Sorry. Again. How to Really Repent: Dane Ortlund

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Sorry. Again. How to Really Repent

Guest:Dane Ortlund

From the series:Deeper, Where Faith Gets Real (Day 2 of 3)

Air date:November 3, 2026

Ann (00:05):

So tell me when you believe a man is really serious about truly wanting to change.

Dave (00:11):

When he gives a bunch of money to church.

Ann (00:15):

Said the pastor.

Dave (00:16):

Yeah. The last part of a man to be converted is his wallet. No, that is a church. Welcome to FamilyLife Today, where we want to help you pursue the relationships that matter most. I’m Dave Wilson.

Ann (00:35):

And I’m Ann Wilson. And you can find us at FamilyLifeToday.com. This is FamilyLife Today. So tell me when you believe a man is really serious about truly wanting to change.

Dave (00:56):

I think men or women, when we get real about who we are and how desperate we need Jesus, when we realize we are at loss completely in life and eternity without a saving Christ.

Ann (01:11):

So you’re saying that’s necessary and you’re looking for that?

Dave (01:14):

Yeah. I mean, I’ve met with a lot of guys who are playing games. You can just feel it when they’re sitting with you. And I think them not being truly honest about their sin, and I’m not saying I haven’t done it. I’ve played games as well. I’m not putting myself above anybody, but I think honesty is part of it.

Ann (01:32):

So would you say if we hide, we don’t grow?

Dave (01:35):

Oh, no question. And I know someone has thought a lot about this. Dane Ortlund is with us back in the studio at FamilyLife Today. Dane, welcome back to FamilyLife.

Dane (01:44):

Thanks, Dave and Ann. Good to talk with you.

Dave (01:46):

Yeah. The reason I know you’ve thought about this a lot is you’ve written about it; you’ve preached about it. One of the things I found very inspiring in your book, Deeper, which we’re going to talk about today— Deeper is a book you’ve written about: how does a person change spiritually?—Real Change for Real Sinners. You write about this and man, I resonated with your thoughts on when a man or a woman or a person gets honest with themselves about who they are, they really change. And again, I know you know this, you’re a pastor at Naperville Presbyterian, you’re a father, you’re an author, you’ve got five kids, so you’re watching this in your own home. But talk about that a little bit. What’s this whole thing called honesty got to do with spiritual growth?

Dane (02:28):

Yeah. Thank you, Dave. Well, actually I would be glad to keep talking about giving money to the church.

Dave (02:35):

That’s where we should be.

Ann (02:36):

Said the other pastor.

Dane (02:39):

But what you just said is so profound and true and right and something that we are professionals at evading and escaping the health fostering discipline, the painful humiliating discipline. Actually, you feel like you’re dying of being honest, taking the mask off and being honest with a fellow brother or sister. And really all we’re talking about guys is the horizontalizing of the gospel. So the gospel is a vertical thing, comes from heaven to us because of what Christ has done. Okay, that’s true. And I receive it individually. What does it look like for the gospel in a church among brothers and sisters to turn on its side and become a horizontal reality? Well, it looks like 1 John 1:7, “If we walk in the light, as he is in the light,”—David, this is what you’re talking about. Walking in the light is what you mean by honesty.

(03:32):

“If we walk in the light, as he is in the light, we have fellowship with one another, and the blood of Jesus his Son cleanses us from all sin.” We are masters, even as believers of self-concealment. And the gospel is the only resource in the world that gives us the courage and the power to speak to another brother or sister, the humiliating reality of where we are really at in our present. It’s easy to say, oh, I struggled with X, Y, or Z and 10 years ago I got over it, but what about where I’m at right now? That’s where the rubber meets the road. So that’s what I wanted to give some time to in this book deeper.

Ann (04:10):

So Dane, you’re saying yes, it’s important to be that and do that before God, but we need a brother or a sister that we’re doing this with on the earth. Let me ask you, so are you saying if we don’t have that with someone, we are not going to go deep and we are not going to change and grow?

Dane (04:31):

Well, yes and no. I mean, I wouldn’t want to make this formulaic and cookie cutter, Ann, and say that if you aren’t doing honesty and walking in the light with another brother or sister exactly in the right way, then you’re stuck and hopeless. No, that would be awful.

