According to interviews, Press to Play (1986, I believe) found McCartney stuck in the middle of the me decade, an aging hippie with gray hair, crinkling eyes, wondering what to do with drum machines and samplers. Even he hated the album and was ready to give up.
It turned out that was a good thing — a major pivot point in his career. The next album was 1989’s Flowers in the Dirt. Still reeling and disappointed with Press to Play, he decided that Flowers in the Dirt would be his last album. He recorded it, threw it on his manager’s desk and said I quit.
His manager convinced him that he should also do a tour. The end result was a record-breaking sold-out tour supporting one of his best albums. He was so happy with it all in the end that, more than 20 years later, he still hasn’t tried to retire again.
When one interviewer asked McCartney about the extreme difference between the two albums he shrugged it off by saying “I didn’t want to get stuck out in America plugging an album I didn’t like.”