#2 You go out on a loss

Retirements in wrestling are a funny thing, and a decision that can't come easy to any legendary Superstar. And though every single retirement from the squared circle is different, many Superstars have spent their final matches on their backs for the three-count.
Though some Superstars have been able to win their final matches (look at Stratus herself in Toronto at Unforgiven 2006), the general consensus is that you lose in your retirement match, for the good of the company.
Fans only need to look back to WrestleMania 35, where Kurt Angle, a former WWE World Champion and Olympic Gold Medalist, lost his retirement match to Baron Corbin. It may not have been the most popular decision with fans, but the win definitely helped Corbin get a heel reaction by the crowd, as now, nearly six months later, he is still bragging about the victory.
Having Flair win at SummerSlam will do a lot more for her career than Stratus winning would have done for the Canadian's, as the Queen continues to build a legacy for herself in WWE.