# Stop Going to Confession Like This. (St. Catherine of Siena Explains Why)

An episode of [AfterMass](https://invisiblenetwork.ai/podcast/1823710125), 20 Apr 2026, 20 min.

Audio: https://traffic.megaphone.fm/APO1789547880.mp3

Book mentioned: https://amzn.to/41PuVEC Most of us Catholics go to confession the same way every time and never stop to ask why nothing is actually changing. In this video, we walk through what Catherine of Siena teaches about how to prepare for confession in a way that actually leads to real contrition, not just saying your sins and moving on. This isn’t about whether confession “works” because the sacrament always works.. but the way you approach it shapes how deeply it changes you. If you’ve ever felt stuck, like you’re repeating the same cycle over and over, this is probably the part no one ever explained to you. This teaching comes from The Dialogue of St. Catherine of Siena, and it lines up directly with what the Church has always taught about repentance, contrition, and the interior life.

## Transcript

[0:00] Most Catholics go to confession the same way.
[0:02] Every single time. We examine our conscience, we
[0:05] list out our sins, we say them, we receive absolution, and then
[0:09] we leave. And for a lot of people, that
[0:11] experience stays almost entirely on the surface.
[0:14] And I know I've been guilty of this because even though the
[0:16] sacrament itself is doing what it's supposed to, the way that
[0:19] we're approaching it hasn't really changed.
[0:21] So the pattern just keeps repeating without anyone
[0:24] stopping to ask what's going on interiorly before we even walk
[0:28] in. You can go to confession often
[0:31] and still find yourself confessing the same things over
[0:33] and over and over again without any real shift in how we see
[0:37] those sins or how we relate to them.
[0:39] And part of that comes down to the fact that most of us were
[0:42] never taught how to prepare for confession in a way that
[0:45] actually engages our heart, instead of just organizing a
[0:48] list and getting through it as quickly as possible.
[0:51] There is a difference between showing up ready to say your
[0:54] sins and showing up already moved by them, already seeing
[0:57] them clearly, and already understanding what they did and
[1:00] why they matter in our relationship with God.
[1:03] And that difference begins before we even step into the
[1:06] confessional, which is the part that usually gets skipped or
[1:09] rushed past or treated like it doesn't really change anything.
[1:13] But luckily for us, there's a St.
[1:14] The church actually calls a doctor, which means that her
[1:17] teaching carries real weight, not just personal opinion or
[1:20] private. And her name is Catherine of
[1:23] Sienna. And what makes her especially
[1:25] unique is that much of what we have from her comes from what's
[1:29] known as the dialogue, which is a recorded conversation between
[1:32] her and God the Father, where he speaks at length about the
[1:36] spiritual life, about sin, and about what actually happens in
[1:39] the soul when someone turns back to him.
[1:42] And within that dialogue, there's a very specific way of
[1:45] preparing for confession that gets laid out.
[1:47] And this isn't a trick or a shortcut, but it's as a way of
[1:50] entering into real contrition, the kind that actually changes
[1:54] how we approach our sin instead of just how we talk about it.
[1:58] And it lines up directly with what the church already teaches
[2:01] about the difference between being sorry in a shallow way and
[2:04] being sorry in a way that's rooted in love for God.
[2:08] So this isn't a new teaching, and this isn't some hidden
[2:11] method that replaces what the church says.
[2:13] It's a deeper look into something that the church has
[2:15] always held, which is that how we go into confession shapes
[2:19] what actually happens in there, and most people never fully
[2:22] think through. The church makes a distinction
[2:24] that a lot of people have heard before but don't really
[2:27] understand enough or slow it down enough to understand.
[2:31] And it's the difference between perfect contrition and imperfect
[2:34] contrition which has everything to do with why we're sorry in
[2:38] the 1st place, not just the fact that you are sorry.
[2:41] So imperfect contrition is when we're sorry because of the
[2:44] consequence of our sin. Maybe we're afraid of the
[2:47] punishment, maybe because we feel guilty or embarrassed, or
[2:51] you don't like what it says about you.
[2:53] And that kind of sorrow is still enough for a valid confession.
