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I'm terribly unproductive from time-to-time, and I think having a constant reminder of a few important items could change that.

If I could get a sticky note, a text editor, or ideally a checklist/calendar to always show as the top window on my macOS High Sierra 10.13.5, then that'd be great.

So far I've looked at using a legacy program called Afloat. Unfortunately this hasn't been continued and requires me to disable System Integrity Protection and for security purposes, I'd rather not do that.

Any recommendations for apps or secure workarounds.

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You can use the built-in Stickies.app in macOS. Go to Launchpad or in the Applications folder in Finder, and launch Stickies.app.

You can create a new note by pressing Command + n or selecting File → New Note from the Menu bar. To float a sticky note on top of all the other windows, press Option + Command + f or select Window → Float on Top from the Menu bar.

You can assign different colours to different notes and independently set them to float on top.

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