Aug. 26, 2026

How Do I Stop Being So Hard on Myself About Money?

Key Takeaways

  • Adopt the same standard of evidence for yourself that you use for other people instead of acting as your own prosecutor, judge, and defendant.
  • Learn to distinguish between conviction, which hands you a specific action item, and shame, which leaves you trapped in a locked room of guilt.
  • Recognize that a con artist telling you to ignore professional advice is a scripted manipulation tactic known as isolating the mark, not proof of your own foolishness.
  • Replace self-punishment with practical financial rules, such as getting everything in writing, using third-party custodians, and enforcing a 48-hour waiting period on rushed decisions.
  • Forgive yourself not as a feeling you wait for, but as a deliberate decision to accept the verdict of grace that God has already signed.
  • Focus on growing through your financial journey rather than carrying the weight of past mistakes that were orchestrated by deceptive predators.

Today, we're diving into the nitty-gritty of self-forgiveness and how to shake off that nagging guilt. Lorraine, our guest, thought she was a fool for trusting a smooth-talking scammer, but we’re here to flip that script. Turns out, she’s got some serious wisdom to share after losing her mom's inheritance to a con artist. How Do I Stop Being So Hard on Myself About Money? We're gonna break down how to get that paradigm shift you've been craving and stop being your own worst critic. So, stick around for some solid advice, and hey, I’ve got a juicy announcement for you at the end!

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Check out the full podcast episode here

We dive into the heart of Lorraine's financial struggles, shedding light on her journey from losing her mother's inheritance to reclaiming her financial confidence. This episode is all about digging deeper into what it means to shift our mindset and how to stop the ruthless self-judgment that often follows financial missteps. Lorraine’s story is a rollercoaster—she trusted a man at church, lost a chunk of her inheritance, and felt like a fool for years. But we flip the script on that narrative, suggesting that it’s not about being foolish; it’s about growing and learning. We lay out practical steps for anyone feeling stuck in their financial journey to break free from that mental cage. Tune in as we emphasize that it’s not about positive vibes alone; it’s about getting the right info and understanding the difference between shame and conviction. This episode isn't just a financial guide; it's a pep talk for the soul, encouraging listeners to forgive themselves and embrace their journey with grace.

Takeaways:

  • Lorraine's journey from negative $1,400 to $125,000 shows that it’s never too late to turn things around, so don't sweat it!
  • When making big financial decisions, always trust the pros – ignoring their advice can lead to major regrets, just like Lorraine learned the hard way.
  • Conviction helps you grow and change, while shame just holds you back – remember to separate the two and focus on what you can do.
  • It's key to treat yourself with the same grace you give others; adopt that same standard of evidence and stop being your own worst critic.

Links referenced in this episode:


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Frequently Asked Questions

How do I stop being so hard on myself about past financial mistakes?

Stop acting as your own prosecutor and judge by applying the same grace and standard of evidence to yourself that you would offer to a friend in the same situation. Separate true conviction, which gives you an actionable next step, from useless shame, which only causes mental torment.

What is the difference between conviction and shame regarding money?

Conviction is specific and points you toward a corrective action or lesson you can apply moving forward. Shame is global, making you feel like a hopeless failure without providing any way to fix the problem.

Why do scammers tell victims to ignore professional financial advice?

Scammers isolate their targets by telling them that professionals like attorneys or accountants do not understand the investment, effectively inoculating the victim against outside warnings before they can be discovered.

How can I practically forgive myself after losing money to a scam?

Self-forgiveness is a decision rather than a feeling you wait for. By accepting God's forgiveness and establishing strict financial rules and boundaries for the future, you can step off the hook for a crime that was committed against you.

