Sketchy Calendar

108 surprisetalk 25 5/22/2025, 11:19:36 PM inkandswitch.com ↗

Comments (25)

koliber · 4h ago
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.

ramses0 · 1h ago
I solved it with different colored calendars in g-cal. Monthly => Rough => Detail => Actual.

Monthly is usually dragging a bunch of "all-day" events across multiple weeks. "school ends", "date night?" (across Fri->Sun), "vacation", "vacation pack", etc.

Rough is kindof planning out the upcoming week or two. I'll drag stuff across Saturday afternoon like "go to park?", and "buy paper towels from Sam's?" in the morning.

Detail is "15-min accuracy" of committed things. Doctor's appointments, birthday party invites, haircuts, or anything that is really "controlling" where I need to be or what I need to be doing at that point in time.

The "actual" calendar is for when I want to reconcile what actually happened vs what I'd planned to happen.

If I'm super "on it" with my detail calendar, maybe I didn't do "clean office" because in actuality I was doing "make dinner", "clean kitchen", and "watch movie with kids".

And integrating with work, sometimes I'll block a section (hour) in "actual" called "Work P1". That's supposed to be "the next item in the todo list", but it is sometimes really helpful to cross-check with "actual" and realize I was really "troubleshooting bug", or "helping coworker on xyz" or "continuing design discussion".

The "narrowing" and "accuracy" is helpful to learn how to do, and the big chunky things like "put fertilizer" and "in-laws visiting" help to make sure I don't schedule too much "detail" in times that already have a lot of external complexity.

8organicbits · 2h ago
I'll add to this to say that I think there are different kinds of todo lists as well. I wrote about [1] a struggle I had with digitizing a whiteboard household chore tracker.

Lately I've been wondering if LLMs can help personalize software. There are so many difference needs users have, yet software is written with a pool of users in mind. I'm very skeptical of LLMs for traditional software projects, but small one-off personal utilities or tweaking existing tools seems more viable.

[1] https://alexsci.com/blog/personal-apps/

racingmars · 6h ago
I'm looking forward to see how this develops.

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!

endlessvoid94 · 52m ago
Things 3 has a sort of recurring todo like what you're describing, where you can set like this: https://culturedcode.com/things/support/articles/2803564/
enricozb · 6h ago
Maybe Sciral Consistency?
Brajeshwar · 10h ago
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.

https://davidseah.com/productivity-tools/

y-curious · 9h ago
Thank you so much for this. I went down the rabbit hole on this guy's website and he is obsessed with categorization. I can't wait to try the emergent task list.

I hope I don't use it for a week and then stop :$

romuloalves · 4h ago
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

n8cpdx · 9h ago
> 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...

storgaard · 6h ago
You can events as tentative in Google Calendar by responding with "Maybe".
jimkleiber · 1h ago
Yes but that would require booking a full-day event for all 7 days in the week if you wanted to say "sometime next week," or at least I assume it would.
deafpolygon · 6h ago
I often put tentative plans in a separate "Calendar" and reassign it to the category if necessary.

Then I can turn "off" the other calendars and see only the tentative plans to zero in on stuff I have yet to deal with.

If I have a shared calendar, I will title it with (tentative) and promote it by removing the tag.

rollcat · 2h ago
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.

WillAdams · 1h ago
I really wish Amazon would either hire these folks, or license their ideas/concepts/applications for the Kindle Scribe.
nicbou · 6h ago
I'm really hoping for a sketchy map. I really wish I could use my iPad Mini to plan motorcycle trips.
WillAdams · 1h ago
I'd really like to see a mapping software which was flexible enough, and informative enough to allow ad hoc hybrid route planning --- hoping to take up bike rafting at some point in the near future, so an idea trip would be:

- park the vehicle near where the trip will ultimately terminate near to a water access point (so need to know about ramp presence and parking)

- pedal in to some remote water area where one can transition from bike to raft

- by water explore a bit, optionally gain access to some area which is remote and not normally accessible by bike, land and possibly ride around a bit (only if area will not be damaged by bike tires)

- exit area by going downstream --- but no rough rapids since I'm not young anymore and have had my fill of fishing gear out of the water and refloating a canoe/kayak, arriving at the vehicle after a fairly easy bit of paddling

If someone has a good suggestion for a map which provides this information in a consistent and reliable and accessible format, I'd be glad --- my first couple of attempts at route-planning have had me opening multiple sites/windows/views to the point where keeping track of which information I was trying to get from which window became a chore.

lugarlugarlugar · 4h ago
They've made a prototype for that: https://www.inkandswitch.com/embark/ Sadly not released.
wonger_ · 2h ago
Someone released a similar trip-planning webapp: https://waypoint.jakelazaroff.com/

Blog post: https://jakelazaroff.com/words/a-local-first-case-study/

AstroJetson · 11h ago
I use pocket mod and make a custom 8 page todo/calendar that I use every day. It works well for me, but I’ve also adapted my life to the way it works.
dfee · 11h ago
In the morning you copy your calendar by hand to the pocket mod? What about dynamic event changes (e.g. additions, subtractions and reschedules)?

There’s something more optimal than my current attempt at strategic daily itineraries (which is quite poor) - a tug between the mechanical and the breathing, flexible and organic.

hiatus · 11h ago
How does it work?
ivape · 5h ago
This kind of exists with things like RocketBook and Neo smartpens. They require special books for the latter:

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).

ErrorNoBrain · 8h ago
i need a digital calendar because i share it and other people put things into the calendar, that i need to know of.

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deafpolygon · 6h ago
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.