(04:45):

The Lord has a different way of working with each one of us. But when John says in 1 John 1, if we walk in the light as he is in light, he doesn’t say, if some of us walk in the light, if those of us who really happen to be wired in such a way that need to do this in order to grow, walk in the light. It’s indiscriminate and universal, if we walk in the light as he is in light. We know that when we have a sin that is taking root within us and we keep it in the dark, that is where it grows strongest. That’s what hell wants us to do. Keep it in the dark where it festers and multiplies, proliferates, grows, gets stronger, the roots go down. But when we pull it out into the light, it’s like a mushroom or something that only grows in the darkness.

(05:31):

It comes out into the light, it withers and dies and we have a chance to grow.

Ann (05:37):

Well, I think you said it so well too when you said the only way we can build spiritual growth is the solid ground of self-despair to the degree that we minimize evil within, we lower the ceiling on how deeply we can grow. And if we view your sinfulness as a bothersome headache more than a lethal cancer, you will see tepid growth, if any. I just sat there reading that like, oh man, that’s so good. And it’s really deep too. I don’t think we ponder that often.

Dane (06:07):

We don’t, do we guys? Would you guys agree with this? It seems to me that when I talk to a godly, very elderly saint who’s been walking with God for decades, they feel more sinful than they ever have before. They’re not. I mean, I’m looking at this person and I’m thinking, you radiate the beauty of Christ. I want to hang out with you and get this contagion. Okay, but what’s going on there? It’s like two lines. One is going up and one’s going down descending, and the one going down is growing and understanding just how sinful we are as we grow and the years go by. The other is therefore understanding how much we in fact need the gospel and need Christ, as opposed to we become a believer and now I begin my life of growth and of sanctification, which means I need the gospel less and less as time goes by.

(07:00):

No, we actually feel our need for it even as we’re growing in holiness, godliness. We feel our need for the gospel more than ever because we’re also growing in an awareness of our sinfulness. So I find that true.

Ann (07:13):

I remember that about Bill Bright. If we had anybody on a pedestal, the founder of Campus Crusade for Christ or Cru, we had Bill on a pedestal for sure. And I remember him always getting up saying, “I am the chief of sinners.” And he’s like, “I could fall tomorrow lower than anybody.” And I’m like, “But really, Bill? Really?” Do you remember that?

Dave (07:35):

I would turn to Ann and say, “No, it’s not him. It’s me.” And you know because you’re married to me, right? I mean, it’s like, no. But here’s my question, Dane. I mean, in some sense, we know what you’re saying is true and yet we still hide. We still keep our sins in the dark. We’re afraid to bring them into the light. Why do we do this and how do we get out of that rhythm?

Dane (07:59):

The reason we do that is we don’t really believe the gospel. Here’s what I mean. We’re all walking through life, and we are pinging back to us an assembled sense of our worth and value and importance and who we are based on what we think others think about us. So I’m walking through life and I’m sort of amassing my sense of self based on what the feedback I’m getting nonverbally or verbally from other people. What am I doing in that moment? That is gospel deficit. What I’m doing is I’m walking around and that well should be full based on what God says of me in Christ. I shouldn’t need to do that. In other words, God has already said, you are my adopted son, and nothing is ever going to take that away from you. Not even you can sin your way out of that.

(08:47):

Okay. So when we are unwilling to take a sin out of darkness into the light before our brother, why are we afraid to do that? Because we’re afraid of losing face, because we’re afraid of being embarrassed. In other words, because we are basing part of our identity on what other people think.

Ann (09:05):

Oh, and we all do that.

Dane (09:07):

We do it. I’m doing it. I’m going to do it tomorrow. So what if we actually stockpiled our hearts with the scripture in the morning with a full sense of who we are as members of the family of God, such that actually we’re invincible. We can walk through life, and we don’t need to suck on the nicotine of human approval to get little drags.

Ann:

That’s a good visual.

Dane:

We’re totally, totally safe and free. So that’s one thought that comes to mind, brother.

