Ben Fleming: The Weight of Regret, Psalm 32:3–5

October 25, 2026 • 00:29:11
Ben Fleming: The Weight of Regret, Psalm 32:3–5
Westside Church
Ben Fleming: The Weight of Regret, Psalm 32:3–5

Oct 25 2026 | 00:29:11

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Show Notes

Regret has a way of convincing us that we’re doing something productive when all we’re really doing is suffering. God recognizes the destruction that guilt can cause us, and through his perfect grace, he creates a space where we can come honestly to him with even our biggest regrets.
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Episode Transcript

[00:00:00] You're listening to a live recording from Westside Church in Bend, Oregon. Thanks for joining us. [00:00:06] Good morning, everybody. I'm Ben Plumbing. I'm the other senior pastor here. We're going to talk through a few things that I just really want to talk about because it's kind of a little bit of me speaking from the heart through my favorite passage in scripture in Luke 15, verse 11 through 32, which is the story of the prodigal son, as well as I want to talk about a theme that I've discovered in my life as I've gotten older, and that is regret. [00:00:32] And I actually think both those things play off each other really well. So I'm actually gonna. I'm gonna kind of superimpose this passage in Psalms over the top of the story of the prodigal son. And I believe that God is gonna teach us some things through that text, because I'm believing more and more that if I'm not careful, my life can be controlled by my regret. And I believe that all of us probably deal with regret in one way, shape or form, you know, and it's big things, little things. This last week, you guys, I was moving some stuff around in the garage. I put my coffee cup down and slid some other things around that were on, and one of those ego batteries, those big batteries, fell off the surface and landed on my toe. And I'm pretty sure I have a broken toe. [00:01:11] So I'm playing injured today. You gotta feel extra bad for me. [00:01:16] We always feel bad for you every time we see you. Okay, great. [00:01:20] You know, I've got. There was this time when my son was 8 years old and I was coaching his little league team. And he made this great play at shortstop, and then he threw the ball to first, and the kid didn't catch it because no kids catch the ball at 8 years old. [00:01:33] And Joel yelled from the top of his lungs at shortstop, these guys stink. [00:01:39] Referring to his teammates. And I screamed so loud at him from the dugout, I can still hear my voice reverberating off of the Northstar Elementary School. Just. [00:01:50] I regret that my wife and I had been married. We got married at 22 years old, each of us, and about two months in, Rebecca, I felt, was being critical about me and the church that we were serving in an unfair way. And she felt like I was being sensitive and defensive, which doesn't sound right. [00:02:10] And I got to this moment, and this is where regrets are built, right? A lot of you guys know this moment. I got to this moment where we were in a bit of an argument. And I knew that I had the option to say something that would feel like it crossed the line. [00:02:25] And, boy, I said it, but I knew it, right? You know, that feeling, that moment where you go, I could say this. And I know. I know what comes on the other end of saying this. [00:02:35] And I don't remember exactly what the buildup was, but they hit a point where I said, it looks like you need to find another church. [00:02:44] Has that been brought up since? [00:02:47] Maybe several thousand times, you know, and it's more of a joke now to us, but there's some regrets in there, right? We've got this. And so it kind of raises this important question to me, because there's obviously much bigger things. You know, there's situations in your marriage or relationships, years lost to addiction, relationship with a child that's become strained or a betrayal of trust or a decision that changes the course of your life in a way that you feel like wasn't right. Right. So it raises these. There's these small things, these big things that raise this big question, what does God want us to do with these things that we can't undo? [00:03:21] What do we do with those things? [00:03:23] Because I find myself more and more, like, ruminating on regrets all the time. [00:03:29] And I've hit this point, especially in the last couple years, where I'm like, is this just like my life now? Like, the older I get, the more I'm ruminate on this. And I'm going to need help to fall asleep at night. And if I go to sleep, I'm going to need more help in the middle of the night, you know, like with some medication or melatonin or something. Like, is this who I am? Like, I don't want to live like this. [00:03:48] And I think that scripture gives us a way through it. It gives us a bit of a blueprint on how to not just ignore our regrets, but actually to grow through them. And in Psalm 32, David says this. He says, when I kept silent, my bones wasted away through my groaning all day long for day and night. Your hand was heavy on me. My