It was a Saturday night in late October, and I was sitting at my kitchen table rewriting a sermon on the widow’s mite for the third time in eight years. The text was Mark 12:41–44. The widow, her two copper coins, the treasury, the observation of Jesus. I had preached it in 2016, in 2020, and now it was coming around again in the lectionary cycle, and I sat there staring at a half-finished manuscript thinking: I have nothing new to say about this passage. Not because the passage is exhausted—it isn’t—but because I am. Or rather, because I have accumulated too much self-consciousness about what I have already said and what it sounded like and whether anyone noticed.

The problem wasn’t the text. The problem was me, sitting in the same chair, at the same table, preparing to stand in front of the same twenty-three people and say something about a story they have heard me tell twice before. I could feel the weight of my own previous sermons pressing on the page. The first time I preached this text, I focused on the contrast between the rich donors and the widow. The second time, I tried to complicate the reading by noting that Jesus doesn’t actually praise the widow—he observes her, and the theological freight is in the observation, not necessarily in a call to imitate. This time, I didn’t know what angle was left. I deleted three opening paragraphs, closed my laptop, and went to bed wondering whether the real sermon was the one I wouldn’t deliver.

I have been the pastor of the same small congregation in Asheville for long enough that sermon preparation has become a particular kind of loneliness. Not the loneliness of being misunderstood or the loneliness of ministry more broadly—those are real, but they are not what I mean. I mean the specific isolation of sitting alone with a text and your own accumulated history of preaching it, trying to find something true to say that you have not already said in a way you can remember. I mean the particular self-doubt that sets in around year ten or twelve, when you realize you have preached more sermons than anyone in your congregation has heard, and the ones they remember are never the ones you are proud of.

The Early Years: Over-Preparation as a Form of Hope

In my first five years of pastoral ministry, I over-prepared every sermon. I mean this literally. I would spend fifteen to twenty hours on a single message, reading commentaries I barely understood, drafting full manuscripts with footnotes, practicing delivery in my office with the door closed. I remember writing a sermon on Isaiah 6 that had four separate introductions, because I could not decide which one was strongest, and I delivered all four of them. The sermon was thirty-two minutes long. Nobody needed that. But over-preparation was its own kind of hope—a conviction that if I worked hard enough, if I studied thoroughly enough, if I found exactly the right illustration and the right structure, the sermon would land. It would do something. People would remember it, or at least feel it, and the preparation itself would be a form of pastoral care.

Some of that was true. A few of those early sermons did land, and I can still tell you which ones. But most of them were too dense, too long, too carefully constructed to sound spontaneous. I was building cathedrals when people needed bread. The over-preparation was not wasteful—it taught me discipline, it taught me to take the text seriously, it formed habits of study that I still rely on—but it was also a way of avoiding vulnerability. If the sermon was well-researched and carefully structured, then its success or failure was a matter of craft, not of me. I did not have to risk being honest if I could be interesting instead.

The Middle Years: Functional Efficiency and Its Quiet Cost

Somewhere around year seven or eight, I got efficient. I had enough sermon manuscripts stored on my hard drive that I could pull structural templates from previous series. I knew which illustrations worked and which ones fell flat. I could write a serviceable sermon in six to eight hours instead of fifteen, and for a season that felt like growth. I was no longer anxious about the weekly deadline. I had systems. I had a rhythm. I had a notebook—a simple black composition book—where I tracked every sermon I preached: the date, the text, the main angle, one sentence about what I was trying to do, and a note about whether it worked. I still have those notebooks. Fifteen years of them, lined up on a shelf in my study, and they are the closest thing I have to a record of my own development as a preacher.

But efficiency has a quiet cost, and I did not notice it until it was already paid. When you can produce a sermon quickly, you start to produce sermons quickly even when the text deserves more time. You reach for the angle you already know works. You use the illustration that landed last time. You stop being surprised by the scripture because you have learned to manage it rather than let it manage you. The notebooks I kept were supposed to prevent this—I could look back and see what I had already said—but in practice, they often became a catalog of shortcuts. I would flip through and find a sermon on a text, see that it had gone well enough, and build something similar. The congregation probably did not notice. They had not been keeping notes. But I noticed, and the noticing became its own kind of isolation. I was preaching to people who could not hold me accountable for repetition because they had not been tracking, and I was the only one who knew how often I was circling the same ground.

That period coincided with the most difficult stretch of my ministry, though not for reasons connected to preaching specifically. Our congregation had navigated a painful conflict over building use—an outside group wanted to rent our fellowship hall for a community program, and the debate split the church council in ways that took eighteen months to repair. During that season, my sermon preparation became almost mechanical. I produced competent sermons because that was what was expected, but I was not present in them the way I had been in the early years. The efficiency I had developed was, it turned out, a way of surviving a season when I did not have the emotional capacity to be honest in the pulpit. I do not regret those sermons. They held things together. But I can look back at that stretch in the notebooks and see the difference between sermons I wrote and sermons I lived.

The Later Years: When Honesty Becomes the Only Option Left

I am not sure when the shift happened, but I can point to a sermon that marked it. It was a Sunday in November, two years ago, and I was preaching on the feeding of the five thousand. I had preached that text at least four times before. I had done the miracle angle, the compassion angle, the discipleship angle, the Eucharistic angle. I sat down to prepare and realized I had nothing new to offer. No fresh insight. No clever structure. No illustration that would make the story land differently than it had before. And instead of forcing something, I wrote a sermon that was essentially an admission of that fact. I told the congregation I had preached this text four times and was not sure I had anything to add, and then I read the passage slowly and said what I noticed this time—just what I noticed, not what I thought it meant, not what it should mean for them, just what I saw. The sermon was eleven minutes long. It was the shortest sermon I had preached in years. And afterward, a woman named Margaret who has been in this congregation longer than I have been alive said to me, That was the most honest sermon I have heard you preach. She did not say it was the best. She said it was the most honest, and I understood that for her, those were different categories—and that honesty was the one that mattered.