Ann (09:37):

I remember this pastor—he was in our church, actually—that he was giving this sermon and he said, “Imagine that the CEO, founder of this huge multimillion dollar company has you come up.” And he says, “I want you to know, you to me are magnificent. You’re a great leader. You are a great mover of people. You are the most amazing person that could ever be in this job that I’ve ever had in this job. And I want you to know this is what I believe in you. I’m always going to believe in you, and you have a spot here.” And he said, “So you start like, yeah, this is who I am.” And then you go downstairs a few floors and these guys are like, “You know what? You’re horrible. You’re a bad boss, but you’re like, I could care less what you say because the CEO thinks I’m amazing.” And I think that’s why we have to keep going back to the Father who’s speaking life to us.

(10:29):

And if we don’t, we start listening to the people that are beside us saying, “You really don’t have anything, or you don’t have what it takes.”

Dane (10:37):

Amen.

Dave (10:37):

Yeah. So the question is, if I understand who God says I am, but I also know the reality is I’m carrying around this sin that I’m hiding, you do such a good job talking about, okay, you’ve got to get that into the light, not just with God vertically. Talk about the horizontal piece. How do we do this with a brother or a sister, or do we do it with a couple? Do we do it with a whole bunch of people? Do we stand in front of the church and do it? What should that look like?

Dane (11:05):

Yeah. Well, nothing cookie cutter here. Each of us is going to have a different context and different set of relationships and so on guys. But here’s what I would say. We don’t want to do it exhaustively, “Let me tell you the 113 things that I battled yesterday,” but redemptively. Actually, we could be very self-focused in how we are bringing sin into the light in a weird way. So here’s what I would suggest. What if someone is listening and saying, I would like to take a step forward by the grace of God in this way, walking in the light. Here’s what I would suggest. Take a week and pray, reflect, maybe journal a little bit, and then a week or so down the road, jot down two or three or four possible names of a person in your church of the same gender who you believe you can be safe with, a trustworthy man or woman, whittle that list down to one person and then gently, cautiously, but courageously just say, “Hey, I don’t know about you, but I am an actual sinner.

(12:11):

Would you be comfortable if you were a safe place for me every so often to just talk very openly about what I’m struggling with? And then would you pray for me? James 5:16 says, confess your sins to one another and pray for one another that you may be healed, not confess your sins to one another and give each other pep talks or fix each other that you may be healed. So when we hear someone confess a sin, it might seem blindingly obvious what they need to do to get fixed, but we don’t do that. We pray for them. Okay. So would you simply pray for me? Could we meet once a month for six months and do this?” So put a timestamp on it so that if it’s not going well, you have an out and then meet with that person and dare to let them know where you really are at.

(13:01):

And I would guess—this has been my experience, Dave and Ann—when you do that with someone, they feel so honored by that. They feel so loved by that. And actually, their own conscience is pricked. They will reciprocate. And before you know it, you have a little mutual two-way walking in the light party going on and both of you are getting traction in your Christian life.

Ann (13:25):

Dane, do you do that at your church? I know that we interviewed your dad, Ray Ortlund, and he actually does this at a men’s group where he preaches the Word and he says, “We just break into twos and guys confess to one another.” Is that something that you’ve seen or experienced?

Dane (13:40):

I’ve seen that happen at my dad’s church and we’re moving in that direction. We are first learning how to honor one another. Now the next step is going to be to learn how to walk in the light together. It’s scarier. So we’re taking this one step at a time, guys. So I’m learning and I’m a toddler in this, but I do have two men in my life. One is 78, one is a peer, my age in his 40s, and they know what is really going on in my life. And I’m not interested in being a Christian without that. Once you taste it, you move from being like a 2D Christian to a 3D Christian. Can I put it that way? Everything clicks into color. You’re like, “Oh, maybe I am a real Christian.” And it’s actually, it’s more of an adventure. It’s much more enjoyable way to live.

Ann (14:31):

We’ve traveled around the world, and I’m always amazed that families around the world bring incredible joy and impact, but they also really struggle with the same issues.

Dave (14:41):

Yeah. I mean, it’s amazing. They all have the same issues. The wife doesn’t like her husband. The husband doesn’t like his wife. They can’t resolve conflict. You name it. They don’t know how really to make Jesus the center of their marriage. It’s the same things we struggle with.

Ann (14:55):

Exactly. But families make a difference in the world. A family centered on Jesus impacts everyone.

