When his retirement began this month, Robert Browning Vaughn II was sitting next to the pool with his wife, Kimi Vaughn, at a Mexican resort in Cabo San Lucas. The trip had long been planned for Mr. Vaughn’s 60th birthday, but the retirement was a late addition. Mr. Vaughn, a former Delta pilot who goes by R.B., had intended to work five more years, but then the airline offered early retirement.

He had been furloughed in the 1990s, but felt that Delta had given him a good career and allowed him to build a schedule around his family’s needs. So he decided to return the favor and help a colleague with less seniority. He also realized it was time for a break after a string of personal tragedies.

“I’ve gotten to do what I dreamed of doing,” he said. “Now, I don’t have to go to another hotel room unless it’s one of my choosing.”

Early in his career, Mr. Vaughn flew internationally, but he switched to shorter, domestic trips so he could more easily return home to help his first wife, who had depression and other conditions, and his son, who has autism. In 2015, Mr. Vaughn’s wife, to whom he had been married for 33 years, killed herself.

He took time off to grieve and care for his son. In 2017, he started dating Kimi, who worked at his son’s school. Mr. Vaughn’s father died that summer, and his wife’s daughter died last year. His mother died in February, and his grandmother died of the coronavirus this summer.

“Burying that many family members in such a short period, each one of those changes your perspective on life,” Mr. Vaughn said. “We’ve had a lot of heartache, but we try to look at the things we’ve been blessed with.”