Five Questions for Pastoral Side Quests

March 14, 2025 Pastor Chris Oswald
Thesis Pastors pursuing specialized ministries or side income streams must subject those pursuits to rigorous examination through five diagnostic questions to ensure they complement rather than compete with pastoral calling and maintain biblical standards for godly discourse.
Series
Type
Topical
Tone
Method
What's in this sermon

The shape of the argument

20 units across exposition, application, illustration, theological claim, and conclusion. The pastor's argument is built from these moving parts.

Pastoral correction · unit #13
"Oswald presents Question One: capacity for dual competence. The diagnostic asks whether the pastor possesses sufficient organizational proficiency and life management skills to maintain generalist ministry while pursuing specialization without either suffering."
Doctrinal loci· 3 surfaced
Pastoral Theology · 18 Ethics / Moral Theology · 5 Doxology / Worship · 1
Bible citations· 3
Proverbs 13:22 | 2 Timothy 2:23-26
Illustrations· 1
  1. personal story · unit #3 — Oswald offers personal testimony of pursuing supplemental income when ministry work left his family in financial difficulty, establishing credibility through lived experience with the tension between pastoral calling and family provision.
Theological claims· 4
  1. Pastoral ministry is fundamentally a generalist calling requiring competence across multiple domains and willingness to do whatever is necessary for the sheep's feeding, safety, and protection. unit #9
  2. Pastoral specialization is historically legitimate and has blessed the church when maintained alongside faithful generalist ministry, as exemplified by Calvin's theological work. unit #10
  3. Scripture's repeated warnings about pastoral money relationships require vigilance because specialization can cloak either financial greed or the pursuit of recognition and larger audiences. unit #11
  4. Contemporary content production economics make controversy virtually necessary for platform growth, creating structural pressure toward biblical ethics violations. unit #18
Quotations· 2
"A good man leaves an inheritance to his children's children, but the wealth of the sinner is laid up for the righteous" — Proverbs 13:22 (unit #6)
"Have nothing to do with foolish, ignorant controversies. You know that they breed quarrels. And the Lord's servant must not be quarrelsome, but kind to everyone, able to teach patiently enduring evil, correcting his opponents with gentleness. God may perhaps grant them repentance leading to a knowledge of the truth, and they may come to their senses and escape from the snare of the devil after being captured by him to do his will" — Paul (unit #17)
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Full transcript

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0 · Oswald frames the sermon as a concerned observation about developing trends in theologically conservative online culture, disclaiming any intent to call out specific individuals while acknowledging his own potential categorization as a 'concerned bro

Sam, Today I am going to discuss my uneasy sense of what's developing in the Theobro culture. Not going to name any names because I don't feel like my concerns are firm enough or as well defined enough to call anybody out. And besides, if I were to do that, I'd probably need to reach out to them first. So these are just things that I'm seeing. And I suppose that I, in recording this podcast, wind up accidentally stepping into the concerned bro category. Cause these are concerns. And that's okay if I get labeled a concerned bro, because I don't care. Anyway, for those of you who are wondering what this is all about, and maybe you're not super online, that's great, by the way, good for you.

1 · Oswald identifies the core phenomenon: pastors maintaining local church ministries while simultaneously pursuing side ventures in content production, enabled by technological and platform changes that have drastically lowered barriers to entry and algorithmic reach

But I'm going to trace this to how I understand this situation to have unfolded. Again, not going to talk about particular people or particular controversies, just the phenomenon at large. And the phenomenon at large is what I would describe as pastors of local churches who also have various on the side are doing. And yet potentially, as my understanding is of past kind of the background it's becoming X is way more free than it used to be when it was Twitter. It's easier to get to algorithmically. It's easier to get to the people who would be interested in you. It's easier to produce content than it's ever been. Doesn't take much money at all.

2 · Oswald traces the historical context: a 'poverty theology' that left pastoral families genuinely impoverished in the 1990s and 2000s, which he critiques as both theologically misguided and practically irresponsible, particularly in its effects on pastors' wives and children

And we walked out of an environment back in the 90s and 2000s. I was a part of this, like a little bit of a part of this, where I think before then a poverty theology had settled in on pastors. And so you would really see fairly often pastors, you know, content in the work of their ministry, not making enough money to take care of their family. And so you would see situations where, honestly I think that. I think a lot of people suffered in pastoral families, wives in particular, but children also, because there was a mentality of like, well, yeah, I'm a pastor, like, what? Of course I'm going to be poor. And of course, like, there's a reasonable level where that's true. I would say poorer might be more consistent to the truth. But there's also a level where a lot of men back in the 90s, earlier than that too, were kind of slackers in that respect. And what they should have been doing is they should have been looking for other ways to supplement their family's income.

