Is there any way to print onto sticky notes a couple of times a day?

There are three routes, and for your use case — short text, several times a day — the third is by far the best.

Feed the note through an ordinary printer. Stick the note onto a carrier sheet of normal paper, print with the note's position set in the document, and peel it off. This works and it is fiddly, and there is a real risk of the note detaching inside the printer, which is exactly the ending you predicted.

Buy printable sticky sheets. Full-size sheets with a repositionable adhesive backing, made for ordinary printers. You print several notes at once and cut them apart. Reliable, and it means preparing a sheet at a time rather than printing on demand.

Use a small thermal label printer. This is the answer. They are cheap, they take rolls of small labels including repositionable adhesive ones, they need no ink at all, and they print a short list in about two seconds from a phone or computer.

Seconding the thermal label printer, with the caveats worth knowing before buying one.

No ink, ever. Thermal printing burns the image into heat-sensitive paper. That is the main reason these are so convenient for frequent short prints — no cartridges to dry out between uses, which is precisely the failure mode of an inkjet used twice a day.

The print fades. Thermal paper darkens with heat, so labels left in sunlight or a warm car will fade over months. For task lists that get thrown away, irrelevant. For anything archival, disqualifying.

Check the label type before buying. Some rolls are permanent adhesive and some are removable. You want removable, and it is not always the default.

Check the software. The cheap ones vary enormously in how pleasant they are to drive from a computer, and that is what determines whether you use it daily or abandon it.

The low-technology option, which is what I eventually settled on after buying two devices: print on ordinary paper, cut, and use a repositionable glue roller.

Those applicators lay down a stripe of removable adhesive and cost very little. You print a page of eight or ten notes, cut them apart with a guillotine, and roll adhesive along one edge as you use them.

It is more steps and it uses a printer you already own with paper you already have. Whether that beats a dedicated device depends entirely on whether you would rather do a small task now and then or buy a machine.

One thing to check if you go the carrier-sheet route: the adhesive strip must lead into the printer, not trail behind it.

A note fed adhesive-edge-last has its free edge lifting as it goes through the rollers, which is how it catches. Adhesive edge first, firmly stuck down, and it usually goes through cleanly.

That said, I lost an afternoon to a note wrapped around a roller once and would not do it again for a daily task.