Stress brought on by Blessings?

So the "Holidays" can be so stressful, the meals, the travel, the cleaning, the packing, the long lines, crowded parking lots, you get my jist... most of the time I work near downtown, an area heavily populated with homeless people.  One day while in a hurry to get from one place to another I noticed a man sleeping on the pavement at the corner of the street and, I was jealous.  Yes, I know you think I'm crazy now, but this guy didn't seem to have a care in the world, while I had a to-do list a hundred miles long just scrolling through my brain, causing painful headaches and unwanted stress.  Ahhh I thought to myself to just layout on the sun-warmed concrete and take a nap in the middle of the day.  No need to worry about holding up a sign for money, or what people would think of me sleeping outside on the ground, or what project needed to be done, or what time I needed to pick up the baby from daycare, or what gifts I had left to buy, it sounded wonderful.

Then I got to thinking, why should I be jealous of this seemingly homeless man? I have so many blessings to be thankful for!  What if being blessed causes stress? Could that be possible?  I've thought about this a lot and think its true in many cases:

Blessing: Challenging career with one of the top 4 Big Accounting firms in the US.
Stress: Pressure from work to work long hours, manage staff, communicate to execs, stay organized and on top of multiple jobs and in touch with multiple clients.  Nightmares about not meeting deadlines or something going wrong. 

Blessing:

Stress:  Am I doing everything right? Is she learning everything she needs to know? Should I put her in gymnastic or dance classes? Is she in the right daycare? Who is going to pick her up/drop her off today? Is she going to wean or potty train soon? Did I pay the daycare? etc....

Blessing:




Stress: Is he truly as happy as he seems? What does he expect from me? What time is he going to get off work? What would he like for dinner? Is he ever going to fix that? Does he think I work too much? Does he know how much I love him? What could I do to make his day better?

Blessing: Nice/newish car to drive

Stress: Why is gas so expensive? Did Raegan spill milk in here again?

Blessing: Lots of family who love us dearly.
Stress: Traveling to Texas can get expensive.  I hate packing.  Why does Raegan ask me where "gigi" is 300 times a day?