strength was sapped, as in the heat of summer. And then I acknowledged my sin to you and did not cover up my iniquity. I said, I. I will confess my transgressions to the Lord, and you forgave the guilt of my sin. [00:04:20] Notice there's, like, a progression here, right? There's silence that turns to acknowledgement that goes to forgiveness. And then there's, like, there's hiding that goes to honesty. And then to freedom. [00:04:29] This is the blueprint that I believe that God wants to lead us through today. And so again, we're going to superimpose this over the top of the Prodigal Son. And so it starts with that. Verses 3 through 4. When I kept silent, my bones wasted away. [00:04:43] And so if you're unfamiliar with Luke 15, Luke 15 has three stories in it that are all about something that gets lost. A lost sheep, a lost coin. And then it's a lost son that we know as the Prodigal son. [00:04:53] And this son, if you don't know the story, comes to his father and he says, and Jesus is telling this story, but it's a. It's a made up story, it's a parable. But he tells the story about this son that goes to his father and he says, hey, I don't want to wait until you're dead to get the money that I'm owed. [00:05:09] And so I would like for you to go ahead and just give that to me now. [00:05:12] And you have to take this in context. That sounds harsh, even just how I just said it. But it's far worse for the Jewish audience that's listening to the sound of Jesus voice. Listen to this son and how disrespectful and awful it would be for him to come to him and essentially say, I would like your stuff, but I'm pretty disinterested in you. [00:05:31] That's the flavor of the story. Dad, I wish you were dead. It's pretty cruel. And it's wild that he would say it. And it might be even more wild that in his story that he's telling that the father agrees to do it. So he divides his property between the sons and this younger son leaves. And Jesus says he goes to a distant country, he squanders his wealth and wild living. And we don't exactly know what that looked like. Jesus doesn't go into detail in this story, but we know that the whole thing doesn't last. The money eventually is lost and it runs out. And then a famine hits the land and this young man finds himself, in order to survive, feeding pigs and eventually eating from the pig slop himself. And so for a Jewish audience, the worst thing that they could possibly do would be to touch and to serve and to help this unclean animal, the pig, in this way. [00:06:20] It's about as low as it could get, essentially. [00:06:23] And so not only has he lost this money and this independence and this kind of idyllic life that he thought he was going to go live, but he's now tending to this animal. [00:06:32] And then Jesus talks about how this young man was so hungry that he filled his stomach with the food the pigs were eating, and he left home by believing that this freedom meant getting away from his father. But here's the kicker. Here he is having lost everything that he thought would really make him free. [00:06:49] Now, this is where regret comes in, right? This is where the ruminating comes in. This is where the replaying of the events of all the mistakes that you've made come in. Now, Jesus doesn't talk about this in the story, but I can imagine is relating as a human being to the idea of this prodigal son, that this would be the time where he replays that conversation with his father. And he thinks about this money that he wasted in a way that he should have. Probably thinks about his tone and his arrogance and how he approached his father. This is the worst spot to be in, eating food that you don't want to with livestock that is unclean. Feeling the shame and probably asking himself the question that I would have asked myself, why was I so stupid? [00:07:27] What happened? [00:07:30] And that's what regret does, right? It takes these things that have happened in the past, and it constantly pulls them on a leash back into the present. [00:07:37] Could have happened years ago, could have happened decades ago for you, and it pulls them back into the present. [00:07:43] And here's one of the bigger problems that that leads to is that the longer this regret is hidden inside of you, the more power it tends to have over you. That's what David says in Psalm 32. He says, When I kept silent, my bones wasted away. He's talking about this inward spiritual reality that is now translating to his. His physical body. Some of us have so many regrets that you feel that ache in your muscles and your bones. You're losing sleep over it. Your ph body, and not just your soul and your spirit are feeling the weight of it. I know that you know this. This feeling. You wake up in the middle of the night thinking about something you wish you'd handled differently, and you find yourself overreacting to new small situations because it reminds you of something you regret. A lot of times, regrets are like a song that gets stuck in your head, you know, and. And it could take something real simple. My wife and I got a new washer dryer when we redid pieces of our house over the last couple