Chapters

00:00 - Untitled

00:00 - The Consequences of Trust

01:34 - Understanding Paradigm Shifts in Financial Confidence

09:02 - Understanding Conviction vs. Shame

16:42 - Understanding Self-Blame and Control

18:25 - The Journey of Self-Forgiveness

27:39 - Transitioning to a New Live Show

Transcript
Speaker A

Hey, if you missed yesterday's show, Lorraine wrote to me and today she wrote back and she told me something she left out the first time. Before she handed the man her mother's inheritance, she paid an attorney to review the contract and guess what? He told her not to do it.And she spent 18 years believing. That proves she's a fool. I think it proves the exact opposite and I want to show you why.Because the same play was run on somebody listening right now. So stick around and we're getting right into it. And make sure you stay to the end because I've got a special announcement for all of our audience.Hello and welcome to Financially Confident Christian. I'm Ralph Estep Jr. And if you missed us last time you met Lorraine. And today I'm going to give you a quick catch up for another new questioner.So here's what you missed yesterday. If you didn't listen to the episode, you can go listen to it. But let me give you a little background. She's 69 years old. She's still working.Lost most of her mother's inheritance to a man she met at church. But here's the best part and the part that she completely left out. That's why you got to go listen to yesterday's episode.She went from a net worth of a negative $1400 in just eight years to $125,000. And she asked me yesterday how to practically live out Matthew 6.I sent her a response and she wrote back and her reply had a question that's been hitting I've been thinking about for days. So today we're going to talk about how do you actually get a paradigm shift? And I'm not talking about that feeling.Stop being so hard on yourself because everybody's already told her that and it hasn't worked once. How do you actually put it down? And if you've ever done the math and you still feel like a failure, today's show is for you.And if you've got a question for the show just like Doreen's, you can get to me by going to financiallyconfidentchristian.com/question We'll put a link in the show notes, but again, that's financially confidentchristian.com/questionWell, like I said, this is the follow up to Lorraine's first email. Here's what she wrote. The second one says, hello, Ralph, thank you so much for your surprisingly quick and detailed response.Great encouragement, insight and godly wisdom. I started to cry after the first few sentences and I'm crying even now as I respond to you. Okay, I'm taking back the apology. And then she put lol.I've asked pastors and other financial people how to navigate my situation and no one has come even slightly close to your detailed and encouraging and biblical insightful response. I feel so helpful, hopeful now with a great sense of direction and relief. I'm going to print your email and keep it where I can see it daily.I'm also going to ask someone to help me be accountable to this Many have told me that I'm too hard on myself. Any advice on how I can have a better paradigm shift? How did you learn to view things as you do?I didn't mention that I sued the scam artist and I lost one of the two property claim lawsuits because of my Christian attorney who a pastor referred to me and made agreements with the opposing counsel on an old boy's handshake without my knowledge and when it came time to deliver, the opposing side denied the unwritten agreement.The portion of the money it was won back, went to pay the attorneys and she puts arc the deceptive thing was that the scam artist had two real estate investment companies. He held paid training classes, he did coaching. He took me to the homes under contract and repair so it looked legitimate and successful.The investment check was written to his company so it looked legit.But Ralph, I consulted with an attorney about the written contract and they warned me not to proceed because I would have no recourse if things fell through.However, Ralph the scammer was so convincing that this method of real estate investing was not understood by many and told me I shouldn't heed the attorney's warnings. I was later told it was likely a Ponzi scheme. Lesson learned, Ralph. Don't assume Christian is a safe label.Never make a decision out of desperation and don't ignore the prompting of the Holy Spirit or godly counsel and be grounded in my identity in Christ and be humble.Lastly, a lawsuit isn't always wise as the enemy can use it to kill, steal and destroy your time, your peace, your resources, your health and your dignity. Of course, forgive. And that includes myself. Now Ralph, I'm still working on that one, but you've helped me start that.So yes, you may certainly use my story and my first name only. And then I love what she ends this with. Think about the struggle she's ended with and this is what she says.She say, may God be glorified and someone or many receive the help and encouragement they need. God's abundant blessings to you, praise and thanks to Jesus. Lorraine. Lorraine, thank you so much.You've really humbled me in what you wrote and I got back to you because this is what I do. If you write to me, if