Preaching Contextually: Navigating Your Cultural Divide

March 16, 2026

Before he preaches, every preacher needs to ask: am I a generational native, or a generational immigrant? Each of us is naturally designed to preach to our own generational cohort. If you are a Gen X’er like me, you speak the language, you get the references. You are a native. But every other cohort? You might as well be a missionary in another country.

This five-part series of blog posts will explore five principles you can bring to your preaching that will more effectively help you communicate as a generational immigrant.

Preachers today face a cultural divide when communicating the timeless truths of the gospel to generations that are not their own. The first principle for effective preaching to a different generational cohort is to understand and embrace cultural differences by contextualizing sermons specifically for them.

Why Contextualization Matters

Contextualization bridges the gap between the biblical message and the lived experience of a particular culture or cohort. Scripture offers examples of this approach: both Peter and Paul adapted their messages to the cultural contexts of Jews and Gentiles.

Just as missionaries can communicate more effectively by immersing themselves in the culture to which they are called, preachers must study and understand the culture of different generational cohorts to connect meaningfully.

Understanding Context

Each generation is shaped by the experiences of their lifetime. Older generations may value stability, tradition, and loyalty. In contrast, younger generations often display skepticism toward institutions and authority figures, having been influenced by political controversies and religious scandals.

These realities shape their perceptions and their receptiveness (and resistance) to faith. Books like Generational IQ by Haydn Shaw and Engaging Generation Z by Tim McKnight can help.

Moving Beyond Assumptions

Preachers cannot assume their listeners share the same cultural reference points or spiritual background they do. The church no longer has a home-field advantage.

Today, preaching is an “away game,” requiring intentional effort to cross cultural and generational boundaries.

Practical Steps for Contextualizing

Here are four ways preachers can start to contextualize their preaching:

Learn listeners’ language and culture: Engage with their media, values, and experiences to understand what matters to them.
Be present: Spend time with people who are different than you—both in person and digitally—to build relationships and understanding.
Incorporate relevant illustrations: Your reference to that John Wayne movie might not connect. Use stories and examples that resonate with listeners’ context.
Address real-life challenges: Speak to the issues your listeners face, such as anxiety, financial pressure, delayed adulthood, or caring for aging parents.

By practicing contextualization, preachers can become cultural translators who make the gospel accessible, relevant, and transformative for everyone.

Putting in the Reps

April 16, 2026

I’ll be honest with you. I’ve been preaching for a while now, and I still walk away from some Sundays thinking, Well, that could have gone better.

There’s no shame in that. In fact, I’d worry about the guy who walks off the platform every week thinking he knocked it clean out of the park. Overconfidence in the pulpit is a little like overconfidence behind the wheel of a tractor — sooner or later, you’re going to end up in a ditch.

I sat down recently with Patrick Lightfoot, lead pastor at Traverse Christian Church in Windsor, Colorado, and something he said stuck with me. He talks about “stage time” — the practice of actually getting up on the platform mid-week and preaching the sermon out loud before Sunday arrives. Not reading it over in your recliner. Not muttering through it in the shower. Actually standing where you stand and speak the words into an empty room.

He calls it “putting in the reps.”

I love that. Because preaching is a craft, and crafts require practice. You don’t sit in the bleachers and become a ball player. You don’t read books about farming and develop a feel for the land. You have to get your hands dirty.

Patrick also talked about watching yourself preach — playing back the recordings and sitting through the awkward “ums” and the rushed transitions and the conclusions that sort of just… trail off. He admits it’s uncomfortable. Of course it is. Nobody enjoys watching themselves on video. I watched one of my sermons once and became briefly convinced that I needed a new career. But that discomfort is where growth hides.

What strikes me most about Patrick’s approach is the discipline underneath the Spirit-dependence. He doesn’t treat those two things as opposites. He plans sermon series a year in advance and still makes room for the Holy Spirit to redirect. He rehearses thoroughly and still steps to the pulpit trusting God, not his notes.

That’s the balance, isn’t it? Preparation isn’t a lack of faith. It’s faithfulness.

Francis Chan puts it in the form of three questions: Am I worried about what God thinks? Do I genuinely love these people? Am I depending on the Holy Spirit?

Patrick has those written on a notecard and tucked in his Bible. They’re a better pre-sermon checklist than anything I could come up with, so I plan to put them in my Bible.

The congregation sitting in front of you every Sunday deserves a preacher who has done the work — and who has also gotten out of the way enough to let God do His.

Put in the reps. Then trust the One who makes them count.

BONUS CONTENT: Here are Francis Chan’s seven questions Patrick Lightfoot mentioned in his recent podcast appearance. Print them off and tuck them in your Bible and see if they don’t shape your preaching.

Am I worried about what people think of my message or what God thinks?—Teach with Fear.

