Hey everyone, welcome back to Grace Over Guilt. I’m Dan Kaufman. If you listened to Monday’s episode, you know we didn’t sugar-coat a damn thing. We walked right into the middle of the storm. The arrest. The sentencing. The divorce. The stuff most people take to their graves. I lived it in real time, and now I talk about it because there’s no healing in hiding.

Today we’re digging into the beating heart of this whole podcast: the difference between guilt and shame, and why grace matters more than either one. Not just as a concept, but as a survival skill.

And I want to take this even further than last time. I want to dig into how this played out in my own mind, how it ties into Stoicism, into Christianity, into therapy, and into the stuff no one likes to talk about: reading, journaling, meditation, and slowing down long enough to face yourself.

This isn’t an episode you listen to on 2x. This is one you sit with.

THE CORE DISTINCTION

Let’s start with the simple truth that punched me in the teeth in jail.

Guilt says, I did something bad.

Shame says, I am bad.

Guilt is about a moment. Shame is about your identity. Guilt is a compass. Shame is a cage.

And let me tell you something uncomfortable: when you strip away all the distractions in your life, when there’s no Netflix, no phone, no noise, no job to hide behind, no social media to numb yourself with, when all you have is a concrete slab, a blanket thin as a tortilla, and your own thoughts bouncing around like drunken raccoons… you get real clear on what’s guilt and what’s shame.

Guilt felt like a spotlight. Harsh, yeah, but pointed. Shame felt like a fog. Everywhere. Constant. Suffocating.

THE SHAME VOICE

Shame talks like it knows you better than you know yourself. It sounds like the voice you think is the truth because it’s been getting louder over the years.

Shame told me:

You’re the kind of man who ends up here.

You’re the guy who destroys his family.

You’re the father your daughters pull away from.

You’re the screwup no one will trust again.

You’re the problem.

The worst part is shame presents itself like a revelation. Like finally, after all these years, after all the pretending, you’re seeing the real you.

But that’s not truth. That’s fear wearing a fake badge.

THE STOIC ANGLE IN THE CELL

I read a lot in jail because I didn’t have a choice. You either read or stare at the ceiling until your brain leaks out. One of the books that messed with me in the best way was Marcus Aurelius’ Meditations.

Stoicism teaches something pretty radical:

You are responsible for your actions, but you are not defined by anything outside your control.

And guess what’s outside your control?

Other people’s opinions.

Your past decisions.

Circumstances you’re already in.

The identity you’ve attached to your worst moments.

Stoics have this brutal clarity:

If you did wrong, admit it.

If you can fix it, fix it.

If you can’t, learn and move forward.

But do not pick up extra weight that doesn’t belong to you.

Guilt fits in Stoicism. Shame does not. Guilt says, Here’s where you fell. Shame says, You’ll never stand again.

I remember reading one line: “The impediment to action advances action”, and laughing because the impediment for me was the size of a damn brick wall. But the truth hit me. My situation wasn’t blocking me. It was exposing me. It forced me to look inward, not outward.

CHRISTIANITY AND GRACE

Now, let me tie in the Christianity side, because it played a massive role for me too.

Christianity has this theme woven through everything:

You are flawed.

You are human.

You are redeemable.

Guilt in Christianity is something you confess, something you repair. Shame is what the enemy uses to convince you you’re unworthy of grace. Guilt says repent. Shame says hide.

There’s a moment I’ll never forget. I was sitting on the edge of the bed in the cell, and I had this verse pop into my head from when I was a kid: “A righteous man falls seven times but gets back up.”

Seven times. Not one. Not two. Seven. Almost like falling is part of the job description.

And it hit me: the fall wasn’t the problem. Staying down was.

THERAPY AND THE TABOO

Let’s get into therapy, because this part needs to be said directly.

There’s still this ridiculous taboo about therapy, especially for men. You can walk into a bar and brag about wrecking your car, losing your temper, cheating, drinking too much, blowing your life up. Totally acceptable. Try saying, I’ve been seeing a therapist. Watch the room get quiet.