you reach out to me, we get back to you.So let me answer your direct question first because she asked me something personal and she said, ralph, how did I learn to live things this way? And here's my honest answer. I didn't learn it from a book. I didn't learn it from a pulpit. I am not an ordained minister.I Learned it from 30 years of working with people doing their accounting and their tax work.I'm a licensed public accountant and for three decades I've sat across a desk from people who they slid their actual numbers across, not the version they post. I'm talking about the real one. And here's what that does to you. I stopped guessing about other people.I've seen the returns behind the vacation photos. I've seen the six figure household with $40,000 in credit debt. And I've seen a retire couple whose paid off beach house has a second mortgage on it.So when Lorraine tells me all her friends have retired and are traveling, I'm not encouraging her. I'm telling her what I've seen. She doesn't know the balance sheets. She knows the paragraphs and the photographs and the social media.That paradigm shift that you're looking for, Lorraine, isn't positive thinking. It's better information. I truly believe that shame runs on comparison and comparison runs on a data set you don't actually have.So today's big idea you asked me about how to stop being so hard on yourself. Everyone's told her to do that, but not a single person, according to her notice, has ever told her how.So today I'm going to give you six things of how to make that correction and how to stop living in that guilt that you feel. So here's the first one and this is going to be so bold. You got to write this one down. You can't be the prosecutor and the judge. You just can't.Read the letter again. And we're going to put a list of it in the show notes. Watch what she does when you go back and review her letter.She extends grace to everybody in this story except one person. The scammer gets a fair description. He scammed me. He was a guy from church. The attorney who cost her case gets scare quotes and an lol.The pastor who referred him gets no blame at all. And then she turns around and Convicts herself. Do you see what I'm saying there? She's playing all three roles.She's playing the prosecutor, she's playing the judge and she's playing a defendant. And the prosecution has an unlimited budget while the defense never gets to speak. Not a single person gets a fair trial in that courtroom.And it's not because the evidence is bad, because the process is rigged. So here's my first practical fix. And it's not a feeling, it's a rule.You gotta adopt the same standard of evidence for yourself that you use for other people. Lorraine, hear me on this. If a 69 year old woman sat down across from you and told you your story, what would you say to her?What would you say out loud? What would you say to yourself now that you see that you already know how to do this? You've done it for everyone else in the letter.She just has excluded herself from the policy. Lorraine, you're not too hard on yourself because you're honest.You're too hard on yourself because you're the only one in the room without a defense attorney. You're entitled to a defense attorney. Here's the second thing. You got to learn the difference between conviction and shame.So many people get this tied up. This is the single most useful distinction I know. And most Christians have never had it explained to them. I'm going to do that right now.Conviction is specific, shame is global. Conviction says you overrode your attorney's warning. Of course that's a thing you did, Lorraine. You said it.You overrode what the attorney said to you. Good looking back at it now with 2020, I shouldn't have done that. That's what conviction says. Conviction allows you to do something about it.But shame says you're a foolish woman and that's who you are. You see the difference there? That shame is never going to help you. Conviction comes with an exit.You could have decided, no, I'm not going to take this advice. But shame is a locked room. Conviction tells you get counsel and follow it next time. Now you know what to do.But shame says you're irresponsible with money. Lorraine, what do you do with that? You can't do anything with that. There's no action item in it. And here's the test, and it takes five seconds.If you're trying to discern between conviction and shame. Does this thought give me something to do? It's really that simple. Does this thought that I'm having right now give me something to do?If you can answer yes, that's conviction. Sit with it, obey it, act on it. That's God.When the attorney said, lorraine, I wouldn't do this because you don't have any recourse, that's conviction. But if it only gives you something to feel, that's not conviction. Cross that out. Conviction changes behavior. Shame just cost you sleep.And Lorraine, you lost a lot of sleep about this and now look at which one she's been running for 18 years. It hasn't produced one change. See, that's the tell. Conviction hands you an assignment. Shame just hands you a verdict.If there's nothing to do with didn't come from God. Now here's another thing I want to talk about. I want to talk about that warning you ignored as the proof he was a professional.This is