Dave (15:01):

That’s why we do what we do. Every single day, we’re trying to help marriages and families here, there, around the world, find Jesus as the center of their marriage and find hope. And then not just see their marriage transform but transform their neighborhood. And let me invite you to join us in this mission. What’s that mean? Pray for us. We need your prayers. But also, I don’t know if you know this, but this ministry is a donor-supported ministry. In other words, people give financially to make this happen, and we would love to have you as a partner.

Ann (15:34):

Because we can’t exist without you, without monthly partners reaching families for Jesus.

Dave (15:40):

So if you’d like to join, here’s all you need to do. Go to FamilyLifeToday.com, click on the donate button right there. And man, wouldn’t it be a joy to be a partner with you? You can help change the world.

Ann (15:56):

Okay. I’m going to ask you guys this question.

Dave (15:58):

Oh no, no, no, no. Don’t ask us.

Ann (16:01):

Because I mean, maybe this is overgeneralizing, but at least for me, it’s been amazing for me to do this with women. And in my world, it has seemed as if most of the time it’s easier for women to do, maybe not do this, but at least have those friendships that give you an access to one another’s lives. But I’ve talked to so many women that will say, “My husband doesn’t have a friend. I’m his only friend,” but they long for their husband to have that relationship with other men. How is women as wives? Do we just pray about that for our guys? Is that the best thing to do?

Dane (16:35):

Well, that would be a great starting spot. We could do a lot worse than that.

Ann (16:40):

Because we want to tell them, “You guys need to go get a friend, but not sure what works.”

Dane (16:45):

Because our wives love us and so they want to see us grow and flourish. Of course. Yeah. I do think you’re right that there’s something in the wiring in female relationships that makes it somehow easier to go there perhaps. I don’t know. All I know is I stink at it and I’m a man and the men I see in my world are not great at it and we do need to grow in it. My wife is my best friend, but there’s also a kind of conversation that I can only have with a man. There are certain things that I can speak to a brother in Christ, and my wife is my deepest best friend, but he understands in a way she doesn’t. That’s true. My wife would acknowledge that too. And it’s true for her. For me, there are certain things she can talk to a woman about that I do not understand though I am her best friend.

(17:35):

So what if every one of us, if we’re married, we have our spouse as our best friend and then another person of the same gender as us who knows what’s really going on in our lives. I think you’re really right in what you said, Ann.

Dave (17:49):

Yeah. And I think for a lot of us men, we’re afraid.

Dane (17:53):

Yes.

Dave (17:54):

We’re afraid of being exposed, being known. I mean, I can’t speak for every man, but it’s like I want to be known. But if I told you what I really struggle with, oh my goodness, I’m afraid of what you would think, not just my wife, but even another guy. And so I think we continue to hide with the shell sort of up that we’ve got. We struggle like everybody else, but pretty much I’m pretty good and I’m probably a little better than you. You know what I mean?

Dane (18:26):

We do that, don’t we? Yeah. We like to say, oh yeah, I’m struggling with some things or this or that, but I’m not going to tell you the specifics. You mentioned my dad earlier, guys. Something I’ve heard my dad say once or twice is we can either be known or impressive. We can either be known or impressive. Someone can know me. I think you’re right, Dave. We deeply desire men and women for someone to know. That’s why Galatians 4 says God in the gospel, we know Him and we are known by Him. But horizontally too, we want to be known, but we also really want to be impressive. And I can try to put up a big front, and no one knows what’s really going on in my life and try to impress others. But actually here’s the wonder of it. When a brother comes up to me and they say, here’s what I’m really struggling with and they’re tearful about it, they’re totally red in the face.

(19:10):

They cannot believe the mess they’re making of their lives, that’s when that man is most impressive to me. That’s actually what is most deeply glorious. So actually being known is the way to enjoy the glory and the respect that we long for as men.

Dave (19:27):

Hey Dane, what would you say in regards to confessing our sin to our spouse? You talked about you have a buddy, you have a brother, you also have your best friend wife. Is it different? Is it similar? Is there a level that’s different?

Dane (19:41):

Wow. I do think it is a little different, Dave, and I would not want to give any married person an excuse to be dishonest with their spouse on the one hand. On the other hand, I do think we want to come back to this idea of redemptive vulnerability versus crass vulnerability. In other words, openness and honesty that is redeeming in the way that it happens. Let’s say you got two 22-year-olds, they’re getting married. They will want to be redemptively honest and open with each other. Do they want to spend hours and hours and hours and hours and hours and hours airing all their dirty laundry?