[2:56] Your sins are still forgiven. Grace is still given.
[2:59] So this isn't about whether confession works or not, because
[3:02] it does every time. The perfect contrition goes
[3:05] deeper than that. Because it's sorrow that comes
[3:08] from love, meaning that we see our sin in light of what it is
[3:12] in relation to God, not just what it does to us.
[3:15] And that you're sorry because you offended Him, because you
[3:19] chose something against him because of what that sin
[3:22] actually is, not just how it made us feel or what it might
[3:26] cost us. And that distinction matters
[3:28] when it comes to what remains after confession, because while
[3:32] sin itself is absolved, the disorder caused by sin, what the
[3:36] Church calls temporal punishment, can still remain,
[3:39] which is where purgatory comes in.
[3:41] And the Saints consistently point back to the same reality
[3:45] that the deeper the contrition, the more the soul is purified,
[3:48] even before anything else has to happen after death.
[3:51] So when we hear something like preparing for confession in a
[3:54] way that leads to perfect contrition, it's not about
[3:58] trying to force a feeling or manufacture something emotional.
[4:02] It's about entering into a way of seeing our sin that is
[4:06] actually rooted in truth, which then shapes the kind of sorrow
[4:10] that follows. Within that same dialogue,
[4:12] there's a passage where God speaks about what happens when
[4:15] someone approaches him in this kind of love and contrition.
[4:20] And he describes a kind of satisfaction for sin that goes
[4:23] beyond just the moment of absolution, where the soul is
[4:27] being purified through love itself, not just through
[4:30] obligation or fear. And that purification isn't
[4:33] limited to what's strictly required.
[4:35] It overflows according to the depth of that love.
[4:39] There's also language about how that love can extend beyond the
[4:43] individual. How a soul united to God in that
[4:46] way can, through charity, participate in reparation not
[4:50] only for their own sins, but for others as well.
[4:53] Which is something that the Church already teaches when it
[4:56] comes to offering suffering, prayer, and acts of love and
[5:00] union with Christ. So again, this isn't introducing
[5:04] something foreign, it's describing how far that union
[5:07] can actually go when it's real. But the key detail in all of
[5:11] this is that this is not mechanical.
[5:14] It's not guaranteed just because we follow a set of steps.
[5:18] It's describing what happens when a soul is truly moved in
[5:22] love and truth. Which is why the preparation
[5:25] matters, because what we're about to walk into when we go to
[5:28] confession, it's not just the removal of sin, it's an
[5:32] encounter with the mercy of God that either stays at the level
[5:35] that you bring into it or goes deeper depending on how disposed
[5:40] you are. So when this way of preparing
[5:42] for confession is laid out, it isn't presented like a formula
[5:46] that we follow once and then it's done.
[5:49] It's describing an interior movement that you enter into
[5:52] before you ever even confess a single sin.
[5:55] Something that shifts in how you see and how you think and how
[5:59] you respond, so that by the time you actually say your sins out
[6:03] loud, you're not just recalling them, you've already encountered
[6:07] them in a completely different way.
[6:09] It unfolds in a kind of order, but it's less about completing
[6:13] steps and more about letting one thing lead to the next.
[6:17] Because you begin by looking at Christ and then that leads to
[6:21] you seeing your sin differently, and then that changes how you
[6:25] feel about it. And then that moves your will so
[6:29] that by the time you reach confession, you're not trying to
[6:31] become sorry on the spot. You already are.
[6:35] And that's the part that most people skip without realizing.
[6:38] Because confession becomes something that you prepare for
[6:40] quickly instead of something that you enter into slowly.
[6:44] When in reality, the depth of what happens in the confessional
[6:47] is already being shaped beforehand by whether or not
[6:51] you've allowed yourself to actually sit with your sin in
[6:54] light of who Christ is and what he's done.
[6:57] The first movement begins with the passion, because the whole
[7:00] point is that your sorrow for sin has to be formed in the
[7:04] right place and according to what is laid out here.
