1. If you find that you’re reluctant to permanently give up on to-do list items, “deprioritize” them instead

I hate the idea of deciding that something on my to-do list isn’t that important, and then deleting it off my to-do list without actually doing it. Because once it’s off my to-do list, then quite possibly I’ll never think about it again. And what if it’s actually worth doing? Or what if my priorities will change such that it will be worth doing at some point in the future? Gahh!

On the other hand, if I never delete anything off my to-do list, it will grow to infinity.

The solution I’ve settled on is a priority-categorized to-do list, using a kanban-style online tool (e.g. Trello). The left couple columns (“lists”) are very active—i.e., to-do list items that I might plausibly do today or tomorrow, with different columns for different contexts (e.g. “Deep work” items for when I have a block of time to concentrate, “Shallow work” items for when I don’t, and before a trip I might temporarily add an “On the airplane” column, etc.). Then going off to the right, I have a series of lower- and lower-priority columns—“Within 1 week”, “Within 2 weeks”, “Within 1 month”, “Within 2 months”, “Within 6 months”, “Someday / maybe”, “Probably never”.

I don’t take the column titles too literally; the important part is that if something doesn’t seem that urgent or worthwhile, I find it very easy and satisfying to drag that task one or two columns to the right. I’m not giving up on it forever! But the further right we go, the less frequently I’ll look at that column. So I get the benefit of a very manageable to-do list without needing to make the irreversible commitment of deleting items that I haven’t done.

(Following David Allen, I also have a “Waiting for…” column for items that someone else is supposed to do. I also have a “Done” column, which is arguably pointless as I just delete everything off the “Done” column every couple weeks, but the deleting ritual is nice because I get another chance to make sure I’ve really finished it, and is also an excuse to feel happy about my recent accomplishments.)

2. If you find that you’re reluctant to delete (or heavily edit) a piece of text / slide that you worked hard on, copy it into a “graveyard” first

I hate the idea of deleting something I wrote, because what if I change my mind and decide it’s better as it is? I’d have to rewrite it, and maybe it wouldn’t come out as good the second time! Gahh!

(Granted, lots of text editors have affordances for going through a document’s history to retrieve deleted text. But I find them a hassle to use.)

Instead, whenever I’m deleting or rewriting more than a couple words, I simply copy-and-paste the current version into a disorganized “graveyard” of text snippets, paragraphs, sections, etc. at the end of the document (or in a separate sister document).

Realistically, I almost never pull anything out of the “graveyard”. But now and then I do pull things out—not only in the course of whatever I’m writing, but also sometimes months after I finish. And more importantly, knowing that the graveyard is there and easily accessible makes me feel more comfortable “killing my darlings” in the first place.

Ditto for editing slides and so on.

3. If you find that you’re reluctant to throw out papers, make it fast and easy to file them

Sometimes I get something in the mail that I probably will never need to look at, but I don’t want to throw it out, because what if I’m wrong and I’ll need it after all? Gahh!

This is what a filing cabinet is for.

In Getting Things Done, David Allen writes “If it takes longer than sixty seconds to file something, you won't file, you'll stack.” (See here for his practical tips on how to hit that 60 second deadline, if you don’t want to buy the whole book. For me, it’s more like 30 seconds, even if I’m adding a new folder to the file, because I don’t bother with the label-maker.)

The “30 seconds to file” rule is much more important than that the filing cabinet be well organized. I always tell myself, “well, if I really need something, it’s in there, I’ll be able to find it eventually, even if I have to spend an hour looking through every single piece of paper”. For example, in my alphabetical filing cabinet, I might well randomly file half my electricity bills under “ELECTRIC” and the other half under “UTILITIES”. Oops. But oh well, whatever. If I’m actually pulling a certain type of document from the file frequently, I can always reorganize it at that time. And likewise, if I’m frequently accessing a folder, then I’ll naturally tend to remember that it exists and what goes in it.

Occasionally my filing cabinet will get too full, but then I can go through it and find lots of things that I was hesitant to throw out 3 years ago but am happy to throw out today. (Or I can buy another filing cabinet.) I also sometimes move files to a much-less-accessible “deep file storage” box if I’m 99% sure I’ll never need them, but want to let them age a few more years before throwing them out—e.g. records that I would only need in the event of a tax audit.

4. If you find that you’re reluctant to delete computer files / emails, don’t empty the trash

I don’t know how common this is, but I have a friend who deletes files or emails and then immediately “empties the trash” to permanently delete them. I cannot fathom why. Obviously you shouldn’t delete files if you expect to ever want them again, but equally obviously, files sitting in the trash aren’t doing anyone any harm, unless you’re actually running out of storage. And even if you are running out of storage, you can sort deleted files by size and permanently delete just the biggest files, and/or sort deleted files by date and permanently delete just the ones that have been sitting in your trash for a sufficient number of months or years.

I find it easier to delete a file or email with the knowledge that I can always change my mind tomorrow.