What a way to start the first one, but hey, I’m writing this at 10:43 PM. And honestly, I’m a little nervous. Maybe it’s the coffee I just drank to help me stay awake as I write.
Let me start this by grounding the first newsletter with the point of this challenge:
This newsletter is meant to be a simple weekly reset for families who want to make progress on debt without feeling overwhelmed. Everything you see below is designed to support that goal — nothing more, nothing less.
My wife’s and my personal goal of paying off our house in 18 months stems from our desire to get rid of debt so that we can create freedom for our family. So we can create margin in our lives. So we can give our boys our full attention as they grow.
I’m so excited for this challenge because I can’t wait to see what other people do with it. And I’m excited to hear what goals and dreams you all have for your families.
This challenge isn’t an 18-month event. It’s an ongoing pursuit of freedom for anyone who wants to jump in. Maybe you’re not ready to jump in, and if so, that’s perfectly okay. But I want to invite you to join regardless! I don’t think you’ll regret it.
The Payoff Challenge will have a slow start. But that’s okay, it just means one thing is true:
The first several issues of The Payoff Challenge Newsletter will undoubtedly grow and evolve. This is actually a huge relief to me because it doesn’t mean it needs to be locked in with no possibility for change. I can try different things to see what works.
This also means that you can actually help shape the newsletter by providing me feedback. Just respond to this email if you do have feedback or suggestions.
Also, this first issue of the newsletter isn’t going to have anyone featured. But if you have signed up for the challenge, there will be many opportunities to be featured in future issues.
Whether you are a participant or merely an observer, thanks for following along in the Payoff Challenge! If you missed it, here’s my announcement of our goal and launch of the challenge.
Community Debt Payoff Snapshot
Yes, current community debt paid is $0. But this is the most exciting number we will ever see because it represents our baseline. We are at the bottom of the mountain looking up. By next week, this number won't be zero anymore. That’s exciting!
Numbers only move if people act—which brings us to this week’s check-in!
Side Hustle Roundup
Shout Out To Your Side Hustles!
Side hustles aren’t required—but for some families, they’re a way to speed things up without cutting essentials. I’m a dad of two so I understand that thinking about side hustles with everything else on our calendar can be stressful! The good news is, if you choose to try a side hustle, you can get really creative with them.
Which is why I’m excited for this section — I get to share with you the actual side hustles people are using to pay off debt. Sign up for the challenge so you can submit your side hustles and get featured in future newsletters. Here are a couple examples of side hustles I have personally tried in the past.
Splitting wood — Where we live has an abundance of wood, ready to cut and split. My brother and I did this all year long for people just wanting some firewood for a gathering or full cords for winter heating.
Making stickers — I actually purchased a Cricut, designed some very simple vinyl stickers, and sold them on Etsy.
Member Spotlight
This Section Will Feature Challenge Participants!
Usually, this section will feature a 'Member of the Week'—someone who sold a car, picked up a side hustle, or made that final payment. Could be literally any type of financial win.
Since we are just kicking off, I want Payoff Challenge participants to be some of the first featured stories. Did you sell something on eBay this week? Did you skip the latte? Or maybe you actually paid off a loan? Tell me about your story so far!
If you want to be featured in the Payoff Challenge Newsletter or related videos on YouTube, Instagram, or TikTok, this is your chance!
Caleb’s Actionable Strategy
Pick the Debt to Pay Off
As we kick off the Payoff Challenge, my first goal is to help you make progress. But I want to help you make progress by simplifying things so you don’t get overwhelmed and quit before you’ve begun!
Action 1 (This Week): Start paying $5 on your smallest debt
Start the challenge by lining up your debts smallest to largest regardless of interest rate. We’re only looking at the balance here. Then while paying minimums on all your debts, put your extra money toward the smallest one. Seriously, even if it’s only $5. This will do two things for you:
First, it’ll provide focus. Now instead of trying to put a little bit on each of your debts, you can simply focus on making progress on only one debt.
Second, it’ll provide momentum. Why should you choose the smallest debt instead of the debt with the highest interest rate?
You could do it that way, but paying extra on your smallest debt first actually helps create momentum and that sticking power you need to maintain your debt payoff until you’re 100% debt free.
If you pay off your smallest debt, you then move to your next smallest debt. Each debt paid off feels so good and helps maintain that motivation. Trust me, it works.
Caleb’s Challenge Update
Progress We Made Towards Our Payoff
528 days until our 10th wedding anniversary.
Our family goofing off during fall pictures
My wife, Bailey, and I are trying to pay off the remaining $70k of our mortgage by our 10th wedding anniversary on June 17, 2027.
We bought our house in 2020 and got a mortgage of $154,200.
As of the beginning of the challenge on Jan 1, we had exactly $70k remaining because I’m only slightly OCD and made enough of an extra payment in December to get us to exactly $70k.
Jan 1, 2026 Balance
Next steps toward paying off the house:
With the launch of the newsletter and the challenge, this coming week will be a tough one to kick off new income methods so upcoming payments towards our mortgage will likely come from two sources: 1) savings we’ve built up for a possible future downpayment and 2) my YouTube channel ad revenue.
But stay tuned as I’ve got a bunch of ideas I’d like to try. Mostly ideas which involve building something that is scalable instead of only trading hours for money.
Next week you’ll see the new balance, partly from our regular monthly payment and partly from our week’s additional payment!
Follow @payoffchallenge!
My plan is to post content every week on YouTube, Instagram, and TikTok to provide updates, give shoutouts, and share strategies to help pay off debt.
Click the links above or look for @payoffchallenge on any of these platforms if that sounds good to you!
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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 (do people still say that?) at [email protected].
Till next week!
Caleb