[7:06] That begins by fixing your attention on the sufferings of
[7:10] Christ in a very deliberate way, in a concrete way where you
[7:14] actually stay with a particular part of His passion long enough
[7:18] for it to change you. So that means choosing maybe a
[7:21] specific scene and staying there, whether it's the
[7:24] scourging or the crowning with thorns, the caring of the cross,
[7:28] the crucifixion, or even a moment like his agony in the
[7:31] garden. Because the point isn't to rush
[7:34] through it all. The point is to let one part of
[7:36] his suffering come close enough to your heart that it begins to
[7:39] draw out love. Because if you instead begin
[7:42] with yourself, your guilt, your embarrassment, with how
[7:46] disappointed you are, you know you can stay trapped in yourself
[7:50] the whole time. But when you begin with Christ
[7:52] and what he endured, your whole focus shifts.
[7:56] And that's where the preparation starts, by refusing to treat the
[7:59] passion like just background knowledge, like a story that you
[8:02] know, and instead letting it become the lens through which
[8:06] you see your sin, through which you look at your sin.
[8:09] Because until you place your sin next to what Christ suffered,
[8:13] it's still very easy to think about it in a shallow way, like
[8:18] it's just a mistake or a weakness or just a bad habit,
[8:22] maybe a something frustrating. And what confession is really
[8:25] dealing with is something that has to be answered by the
[8:28] suffering and death of the Son of God.
[8:30] So once you're actually there, staying with a very real moment
[8:34] of the Passion and not moving past it too quickly, the next
[8:37] movement is letting that scene become personal in a way that
[8:40] most people instinctively avoid. Because it requires us to stop
[8:44] looking at Christ's suffering as something general and begin to
[8:48] recognize that what you're looking at is directly connected
[8:52] to what you are about to confess.
[8:54] That is heavy. So instead of thinking about the
[8:57] crucifixion or maybe the crowning with thorns as
[9:00] something that happened because of sin in a broad sense, you
[9:04] begin to make a very direct connection where you understand
[9:08] that what Christ is enduring is tied to your sin, the actual
[9:12] sins that you're about to bring into confession, and not just
[9:15] the sin of humanity in general, not the sin of just the world,
[9:20] but you personally. And that shift can change the
[9:23] entire posture of your heart, because now you are no longer
[9:26] looking at his suffering, just observing it.
[9:29] You're standing in front of it with the awareness that your
[9:32] choices are not separate from it.
[9:34] And that kind of realization doesn't leave you in a place of
[9:38] vague guilt or self consciousness.
[9:42] It instead brings you into kind of sorrow that is focused
[9:45] outward when you're not primarily upset with yourself
[9:49] for failing. Instead, you're grieved by what
[9:52] your sin is in relation to Jesus.
[9:55] And that's where the beginning of real contrition starts to
[9:58] form, because the sorrow is no longer centered on how you feel
[10:02] about it yourself. It's instead rooted in what your
[10:05] sin actually is when it's placed next to Christ and what He
[10:09] adored. As that connection settles in,
[10:12] where you're no longer looking at his suffering from a
[10:15] distance, but instead recognizing your particular,
[10:18] your direct place in it, then the next movement is allowing
[10:22] that to lead you into a real sense of humility.
[10:25] And not performative or exaggerated, no, but something
[10:28] that's grounded in truth, where we begin to see clearly that
[10:33] what we are looking at is not something that He deserved to
[10:36] endure. And that realization shifts the
[10:40] weight of what we're seeing, because instead of stopping at
[10:43] the awareness that he suffered because of our sin, we begin to
[10:46] understand that the suffering itself belongs to us in the
[10:51] sense that what he took on is what sin actually warrants.
[10:55] And that recognition doesn't come from trying to tear
[10:58] yourself down or convince yourself of something
[11:00] emotionally. It comes from seeing the order
[11:03] of things as they really are. So you're standing there looking
[11:08] at Christ, knowing that what he is enduring is connected to what
[11:12] you're about to confess, and at the same time recognizing that
[11:17] there's nothing in him that deserves it.
