“You Don’t Want To Admit This Is Screwed Up”

Summary

Episode Overview

Podcast: The Ramsey Show Highlights
Episode: “You Don’t Want To Admit This Is Screwed Up”
Date: January 14, 2026
Hosts: Dave Ramsey & Rachel Cruze
Theme:
This episode spotlights a candid conversation with a 37-year-old caller who, after years of steady success as an engineer, made a series of risky choices—buying a large house with little down, quitting his job, and trying to salvage the situation through Airbnb. The caller now faces financial quicksand and seeks advice from Dave and Rachel about whether to sell his house and how to get back on track.

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Key Discussion Points & Insights

1. Caller’s Backstory & Main Financial Dilemma

• Caller reveals he was financially secure but made two major missteps:
  • Bought a large house with 3% down & PMI, hoping house hacking would work easily.
  • Quit his job, believing his savings would tide him over.
• Tried house hacking and then pivoted to Airbnb, with limited success.
• Now wonders: "Should I sell my house?" ([00:12–00:44])

2. Transition From Engineering to Financial Trouble

• Rachel Cruze and Dave Ramsey ask for clarification.
• Caller explains living arrangements:
  • Stayed in his house during renovations.
  • Moved in with a friend, helping babysit their kids, while Airbnb-ing his home. ([01:05–01:24])
• Reveals he is 37 years old. ([01:29–01:31])

3. Ramsey & Cruze’s Immediate Assessment

• Dave Ramsey: Advises returning to “solid ground”—get a job as an engineer and sell the house. ([01:32–01:58])
• Rachel Cruze: Questions what’s holding him back. ([01:58–02:02])

4. Reluctance to Return to a 9-to-5

• Caller says he tried job interviews but finds himself “not suited” for traditional work and prefers entrepreneurship. ([02:02–02:15])
• Dave Ramsey: “Why are you not suited for a 9 to 5? What's wrong with you?” ([02:15, 02:48])
• Rachel Cruze: Suggests he may just be entrepreneurial rather than unsuited to 9-to-5. ([02:57–03:00])
• Dave clarifies: “You're suited for it. You don't want to do it.” ([03:02])
• Core message: Preference doesn't matter when you’re “neck deep in quicksand.” ([03:17–03:23])

5. Financial Assessment — The Numbers

• Caller shares financial stats:
  • Airbnb income broke even in 2024, but lost $10k–$15k in 2025. ([03:30–03:47])
• Dave: “If this was a business unit at Ramsey, we would close the thing and call it failed.” ([03:50–04:00])
• Caller may be falling into a “sunk cost fallacy.” ([04:17])
• Dave: “Yeah, definitely. 100%.” ([04:21])

6. The House Situation: A Sunk Cost

• Caller bought home for $650,000, put $100,000 into renovations.
  • Zillow estimates value at $615,000; Redfin at $580,000. ([04:40–04:53])
• Dave calculates: “You have $750,000 invested in a house that's worth $600,000.” ([05:03–05:11])
• Rachel Cruze: Urges to get a professional realtor’s assessment. ([05:39])
• Caller admits he started this process but wanted Dave’s direct advice. ([05:56–05:59])

7. What To Do Next: Action Steps

• Dave: “Facts are your friends. You're in trauma and you need to sell this thing if you can. And you need to retrace your steps and get back on solid ground.” ([06:04])
• Suggests focusing on income and survival first, then building towards entrepreneurial pursuits.

