Self-plug: I created https://recalendar.me/ (open-source and always free) to solve this from a different perspective. It allows creating highly customized PDF calendars for e-ink tablets like ReMarkable. This gives you the "sketchy" part, making it more natural to input, doodle, make notes. But extensively utilize PDF links to make it easy to navigate the calendar. Plus other features, like pre-filling anniversaries/birthdays, custom templates per day, week, month, etc. to make it yours, fitting your particular needs. For example, I added an extra page after each Thursday, cause I always had some notes after therapy session then.
Unfortunately, something that's fundamentally hard to do with this approach is having a dynamic sync with an online calendar. That's because ultimately it's a PDF, with some device-specific layer with writing on top of it.
But in some ways, it could be seen as feature - I find it useful to copy "manually" the events to my ReCalendar. That automatically makes me reflect on them or just help me remember they're happening!
I struggled with this problem for a long time. I sort of solved it.
The key was to realize that there is a difference between a calendar, a todo list, and an agenda.
A todo list is a list of things that need to be done but usually don’t have a specific time when they need to be done at. They can have priorities or deadlines or fuzzy target dates like “next week.”
A calendar is for storing future concretely scheduled events.
An agenda is a list of things that will happen soon.
Each day I pull things from my calendar, todo list, and prior agenda and create my daily agenda. I also keep notes, doodles, clippings, and references in my agenda.
I use Google calendar as my calendar. It meets my expectations.
For my todo list I use Notion. I break it down into “next, soon, and later”. I add ad-hoc sections like “after the vacation” when needed. Some todo items are scheduled for a specific day or “not sooner than.” I add these to my calendar with an email reminder so they don’t take up any mind space until needed.
Finally, the daily agenda. I use Notion but could probably use a physical notepad. I like being able to archive them as sometimes I need to check when I did something or pull some details from notes. With a digital agenda I can file it into an archive easily.
This is not perfect but it helped me reconcile the rigidity of calendar tools with the need to do keep things freeform in the short term.
If you want to try something in these lines, David Seah has some pretty awesome printables perfected over the years. I’ve used them like 10+ years ago, and I still like to print out some copies and tinker around. However, I have changed my ways of using pen and paper. His work is extremely detailed. I heard many restaurants have standardized on some of this work.
There was a program a long time ago, classic Mac OS days, and I don't remember the name of it but I think it was "<something> Consistency". I loved it because tasks in it were "loose," in the sense that something like "water the plants" didn't have to happen on a strict 7-day repeating event. It could be defined as "should be done 6-8 days after the last time I did it." So when you hit "done" on the current "water the plants" task, it automatically fuzzy-scheduled the next "water the plants" event with a target date of 6-8 days after when you clicked done. You could have the range prefer some days but be "acceptable" for a wider range of days.
Someone once told me emacs org-mode might be able to schedule recurring tasks somewhat like this. But any time I see a new calendar/to-do manager application, I hope the designers keep this "fuzzy" repeating event idea in mind!
LLMs are good enough that if you can stand up a small video capturing app on your iphone, then you can live transcribe. I believe the LLMs are good enough that if you just write legibly, then you can give it ad-hoc commands in any way you want (e.g "Add this to iCal").
I'm expecting something like this to be part of the suite of devices OpenAI will release. Shifting away from tapping things into phones all the time to leveraging all of the mechanical things we do outside of phones.
The product would be an aesthetic document scanner with a mic, so you can make comprehensive notes with additional voice transcribing. Seems like an ideal thing to have on a scratchpad desk for quick notes, because eink note-takes are actually really good now days (just overpriced).
> If you have tentative plans like “lunch with a friend sometime next week” there is no obvious way to add this to your calendar in a way that differentiates it from an important appointment that can’t be missed.
Does Google Calendar not let you mark events as tentative? Outlook does and I’ve always taken that for granted.