[11:20] Which leads you to acknowledge that the disorder, the
[11:23] punishment, the weight of it is something that you brought
[11:26] about. And that clarity produces a kind
[11:29] of humility that's steady and sober because it's rooted in the
[11:34] truth rather than reaction. And that humility changes how
[11:38] you approach confession, because you're no longer going in trying
[11:42] to explain yourself, or trying to soften what you've done, or
[11:45] trying to frame it in a way that feels easier to say because it's
[11:49] embarrassing. You're going in there having
[11:52] already faced the reality of it, which makes your confession more
[11:57] honest, more direct, and more aligned with what's actually
[12:01] there. From there, the focus turns even
[12:03] more specifically to the blood of Christ.
[12:06] And instead of moving away from what we've been looking at, you
[12:09] remain there and allow that detail to come forward.
[12:12] Because his blood is not just a part of the scene, it's the
[12:16] price of what you're looking at. And the church has always spoken
[12:19] about it in that way, as something with real value,
[12:22] something that was poured out for the forgiveness of sins.
[12:26] So as you're staying with that, we are not trying to force a
[12:29] reaction out of ourselves to produce a certain kind of
[12:32] feeling that we're going to experience.
[12:35] But we're allowing the reality of it to speak on its own, which
[12:38] means that we're looking at what our sin costs in a way that
[12:42] begins to Draw Something out of us that isn't coming from
[12:45] pressure or guilt or obligation. It's coming from seeing clearly.
[12:50] And what begins to form there is a kind of love that isn't just a
[12:55] fleeting moment. It stays with you because when
[12:58] you're faced with that kind of sacrifice and you recognize your
[13:03] place in it, it moves your will in a steady way where we begin
[13:08] to desire to respond. And you feel it.
[13:12] You want to live differently. You don't want to return to the
[13:15] sin that you're about to confess.
[13:17] And you even learn to accept difficulty or sacrifice in your
[13:21] own life in a way that's united to what you're looking at.
[13:25] So instead of trying to stir something up before confession,
[13:28] you're allowing this to shape you.
[13:30] And this isn't something that can be rushed or controlled.
[13:34] And you can't generate this feeling.
[13:36] It's something that you receive by staying there long enough for
[13:42] that love to take effect. And as all of this settles in
[13:46] where you've stayed with his suffering, you've recognized
[13:50] your place in it. And then you've allowed that to
[13:52] shape how you see your own sin. The final piece of this widens
[13:57] what you're bringing into confession because your sorrow
[14:00] is no longer limited to just what you've done personally, and
[14:03] so it begins to extend outward. So instead of approaching
[14:06] confession only with your own sins in mind, you kind of start
[14:10] to carry a sorrow for sin itself, for the ways that God is
[14:14] offended more broadly, for the reality that what you're
[14:18] confessing is a part of something larger.
[14:20] And that doesn't distract from your own responsibility, but
[14:24] instead deepens it because you're no longer isolated and
[14:27] how you see it. And that kind of sorrow isn't
[14:30] something that people usually think about before confession
[14:34] because the focus tends to stay on us, on the individual.
[14:37] It's very contained. But when your love for God
[14:41] begins to take shape in a real way, it naturally expands and
[14:45] you begin to care about what offends him beyond just your own
[14:48] actions. So by the time that you walk
[14:50] into the confessional, you're not just bringing your sins,
[14:54] you're bringing a part that has already been moved in a way that
[14:57] goes beyond yourself and that changes the way that you confess
[15:01] because your sorrow is no longer narrow or self focused.
[15:05] It's aligned with how God sees sin, which is always in light of
[15:10] love. So what's happening through all
[15:12] of this is that you're not walking into confession trying
[15:15] to become sorry in that moment. You've already let the truth of
[15:19] your sin reach you beforehand, which changes the entire
[15:23] experience because you're no longer relying on whatever you
[15:26] happen to feel when you step into the confessional.
[15:29] You've already looked at Christ. You've already made the
[15:32] connection. You've already faced what your
[15:35] sin is in relation to Him. And you've already allowed that
[15:39] to shape your sorrow so that when you confess, you're not
[15:42] scrambling to recall or react. You're speaking from something
[15:46] that has already been worked into you.