years. Some of you know about that saga that I'm still not willing to share too much about because it hurts too much right here. [00:08:42] But over the Course of it, we got rid of our washer dryer that we had had since we got married 16 years ago, and we got this new washer dryer. And by the way, in the middle of it, one of the worst marriage situations I have been in is we're picking up this washer together, and I'm trying to get it out of the house, and I threw out my back in the process, and I'm now in a corner with a bunch of old washer water on the ground, and I'm just laying down behind the washer, and my wife asked the worst question any insensitive spouse would ever ask. And she says, can I help you? [00:09:16] And I'm like, how dare you? Don't talk to me. Just leave me to lay inside of this water all by myself. [00:09:25] That's a whole different story that I'm going to therapy for. But we get this new washer dryer. And you guys, have you seen these new washers? [00:09:34] They sing. [00:09:36] I hit start on the button, and it goes blend. [00:09:41] And I'm like, I don't need this. [00:09:44] What are you doing? [00:09:45] You know, the old cycle used to end, and my old dryer would be like. [00:09:50] And then if you didn't open it for a few hours, eventually the ants just got a little shorter, you know, I was like, just like, dude, let's go. Hurry up. But it sings to you. And I hear that blend. [00:10:01] And I will sing that for the next 24 hours. That little tune, you know, it's the same thing. When I hear the beginning of hello Darkness, my old friend, you know, hello, Darkness, my friend, you know, Call Me maybe does this to me. There's lots of songs. And you guys know that feeling when a song gets stuck in your head, it takes, like, a note, and then that can stick with you for a week's time if you're not careful. [00:10:25] And the same thing happens with regret. It's a little note. It's a little something. Somebody talks to you in a certain way. [00:10:31] You hear specific words. You see a show, like, you smell a smell. And all of a sudden, like, these things can just manifest themselves inside of your head and inside of your soul. These regrets, they're so sticky. [00:10:43] And by the way, the older we get, if we don't manage to work through these, the more we just kind of stack up those regrets we accumulate more and more and more and more of them to then where everything all of a sudden triggers this kind of reaction or idea inside of our minds. [00:10:58] Sometimes we spend years trying to outrun the consequences of these choices. And sometimes we become convinced that the best way to deal with our regret is to just bury it. We're not going to talk about it. We're not going to bring it into the light. I'm a very mature person. I can handle this all by myself. And so I'm going to hold onto it all by myself. But here's what I've learned about buried regret, if you haven't learned it yet. What we refuse to acknowledge continues to have a dramatic amount of influence over us. [00:11:27] Now, there's this important distinction we need to make between guilt and shame here, right? [00:11:32] Guilt says, I did something wrong. Shame says, I am something wrong. [00:11:37] And so guilt can be a gift when it awakens our conscience and it moves us toward repentance and repair and growth. But shame tends to move in the opposite direction. Shame doesn't invite us to move forward. It continues to pull us back into our hiding places. [00:11:50] And then we hide behind anything at all. Busyness, accomplishments, humor can hide behind all of it. But one thing leads to wisdom, and one thing leads to a prison. [00:12:02] And so it goes on in Psalm 32, and it says, then I acknowledged my sin to you, and it did not. I did not cover up my iniquity. [00:12:10] So let's return again to the prodigal son, Jesus's story. [00:12:13] He's hungry, he's humiliated, and he's sitting with pigs. And then Jesus says something in Luke 15:17 that I believe is profound. It says, he came to his senses. [00:12:24] And when he came to his senses, some translations say, when he finally came back to himself, it's almost like this guy's been living outside of himself, right? It's like his decisions have taken him so far from who he was meant to be that he barely recognizes his own life anymore. But then something changes, and he does this great thing where he begins to project forward, begins to think about his father's house. He begins to think about the food that's available there and the warmth there. [00:12:52] And he remembers that even his father's hired servants have food to spare. [00:12:59] And so he realizes that he can go home, but he's gotta figure out something to say. And so he begins to rehearse this idea. And he says, I'm gonna say, father, I've sinned against. You no longer need worthy to be called one of your sons, so make me like one of your hired servants. And so this young man doesn't come up with this list of excuses finally, right? He's not saying, look, if you wouldn't have been so mean and controlling to me, Dad, I never would have left. That's not what he's finally presenting with. [00:13:25] He's