In jail, therapy wasn’t optional for me. My choices were:

Face myself or get swallowed by shame.

Therapy taught me something huge: guilt is specific. Shame is vague. The moment you take something vague and start breaking it down, it loses 90 percent of its power.

Therapists are basically emotional mechanics. You walk in with an engine that’s smoking and stalling, and they say, Let’s look under the hood. Shame hates that. Shame thrives when the hood stays closed.

MEN DON’T TALK ABOUT THIS ENOUGH

Men are conditioned to think they can out-tough shame. That’s like trying to out-muscle quicksand. The harder you fight it alone, the deeper you sink.

Every time I sat with a therapist, I realized I wasn’t broken. I was untrained. I had emotional muscles I’d never used. Therapy didn’t “fix me.” It helped me understand myself so I could stop swinging blindly.

READING, JOURNALING, MEDITATION

This is where the healing became a practice, not an event.

Reading gave me perspective. Stoicism. Scripture. Self-development. Even biographies. People who went through hell and came out stronger reminded me I wasn’t a special case of brokenness.

Journaling was huge. I’d write down the shame thoughts, and the minute they were on paper they looked ridiculous. Shame only thrives when it stays in your head. Once it moves to ink, it loses its costume.

Meditation was the first time in my life I learned to slow down the mind. Not shut it up. Just slow it down. When you slow it down, guilt becomes something you can look at. Shame becomes something you can challenge.

GUILT AS A TEACHER

The big turning point for me was reframing guilt.

Guilt isn’t the enemy. It’s a teacher. It points toward what needs repair. It gives you clarity. The trick is not letting guilt morph into a lifelong identity.

Guilt says, You broke trust.

Shame says, You’re untrustworthy.

Guilt says, You hurt someone you love.

Shame says, You don’t belong in relationships.

Guilt says, You missed the mark.

Shame says, You are the mark.

That’s the difference between change and collapse.

THE REBUILDING PROCESS

Rebuilding your life is slow. It’s unglamorous. It’s painful. But it’s real.

Here’s what the process looked like for me.

Step one: Tell the truth. To myself. Out loud. Shame hides in lies.

Step two: Own what I did wrong without owning things that weren’t mine.

Step three: Make small changes I could actually sustain.

Step four: Accept grace. From God. From my parents. From the people who didn’t abandon me.

Step five: Build new evidence about who I am. Not with talk. With action.

Your identity doesn’t change because you declare it. It changes because you behave in a way that supports it.

THE STOIC PRACTICE OF INTERNAL CONTROL

Marcus Aurelius wrote something that ended up becoming a mantra for me: “You have power over your mind. Not outside events.” That line alone could break a million people out of their shame spirals.

You can’t change the past.

You can’t change other people’s reactions.

You can’t control the fallout.

You can’t rewrite the story that already happened.

You can control what you do today. Right now. This minute.

CHRISTIAN REDEMPTION

The Christian version of this is just as powerful:

God doesn’t wait until you’re polished to work with you.

He meets you in the mess.

Grace isn’t the reward for getting your act together. Grace is the reason you can stand back up and try again.

PRACTICAL TOOLS THAT SAVED ME

Let me break down the toolbox I still use.

Journaling to separate fact from story.

Reading to remind myself I’m not alone in this human circus.

Meditation to actually hear my own thoughts instead of drowning in them.

Therapy to challenge the lies I tell myself.

Prayer and Scripture to reconnect with something bigger than my screwups.

Stoicism to keep me grounded in responsibility.

Grace to keep me human.

Grace over guilt. It isn’t a slogan. It’s my operating system. Because guilt can be fuel, but shame will burn your entire life down.

If you’re dealing with shame right now, hear me: it’s lying. You’re not unfixable. You’re not beyond redemption. You’re not your darkest moment.

You are a human who messed up and still gets to write the next chapter.

Grace over guilt. I’ll see you on Friday.