3 · Oswald offers personal testimony of pursuing supplemental income when ministry work left his family in financial difficulty, establishing credibility through lived experience with the tension between pastoral calling and family provision

And I have tried. I don't think I've always succeeded. I certainly have never succeeded in making, you know, my family's life extremely comfortable. But when things got stupidly bad because of ministry or you know, the orphan, I would, I would go do somewhat successful or we left for Kansas. This kind of problem that people were having full toward, I think just a family to have income wise. And it wasn't.

4 · Oswald credits Mark Driscoll with challenging poverty theology and modeling pastoral side income through content production, establishing Driscoll as the inadvertent architect of the current content-production model even among pastors who have since rejected his theology

He began to really push back against that and say, you know, pastors, men, it's not okay for your family to be poor just because you're in the ministry. You need to go out and make some stuff happen and take care of these folks. And it was Oscill Driscoll who had kind of a model for that in that he was both a content producer, he was a relatively prolific writer and produced a bunch of other kinds of content. And this is before podcasts were super popular, but he was definitely bringing in a second stream and was able to take care of his family because of that.

5 · Oswald traces the genealogy: contemporary theologically conservative pastors have retained Driscoll's emphasis on pastoral hustle and family provision even while abandoning his theology, resulting in a culture committed to side income but without the traditional trades Driscoll might have envisioned

Well, a lot of guys these days who are in the theobro camp and really don't align theologically with Mark Driscoll at all anymore and have moved way more toward the far right side of the theological spectrum and are open advocates for patriarchy and so on and so forth. Well, a lot of those guys, I think, carried that essential lesson forward that Driscoll pounded into them. There were a lot of these guys who were part of that movement in one way or another or influenced by it. And so they are admirably dedicated to the hustle, which I love. I feel like I want my family motto to have always been, you can just do things. Because the truth is that we live in this incredible country with incredible opportunities and we have so much freedom and so many resources. If we screw up that. And it's okay if you don't and you can really go out and neo bro guys aren't content to let their thousand dollar a year. They're like, well, that's a start. That's probably not going to be enough for my family. So that's good.

Where this fits

Recent preaching context

The three sermons immediately preceding this one in the preaching schedule.

Mar 13, 2025
God is actively dismantling the disorienting effects of Darwinian thought through an unlikely coalition of tech oligarchs and reality-respectors, relocating humanity to its proper place above creation but beneath the Creator, and restoring a coherent understanding of time.
March 14 · This sermon
Five Questions for Pastoral Side Quests
Pastors pursuing specialized ministries or side income streams must subject those pursuits to rigorous examination through five diagnostic questions to ensure they complement rather than compete with pastoral calling and maintain biblical standards for godly discourse.
Take it further

Discuss · apply · pray

Small groups
6 discussion questions
Chris described pastoral ministry as fundamentally generalist work—shepherding the flock in feeding, safety, and protection across multiple…
Daily readings
5-day reading plan
This week we examine five diagnostic questions that help pastors discern whether specialized ministry enhances or undermines their fundamental calling to feed, guard, and protect the flock.
Prayer
Grace for Faithful Generalist Calling
Father, we come before you as undershepherds, grateful that you have called us to pastor your flock with faithful simplicity and gospel-cent…
Family table
When a Pastor Has Other Gifts
This prompt invites kids to think about how pastors (like their own pastor) are people with many gifts and responsibilities, not just one th…
Couples
Calling, Competence, and the Care of Our Home
The sermon pressed the question of whether a pastor can faithfully pursue specialized work alongside his primary calling. What conviction or…
Memorize
2 Timothy 2:23-26
This passage directly addresses the pastor's ethical vulnerability when specialization and platform-building create structural pressure toward controversy and quarreling—the very diagnostic danger Chris identified in contemporary content production economics. Paul's call to avoid foolish controversies and maintain gentleness in correction anchors the sermon's warning that pastoral specialization must never compromise the shepherd's fundamental character and commitment to truth-seeking over audience expansion.
Small-group discussion

