“Am I Allowed To Go on a Free Cruise Even Though I’m in Debt?

Summary

Episode Overview

Main Theme:
This episode of The Ramsey Show Highlights centers around a listener's question about whether it's acceptable to go on a free, company-sponsored cruise while actively paying down debt (“baby step two” of the Ramsey program). The hosts, with their characteristic insight and humor, discuss not only the practical side of financial choices but also the deeper mindset and behavioral shifts required for lasting change. The core message is about discipline, intentionality, and reconstructing one's relationship with money, especially while working toward financial freedom.

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Key Discussion Points & Insights

1. Listener Dilemma: Vacation While in Debt?

[00:09]

• Caller Jesse's Situation:
  • Received a reward from work—an all-expenses-paid cruise.
  • In baby step two, actively paying down debt ($5k in consumer debt, $14k car loan, down from $7k recently).
  • Wonders if he’s breaking the Ramsey rules by going, even though it’s free except for minor “fun money.”

Practicality:

• Company pays for everything, including room, board, travel to the port, and paid time off.
• Minor out-of-pocket spending for optional excursions or personal fun.

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2. Ramsey's Response: “It’s Not About Permission”

[00:37 - 01:31]

• Dave Ramsey:
  • “You’re allowed to do whatever you want to, Jesse.” (00:37)
  • Emphasizes intent over rigid rule-following. The central idea: spending is not the villain—rationalization is.
• Discusses that baby step two is about total focus, not deprivation for deprivation’s sake.

Notable Quote

"The reason that we teach people to stay out of restaurants and stay out of vacations while they're in baby step two is total focus...I have one job, and that's to defeat the debt. Because if I live like no one else later, I can live and give like no one else. I'm paying a price to win." — Dave Ramsey [01:53]

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3. Mindset Shift: “Altitude, Attitude, and Angle of Your Heart”

[02:43 – 04:10]

• Mindset Over Mechanics:
  • Ramsey stresses reframing how one talks to themselves about money and deprivation.
  • It's not about “asking permission” but seizing the opportunity to reset habits and thinking.
  • Jesse is encouraged to focus on gratitude, not entitlement.

Notable Quotes

“You need to frame it up with, ‘I'm going to do this. I don't need Dave's permission to do it for sure. You're like a grown man and you hit your metrics. Okay, but I'm going to do this. But I'm also going to make sure that the altitude and the attitude and the angle of my heart is permanently changed.’” — Dave Ramsey [02:43]

“What I figured out is that you have to change the altitude, the attitude, the angle of your heart permanently regarding these things. So you never again talk yourself into something that down deep, you know, you shouldn't be doing.” — Dave Ramsey [03:15]

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4. The “Brownie Pan” Analogy: Self-control and Boundaries

[04:17 – 05:36]

• Boundary Setting:
  • Hosts use an analogy: saying “just a little” can become a slippery slope (similar to nibbling one brownie after another).
  • Emphasizes the importance of setting—and sticking to—clear boundaries, both financially and in self-talk.

Notable Moment

“It's like when you say, I'm not eating any sweets and then somebody makes the pan of brownies...already you've gone past. Now you can...But then what do you do? You slice off a little piece and...before you know it, you've ate the pan of brownies.” — Co-host [04:35]

“That's the danger. The danger is not the actual slice. The danger is I'm still going back to the brownie pan.” — Dave Ramsey [05:26]

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5. Practical Tools: Automating Smart Habits

[07:28 – 08:51]

• Automation:
  • Dave shares his own experience of putting smart money habits on autopilot (prepaying bills, automatic investments) for built-in discipline.
• Cites David Bach's Automatic Millionaire principle: let automation do the heavy lifting for your financial progress.

Notable Quotes

“I have automatic discipline all the way through this... put everything on automatic so that you're automatically doing smart stuff.” — Dave Ramsey [08:27, 08:43]

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6. The Deeper Lesson: Vocab Rehab and Emotional Reset

[06:09 – 07:10]

• The pendulum of cultural mindset has swung too far towards entitlement (“I work so hard, I deserve [this]”). The Ramsey approach aims to swing it back toward humility and responsibility.
• “Vocab rehab” is about changing not just behavior but how you speak to yourself about money and worth.