8. Essential Money Priorities & Tough Love

• Caller has only about $10,000 in non-retirement savings. ([06:30–06:32])
• Dave: “You gotta get a job, man.” ([06:32])
• Rachel: Recommends book “Find The Work You’re Wired to Do” to help caller determine purpose—but stresses urgency of stable employment. ([06:35])
• Dave:
  • “The first thing you're suited to do is buy food, lights and water. The second thing you're suited well to do is pay your stinkin' bills. The third thing...find something that's a style of work you enjoy...But you don't really have a lot of choices right now, man, because you've done screwed this up.” ([06:53–07:16])
  • “You do not get to...do something that you saw on TikTok…when the mathematics around it don't math 100%. That's called…You can't.” ([07:32–08:14])

9. Grounding Ambition with Reality

• Dave: “The math does not form to your desires…The math forms to the math.” ([08:15–08:21])
• Rachel: Reflects on her own experience, working jobs she didn’t love to “close the gap so that the math maths.” ([08:28])
• Dave (on waiting for dreams): “God designed me to be on the stage. Good. And in the meantime...you're also destined to wait tables.” ([08:59])

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Notable Quotes & Memorable Moments

• Dave Ramsey:

  • “Sometimes if you wake up from a nightmare and you're standing knee deep in the swamp, the best thing to do is to return to the last time there was solid ground and retrace your steps.” ([01:32])
  • “You just don't want to get. You don't want to admit that this screwed up.” ([04:13])
  • “You have $750,000 invested in a house that's worth $600,000.” ([05:03])
  • “Facts are your friends. You're in trauma and you need to sell this thing if you can.” ([06:04])
  • “The first thing you're suited to do is buy food, lights and water…But you don't really have a lot of choices right now, man, because you've done screwed this up. Hello. You've made a mess.” ([06:53–07:16])
  • “You do not get to…do something that you saw on TikTok…when the mathematics around it don't math 100%. That's called…You can't.” ([07:32–08:14])
  • “The math does not form to your desires. The math forms to the math.” ([08:15–08:21])
  • “God designed me to be on the stage. Good. And in the meantime, that means you're also destined to wait tables.” ([08:59])

• Rachel Cruze:

  • “Right now you're not really in a phase where you can do exactly what you prefer.” ([03:17])
  • “You have to work and you have to do the things that close the gap so that the math maths.” ([08:28])

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Timestamps for Important Segments

• 00:06–00:44: Caller shares backstory and financial issues
• 01:05–01:31: Living situation and age
• 01:32–01:58: Initial advice—retracing steps
• 02:02–03:17: Hesitation to return to regular employment
• 03:30–04:17: Airbnb numbers and “sunk cost fallacy”
• 04:40–05:32: Revealing the house’s true cost vs. value
• 05:39–06:04: Realtors and the need for facts
• 06:30–07:16: Realistic priorities, money strategies
• 07:32–08:21: Fusing dreams with reality: math trumps desire
• 08:28–09:17: Rachel and Dave on working through the difficulty and building dreams responsibly

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Tone & Takeaway

Throughout the episode, Dave and Rachel strike a balance between empathy and tough love. There’s an emphasis on:

• Facing facts, not wishes, when it comes to money
• Taking immediate corrective action, even if it’s humbling
• Recognizing when ambition collides with financial reality

Essential message:
You can't let pride or sunk cost keep you stuck. Sometimes the path forward means starting over, taking any good-paying job, and living in reality—not dreams or TikTok fantasies—until you’re back on solid ground.

Transcript

[Dave Ramsey]

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[Caller/Guest]

I used to make good money as an engineer, and I was on Baby Step 4 Before I knew what the baby steps were.

[Dave Ramsey]

Good.

[Caller/Guest]

Then three years ago, I made what I realize now. Two major mistakes in a row. I bought the biggest house I could buy with 3% down and PMI thinking that house hacking would be easy. I'm now doing Airbnb. And then a few months after that, I quit my job because I was miserable there, thinking I had enough savings. I can give you some financial details, but I'm wondering if you think I should sell my house.

[Rachel Cruze]

Tell us more. What's.

[Dave Ramsey]

Yeah, tell us more.

[Caller/Guest]

Yeah, so I quit my job, and then I realized that I would not be making my mortgage if I were to do house hacking. So I. I pivoted and then started doing Airbnb.

[Rachel Cruze]

Okay, and where are you living?