[15:49] And that's the difference between a confession that stays
[15:52] at the level of words and a confession that comes from a
[15:55] place that's been prepared. Because the sacrament itself
[15:59] isn't lacking. The grace is there, but the way
[16:02] that you receive it can either stay limited or go deeper,
[16:06] depending on what you brought into it.
[16:08] So instead of confession being something that you repeat
[16:12] without much change, it becomes something that actually begins
[16:15] to cut into the root of what you're confessing, because
[16:18] you're no longer treating sin lightly or vaguely.
[16:21] You've already seen it for what it is, and that changes how you
[16:25] turn away from it. A lot of people go to confession
[16:27] just trying to stay in a state of grace, which is good, You
[16:31] know, that's great, and that matters.
[16:33] But if that's the only way you ever approach it, it can stay at
[16:36] the level of maintenance where you're managing sin instead of
[16:40] confronting it in a way that begins to break it.
[16:43] Because if the only reason that you're sorry is that you don't
[16:46] want to be separated from God, or that you don't want the
[16:49] consequences that come with sin, you can keep returning to the
[16:52] same things without ever really seeing them clearly.
[16:55] And that's why you can feel like you're stuck, even though you're
[16:59] doing everything that you're supposed to be doing externally.
[17:01] And this is where people get frustrated, including myself,
[17:04] because we assume that something is wrong with us, or that we're
[17:08] just weak, or that this is how it's always going to be.
[17:11] But in reality, we've never been taught how to approach
[17:14] confession in a way that actually engages our love for
[17:18] God instead of just our fear of losing Him.
[17:22] So confession becomes something that we do regularly, but not
[17:25] something that changes how we relate to our sin at the root.
[17:29] And over time, that can turn into a kind of routine where,
[17:33] yes, we're honest, we're sincere, but we're not going
[17:35] deep because we've never really been shown how to prepare our
[17:39] heart to actually go there. There's also a short prayer
[17:42] that's attributed to Saint Catherine of Siena that fits
[17:45] into this kind of preparation really well.
[17:47] And it's not complicated. It's just a way of asking God to
[17:51] actually do in you what you've been trying to enter into.
[17:55] Because at the end of the day, you can place yourself in the
[17:58] right position, you can stay with the passion, and you can
[18:01] think through all of this clearly, but you still need
[18:04] grace to move your heart. So before going to confession
[18:07] next time, you can pray something like this, just slowly
[18:10] without rushing it and just letting each line land as you've
[18:14] already spent time reflecting. Then I'm going to put it on the
[18:16] screen, but it says, Holy Spirit, come into my heart by
[18:21] your power. Draw me to God and give me true
[18:23] charity with holy fear. Protect me from every disordered
[18:27] thought. Warm me with your love so that
[18:29] what is difficult becomes light. Help me and everything I do.
[18:34] And the point of something like this isn't to add just like
[18:38] another thing to check off. It's really simply to ask for
[18:42] the interior help that we actually need, because
[18:45] everything that we've talked about up until this point
[18:48] ultimately depends on Grace doing what you can't do on your
[18:52] own. So the next time you go to
[18:54] confession, instead of walking in there with a list that you
[18:57] put together maybe 5 minutes before, I know I've been there,
[19:00] take the time beforehand to actually sit with what you're
[19:04] bringing into the confessional. Place it in front of Christ,
[19:07] stay there long enough to see it clearly, and let that shape how
[19:11] you enter into the sacrament. Because confession isn't just
[19:14] about saying your sins and then being done.
[19:16] It's about whether you've actually allowed yourself to
[19:20] encounter your sins in truth before you speak them.
[19:23] And that begins long before you step into the confessional.
[19:26] And if you do that consistently, you will start to notice that
[19:29] you're not just repeating the same cycle and the same sin,
[19:32] even though there are those sins that we fall back into.
[19:36] But instead, you'll begin to see that you're beginning to
[19:38] understand your sin differently, and you're beginning to respond
[19:41] to it differently and approach God differently because you're
[19:45] no longer keeping everything at the surface.
[19:48] You're letting it go deeper where it actually has the
[19:51] ability to change something in you.
[19:53] That's all I have for today. Thank you guys so much for
[19:56] listening. I will see you guys next time.
[19:59] Bye.

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