The author may also want to consider removing the notion of "caught up" from his vocabulary. Although it's not covered in the Now Habit, it's discussed in other respected books on procrastination and time management.
I used to beat myself up a lot with the idea that there was a (poorly defined) state of having gotten "caught up" on life tasks like those the author describes at which point all would be well.
The problem is that it doesn't really exist - there's always more to do than you can actually do - and denying that fact keeps you from living in the present. There are simply activities you choose to do and activities you choose not to do - that's it.
While it may sound absurdly simplistic, this one change in thinking had a huge impact on both my personal productivity and happiness.
FWIW, YMMV, etc.