Peter J. Strauss’s life as an attorney, speaker and single father of four children ages 1 to 10 leaves him little time for himself.

He catches a break in a place most people try to avoid: “I love going to the dentist,” says Mr. Strauss, of Hilton Head Island, S.C. “It’s 45 minutes when I know nobody is going to interrupt me. You can’t reach me and you can’t ask for anything,” says Mr. Strauss, author of a book on self-insurance for businesses. Although he has perfect teeth, he gets them cleaned three times a year instead of the usual two. The visits are so dull that he sometimes falls asleep in the chair.