In this issue of The Payoff Challenge:

  • Community Debt Payoff Snapshot

  • Submit your debt payoff totals for this week!

  • Weekly Action: Lower your internet speed

  • Money News: AI agents and managing personal finance

  • New video: Review of Ramsey-Friendly Bank Account!

  • My Home Payoff Update

Disclaimer: Some links in this newsletter are affiliate links and provide compensation for clicks and sign ups.

Happy Mother’s Day (a day late) to all you hard-working moms out there! To my own mom, because I know she’s reading this, you’re the best.

Alright, let’s jump into this week’s numbers.

Community Debt Payoff Snapshot

Low week of submissions this week (just us) but that’s okay because we still made progress on our house balance.

We paid off a total of $1063 last week! That’s almost what we spent on our honeymoon back in 2017. We definitely didn’t go all out. We were young and had bills to pay.

$1063 is also the equivalent of 288 gallons of chocolate milk.

Numbers only move if people act—which brings us to this week’s check-in!
Weekly Check In!

How Much Did You Pay Off This Week?

⏱ Takes under 60 seconds. Any amount. Any debt.

This isn’t about how big the number is—it’s about progress. If you haven’t made a payment yet, consider this your nudge to go make one right now. Missed a week? Just submit the total since your last entry.

Submissions will be included in future week’s Snapshots!

Caleb’s Actionable Strategy

Just Ask for a Refund

Recently, I’ve had two purchases that I messed up on and I acknowledge that. With both, I told them I messed up and asked for a refund and they granted it to me, saving me some moolah.

Action: This week, check if you can do a return or get a refund on something you thought you couldn’t.

Here’s what happened: I had been paying for monthly Amazon Prime and was planning to end the subscription, but then I forgot and got charged for it. I reached out, told them I meant to cancel and asked for a refund and they gave it to me.

Another time when we were planning our ski trip for February, we booked a non-refundable two-night stay at Hotels.com. When we changed our plans, I asked if they would be willing to refund. They couldn’t do the whole thing but they did give us one of the two nights back.

I’m not saying lie about your situation. Just be honest about messing up. I feel like especially for companies that aim for high quality customer service, they’ll likely try to work with you because they want you to remain a customer. I’ll certainly still be a customer of both of these companies.

And it could save you some money that could go towards debt payoff!

Member Spotlight

I Want To Celebrate Your Wins!

But I can’t do that if you don’t tell me about it. So fill out this short form about the debt you’ve paid off and your current wins!

Any amount of debt payoff is worth celebrating here in the member spotlight.

Personal Financial News

JP Morgan Will Roll Out AI Agents Soon

Apparently, JP Morgan is partnering with Mirakl to create AI agents that can actually help with purchasing for both consumers and businesses along with a lot of other financial tasks.

From what I can tell, it could be great for security of finance, but I grow increasingly wary of how AI could make people even more ignorant of their financial situations than they already are.

Your take-away: Nothing helps you change your financial future than you knowing your own situation and making intentional progress.

That’s why I want to help everyone budget money and make intentional decisions about their money instead of letting an AI make decisions for them. I still think it’ll be interesting to see how this affects finance in the near future. While AI absolutely has the capacity to help people manage their money, I just don’t tend to think having it manage everything is healthy. Read more here.

New video alert! I just reviewed the partner credit union of Ramsey Solutions. Check it out if you haven’t seen it yet.

Caleb’s Challenge Update

Progress We Made Towards Our Payoff

Goal: Pay off our remaining mortgage ($70k) by our 10-year anniversary on June 17, 2027.

409 days left

Mortgage Balance on January 1st, 2026: $70,000

Current Mortgage Balance: $62,410.90 (▼$1,063.12 since last week)

Balance paid off since start of challenge: $7,589.10

Source: Paycheck, savings, interest, Etsy poster sales, selling scrap metal, bicycle, TV cabinet

*This includes monthly principal payments as well as additional payments.

Current Mortgage Balance

This week, I sold a bench on Marketplace! We also had our May mortgage payment come out. Making progress!

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That’s it for this week! I already can’t wait for next couple week’s editions as we start getting numbers to include. If you have any feedback, respond to this email or drop me a line at [email protected].

Till next week!

Caleb

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