"As I grapped with some of the more difficult items on the to-do list though, I faced a discouraging number of "boomerang errands": errands that I thought I was getting rid of but came right back to me.  Eighteen months overdue, congratulating myself on crossing the task off the list I went to the dentist to get my teeth cleaned, only to discover I had decay under one filling. I had to return to the dentist's the next week.  Boomerang.  I asked the building super to fix our bedroom wall light, but it turned out he couldn't do it.  He gave me the number of an electrician. I called the electrician.  He came, he took the light off the wall, but he couldn't fix it.  He told me about a repair shop. I took the light to the repair shop.  A week later, I picked it up. Then the electrician had to come back to install it.  Then the light worked again.  Boomerang, boomerang, boomerang."

One of the most frustrating parts of working towards cheerful productivity is hitting checklist items that generate more checklist items.  I've felt tension creep in but hadn't really looked at it squarely until Gretchen Rubin articulated it so well above.  It can be tempting to put off an appointment, or delay making a call because you have good reason to suspect it will usher in additional 'to-do's.'  There is that tendency to let those sleeping dogs lie and tackle more straightforward tasks which provide a bit of instant gratification. 

My goal has been to incorporate these time-eaters into the schedule and slowly cross them off,  however many steps that requires. Less shirking, more facing and finishing.  My challenge has been to be as chill possible as those issues get untangled.  Sometimes that simply requires a quick pep talk to self.  Sometimes, like when the automated voice on the other end of my call to the insurance company informed me, "Your estimated hold time is now…. 47 minutes." I hang up, mutter a bit under my breath, and start in again fresh at a better time.