the heaviest thing in your letter and I want to take my time with it. You said you consulted an attorney, even paid for it. The attorney read the contract and told her, don't do this, you have no recourse.And what did the scammer say? The scammer told her his method just wasn't understand or understood by many people and that she shouldn't heed that warning.And she's carried that for 18 years as exhibit A against her. Again, she's proving her case against herself. Well, I want to enter it is exhibit A against him.Because that move, and if you've heard somebody say this, if you've ever heard, don't listen to your advisor, they don't understand this. That's not something they improvise. That is a scripted play. It has a name. It's called Isolating the Mark. I've seen this way too many times.Every serious con includes an inoculation against outside counsel. Now that's a fancy way of saying it because the con man knows exactly what the professional is going to say when they read the paper.I see these all the time. Clients will send me something and said, ralph, tell me if this is too good to be true and I'll read it and I'll say it's too good to be true.They'll call me a week later, they'll send me an email like, well, I told the guy what you said and he told me you just didn't understand, Ralph. So I did it. Well, that's why the con person is doing this. He wants to get ahead of that.He tells you the warning is coming and he tells you what it means before you even hear it. And look at everything else he built to make that work. Think about the scam he played here a two real investment companies.He had paid training, classes and coaching. You're not just going to make money. You pay to learn from him, which makes him the teacher and you the student.He even did site visits under contract and under repair and a check made out to a company, not a person. That's not a guy who was lucky with a gullible woman. This is an infrastructure. This was a well developed con.That's a career and you were the one to stop on it. So if you're listening right now, I want you to write this down because this is the whole episode for you right now.If anyone ever tells you not to listen to your attorney, not to listen to your accountant, not to listen to your pastor, that is your answer. You don't even have to evaluate the deal. The advice to ignore counsel is the fraud.Anybody that gives you a legitimate deal, a truly legitimate deal, is going to survive an attorney. It's going to survive an accountant reading them. That's the entire point of an attorney. He didn't beat your judgment.He knew your attorney would beat him, so he got you to it first. That's not you being foolish. That's him being good at his job. He's a good scammer. I want to add one correction to your lesson list.Your lesson list is better than most of what I read in most finance books and I want to affirm almost all of it. Don't assume Christian is a safe label. That's correct. And she paid for that one twice. Once with the scammer and once with the attorney.You said there never make a decision out of desperation. Correct. Don't ever make a rushed decision or decision out of desperation. You said, don't ignore godly counsel. That's correct.And I want to add this because Lorraine, God did answer you. The attorney was the answer. You had it in your hand. You had it in writing. Now one of the things you said is a lawsuit isn't always wise.They can be hard one and true. You won a claim and the recovery went to the lawyers. That happens more than people know. That happens all the time.But there's one item on that list I want to take off and I'd ask you to hear me out on this one. You wrote, be humble and that's honorable, Lorraine, but humility was not your problem. Humility was the tool the scammer used against you.You deferred to a confident man over a credentialed professional. And your own gut told you that. That's not a shortage of humility. That's a shortage of authority. Predators like this person love humble people.This is why they go in the churches. Because the church is full of humble, good, humiliating people. Humility is the doorway they walk through. So I'd replace it. Not be humble.Be humble before God and be hard to move by men. Meekness in scripture is not weakness. It's strength that answers to God instead of to whoever is loudest in the room.And notice she already put the Russian right there on her own list, right next to the wrong one. Be grounded in my identity in Christ, Lorraine. That's the fix. That's the one that makes her hard to move. You don't need more humility.You needed more authority to be humble before God, hard to move by men. That's the whole lesson. But Lorraine, you've alluded to something big here. And you got to know why self blame is so hard to put down.She says many people have told her she's too hard on herself. And why hasn't it worked when people told her that? Because self blame is doing a job for her. And not a single person has addressed the job.Because here's the trait underneath of it. If it was my fault, then I have control and I can prevent it next time.If it wasn't my fault, if a professional criminal simply targeted me, then the world is dangerous and random and I can't guarantee it won't happen again. That self blame feels like