Speaking of Outlook, they used to have a board view that I think was conceptually quite close to achieving the large free form canvas experience of a paper calendar. Retired years ago though. https://www.computerworld.com/article/1616186/how-to-use-out...
Excited to see what comes out of this.
Like many others, I struggle to keep up with a Calendar app. They don't give satisfaction when using them, making it harder to stick with them day after day.
Using pen & paper, I have a hard time following my schedule because I don't receive notifications when an event or time block is about to start. LOL
I'm surprised the author doesn't use color coded labels (e.g. red=important, yellow=Hold-Event, etc) to solve a huge portion of their described problems ... as well as using Tasks functionality (that you can find from Google Calendar, Outlook, etc)
I am curious to see how this unfolds. I know that for many people, myself included, that the main appeal of a digital calendar is the edit-ability of it. I can move, edit, and even copy. And it's in text format (as opposed to ink) so that also means "readable" (in contrast to the chicken scratch that is my handwriting) and searchable.
I think the idea is for the top part of each day's view- the little square that lists the date- to be what's visible when you're looking at an entire month.
If so, I like it! Gives the option to work on both time scales at once.
The whole idea is lovely, pen tablet drawing is so much more expressive than any other form of input we have
Remarkable to see this blog post, just a few days after I'd seen the HEY Calendar [0] for the first time, and asked an LLM about how I could recreate its unique features within my macOS calendar app of choice: Flexibits Fantastical [1]. I didn't get very far with it, but for those interested, here's what I think are the "sketch-based" features (per author's post) that HEY allows for that are sorely missing in all digital calendar software:
- Bar at the bottom of the GUI called "Sometime this week" that shows tasks/events that mentally fit into the frame of "should be done sometime this week, just not sure exactly when"
- Habits (that you can easily check off if completed) [plus associated aggregate tracking]
I like it that Apple's Calendar app now includes scheduled TODOs from Reminders.
I love checklists (early adopter and fan of Trello; sadly it's well past its peak), so Reminders is now a natural way to organise them. I can add a due date (and optionally, time), when I will get a notification. Overdue reminders still show up in the "today" view.
So for things like "lunch with a friend", I just set due date to whenever I should follow up, postpone until actually scheduled, and it continues to show up both in my reminders and in the calendar. It works for me.
As for the more free-form stuff, I keep a journal in Notes. I have a shortcut that looks for today's note in the "journal" folder, and if none is found, creates it; then it inserts the current timestamp. I can just start writing whatever comes to my mind.
Since the journal is already organised by date, I can always look back. I only wish I could run the shortcut straight from the Notes app.
Unless I read this wrong, it sounds like the author is after a calendar background template that they can write over on their tablet (or ReMarkable/etc) device.
I mean that's basically what that last screenshot looked like to me...
Sketchy Calendar
(inkandswitch.com)156 points by surprisetalk 22 May 2025 | 46 comments
Comments
Unfortunately, something that's fundamentally hard to do with this approach is having a dynamic sync with an online calendar. That's because ultimately it's a PDF, with some device-specific layer with writing on top of it.
But in some ways, it could be seen as feature - I find it useful to copy "manually" the events to my ReCalendar. That automatically makes me reflect on them or just help me remember they're happening!
Of course, YMMV, good to have different options!
The key was to realize that there is a difference between a calendar, a todo list, and an agenda.
A todo list is a list of things that need to be done but usually don’t have a specific time when they need to be done at. They can have priorities or deadlines or fuzzy target dates like “next week.”
A calendar is for storing future concretely scheduled events.
An agenda is a list of things that will happen soon.
Each day I pull things from my calendar, todo list, and prior agenda and create my daily agenda. I also keep notes, doodles, clippings, and references in my agenda.
I use Google calendar as my calendar. It meets my expectations.
For my todo list I use Notion. I break it down into “next, soon, and later”. I add ad-hoc sections like “after the vacation” when needed. Some todo items are scheduled for a specific day or “not sooner than.” I add these to my calendar with an email reminder so they don’t take up any mind space until needed.