Notable Quotes

“The words that we use and the way we talk to ourselves and even the tone...reflects whether or not is your heart right on this.” — Dave Ramsey [05:36]

"The pendulum has swung too far to the consumer side, where he says, everything's okay...And all we're doing is swinging the pendulum back to the other side and go, you don't deserve nothing. Shut up. You broke people." — Dave Ramsey [06:43]

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Memorable Quotes & Moments With Timestamps

• “I don't need Dave's permission to do it for sure. You're like a grown man and you hit your metrics.” — Dave Ramsey [02:43]
• “If I live like no one else later, I can live and give like no one else. I'm paying a price to win.” — Dave Ramsey [01:53]
• “You have to change the altitude, the attitude, the angle of your heart permanently regarding these things…never again talk yourself into something that down deep, you know, you shouldn't be doing.” — Dave Ramsey [03:15]
• “That's the danger. The danger is not the actual slice. The danger is I'm still going back to the brownie pan.” — Dave Ramsey [05:26]
• “Put everything on automatic so that you're automatically doing smart stuff.” — Dave Ramsey [08:43]
• “The pendulum has swung too far to the consumer side...All we're doing is swinging the pendulum back...You broke people.” — Dave Ramsey [06:43]
• “Vocab rehab.” — Co-host [06:40]

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Recommended Mindset (As Stressed in the Episode)

• Gratitude over entitlement: “I've chosen to be grateful that I do this...the company gave me this because otherwise I wouldn’t be able to do it this year.” [06:25]
• Discipline over rationalization: Any “splurge” must not turn into a habit.
• Automation for success: Make smart choices automatic to avoid slip-ups.
• Permanent change: Shift your self-talk and internal narrative around money.

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Conclusion & Takeaways

• Is it OK to go on a free cruise while paying off debt? Yes, if it's truly free and you’re not rationalizing deeper spending patterns.
• The true battle: Changing internal attitudes and self-talk about money, not just following external rules.
• Practical wisdom: Put automation in place; celebrate small wins, but maintain discipline and gratitude.
• Final lesson: The journey to financial freedom is mostly emotional and psychological; "reset the tapes" in your brain for real, lasting change.

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Transcript

[A]

If your private student loans are in default, you're not out of options. Go to yrefi.com Ramsey I work for.

[B]

A great company and I did fairly well last year. And so they were taking my wife and I on a cruise in February, along with a lot of the people who had also gotten the metrics. And I was just wondering, I'm in baby step two, and so I know I shouldn't be on any vacations or going out spending, but am I allowed to have an allotted a side job to use on the staycation? And yes, I get paid for it.

[C]

Is it just. You just pocket money?

[A]

You're allowed to do whatever you want to, Jesse. But you know, what would we do if you're in baby step two, this cruise is not costing you anything.

[B]

No, I get paid the whole time I'm gone. I get room and board and the company vehicle down to the port.

[C]

Okay, so just pocket money for meals or whatever.

[A]

Should be included on the cruise, right?

[B]

It is a little bit of money just for, like, excursions or to have a little fun, because this is the only vacation that I'm quote, unquote, planning.

[C]

So what if you planned. If you planned it out and you've looked at it, what do you think is the number of the amount of money you think you would need for it that you would spend?

[B]

Oh, yes, we did it last year and I did like bare bones. So I didn't spend anything. And I know that we could do it again like that.

[A]

But don't talk to me about I don't ever get to go on vacation. I did a cruise last year.

[C]

That's the plan.

[A]

Oh, whining.

[C]

Wait, let me. Let me get you back to your senses. How much debt do you have?

[B]

Okay, so I got about 5 in consumer 2 cards that started listening to y' all in November. So I've already cut that down from 7K. And then I got my car and that's about 14. That's it.

[A]

I would go, Jesse, but what I would do is I want you to reframe this in your head, okay? The reason that we teach people to stay out of restaurants and stay out of vacations while they're in baby step two is total focus that I have one job, and that's to defeat the debt. Because if I live like no one else later, I can live and give like no one else. I'm paying a price to win. Okay? And that's how you frame this decision in your head. Not Dave, I want to go on vacation. We're not going to get to you on vacation for a long time and we went on a cruise last year. But come on, man, wait, let me.

[C]

Frame it to you.

[A]

I'm sorry. No, I mean really, you need to frame it up with. I'm going to do this. I don't need Dave's permission to do it for sure. You're like a grown man and you hit your metrics. Okay, but I'm going to do this. But I'm also going to make sure that the altitude and the attitude and the angle of my heart is permanently changed.

[B]

Oh, yeah.

[A]

Away from the rationalizations and the justifications that allowed me to get into this mess in the first place.

[B]

Yes, sir.

[A]

That's why we do this, because we're trying to shock your spirit into saying you're not entitled to vacations or eating out. Those are entertainment, luxury items while you're broke, people. And I want to, I want people's spirit to be shocked. That's what happened to my spirit. I didn't have the option of doing it voluntarily. It was snatched from me because I was so stupid I went bankrupt. So I got you beat hands down on stupid. Right. And listen, I thought whining was a little known form of prayer, so I had whining down too, you know. But what I figured out is that you have to change the altitude, the attitude, the angle of your heart permanently regarding these things. So you never again talk yourself into something that down deep, you know, you shouldn't be doing. I think this is fine mathematically.