responsibility. It's actually a bid for control. That's why that phrase of stop being so hard on yourself never lands.You're not asking, you're to feel better. You're asking to give up the only steering wheel you think you have. So don't take it away, just replace it.Lorraine, you want to prevent it from happening again, Good. That's a healthy desire. The thing that prevents it is not self punishment. It's a rule.Like we said yesterday, the third party custodian everything in writing, never override professional counsel and a 48 hour rule on any decision. Anyone is rushing you. Rules protect you, shame just watches you. And once you have the rule, you don't need the guilt.The guilt was a substitute for a system. You've been using that shame as a security system. It doesn't work, it's expensive. So trade it for a rule. I want to land one more thing. Lorene.Forgiving yourself is not optional. You wrote it right in your letter. You said forgive and that includes myself. But I'm still working on that one.I want to name what's actually happening in that sentence, gently. If God has forgiven you and you refuse to forgive yourself, you've set your judgment above his verdict.And most of us feel like that's humility, but it's not. Humility accepts the ruling. If you're refusing to close a case that God has already closed, that's not being modest.It's a quiet appeal of a decision that came from a higher court than yours. I don't know about you, but I think God's decision is the highest court in the land.And what you're basically saying is God, yeah, you said to forgive myself, but I can't because I think there's something higher. Practically self forgiveness isn't a feeling you wait for. It's a decision you make repeatedly until the feeling catches up.And Lorraine is not going to arrive at first. It's late to the station and it's only usually after you obey it day in and day out. One more thing, and I mean this.Forgiving yourself is not the same as saying it didn't matter, it mattered. It cost you a house, it cost you 18 years. It cost you your sense of safety. And forgiveness doesn't shrink the loss.It just takes you off the hook for a crime you didn't commit. This is what we get so messed up. It's not a feeling. You're not required to feel forgiven before you agree to be forgiven.Sometimes you just gotta agree first. Yes, Lord, I accept the forgiveness. But you might still feel like you're not.But that feeling comes later and it comes to people who stop arguing about the forgiveness that was already granted. Now, Lorraine, you told me you cried when you read my email and you're still crying when you wrote back.But I don't think that's because I told you anything you didn't already know. I think you cry because somebody finally said it out loud and you're allowed to believe it. Here's what faith doesn't promise.Unfortunately, it doesn't promise the man is ever caught, he may go on and scam more people.It doesn't promise the 18 years are going to come back or that the money reappears or that you're ever going to fully understand why God let that thief walk into the church and out with your mother's house. Those are questions that may never get answered. But it does promise us one thing. And I want you to hear this super loud and clear.It promises that the verdict on you is already in. It was signed in blood on a cross. And it's not up for Appeal, including by you.Romans, chapter 8:1 says, so there is no condemnation for those who belong to Christ Jesus. I want you to read the word no. No, not less, not manageable. None. And notice what it doesn't say.It doesn't say there's no consequence, Lorraine, you've suffered the consequences. It doesn't say there's no loss. You've had real loss. And it doesn't say there's no lesson. You've learned a lesson, Lorraine.You've got the consequences and you're living in them. What it does say is there's no condemnation. The loss is real, but that verdict against you is not.And, Lorraine, you've been serving a sentence in a case that was dismissed 18 years ago and nobody told you could leave the courtroom and go home free. Lorraine, you asked me how to get a paradigm shift. Here it is, and it's in one sentence.You've been treating your worst day as evidence about who you are when it was only ever evidence about who he was. Put down his file. It was never yours to carry. You said you're still working on forgiving yourself. Working on it isn't failing at it.It's the only way anybody has ever done it. It isn't going to happen overnight. It's a process. And when a woman who ends a letter about her own robbery, what did she say in her first one?She felt like she was raped. Any woman who ends a letter about her own robbery with these words, may God be glorified. Let me tell you right now, that gave me goosebumps.She's not behind on her healing. She's ahead of most of us. So here's my win for today. I want you to write down the harshest sentence you say to yourself about money.What is the harshest sentence you repeat to yourself? I want you to write down the exact words. It'll take you five minutes. What is the harshest sentence you say to yourself about money?And under it, I want you to write one question. Does this give me something to do? Does this give me something to do? If the answer is yes, write the action