It is often really hard to determine what success it when you are a pastor. Leadership books encourage you to clarify the win so that you are not just doing stuff and wasting time and money. But at the end of the day, there is not always a clear scoreboard for life transformation.
But one benchmark that we celebrate as a church, and I personally enjoy being a part of, is seeing folks get baptized. Last night we baptized 6 more people in our church family. We had lots of people there to celebrate with those being baptized and overall it was just a sweet night. Those kind of nights feel like winning.