Jen Wilkin Takes a Second Look at the Sermon on the Mount

A decade ago, a little-known Bible teacher named Jen Wilkin published her first Bible study, an exploration of the Sermon on the Mount. She challenged herself and her students to wrestle with Jesus’s “inaugural address”—his vision for his kingdom. Ten years later, she’s still teaching Matthew 5–7 and has published an updated Bible study.

I asked her to reflect on what she’s learned, how the world has changed, and what she hopes a new generation of women will gain from the most famous sermon of all time.

What’s been the biggest blessing in teaching the Sermon on the Mount? How has it transformed you?

Like many other Christians, I wrestled with a clear understanding of what my relationship to the law should be. Was I bound by it? Was it no longer relevant for me because of Christ’s perfect obedience? The Sermon on the Mount gave me a clear articulation of the ethics of the kingdom of heaven. It gave needful conviction and a clear delineation of the way of holiness. And it gave assurance as well.

The Sermon on the Mount gave needful conviction and a clear delineation of the way of holiness. And it gave assurance.

Until I studied the Sermon, I held a weak understanding of discipleship, particularly in the area of obedience. Jesus’s teaching about the necessary pairing of internal righteousness with external righteousness transformed my understanding of the work of the Spirit in our sanctification. It gave me language for the difference between a legalist and a lover of God’s law, and it gave me a framework for living as someone whose “righteousness exceeds that of the scribes and the Pharisees” (Matt. 5:20).

Sometimes we see new things when we go back and study a portion of Scripture again. What did you notice the second time around that you missed the first time?

All my studies originated in a living room before they ever found their way to a publishing house. Most of what I’ve published I’ve taught multiple times beforehand. I first taught the Sermon on the Mount to a group of about 10 women in 2002. This new release is the fourth or fifth time I’ve gotten to teach this content, and every time I find more treasures.

Since the 2014 release, I’ve spent a great deal of time in Genesis and Exodus. This time through the Sermon on the Mount, I was surprised by how many connections to that Old Testament narrative can be found. Like others, I’ve said the Lord’s Prayer thousands of times, to the point that it can become overly familiar. For the first time, I heard the language of God’s provision in the wilderness wandering in its lines. Daily manna, forgiveness for our ongoing sins, faithful leading—they were God’s provision then, and they’re ours still as we walk the wilderness of our time on earth, traveling toward the fullness of the kingdom of heaven.

What are some important interpretative strategies to remember when reading the Sermon on the Mount?

It’s essential to see the Sermon as a cohesive unit with a flow of thought. Like any other good sermon, it has a crafted beginning, middle, and end. We typically hear teachings over small, familiar portions of its content like the Lord’s Prayer or the Beatitudes, but we rarely get to consider it in its entirety. In a sense, we’re overly familiar with sections of the Sermon but unfamiliar with how those sections fit together. Studying the Sermon as a whole gives us the context we need to understand its individual parts.

But we also need to study the Sermon within the context of the Gospel of Matthew. It matters that it was preached at the beginning of Jesus’s public ministry versus at the end. Seen in its place in the timeline of Jesus’s ministry, we know to read it like an inaugural address. Jesus is telling his followers exactly what they can expect, both to redirect wrong expectations and to shape a positive vision of the kingdom.

What did you learn from the first edition of the Sermon on the Mount study? What seemed to resonate with women most? What did they wrestle with most?

I learned women were indeed hungry for a line-by-line study that asked something of them as thinkers. I saw this as I taught in my living room, but I didn’t have a sense of how widespread the hunger might be.

Daily manna, forgiveness for our ongoing sins, faithful leading—they were God’s provision then, and they’re ours still.

This was the first study I ever published. I think everyone involved wasn’t sure whether it would make its way very far into the world. It was longer than the average study, and it required a fair amount of work on the part of the participant. My approach to curriculum writing is to raise dissonance for the learner—to ask them to feel and sit in what they don’t know. This wasn’t a common approach to women’s Bible studies in 2014. Even the women in my local study didn’t love it when I asked them to wait to consult commentaries until after they’d completed the entire lesson. Would women who didn’t even know me embrace the method? But they did!

In terms of the teachings, I heard what I’d experienced myself: many women had never had the opportunity to see the Sermon as a continuous whole, and their understanding of its individual parts changed dramatically as they viewed the sweep of the entire message. The confusing or confrontational passages grew in clarity, and the familiar ones grew in depth. In particular, the portion that reorients the Ten Commandments hit home—as it had for me.

What can be difficult or confusing about Jesus’s words in the Sermon on the Mount?

Jesus packs his longest recorded message with hard words. He speaks of persecution as normative and worry as irrational. He decries not just megawatt sins like murder and adultery but also the more subtle, related sins of anger and lust. He tells his followers to cut off offending hands. He demands single-minded allegiance. His view of the blessed life is by all earthly standards accursed.

The boldest of modern preachers may place one or two convicting phrases in a sermon. Jesus’s preaching is relentless in delineating the difference between citizens of the kingdom of earth and citizens of the kingdom of heaven. We’ve grown unaccustomed to such directness, to calls to costly commitment, and it can take some time for us to absorb the sense of the Sermon as a whole. But with patience and repeated reading, it yields rich fruit.

What has changed in the world since you released the first edition of this study? How do you think the Sermon on the Mount can help us today?

The first edition released in 2014. When I first read this question, I thought about all the changes to my own life—I was parenting teens, and now I’m a grandmother. I’d just published Women of the Word, a book I didn’t expect anyone but my family would read. Because I typically write studies over entire books of the Bible, I had mixed emotions about this study being the first one to publish, but I knew how influential the Sermon had been on my formation. Ten years later, I’m so glad it was the first one to venture out into the world.

And that world has seen much in those 10 years. I googled the headlines from 2014, and they were surprisingly similar: Ukraine, Israeli-Palestinian conflict, mass shootings, fears of an Ebola pandemic, the deaths of influential people. And yet we’ve grown familiar with the phrase “in these unprecedented times” in the past decade. Within Christian circles, our post-Christian reality has begun to sink in. It’s clear that to be a devoted follower of Christ will mean the very things Jesus indicated in the Sermon: rejection, persecution, and the daily renewal of our commitment to follow where he leads. His exhortation to long for a future kingdom and live as its citizen now has never been more needed.