6 questions for your group this week

  1. Chris described pastoral ministry as fundamentally generalist work—shepherding the flock in feeding, safety, and protection across multiple domains. What does this generalist calling look like in the real life of a pastor you know or have observed?
    → When you think about that pastor's life, where do you see the weight of trying to be competent in many areas at once?
  2. The sermon acknowledged that specialization—theological writing, counseling expertise, speaking—can genuinely bless the church. But what warning does Scripture place around a pastor's pursuit of specialized recognition or financial gain, and why does that warning matter?
    2 Timothy 2:23-26
  3. Chris presented three diagnostic questions a pastor should ask before pursuing a specialized pursuit alongside generalist ministry. Of those three—capacity, competence, and complementarity—which one do you think gets neglected most often, and what happens when it does?
  4. The sermon highlighted a fallen condition: contemporary content production economics almost require controversy to build an audience, creating structural pressure toward ethical compromise. How have you witnessed this dynamic at work in Christian leadership, whether in your church or beyond?
    → What makes it hard for a pastor or Christian leader to resist that pressure?
  5. The gospel humbles us and fills us with gratitude for Christ's finished work. How does that gospel posture—gratitude rather than striving for recognition—reshape how a pastor should think about building a platform or specialized reputation?
    → What would change in a pastor's life if his primary audience was the joy of his own flock rather than a larger audience?
  6. Proverbs 13:22 speaks of the righteous leaving an inheritance for their children's children. In light of this sermon, what kind of inheritance—in terms of pastoral character and faithful generalist work—do we want our shepherds to leave the church?
    Proverbs 13:22
Draft · pending review
Daily readings · Monday–Friday

5-day reading plan

This week we examine five diagnostic questions that help pastors discern whether specialized ministry enhances or undermines their fundamental calling to feed, guard, and protect the flock.

Monday 2 Timothy 2:23-26

Paul instructs Timothy to avoid foolish controversies and instead pursue gentleness, teaching, and patience—the bread-and-butter work of a shepherd. The generalist pastor cultivates virtue across the whole spectrum of congregational care, not only in specialized domains. We are called first to the undramatic faithfulness of feeding our flock in all seasons, not to the pursuit of distinctive expertise at the expense of the whole.

Tuesday Proverbs 13:22

The righteous leave an inheritance to their children's children, while the sinner's wealth is laid up for the just—a reminder that how we steward resources reveals our hearts. As pastors consider specialized pursuits, we must examine whether the economics of those pursuits tempt us toward the idolatries of wealth accumulation or platform growth. The gospel humbles us as we recognize how easily specialization can become a vehicle for covetousness dressed in the language of ministry effectiveness.

Wednesday 2 Timothy 2:23-26

Paul's charge to Timothy emphasizes steadiness, instruction, and correction done with patience and gentleness—disciplines that demand organizational clarity and margins. A pastor pursuing specialization without the capacity to manage both faithfully will find either the flock neglected or the specialized work compromised. We must ask honestly: Do I have the life rhythms, the systems, and the personal discipline to give full attention to both, or am I deceiving myself about my actual bandwidth?

Thursday 2 Timothy 2:23-26

Timothy is called to be "apt to teach," which assumes he has actually developed the competence to handle Scripture well and instruct others faithfully. Specialization without genuine skill development wastes the pastor's time and damages his witness to the flock who know when competence is lacking. We serve the sheep best when we undertake specialized work only after proving that we possess real capacity and expertise in that domain.

Friday 2 Timothy 2:23-26

Paul's call to avoid futile controversies and pursue instruction and correction reminds us that the pastor's specialized gifts matter only insofar as they serve the central work of feeding and guarding the flock. Our deepest question is not whether we have a passion for a specialized pursuit, but whether that pursuit actually strengthens our generalist calling or diverts our best energy away from the sheep entrusted to us. The natural response is to rejoice when specialization genuinely serves the whole, and to lay it aside when it competes for the pastor's primary allegiance.

Draft · pending review
Pray together this week

Grace for Faithful Generalist Calling

Father, we come before you as undershepherds, grateful that you have called us to pastor your flock with faithful simplicity and gospel-centered care. We confess that we are often drawn to specialization and platform—to the recognition that comes with expertise in a single domain—and we struggle to embrace the generalist calling that feeds, protects, and knows your sheep in their particularity. We know that our hearts are prone to the subtle idolatries of influence and financial security, and we need your Spirit to expose where ambition has begun to cloak itself in the language of ministry (2 Timothy 2:23–26).