Do I genuinely love these people? — Teach with Love

Am I accurately presenting this passage? — Teach with Accuracy

Am I depending on the Holy Spirit’s power or my own cleverness? — Teach with Power

Have I applied this message to my own life? — Teach with Integrity

Will this message draw attention to me or to God? — Teach with Humility

Do the people really need this message? — Teach with Urgency

Prepare for the Way You Preach, Not the Way You Prepare

September 3, 2026

Tony Johnson was back on the podcast this week, and he said something in the first five minutes that I haven’t stopped thinking about: “I was preparing for a different style of preaching than what is natural for me.” He was preaching based on the way he prepared, rather than preparing for the way that he preaches. Read that twice. I had to.

Tony told me he used to build these meticulous outlines — detailed enough that he could hand them to someone else and they could preach the message. But when he got up to preach, he wasn’t using the outline at all. He was following the red circles and blue stars he’d scribbled on it. The notes were theater. The real preparation was happening somewhere else entirely.

So he blew it up and started over, building a process that matches how his brain works. Mondays through Wednesdays, he just lives in the passage: reading it, praying over it, letting it marinate. No writing. He calls this white space, and he’s convinced it’s one of the most underused tools in a preacher’s kit. Some of his best material shows up at two in the morning on a trip to the bathroom, not at a desk with a deadline looming. Thursday, he sits down and builds a mind map, breaking the message into four or five movements he can hold in his head rather than a manuscript he has to follow. Less prep time. More authenticity. A sermon that feels discovered rather than delivered.

Now, Tony’s got a teaching team of five to seven preachers to coordinate, which most of us reading this don’t have. But don’t let that get in the way of the real point. If you’re the only voice at a church of 125, you can still build a team around your preparation, even if you’re the only one standing up on Sunday. Ask a few trusted voices in your congregation what they think people need to hear. Let your spouse hear you talk about something you love and compare that energy to your preaching voice. Tony’s litmus test was simple: are you performative, or are you proclaiming something that’s naturally been embedded in you?

He also mentioned something that stuck with me. 2|42 has moved away from Tony underlining scripture on a screen when he preaches and gone back to him simply holding a Bible in his hand. No graphics, no bumpers, just him, the text, and the room. Turns out people aren’t as hungry for polish as they are the Word.

Find the process that fits how God wired you. Then get out of your own way.

Better preaching makes a bigger impact.

Episode Summary

Discover how preacher Tony Johnson transforms his approach to sermon preparation, emphasizing authenticity and responsiveness. Learn practical tips on adapting your preaching style, engaging your congregation, and cultivating your unique voice.

Standing in the Middle

March 9, 2026

“And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others.” (2 Timothy 2:2)

My Biological Ancestry

My family’s American experience began ten generations ago when my seventh great-grandfather, Johann Jacob Weller, arrived in America in 1737. Four generations later, my third-great grandfather—Johann’s great-great grandson—moved to northeast Indiana. That’s where he and four successive generations of Wellers rest at Cedar Chapel Cemetery. It’s where they’ll lay my bones one day to await Christ’s return.

My Spiritual Ancestry

As fascinated as I am with my family’s genealogy, I am more intrigued with my spiritual family tree. I wish there was a good website for tracing the ancestry of my spiritual fathers and mothers.

I learned about Jesus from my dad, Larry Weller. My childhood preacher, a man named Jim Platner, led my father to faith in Christ. Jim tells me he became a Christian through the influence of, among others, a preacher named Hank McAdams.

That’s as far back as I can trace my spiritual heritage.

If Brother McAdams were still living, I’d be fascinated to find out who told him about Jesus. And who told that person. And the one before.

In eternity I think I’ll have all the time in the world to meet every person in that long line reaching all the way back to Jesus. Jesus discipled Peter, who told Clement about Jesus, who told Ignatius, who told Polycarp, who told Irenaeus, who told someone, who told someone else, all the way down the line to Hank McAdams, Jim Platner, Larry Weller, and eventually me.

Christians Stand in the Middle

That’s because all those folks lived according to 2 Timothy 2:2—“And the things you have heard me say in the presence of many witnesses entrust to reliable people who will also be qualified to teach others.”

If you’re a follower of Jesus, you’re called to stand in the middle between the generation who led you to Christ and people who have not yet become followers of Jesus.

Preachers Stand in the Middle, Too

In 2020 I began meeting with a group of younger preachers for coaching and encouragement. These guys ranged from their late twenties to early thirties, and each were first-time preachers.

By that time, I had been preaching nearly every Sunday for twenty-three years, so I had a lot to say. I’ll leave it to them to decide whether I had much to offer.

We talked about preaching. We explored leading in the context of a complicated time in our nation’s history (remember, it was at the start of the pandemic). Our topics ranged from the mundane—like how to prepare a sermon—to deeply personal subjects like how being in ministry impacted our wives and children.

As I move into my fifties, investing in the next generation of servant leaders feels more important to me than ever.

There was a slogan on the wall of the chapel at the college I attended: “God give us preachers.” This rallying cry is as relevant and needed today as it was forty years ago when I first read it.

It is a prayer, but it is also a reminder that I am the answer to that prayer, because I stand in the middle between the preachers who taught me and the ones who will pick up the mantle of proclaiming God’s Word to a new generation.

Evangelism is the responsibility of every Christian. But it’s important that preachers understand their responsibility to stand in the middle pulpit.

Fresh preaching insights await.