First of all, it is NOT failure. As a pastor, I've failed. Some times it's big failures, some times it's small ones. I've read leadership books that say it's good to fail because it means you're trying and taking risks. It would be far worse to not even try. But failure is not the most difficult part of being a leader.
"Everything rises and falls on Leadership." I've heard and read that quite a bit. I'm not sure who coined it first (was it John Maxwell or Mike Slaughter?). Notice it's not "some" things rise and fall on leadership. No, it's "EVERYTHING." You see, that's the hardest part of being "The Leader" or the one in charge; the one who is ultimately responsible. Look at baseball managers. They get criticized when the team is losing, but they're geniuses when the team is winning. Lose enough, and the manager is fired. It doesn't matter if the players are terribly worse talent than every other team in the league, or the ownership isn't willing to spend more money, or any number of other people who could have done their job better. The Manager is ultimately responsible for the baseball team on the field, so if the team is losing, then the manager is out, and a new leader is brought in.
The hardest part of being "the leader" is: The Pressure of Ultimate Responsibility. It nags at me nearly everyday. Sure, I can place blame on other people or things: church members, the District Superintendent, the Bishop, "the community transitioned but the church didn't," "people just don't give like they used to," ... there's tons of reasons we can look at and analyze, but ultimately, I am responsible for the church that I've been sent to. God's given me a responsibility for this time, and this place...these people. Because, "everything rises and falls on leadership," right?
I'm not sure many people in the pews realize this pressure that the pastor faces. I'm not talking about a "woe is me" "everything is my fault" attitude. But it's just the pressure of being a passionate owner of the responsibility for the direction of the organization. Knowing that pretty much every problem, tension, failure or success you face is somehow related to you either directly or indirectly.
So, if you're wondering what stresses out your Pastor, President, CEO, or other leader, now you know. No matter how many times he or she tells oneself or hears "it's not your fault," it doesn't matter, because deep down, the leader knows who is ultimately responsible regardless of fault or blame. The leader will always think, "If I was just a better leader, we could overcome and make it through..."
How do you handle that? I guess you have to realize who it is that is really in charge, and it's not you. AND, you have to realize that Leader is more capable and powerful than anything you ever even imagined, a very trustworthy leader. Who is it? God: Father, Son and Holy Spirit. He has this way of accomplishing things, directly and indirectly, in spite of the shortcomings of the people He sends. He is The One on Whom everything actually rises and falls. Jesus Christ. (Colossians 1:16-17, Ephesians 1:20-21)
How else do you handle it? Like a 162 game baseball season: you win some, you lose some. You brush it off, forget about it, and "get 'em next time (or next season)."