Yet the gospel humbles us as we grasp that Christ himself was the consummate generalist, ministering to every dimension of human need—healing, teaching, rebuking, comforting, and laying down his life. In his substitutionary sacrifice, he has freed us from the tyranny of self-promotion and given us the capacity to serve without the constant calculus of personal gain. We are no longer enslaved to our own glory; we belong entirely to him.

Give us wisdom, we pray, to evaluate any specialized pursuits by asking whether we possess the organizational capacity to sustain both generalist faithfulness and focused expertise without either suffering. Grant us honest assessment of our actual competence—not the competence we wish we had, but the competence we truly possess—so that we do not waste the church's time or our own energy on pursuits that lack genuine skill. Most of all, grant us the grace to see specialization not as an escape from the humble work of pastoral care, but as a complement to it, a way to serve the flock with richer resources and deeper love.

We commit ourselves afresh to the generalist calling, knowing that in feeding your sheep—in all their messy, particular, non-viral complexity—we are serving the Chief Shepherd himself (1 Peter 5:1–4). To him be all glory and dominion forever.

Draft · pending review
Sunday-evening family table

When a Pastor Has Other Gifts

For the parent

This prompt invites kids to think about how pastors (like their own pastor) are people with many gifts and responsibilities, not just one thing. It's a chance to explore how doing *lots* of things well is harder than it sounds, and why wisdom matters when we're tempted to add more to our plate.

Pastor Chris talked about pastors who are really good at writing books, or teaching Bible studies, or starting new ministries—things *beyond* taking care of the congregation on Sunday. If you were a pastor, and you were really, really good at something extra (like writing or counseling or leading a big project), how would you know if doing that extra thing would help the church or hurt it? What questions would you ask yourself?
works for ages 9+ — younger kids can listen and share simpler thoughts with help
Draft · pending review
Couples · three questions over coffee

Calling, Competence, and the Care of Our Home

  1. The sermon pressed the question of whether a pastor can faithfully pursue specialized work alongside his primary calling. What conviction or question did that tension surface in your own heart about how we're stewarding our time and energy together?
  2. Chris talked about the danger of letting platform or recognition subtly reshape our priorities. Where do you sense that temptation showing up in our marriage—not just in work, but in how we spend ourselves, or what we're reaching for?
  3. If the sermon's diagnostic questions about capacity, competence, and complementarity apply to any pursuit or ambition in your life, what's one thing you'd like me to pray for you about this week as you think it through?
Draft · pending review
Memory verse this week

2 Timothy 2:23-26

Have nothing to do with foolish, ignorant controversies; you know that they breed quarrels. And the Lord's servant must not be quarrelsome but kind to everyone, able to teach, patiently enduring evil, correcting his opponents with gentleness. God may perhaps grant them repentance leading to a knowledge of the truth, and they may escape from the snare of the devil, after being captured by him to do his will.

Why this verse: This passage directly addresses the pastor's ethical vulnerability when specialization and platform-building create structural pressure toward controversy and quarreling—the very diagnostic danger Chris identified in contemporary content production economics. Paul's call to avoid foolish controversies and maintain gentleness in correction anchors the sermon's warning that pastoral specialization must never compromise the shepherd's fundamental character and commitment to truth-seeking over audience expansion.

Draft · pending review
Where this was preached

About the church

Providence Community Church
Lenexa, KS
Sundays · 10:00 AM
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# Providence Community Church

A church preaching expository sermons through the books of the Bible.

## Sermons
- [Glory to the Shepherd, Not the Sheep (2025-03-02)](/ProvidenceLenexa/sermons/2025/03/glory-to-the-shepherd-not-the-sheep)
- [The Whole World Has Gone After Him (2025-03-09)](/ProvidenceLenexa/sermons/2025/03/the-whole-world-has-gone-after-him)
- [Reading that Russian at 5 A.M. (2025-03-13)](/ProvidenceLenexa/sermons/2025/03/reading-that-russian-at-5-a-m)
- [Five Questions for Pastoral Side Quests (2025-03-14)](/ProvidenceLenexa/sermons/2025/03/five-questions-for-pastoral-side-quests)

## About
- [About the church](/about)
- [Plan a visit](/visit)

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