Finally, the daily agenda. I use Notion but could probably use a physical notepad. I like being able to archive them as sometimes I need to check when I did something or pull some details from notes. With a digital agenda I can file it into an archive easily.
This is not perfect but it helped me reconcile the rigidity of calendar tools with the need to do keep things freeform in the short term.
https://davidseah.com/productivity-tools/
There was a program a long time ago, classic Mac OS days, and I don't remember the name of it but I think it was "<something> Consistency". I loved it because tasks in it were "loose," in the sense that something like "water the plants" didn't have to happen on a strict 7-day repeating event. It could be defined as "should be done 6-8 days after the last time I did it." So when you hit "done" on the current "water the plants" task, it automatically fuzzy-scheduled the next "water the plants" event with a target date of 6-8 days after when you clicked done. You could have the range prefer some days but be "acceptable" for a wider range of days.
Someone once told me emacs org-mode might be able to schedule recurring tasks somewhat like this. But any time I see a new calendar/to-do manager application, I hope the designers keep this "fuzzy" repeating event idea in mind!
https://shop.neosmartpen.com/collections/journals-notebooks/...
LLMs are good enough that if you can stand up a small video capturing app on your iphone, then you can live transcribe. I believe the LLMs are good enough that if you just write legibly, then you can give it ad-hoc commands in any way you want (e.g "Add this to iCal").
A cheap document reader gets your half way there:
https://www.amazon.com/Kitchbai-Document-Visualiser-Micropho...
I'm expecting something like this to be part of the suite of devices OpenAI will release. Shifting away from tapping things into phones all the time to leveraging all of the mechanical things we do outside of phones.
The product would be an aesthetic document scanner with a mic, so you can make comprehensive notes with additional voice transcribing. Seems like an ideal thing to have on a scratchpad desk for quick notes, because eink note-takes are actually really good now days (just overpriced).
Does Google Calendar not let you mark events as tentative? Outlook does and I’ve always taken that for granted.
Speaking of Outlook, they used to have a board view that I think was conceptually quite close to achieving the large free form canvas experience of a paper calendar. Retired years ago though. https://www.computerworld.com/article/1616186/how-to-use-out...
Using pen & paper, I have a hard time following my schedule because I don't receive notifications when an event or time block is about to start. LOL
If so, I like it! Gives the option to work on both time scales at once.
The whole idea is lovely, pen tablet drawing is so much more expressive than any other form of input we have
- Bar at the bottom of the GUI called "Sometime this week" that shows tasks/events that mentally fit into the frame of "should be done sometime this week, just not sure exactly when"
- Habits (that you can easily check off if completed) [plus associated aggregate tracking]
- Tracked/Logged-Time (a.k.a. "retrospective calendaring")
- Freetime visualization (the HEY Calendar visually highlights long uninterrupted blocks of freetime)
- Add images or a label to a specific day (without being an event itself; a purely graphical signifier)
- Built-in countdown-type events, with associated UI element that counts down for you
My main desire is not switch calendaring platforms, but to figure out how to 'bolt-on' these capabilities in what I'm already living in.
--
[0] https://www.hey.com/calendar/
[1] https://flexibits.com/fantastical
I love checklists (early adopter and fan of Trello; sadly it's well past its peak), so Reminders is now a natural way to organise them. I can add a due date (and optionally, time), when I will get a notification. Overdue reminders still show up in the "today" view.
So for things like "lunch with a friend", I just set due date to whenever I should follow up, postpone until actually scheduled, and it continues to show up both in my reminders and in the calendar. It works for me.
As for the more free-form stuff, I keep a journal in Notes. I have a shortcut that looks for today's note in the "journal" folder, and if none is found, creates it; then it inserts the current timestamp. I can just start writing whatever comes to my mind.
Since the journal is already organised by date, I can always look back. I only wish I could run the shortcut straight from the Notes app.
I mean that's basically what that last screenshot looked like to me...