next to it. That's conviction.And then go do it. If it only gives you something to feel, I want you to take and draw a line straight through it. That shame, and it didn't come from God.Not journaling, not affirmation, just one sentence and one question. You can't argue with a feeling, but you can audit a sentence, get it out of your head and onto paper, where it is an answer to itself.Now, Lorraine, I found a Bible verse for today that I think is going to be encouraging. It comes from Second Corinthians, chapter 7, verse 10.It says for kind of sorrow God wants us to experience leads us away from sin and results in salvation. There's no regret for that kind of sorrow. But worldly sorrow which lacks repentance results in spiritual death.Paul draws the exact line I drew in step two and he drew it 2,000 years earlier. There is a sorrow that moves you and a sorrow that just eats you. Godly sorrow got Lorraine her lessons list. Lorraine is genuinely wiser.She'll never make those decisions again. That's a good kind. And Paul says you don't regret it. Worldly sorrow is the 18 years of self punishment that produce nothing. Just think about that.The same event, two completely different sorrows. You've been carrying both and only one of them is from God. So it's time to let that go.How about we pray and then I've got a special announcement to make. Heavenly Father, again today I'm praying for Lorraine. What a strong woman. And she came back to us later, Lord, and I thank you for that.I thank you for giving me the ability to reach people and the ability to talk to people. Lord, I know that you speaking through me, but she's still carrying a case against herself that you closed a long time ago.She told us she's still working on forgiving herself, Lord, meet her in that working. Help her to understand that, Lord. Take that prosecutor's voice out of her head and let her hear your gentle voice instead.Give her the sermon she's asking for and make her hard to move by confident men who are trying to scam her. Lord, bless that person. She's asking to hold her accountable and give her the right one, Lord.And thank you that she got a warning she couldn't use then, but let her trust her own gut now, Lord. And Lord, she asked that this be used for someone else's good. Lord, I just ask that you would do that.I know somebody that's watching or listening right now is learning from this, Lord, and I just praise you for that. Somebody right now is sitting in that same shame and doesn't know it's not theirs. Lord, help them to break that shame. And I ask this in Jesus name.Amen. Friend, if you've been quietly serving a sentence for something that was done to you, I hope today felt like a door opening.Nothing about the past has changed in the last little bit of time. What's changed is who the evidence is actually about. So here's my takeaways for today.Give yourself that same standard of evidence you give everyone else. Say it out loud today. And remember, conviction gives you something to do. Shame only gives you something to feel. Audit that sentence.And if anyone ever tells you, hear me on this, please hear me on this. If anyone, anyone ever tells you to ignore your attorney, ignore your accountant or your pastor, that is your answer. You don't need more humility.Humble before God, hard to move by men and trade that shame for a rule. Everything in writing, third party custodian, 48 hours on anything rushed. And forgive yourself by decision, not by feeling.That feeling is going to come later. And Lorraine, I just want to say thank you for letting us use your story. Somebody needed it, Lorraine.And I'm telling you right now, there are people that are being moved by your words. They've moved me and they've moved my team. And if you've got a question for this show, I would love to hear it.You can reach me by going to financiallyconfidentchristian.com/voicemail. We'll put a link in the show notes, but again, that's financiallyconfidentchristian.com/voicemail.Now, before I go, I told you I had something I wanted to mention. I've got something to tell you.Starting on Monday, August 31, this show is going to be a brand new live show and it's going to be called Becoming Financially Confident. It's going to be live every weekday at 11:30am Eastern. It's going to be a full hour with me and a co host. No more just Ralph blathering on.You're going to listen to me and my co host and we're still going to talk about real bills, we're talking about real numbers, no jargon and of course, no shame. And my favorite part is live chat is going to be part of the show so you can get your questions answered right on air.The podcast isn't going anywhere. The live show is where we go deeper in real time. And if 11:30 doesn't work for you, don't worry about it.We're going to go live at 11:30 Eastern and we'll show you how to do that right in the show notes and then the whole show gets released as a podcast episode later that day. So you can choose to be with us there live or you can catch us on your drive home.And again, it starts on Monday, August 31st at 11:30am Eastern and I would love to see you there. So thank you so much for joining me today. I want to encourage you. We've had a great two days stay financially savvy.May God bless you and you have a truly great day. It.