not saying, look, it was. The economic factors were kind of. I was going through a difficult season and you don't understand, but I'd like to come back. He just says, this is what I'm going to say. I'm sinned and I was wrong. [00:13:38] And that's how genuine repentance works. All of a sudden, a lot of the excuses and the extra language goes away and repentance comes into the picture. And I want you to know that repentance isn't just feeling bad about what happened. My dad used to say this. I would sometimes say, I'm sorry. And my dad would say, are you sorry that you got caught or are you sorry? And I would say, that's not fair. [00:14:07] Repentance is not just feeling bad about what happened. It's being honest about what happened and then allowing that honesty to change your direction. [00:14:16] It carries this idea of a changed mind, a transformed way of seeing and thinking. [00:14:24] And throughout Scripture, repentance is connected to this turning, this change in direction of life. And so Luke 15:20 says this. As he got up and he went to his father, so he got up, he stopped rehearsing his failures, and he started moving toward home. And maybe that's what you need to hear today, is that you can't change what happened. That's 100% true. A lot of the mistakes that you made and the. The wishes that you have, they can't be fulfilled. And you can't go back and fix all of them. But you can get up and you can go home. And so maybe going home for you isn't getting out of a pigsty and then returning to actual home. Maybe it's a phone call that you need to make an apology, that you need to tell a truth that you need to help someone understand or realize for yourself. That's the get up and the going home. And confession means coming honestly before God and saying, God, here's what happened, here's what I did, here's what I wish I would have done differently. And here's what I don't know how to fix. [00:15:22] I don't know how to fix all this. [00:15:25] And here's what I've been carrying, right? There's something freeing about that honesty. Have you ever had that feeling of release that comes from honesty? And David talks about it in this Psalm 32. He says, Then I acknowledge my sin to you and did not cover up my. Iniquity he doesn't say. And then finally I figured out how to fix everything. [00:15:43] Come on, maybe you're like me and you can ruminate long enough on these regrets where you're finally gonna figure out a fix. And you've been working on that fix for 30 years. [00:15:53] He says, I acknowledge. That's it. He stops hiding. [00:15:57] Now. Grace is not opposed to honesty. We need to understand grace is actually what makes the honesty possible in the first place. [00:16:04] Because if you believe that you're loved by God, you won't spend your life protecting this false image that you have of yourself that you would like to project on other people. [00:16:13] You can acknowledge your failures without those failures becoming a part of your identity. [00:16:20] And so I think confession says, I'm not going to pretend what happened didn't happen, but instead it says, but I'm not. I'm also not going to believe that what happened is all that I actually am. [00:16:35] And then Psalms 32. 5 says, you forgave the guilt of my sin. [00:16:40] Now we come to what is the most important and remarkable part of the story that Jesus is telling. [00:16:47] Says the young man is walking home. He's rehearsed his confession and he knows what he's going to say. Oh, you guys, I love rehearsing conversations that I'm going to have that are difficult conversations. You love doing this, and then they're gonna say this, I'm gonna say that. And then the worst is when you get into those conversations, you get on the back end of them, you go, oh, I know what I should have said. [00:17:05] And I slam dunked right on their face. [00:17:10] That's just what I think. Maybe this guy's a little unstable. Yeah, well, today I am. [00:17:18] Alright, catch me at the 11 and see if I figured it out by then. [00:17:24] It says he's walking home and he's rehearsing. Okay, Father, I've sinned against heaven and against you. Okay, I'm no longer ready to be called your son. Make me like one of your hired servants. Okay, that sounds really great. [00:17:33] Full of anxiety, right? I bet he's wondering, like, what's dad gonna say? How angry is he gonna be? And is he gonna say the worst words that I don't want to hear ever? And is he gonna say, I told you so? [00:17:46] I don't want to hear that. [00:17:49] And then Jesus says this. He says, while he was still a long way off, his father saw him and was filled with compassion for him. And he ran to his son and he threw his arms around him and he kissed him. [00:18:04] Now listen to the sequence again, he sees him. He feels compassion. The father runs and the father embraces him and the father kisses him. [00:18:14] And only then does the son get to begin his confession. [00:18:17] You notice that all of that happens before the confession. The embrace happens before this explanation. [00:18:27] And so the father isn't standing on the porch with his arms crossed, tapping his foot, but instead