Your "maybe someday" lists -- what your approach to using them?

I have long lists of interesting stuff I might do, collected in “maybe someday” buckets. Over the years I collected these in OmniFocus, then migrated to Todoist, and several other playpens.

I intend to wean myself off of the OmniFocus / Todoist / task manager software category permanently – I don’t want to play that game anymore. I find that the calendar and Due are just fine for the “must do” category of tasks. For that matter, an index card is just fine too; if I didn’t tend to lose them.

But I don’t want to lose track of my “maybe someday” ideas. I would like to find a way to have them percolate up for consideration from time to time. The practice of structured, scheduled daily reviews is not for me – too much organization feels compulsive and drives me nuts.

You could set up a recurrent reminder in Reminders to review your “maybe someday” list. Your list can be in whichever document you choose.

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either a recurring reminder, or a monthly meeting with yourself and with the list as the agenda?

I don’t have a lot of these at the present, but I do have something that I review every year to see how my life as it is compares to my life as I would like it to be.

For things like that, I think a physical notebook or some other source would be well suited. Something you can periodically pick up and page through, perhaps crossing out things you’ve done or that no longer interest you.

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The length of my someday/maybe list is probably somewhat embarrassing! Currently working with it in two different ways:

  • A weekly reminder that triggers selection (powered by an iOS Shortcut) of a random item from the list. On selection: do it, schedule it appropriately, delete it, etc. If I have capacity to tackle more than one in a week, then I do. Some of my someday/maybe items require more than a week to take on, in which case I don’t take on another until I’m done with the last.
  • A bi-monthly reminder to sweep the list and prune or hoist where appropriate. Nothing too exhaustive or rigorous, just a quick eyeball. Aim is to derive value from the list without it becoming a chore or a time suck.

I put all my someday/maybe ideas into lists. Right now most arestill in DEVONThink but they are migrating out of htat and into Obsidian. It started as one big monolithic list but as I got more and more into it I started splitting it into logical groupings of cool ideas. I like to have it about 1 to 1.5 pages or screens at a time and if it gets longer I split it. Right now there are 69 separate S/M lists in my system.

What I have done in the past is at least re-read all ym S/M lists at my regular quarterly reviews at the equinoxes and the solstices. That’s when the seasons change and fits in well with farming. I “put to bed” all the projects in Omnifocus that I was working on the past season that will now hibernate for a while and they go into my S/M lists. Similarly I will bring into OF any things from the S/M lists that I could or would like to work on in the next season. The process is manual and I find that the friction of doing it that way is a good thing. It forces me to really evaluate what I am bringing into the task management system and also to clarify the outcomes and do at least minimal project planning.

Once they are all into Obsidian I think I can have them resurface by some creative scripting of the open random note from search and open random note tools in Obsidian. OTOH since I always review them 4 times a year I may not need to get them in my face by some automatic procedure.

My view is that a long and extensive S/M list shows that you have lots of varied interests. I have never worried how long my lists got or how many I ended up with. However, at my year end quarterly review at the winter solstice this past December I ended up doing a MAJOR culling of my S/M lists. Because I was curious I actually counted the number of things in them both before and after the clean-out. I started with over 1800 individual items on my lists but by the end of January (yes, the year end review took that long!) I had whittled it down to 846. I found duplicates, or near duplicates, I found things that no longer interest me, I found things that I know I will never do and I found things I decided to dump figuring if it really does become important I’ll think of it again. That last was the biggest set of stuff to get rid of. Now my lists are growing again but they are very manageable and I know I’ll take a look at them every so often.

As I move them into Obsidian I am also taking that opportunity to cull the items again and expand on a few as I have additional ideas for those projects.

Weekly or even monthly reviews of S/M are way too much for me. My quarterly schedule seems to fit well for me with an every few years or so major overhaul like I just finished this year. The last time I did an overhaul like that was over 5 years ago so it’s a very irregular thing.


1800 to 846? I’m a small fish, then. My list current stands a t 582.

I appreciate that view of varied interests! And that a delay after capturing something can help in deciding how important/valuable that thing might be. Likewise, I’m not actually that worried about how long my list gets… just aware that it’s all too often easier to add something to a list than it is to do whatever it takes to get an item off that list…


These are good thoughts, everyone. Thanks esp. @tjluoma and @jsamlarose.

@OogieM an Obsidian vault is an attractive idea. A few weeks ago I started a Tech Notes vault to note all software and hardware additions and changes, configuration changes, and bug fixes. Including web services, plugins, etc. The Obsidian plug-ins Checklist, MetaEdit, Tracker, and, especially, DataView have made that vault an active resource. It would be small step to use the same approach in a maybesomeday vault.

I have hundreds (countless, in a sense) of maybesomedays going back decades. I would never delete anything on those lists. A bit of organization will not make them occur, but it will add pleasure to reflecting on the possibilities.

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Apple Stickies.
Yes, I said it, use it, and still love it after all these years. :slight_smile:

I just completed a database design project in GoodNotes and Obsidian that went much faster than normal. 5 days from concept to working code (on the bench) with the new database additions. We do our first live test with sheep later today. But I’ve not yet investigated any of the 4 plug-ins you mention. Could you expound on what they do and how you use them in your Tech Notes? Maybe in another thread?

Also, are you creating separate vaults or keeping things in one big Obsidian vault? I started out thinking I’d have separate vaults but found myself wanting to link into them so decided to pull everything into just one vault. So far no issues even wne I move the vaults to my mobile devices (iPad and iPhone)