I feel bad when I drop him off, but I try to think of it as a vacation for him also. Sometimes he gets very excited, other times he doesn't seem so thrilled. We usually try to kennel no more than a few times a year. My next door neighbor will watch him for short weekend trips. I don't feel totally safe leaving him at home, what if there was a fire or something else catastrophic. A kennel is probably the safest place for him to be, I don't have to worry about him running away or not listening to someone else. I am really the only one he obeys. I usually get over feeling terrible, enjoy my vacation and look forward to picking him up again. Most times we have another neighbor get him and drop him off at our house, so he is here the minute we walk in the door.