging the digital and analog divide, but it quickly showed how much more progress needs to be made.

The Smart Planner builds on the company's existing Paper Tablet and Pen+ smartpen technology, which can transfer handwritten notes jotted down with a smartpen in a specially-designed notebook to a smartphone.

A camera in the pen scans a microscopic pattern on the paper to know exactly what page and where on that page the pen is writing, Jensen told the Tribune-Review. That technology is what allows the pen and Smart Planner to know when you're putting next week's meeting into your planner and a reminder to buy dog food tomorrow.

In-app instructions make it easy to connect the pen to your phone. Syncing with either Apple, Google or Outlook requires you to go into "Settings" and then "Authentication Center," which isn't intuitive.

The pen's battery life was never an issue.

The planner-pen combo requires a steep investment for the first year. The planner itself is $29.99, very reasonable for a top-notch planner. The smartpen is only available in Moleskine's Smart Writing Set, which includes the Pen+ and a Smart Notebook and is $199.

Assuming all the technology stays the same year to year, you'll only need to buy the planner for 2019.

I'm not sure if Moleskine's Smart Planner will be my go-to for 2018, but in the spirit of New Year's resolutions, I'm willing to give it a shot.

For the month of January, I'll put the Smart Planner and Pen+ through its paces as my primary calendar. We'll see how it handles my chicken-scratch handwriting for 31 days when it really counts.

Check back on Feb. 1 for an updated review. Put it in your planner if you have to.

Aaron Aupperlee is a Tribune-Review staff writer. Reach him at, 412-336-8448 or via Twitter @tinynotebook.

Moleskines smart planner attempts to bridge the divide between analogue and digital.
Andrew Russell | Tribune-Review
Moleskines smart planner attempts to bridge the divide between analogue and digital.
Moleskines smart planner attempts to bridge the divide between analogue and digital.
Andrew Russell | Tribune-Review
Moleskines smart planner attempts to bridge the divide between analogue and digital.
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