[B]

Okay. Yeah. And on Jade's point of view, I just wanted to add this real quick. I am picking up a side job this year too, so doesn't matter.

[A]

That should all go towards the death.

[C]

It's still, it's, it's. What we're talking about is you set the boundary. And once if you have said to yourself, I'm getting out of debt, that's the priority. If you let these little things start sneaking past the goalposts more and more sneak past. It's like, it's like when you say, I'm not eating any sweets and then somebody makes the pan of brownies. Well, already you've gone past.

[A]

Now you can now you.

[C]

But then what do you do? You slice off a little piece and you go, I'm just going to have that little piece. Then you go back in and you slice off another little corner and another little corner and before you know it, you've ate the pan of brownies.

[A]

Are you following me around?

[C]

I saw you. That's what we all do. We've all done it. And that's a great way to think of it. You got a pound of brownie because they gave you the free trip. You get to decide how much you slice off. Don't slice any of it off. You already have. The pan is just sitting there.

[A]

And you know what we're doing. You have to set new neural pathways in your brain.

[C]

Yeah, that's the real part that says.

[A]

I'm done with this crap. So I would go, but I'm gonna. You know, your. Your side hustle is to set the new neural pathways and go, I'm going to. But I'm going to be unbelievably disciplined about this slice.

[C]

Yes, Very disciplined.

[A]

Because I know the danger is not the actual slice. The danger is I'm still going back to the brownie pan.

[C]

Yes. Throw the pan away after this slice.

[A]

That's the thing. That's what it is. I mean, that's what we're trying to. You have to permanently change the way you talk to yourself about this. The words that you use out of the abundance of the heart the mouth speaks, the Bible says. And so the words that we use and the way we talk to ourselves and even the tone that we use to ourselves about talking ourselves into or out of something reflects whether or not is your heart right on this. And that's the thing. So, guys, that's the lesson. The takeaway from Jesse's call, because it's a good call and Jesse's obviously a good guy and he's obviously a high producing dude.

[C]

And when you go out there, though, take a step further. What Dave just said. When you go out there, Jesse, what you can't do is, well, I can't spend any money. I can't do.

[A]

No, no.

[C]

You have to form the words of what you want, which is. I'm choosing. Everything's a choice.

[A]

I've chosen to be grateful that I do this. Yeah. The company gave me this because otherwise I wouldn't be able to do it this year.

[C]

Yes.

[A]

Because this year we're not going on.

[C]

Vacation, but paying off my debt is my priority.

[A]

Exactly.

[C]

And that's how you talk to yourself.

[A]

Reset this whole. This whole set of tapes that's running in your brain, man.

[C]

Vocab rehab.

[A]

That's why we do some of the things we do, y'. All. It's like the. And what we're doing is the pendulum has swung too far to the consumer side, where he says, everything's okay. Just push the submit button. Load the Cart. Right, right. And I can impulse anything I want and I work so hard and I deserve. And all these things we tell ourselves. And all we're doing is swinging the pendulum back to the other side and go, you don't deserve nothing. Shut up. You broke people.

[C]

It's like you're quoting the book. Good job.

[A]

Your book? Yeah, the new one.

[C]

The new one that's out today.

[A]

What no one tells you about money, the real key to getting unstuck from someone who's been there. It's the emotional part of this.

[C]

That's right.

[A]

And that's what we're dealing with. The neural pathways, the behavior shifts, all of those things. And you know the feedback loops you put for yourself.

[C]

Yes.

[A]

You know, one of the things that goes with this, too. And Jay, I know you talked about this in there as well, indirectly, not exactly the way I'm going to say it, in other words. But one of the things I did, Jesse, when I was at your thing is completely different from your question, but it fits in the same bucket of stuff. I don't do things mechanically, tactically, with how I pay things that aren't automatically always getting me the discount.

[C]

Okay.

[A]

Okay. So before there was online bill pay, because there was no online. I prepaid my utility bills to get the discount. To get the discounts. Prepaid to get the discounts. And I set it on an auto calendar. Right. I have automatic draft to this day on my checking account that goes straight into a mutual fund every single month automatically out of my checking account so I don't accidentally forget it.

[C]

That's right.

[A]

I have automatic discipline all the way through this. There was a guy out 100 years ago when one of my first best sellers called Automatic Millionaire, his name is David, David Bach. It was a best selling book. He said, just put everything on automatic so that you're automatically doing smart stuff.

[C]

Automate smart. Yes.

[A]

And you don't have to think about. You don't have to built in discipline with the systems. Not like I'm going to grip my teeth and do this every time.

[C]

That's right. That's right.

[A]

And that's the same kind of thing. We're resetting how we view this. And what's the attitude, the altitude and the angle of my heart on this stuff. Why Refi Refinances defaulted private student loans for struggling borrowers. Learn [e-mail] Ramsey.