"Once I start I'll be there all night"
There's a fear that goes the other way from the last one. If you open the heap, you'll be in it for hours. One item leads to another, the insurance needs a document, the document needs a login, the login needs a reset, and it's midnight and you've done half of it. Better not to start.
This is a fear about the heap having no edge, and the answer is to give it one. The sweep in chapter 21 is fifteen minutes with a timer, and when the timer goes, you stop, whatever you're in the middle of, and write a dated line for where you got to. That's the whole protection. You never open the heap without a way out, and the way out is a clock.
An earlier book in this series is about switching between tasks, and one of its tools is a stopping point named in advance, so that you can leave a thing cleanly and come back to it. The sweep borrows the idea. Fifteen minutes is the stopping point, every day, and because it's every day, nothing has to be finished tonight. What's left at the timer is left for tomorrow's sweep, which exists, which is the difference between a fifteen-minute sweep and an all-nighter. The all-nighter happens because you believe this is the only chance. The sweep removes that belief by being there tomorrow.
And the heap is finite. This is the thing the fear gets most wrong. It feels bottomless because you've never seen the bottom, because you've never listed it, and the carry from chapter 3 makes eleven items feel like fifty. Chapter 22 is about listing the lot once, and most people who do it find it fits on one side of a page and that the ten-minute items, done then and there, take the page down by half in an hour. What's left isn't a night's work. It's a week of sweeps.
There's also the chain, the item that needs a document that needs a login. Chains are real and they're the reason for the dated line. When an item hits a wait, the password reset email, the document from the garage, you write "Thursday, insurance, once the reset's come" and move to the next item. You don't sit in the chain. The chain is what makes fifteen minutes feel like all night, and the dated line is the exit from it.
You won't be there all night. You'll be there fifteen minutes, and then the timer, and then tomorrow. The heap has an edge now, and it's the clock.