I don't second guess much. I don't think of myself as overconfident....although I'll admit that I often think everyone else is just a little nuttier than I am. I'm just of the mind that once a decision has been made, even if the whole situation goes pear shaped (to quote my British friends), it's a waste of energy to go the 'if only I had..." route.
Perspective is everything, and the bigger the failure, the more distance you need to look at your failure objectively and learn from it. I think I'm finally in the phase of learning from our church plant's failure six years ago.
Here are a few ways I'm thinking about all that.
We didn't fail at church planting. We learned how to pray.
Kelsey is the one who gave me language for this one. Prior to planting, I didn't know much about pouring my guts out before God. I didn't really get there until it was obvious that I was not Rick Warren, and if I was, that Rick Warren was failing miserably in our corner of Cincinnati. In that season, we started this goofy little prayer meeting on Saturday nights. That meeting was life to Kelsey and I in a way that our best Sunday morning never was. When that season passed, we found out we had become intercessors. I'm not planting at this point in my life, but I'm still a prayer guy.
My leadership was not as bad as I thought.
Five years ago, I felt like I had DORK tattooed across the back of my head. With a little perspective, I'm seeing that I wouldn't have done a lot differently - especially the decisions that were made in crisis mode. It seems like the harder the decisions, the more likely I was to have made the right call.
My preaching was not as good as I thought.
I used to think some people came to hear me preach. That might have been true, but it was kind of like how someone might pack a lunch to go have a picnic if they were sure they were going to see a train wreck. I discovered some of my notes the other day and thought "what the heck? Those poor people....". It wasn't all bad....but some of it was really bad. At the same time, there were some great raw ideas. I discovered a message that I'd forgotten about - one where I declared us to be a beta church. In other words, like beta software, we were quirky, but we were doing things that hadn't been done before (at least by us). Regrettably, I then launched into a 12 minute explanation of what an early adopter was. Great idea, bizarre execution.
I launched too quickly.
I was still of the mind that church was Sunday morning, and the sooner I could get to Sunday morning the happier I was. Add that to the fact that I was not (still am not) a great small group leader. We hadn't reached critical mass and it took the whole congregation to operate the church, leaving no one in the actual service (an exaggeration, but not by much....). I should have forced myself to be a better small group leader rather than tried to force my small group to be a better full service church.
I was blessed with an amazing advisory board.
God gave us three young couples who loved Jesus and us. They were remarkably kind to us in every season. Years later, I have a wave of emotion when I think of any of them.
I was in a radical season of reformation myself.
The 3 1/2 years that we went from launch to splash down were remarkably reformative for me. (Spell Check says I made that word up, but I like it.....). I was 30 or 31 starting out - seven years of ministry under my hat, in a wineskin that should have been hung out to dry long before. In that God spoke incredibly clearly to me about doing things differently. My guess is that I was changing internally so quickly that it was hard for people to track with me.
I'm done saying never.
When it was all finished, I said never again. I was probably too young and wounded to speak at that point. I have no real plans, but I don't say 'never again' anymore. God's too big, too complex, and too exciting for that. Plus, I think I've learned a few things....