he does something that, again, in the context for these Jewish listeners, is crazy. Because this father, this dignified patriarch of the family, would have had to like, first of all, they just didn't run. That wasn't the thing. Running wasn't there for the older father of the household and the property. And what he would have had to do, not just to run, is that he would have had to grab his robes and then pull them upward while he ran. And so the listeners hearing Jesus story, they're going, this is not going to happen ever. [00:19:04] That's not what a dad does. It's not what this guy does. That is. That's a feminine act to pull up your robes, to run. Who is this guy? And some of them are probably getting the idea that Jesus is saying, and I'm trying to tell you a picture of the father. I'm trying to tell you what God is like. And they're going, there's no way that God would ever do anything like this. Not the God that has created all these rules for us to then follow. Not the God that we stand around just being afraid of all the time. Not the God that seems so distant and far away, that hasn't fulfilled so many of the dreams that we have. This is not God. And Jesus is saying, let me tell you about God. God would stand out on his porch. Which means, by the way, this probably wasn't the first time that he had done it. He's standing out there waiting for the son that had betrayed him, that it asked him to go ahead and die so that he could have his money. And he's standing out there day after day after day, hoping he comes to them. When he sees him, the words can't even come out of his mouth before there's an embrace and a running and a huge wet kiss on his cheek. [00:20:05] And this poor kid is going, dad, I'm trying to tell you something. And he's like, you're home. [00:20:15] The kid pushes him off. You know, okay, I've been thinking about this, Dad. [00:20:24] I sinned against heaven, against you, and I'm no longer worthy to be called your son. [00:20:29] He doesn't even get to the part about being a hired servant. [00:20:33] Before the Father's like, yeah, yeah, shut up. Hey, get, get everything out for him. Let's put his bed, the best robe on him and bring. Put his finger back, his ring rack on his finger and his sandals on his feet and bring the fattened calf and kill it and let us feast and celebrate. [00:20:48] Why? Because the son of mine was dead and he's alive again and he was lost and now he's found. [00:20:55] Can't even make an argument, this prodigal son, before there's a feast being thrown in his honor. [00:21:02] And the thing that I want to kill inside of each and every single one of our souls today, our religious souls, the thing I want to take out of each and every single one of us today is this idea that we finally came around to faith, that we finally accepted Jesus Christ as our Lord and Savior and we're satisfied with living as a slave inside of the house and the church that belongs to God. [00:21:24] That was never the intention. And holding onto all these regrets and simply writhing around inside of our beds at night wishing we would have done something different. Look, I understand that we should have done something different, that we've made mistakes, that we wish life would have turned out differently. But this walk alongside Jesus, this walk of being in the Father's house was never meant a place that we kind of just happened to get so that we could sleep on the floor and have a few real meals. But instead you were called to be a son or a daughter of God. There's a celebration and a festival and all these things that belong to you, not because you handled yourself well, but because you simply belong to Jesus. [00:22:01] That's the entire idea behind this faith. [00:22:05] It's not that this son went out and invested wisely, but this son was dead. And now he's alive and he was lost and now he's found. [00:22:14] Now we like this idea, we preach it, we sing about it, we extend it to other people. But when it comes to our own failures, we love to make an exception. [00:22:22] Yes, God forgives people, but you don't understand what I did. God is gracious, but I should have known better. God loves me, but I don't deserve to be happy. [00:22:31] We love these little perpetuating, self deprecating, false, humble ideas. [00:22:37] And in a strange way, we end up behaving as though our regret is more powerful than God's grace. [00:22:45] As though the cross is sufficient for everyone else's failures, but somehow inadequate for ours. [00:22:52] David doesn't only say, I confessed my sin. He says, you forgave the guilt of my sin. [00:23:00] David brought his sin into the presence of God. And what he discovered was that there was mercy. I Love that. Romans 5, 8 says it real simply like this. God demonstrates his own love for us in this. That while we were still sinners, Christ died for us in the very act of our sin and of our lives and of our regrets. [00:23:16] Christ died for us in that moment while we were a long way off. [00:23:23] And so the epilogue of all this is actually that Jesus tells a story about two sons. [00:23:29] The older brother carries a different kind of