[Caller/Guest]

To renovate. During this time? I was in the house. During renovations. I was living in the house. Sorry. Yeah, I was living in the house. And then while I was Airbnb. While I Airbnb my house, I was living with my friend that have a couple of kids, and I was helping them.

[Rachel Cruze]

Oh, gosh.

[Caller/Guest]

Babysitting in a game.

[Dave Ramsey]

How old are you?

[Caller/Guest]

I am 37.

[Dave Ramsey]

Okay. All right. I mean, sometimes if you wake up from a nightmare and you're standing knee deep in the swamp, the best thing to do is to return to the last time there was solid ground and retrace your steps. And so that would, in this case, sound like get a job as an engineer and sell the house.

[Caller/Guest]

Yeah.

[Dave Ramsey]

And then you would have your life back.

[Rachel Cruze]

Yeah.

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[Rachel Cruze]

What prevents you from doing that in your mind?

[Caller/Guest]

I was interviewing for some engineering jobs in 2025. It was difficult to come back after taking some years off. And I also know that I'm not suited for a 9 to 5 now, and I'm pursuing.

[Dave Ramsey]

Why are you not suited for a 9 to 5? What's wrong with you?

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[Dave Ramsey]

Ramsey, why are you not suited for a 9 to 5. What's wrong with you?

[Caller/Guest]

That's a great question.

[Rachel Cruze]

Are you trying to say that you're entrepreneurial?

[Caller/Guest]

Yeah, I believe so.

[Dave Ramsey]

Yeah. You're suited for it. You don't want to do it. Okay. I don't blame you for that. I don't blame you for that. I'm entrepreneurial, too, and I wouldn't want to be trapped somewhere. I don't. I don't have an issue with that, but. So what we're saying is not suited for is not the right phrase. What we're saying is it's not preferable for you.

[Rachel Cruze]

But right now. Right now, you're not really in a phase where you can do exactly what you prefer.

[Dave Ramsey]

Exactly. Preference is no longer a point. You're neck deep in quicksand.

[Caller/Guest]

So I'm wondering if. If I give you some numbers if you think I am in quicksand. So in 2024, I broke even with my mortgage with the Airbnb, and then in 2025, I was negative 10 or 15,000 with my Airbnb.

[Rachel Cruze]

Is the Airbnb where?

[Dave Ramsey]

Does this sound like it's fun to you? None of this sounds fun to me. If this was a business unit at Ramsey, we would close the thing and call it failed.

[Caller/Guest]

Yeah. I'm wondering if an alternative is. Yeah, maybe.

[Rachel Cruze]

Why are you reluctant to. Why? Hey, why are you going to sell the house? Yeah.

[Dave Ramsey]

You just don't want to get. You don't want to admit that this screwed up.

[Caller/Guest]

Yeah, I. I think I might be falling into sunk cost fallacy.

[Rachel Cruze]

Okay.

[Dave Ramsey]

Yeah, definitely. 100%.

[Rachel Cruze]

What? Tell us. Tell us the.

[Dave Ramsey]

Can you sell the house for as much as you owe on it?

[Caller/Guest]

Yes, I believe so. I put about a hundred thousand into it, renovating it.

[Dave Ramsey]

Oh, you'd lose that. I mean, what would the house sell for?

[Caller/Guest]

Yeah, the. So I'm looking at Zillow and Redfit right now. I bought it for 650. Zillow saying 615, Redfin saying 580.

[Rachel Cruze]

Oh, so you're not going to get the money out of it, but you.

[Dave Ramsey]

Put a hundred down or you put 100 in it after you bought it for 650.

[Caller/Guest]

100 into it after buying it.

[Dave Ramsey]

So you owe 7. You have $750,000 invested in a house that's worth $600. $600,000.

[Caller/Guest]

You know better than I did.

[Dave Ramsey]

Well, I mean, is that what you're telling me?