Ann (20:19):

That’s what we did, Dane.

Dane (20:21):

Okay. Well, that might be healthy.

Ann (20:23):

No, it wasn’t.

Dave (20:24):

We’re here to say it was very unhealthy. Okay. We didn’t know it at the time, but now we say the same thing you’re just about to say is that’s not redemptive.

Ann (20:32):

Yeah. Keep going with that.

Dane (20:34):

Yeah, just to be wise. It’s a matter of wisdom, not like I’m just going to air everything before you. That can actually be quite hurtful. Maybe it scratches an itch in me as the one confessing it because I feel like I’m being so open and honest in something, but that’s all. You’re asking your spouse or your fiancé to bear an enormous weight. So what is loving is to say, “What if I’m in their shoes, what do I want to know?” And that’s what we want to do.

Dave (21:01):

Yeah. And I think as you go back to James 5:16, talk about confess your sins to one another. In some sense you’re like, “Wait, wait, wait. Aren’t we supposed to confess our sins to God?” Yes. But he also says one another. And again, that’s not standing in front of the hundred people, but it is brother, sister, and your spouse. And pray for one another that you may be healed. I think often we think healing is physical, and I think there’s obviously that sense there, but it’s deeper, isn’t it? It’s like, wow, he’s talking about no, you want to grow in Christ. That’s going to propel you toward that kind of healing where your soul is set free so that now you’re not in the dark, you’re not hiding, you’re not putting on a mask. You are literally being known by Christ and by a brother or sister.

(21:45):

And now you’re on a path to a true healing of your soul that leads to real growth in Christ. Am I right?

Dane (21:53):

I love the way you just put that, Dave. Healing is wholeness. You’re integrated. Integrity, you’re one. In other words, when you’re hiding and got things in the dark where they’re festering, there’s two of you. At that point, there’s two Danes. There’s the real Dane that I am behind the mask, and then there’s the Dane that I’m preening and parading around the world with. But when I confess my sins to someone else, then the two become one. It’s much simpler and less exhausting as a way to live. And you’re whole, and I agree with you, brother, the healing there is not so much physical healing. It’s internally, you are becoming whole. Shalom is washing over you as a human being.

Dave (22:34):

Yeah. And I tell you what, you’re listening right now and you’re thinking, Hey, I stumbled upon this. Or maybe you were intentional today to listen to FamilyLife Today. And here you are, you want a first step to a new life. And I know there’s a brother or a sister going, don’t say it, don’t say it. You need to find a brother or a sister that you can be real with, take off the mask, bring what’s in the dark now into the light with God, with a brother or sister, possibly a little bit with your spouse. And that’ll be the best first step to real change. Amen. Start today.

Ann (23:14):

Okay. You may not know this, but we want to hear from you.

Dave (23:18):

Yeah, like literally hear you.

Ann (23:21):

You can leave us a voice message with your questions, concerns, praise reports, or whatever. Maybe Dave said something that you totally disagree with.

Dave (23:32):

Why’d you have to pick on me? Maybe it’s you said something.

Ann (23:35):

Maybe, probably.

Dave (23:36):

Or maybe it was inspiring. See? See, I was nice.

Ann (23:39):

No, I know you’re always nicer than me.

Dave (23:42):

I don’t think so. Or maybe you just want us to answer a question or explore a certain topic. Whatever you want to say, you get to call and say.

Ann (23:51):

All you have to do is go to Speakpipe.com/FamilyLifeToday. Again, that’s Speakpipe.com/FamilyLifeToday or get the link in the show notes.

Dave (24:05):

Again, it’s Speakpipe.com/FamilyLifeToday. Another great day with Dane Ortlund. Just love having him in here talking about some deep stuff.

Ann (24:15):

Yeah. And his book is called Deeper.

Dave (24:17):

Deeper.

Ann (24:18):

Real Change for Real Sinners. Isn’t that real?

Dave (24:21):

And that’s us, real sinners that need real change, and you can do it. And again, the book is called Deeper. You can get your copy at FamilyLifeToday.com. Just click the link in the show notes. We got one more day with Dan. We’ll see you tomorrow.

Ann (24:45):

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