regret. And so while this younger son was wasting inheritance, the older brother was doing everything right. Come on, we got some older brothers in the house today. [00:23:41] Yeah, I know about doing everything right while all you irresponsible morons go out and spoil Dad's money. [00:23:48] I've been here the whole time. [00:23:50] He worked hard. He was responsible. He'd done what was expected of him. [00:23:55] And when the younger brother returns, the father throws a party. And the older brother becomes furious and refuses to join that party. [00:24:02] And then he says in Luke 15:29, he says, look, all these years I've been slaving for you and never disobeyed your orders. [00:24:12] Could you hear that? [00:24:13] The older brother spent years doing the right things, but he's been keeping score. [00:24:21] He's been accumulating a different kind of resentment, a different kind of regret. [00:24:27] I've worked so hard and I've given up so much, and I've done everything that I was supposed to, and what did I get? [00:24:35] I love that. He says in the text. He says, look, you've never given me permission to go out and get a fattened calf for my friends. [00:24:41] And I imagine one of my kids saying that to me someday. And it just makes me laugh, you know? [00:24:45] You know, Jovi did this, and you never gave me a chance to get a fattened calf for me and my buddies. [00:24:51] What's wrong with you, Dad? [00:24:53] I just want to hear my son say fattened calf. [00:24:59] Sometimes regret doesn't look like a person grieving mistakes, and maybe this is you. Sometimes regret looks like a person resenting all the things that they think they missed. [00:25:10] The older brother's problem is that he came to see his relationship with his father as a transaction. [00:25:18] This doesn't sound like a son that enjoys being with his father any more than the younger son did. [00:25:24] He sounds like an employee that feels like he's underpaid. [00:25:28] And his father says, my son, you're always with me, and everything that I have is yours. And the older son who's been so focused on what he thinks he's missed out on, has lost sight of what he had the whole time, the entire time. [00:25:49] The sacrifices that we made that seem to have gone unnoticed sometimes can be the most haunting of things. And if we're not careful, that regret doesn't stay as regret. But then that evolves into bitterness. [00:26:02] So much of our regret evolves into anxiety and this kind of regret evolves into bitterness. [00:26:09] You resent other people's joy. [00:26:14] You compare your lives constantly to what might have been and what other people are doing. [00:26:23] And then the story just kind of ends there. And I wonder if Jesus leaves this story unresolved on purpose. [00:26:31] We don't find out if he joins the celebration and he figures it out and. [00:26:35] And I wonder if it's because the invitation actually kind of remains open ended to him. [00:26:42] The father's gone out to both sons. He runs to meet the rebellious younger son and he heads outside to be with the older son. [00:26:52] But neither one of them are intended to stay outside. [00:27:00] One has to release shame. And I wonder if that's something for many of us here today. It's time to release the shame and the regret that if left unattended, will continue to, if not, begin to control your life. [00:27:16] And then all of a sudden, when you're in your 50s and your 60s, you'll be continually thinking back to this move that you made or didn't make in your 30s. [00:27:25] You gotta release that shame. [00:27:27] Now. The other son doesn't have that task ahead, but instead he must release his resentment. [00:27:33] And the tie that binds both brothers together is that they both are in desperate need to receive grace. [00:27:43] And so I want to return to this question that we started with, right? What do we do with these things that we can't undo? [00:27:50] Because I think all of us have something to carry. There's some kind of weight and some kind of burden that you're feeling today. [00:27:56] And maybe it's that weight of regret, or maybe it's that weight of resentment. [00:28:01] And I want you to hear something today. God isn't asking you to pretend that nothing in your past happened. [00:28:08] But God is inviting you to stop allowing your past to become everything that you are. [00:28:19] And what we are after, you guys, as a church, as Christianity, we're after this access to the Father, which we are given freely because we're his children. [00:28:28] We're a child of the King. [00:28:31] I love. I'm going to ruin it. But there's this great Tim Keller quote that we've used a few times here where it says the only person that can get access to the king to bring him water at 3am in the morning is a child. [00:28:45] We have that kind of access that. That inroad to the father. [00:28:50] And so you have to know today, as we finish our time together, that the door is always open. You can always go home. [00:29:00] It's time to move past this regret and this resentment and into the grace of God. Amen.

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