That moment did not transform my preaching overnight. I still write full manuscripts. I still study commentaries. I still spend Saturday nights at the kitchen table. But something has changed in how I understand the task. I am no longer trying to be interesting. I am trying to be honest, and the difference is not semantic. Being interesting is a craft goal. Being honest is a relational one. Interesting sermons can be delivered to strangers. Honest sermons require people who know you—and the particular loneliness of long-tenure preaching is that the people who know you best are also the people you are most afraid of being honest with, because they will see through you if you are not, and they will hold what they see.

The Notebook System and the Problem of Accumulated Manuscripts

Let me say more about the notebooks, because they have become central to how I think about sermon preparation over the long haul. The system is simple: one composition book per year, one line per sermon. Date, text, title, one-sentence summary of the angle, one-sentence note on how it went. That is it. The notebooks are not a sermon archive—I keep manuscripts on my computer—but they are a pattern archive. They let me see, at a glance, what I have preached and how I have approached it. When the lectionary cycles around, I can check the notebook before I start preparing and see what I said three years ago and six years ago and nine years ago. This has prevented repetition, but it has also created a new problem: I can see my own patterns, and some of them are not flattering. I lean toward certain texts. I avoid others. I have preached on grace more than judgment, on comfort more than challenge, on the Gospels more than the Prophets. The notebooks have made me more self-aware, and self-awareness in preaching is a complicated gift. It can make you better. It can also make you cautious in ways that are not faithful.

Last year, I began experimenting with a different approach to organizing the accumulated history of my sermon manuscripts. After fifteen years of scattered files—some in Word, some in Google Docs, some in an old version of Pages that no longer opens properly—I needed a way to see patterns across series, texts, and years. I started using an AI writing app designed for structural organization not to generate sermon content—I have no interest in a machine writing my sermons—but as a documentation tool to sort, tag, and surface connections between manuscripts I had not looked at in a decade. The distinction matters. The Authors Guild, in their AI Best Practices for Authors, draws a careful line between using AI as a research or organizational aid and using it to replace the writer’s own voice and thinking. That line is one I have tried to honor. What I needed was a way to see what I had already said so I could stop repeating myself without losing the threads worth picking up again. The tool helped me map fifteen years of preaching in an afternoon, and what I found was both humbling and clarifying: I have said certain things well and certain things poorly, and the difference is almost always whether I was honest or merely competent.

I should note that the question of what tools are appropriate for sermon preparation is not one I take lightly. The Purdue OWL’s creative writing resources frame sermon writing—rightly, I think—as a creative practice subject to the same invention and revision challenges as other forms of creative nonfiction. The weekly discipline of generating original work against accumulated self-doubt is not unique to preachers, but it has a particular shape in the pulpit because the audience is fixed and the relationship is long. The writer’s development compounds over time, and the self-consciousness that comes with experience is not a problem to be solved but a condition to be worked within.

Shorter Sermons and the Theological Conviction Behind Them

Two years ago, I began writing shorter sermons. I want to be clear that this was not a concession to shorter attention spans or a response to declining attendance. It was a theological decision. I had come to believe that I had been using sermon length as a substitute for sermon depth—not theological depth, but relational depth. A twenty-five-minute sermon can hide a preacher. It gives you room to circle, to qualify, to illustrate your way around the thing you actually need to say. A twelve-minute sermon forces you to say it. There is nowhere to hide. And I had reached a point in my ministry where hiding in the pulpit felt like a violation of the trust the congregation had placed in me. These people know me. They have watched me age. They have buried their people with me. They do not need me to perform competence for twenty-five minutes. They need me to tell them what I have seen in the text and what I am struggling with, and then sit down.

The shorter sermons are harder to write, not easier. Cutting is harder than adding. Every sentence has to carry more weight. I spend as much time on a twelve-minute sermon as I used to on a twenty-minute one, because the editing is more demanding. But the result is something I can stand behind more fully, because there is less of me in the way. The widow’s mite sermon that I was rewriting on that October night—the third time I had preached it—I eventually delivered in nine minutes. I read the text. I said that I had preached this passage twice before and that both times I had tried to make it mean something, and that this time I wanted to just sit with it. I said that the widow gave everything she had and that Jesus noticed, and that I did not know what that meant for us and I was not going to pretend I did. Then I sat down. Margaret told me it was honest. I think she was right, and I think that is enough.

What the Loneliness Teaches

I do not have a resolution for the loneliness of sermon preparation. It does not go away. If anything, it deepens with time, because the longer you preach to the same people, the more you are aware of the gap between what you say and what they need, between what you intend and what they hear, between the sermon you deliver and the one you could not bring yourself to write. That gap is the loneliness. It is not a failure of craft or a sign that you are in the wrong vocation. It is the cost of doing this work among people you know, for years, without the buffer of novelty or distance.

What I can say is that the loneliness has taught me something I did not expect. The sermon that matters is not the one people remember. It is the one that was honest. And honesty in the pulpit, for a preacher who has been in the same place long enough to run out of fresh angles, means standing up and saying what you see in the text even when—especially when—you are not sure what it means. The widow gave two coins. Jesus watched. I have preached that story three times now, and I am still not sure what to do with it. But I am more at peace with not knowing than I used to be, and I think that peace is what the congregation actually needs from me. Not certainty. Not novelty. Just the willingness to keep showing up with an open Bible and an honest silence, and to let that be enough.