We’re in the thick of our annual Stewardship season at church, and so far, so good—the letters are out, the committee has worked well and diligently, the stewardship moment was rock solid…and we had the cherub choir sing (even Scrooge’s heart would have melted).   The pledge cards are arriving, and we’re getting there.

We’re feeling that combination of cautious optimism and…what?…maybe it’s “optimal caution.”

O.k., so I just made that term up.

But I think of “optimal caution” as something like “cautious optimism for the ‘glass half empty’ set.”

In that vein, maybe it’s just the sense that we’ve reduced the missteps, whether those were typos in the mailings (honestly, how many English majors can one congregation have?), forgetting to follow up personally (some people don’t know how to say that while they still love the church, their circumstances have changed), or speaking of the year ahead like a disaster to be averted rather than an unfolding promise to be claimed (never ask the Buildings and Grounds people to write the Stewardship letter. “Asbestos” actually means “no pledges” in Koine Greek. You can look it up).

Of course, pastors can make plenty of missteps at this time of year, too.

A colleague of mine once crafted a warm, newsy, personal note to go alongside the stewardship letter to a member she hadn’t seen since last December…only to find out that the woman had died in Florida that spring, and that her living daughter was not so pleased with the chipper, utterly well-intentioned “How’ve you been?!” message her mother had received from her erstwhile pastor.  Needless to say, that was the end of that, and losing the pledge was the least of it.

So…everyone on our committee is pretty sure we haven’t done any of those things. Now we just wait.

But it’s hard.

It’s hard because it does feel like a referendum on how things are going, even when you know it’s not that simple.

It’s hard because you feel like you’re not just fundraising for an organization, but actually for the Kingdom of God, and that Jesus might be kind of bummed about your numbers even if nobody else is.

It’s hard because we want the church to be an enormous come-as-you-are party, and we work hard to make it just that, only to glimpse the shame and anxiety that can surround people’s relationship with money in ways that only Stewardship season can seem to reveal, and to encounter their painful suspicion that our eleven months of extravagant welcome are really just another sales pitch.

It’s hard because the world’s needs are so great, and that we want people to be generous and responsive to whatever God places on their heart and conscience, even if that means we come later—and yet, the harder we have to make due, the less we’ll be able to do the things that only a church can.

It’s hard because, at the same time, to acknowledge all this can seem as self-serving as asking for capital improvements to the Parsonage, and so many pastors feel as if they don’t dare try.

Maybe it’s no wonder, then, that so many of us learn to come into Stewardship season, optimally cautious, rather than cautiously optimistic.

Maybe that’s the biggest misstep of all.