The Digital Planner is an impressively thorough tool for the iPad and Apple Pencil. It’s designed to model physical planners for organizing your goals, tasks, schedule, and thoughts.

Technically, it’s an interactive PDF built to be used within an app like GoodNotes. The big advantages are free form note taking with a Pencil, a smart organizational design, and GoodNotes can search handwriting.

Day One is a journaling and diary app, built primarily for the digital age. You can type entries and add photos and files, automatically scoop up social activity, automate certain things with IFTTT, and more. While Day One has gained the ability to add sketches to entries, it’s still primarily a digital-first app, not a mimic of a physical counterpart. It also doesn’t do very much with features like organizing tasks, tracking moods, or other quantifiable data beyond tags (which are implemented quite well).

I really wish there was a hybrid of these two products.

Digital Planner comes from the Focus Course (built by my friend Shawn Blanc and the people behind The Sweet Setup). I really like their emphasis on sitting down with a writing instrument to think about your day, week, goals, and more. Combining some advantages of digital tools with the physical sensation of writing has been a great experience in that regard.

But part of Digital Planner’s approach involves tracking data that only digital apps can quantify in a useful way—completing tasks, tracking habits, tagging entries for collection, review, or even sharing. Digital Planner is an impressive tool, but still just a PDF at heart.

While I have found a couple iPad apps that are in the direction of uniting these two experiences, they fall too far short for me to give them a serious try. The closest I’ve found is Pencil Planner & Calendar Pro. The UI is interesting though somewhat foreign, and it combines some things like Pencil writing and bringing in my digital calendar events while still allowing sketching on the calendar.

But Pencil PLanner & Calendar Pro (it just rolls off the tongue!) doesn’t capitalize on quantifiable data. I can add tasks but there’s no checkbox to tap. I can set a mood for the day, but it’s just a circle drawn around an icon, not something I can view on a monthly basis. Plus, it uses a home-grown sync option, (not iCloud, which I would prefer), and I can’t find a mention on whether it’s E2E encrypted.

I think there’s a great opportunity to meld the benefits of physical journaling and planning with the advantages of digital tools and data. I recommend both Digital Planner and Day One as great products in their own right. But I’d also love to see what’s possible in a hybrid of the two.

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