"I don't know where to start with it"

Some items aren't boring so much as opaque. You don't know what the form wants. You don't know which login. You don't know whether the insurance thing needs a phone call or a website or both. The item isn't small. It's unclear, and unclear feels big.

Look closely at what's blocking it, because it's almost always one thing. Not the whole item. One step, usually the first, and usually a piece of information. A reference number. A password you've forgotten. Which department to ring. Whether the school wants the form back on paper or by email. The item behind that one step is four minutes. The one step is what's making it feel like an afternoon, and the one step is usually two minutes on its own, if you name it.

So name it. Not "sort the insurance" but "find the policy number". Not "do the school form" but "check whether it goes back on paper". When the item on your list is the unknown step and not the whole thing, the felt size collapses, because the unknown step has a size and the whole item, wrapped in fog, didn't.

Then notice what the unknown step usually is. It's a phone number or a login. That's most of them. Admin lives behind those two things, and both of them are findable in under two minutes, and the finding is the whole of the hard part. The password reset email arrives, you're in, and the item is what it always was, which is a form. In my observation, the items that sit longest in the heap are not the dull ones. They're the ones with a fog on them, and the fog is one missing fact.

There's a version of this where the first step is a person. You don't know what the form means and you'd have to ring and ask. That feels enormous and takes three minutes, and the person on the other end answers this question all day and won't think anything of it. The dread of that call is almost entirely the dread of appearing not to know, and the person you'd be appearing to has never heard of you.

When an item has been on the list for more than a week and it isn't boring, ask what the one thing is that you don't know. Write that down instead. That's the item now, and it's the smallest one on the list.