[Caller/Guest]

I don't know if I got an appraisal if it would be worth more. I'm Guessing it would be okay, but.

[Dave Ramsey]

I mean, you're telling me you paid $650,000 for it, plus you put 100 into it, meaning you have 750,000 in this house. Correct?

[Caller/Guest]

Correct.

[Dave Ramsey]

And you don't think it's worth anywhere near that, is what you're telling me?

[Caller/Guest]

I don't know.

[Rachel Cruze]

Get a real estate agent. Go, go, go. On our site, you need to go to ramseysolutions.com and just in the box, type in real estate agent. It'll take you where you need to go. And you need to have somebody come out there. Okay, and what did they say? What they, what would they list it for based on what they saw?

[Caller/Guest]

I started doing that step and then I was like, I'm going to talk to Dave directly.

[Rachel Cruze]

Facts. And now I'm telling you, go do it. See it through so you can see what the actual numbers are.

[Dave Ramsey]

You need to have numbers. Facts are your friends. You're in trauma and you need to sell this thing if you can. And you need to retrace your steps and get back on solid ground. And then from there think about how you can come up with some career choices after you're making a living again. How much money do you have in the bank in retirement or say not retirement, non retirement investments?

[Caller/Guest]

Probably like about 10,000.

[Dave Ramsey]

Yeah, you gotta, you gotta get a job, man.

[Rachel Cruze]

We'll send you find the work you're wired to do because I think you don't know what you want to do and I think you're just kind of coasting. And this idea that you might be an entrepreneur, I'm glad that that's so. But we need to get some, some beef around that and figure out what that's going to be in the meantime. Yeah, we'll send you the book. But you also just need to get a job.

[Dave Ramsey]

Yeah. So the first thing you're suited to do is buy food, lights and water. The second thing you're suited well to do is pay your stinking bills. The third thing you're well suited to do after you've done those two things is find something that is a style of work that you enjoy, meaning entrepreneurial and more freewheeling than in a 9 to 5. But you don't really have a lot of choices right now, man, because you've done screwed this up. Hello. You've made a mess. And so you got to get the shovel out. The barn is full of poop.

[Rachel Cruze]

Today is J O B. Yeah.

[Dave Ramsey]

There's some shoveling that needs to be done here. So you Got a mess. Wow. So you do not get to as an adult, boys and girls, ladies and gentlemen, Do something that you saw on TikTok. That feels fun or good or well suited, whatever the phraseology we want to use is when the mathematics around it don't math 100%. That's called. You know, you can't.

[Rachel Cruze]

That's not reality.

[Dave Ramsey]

The math does not form to your desires.

[Rachel Cruze]

No.

[Dave Ramsey]

The math does not form to your suited. The math forms to the math.

[Rachel Cruze]

The math. When Sam and I were getting out of debt, we knew we wanted to start a business. But that takes time. Right. You got to build it up. And so in the meantime, you have to work and you have to do the things that close the gap so that the math maths. So you can continue to accomplish your goals financially while you accomplish your goals career wise. You have to do it all at the same time. You can't just go, well, I want to be an actress or, well, I want to own a business and I'm not going to do anything until I have that success. That's not real.

[Dave Ramsey]

God designed me to be on the stage. Good. And in the meantime, that means you're also destined to wait tables. That's what that means every time. I mean, we're in Nashville. How do you get the next country music star's attention? Waiter. That's exactly how you get it, right?

[Rachel Cruze]

Yes.

[Dave Ramsey]

And so, I mean, you know, there's calluses that are involved in these things. Okay. Yes. You know, God designed me. I'm suited for. I'm good. Me too. We all are wonderfully made. We have these. That's why we have finding the work you're wired to do that we're going to send to Chris. Okay, that's all great, but you don't get to use this specialness card to try to violate mathematics. It just. It'll destroy your life. It's too harsh. It's mean out there, boys and girls. Mean out there. Create your free every dollar budget today. The simplest way to budget for your life.