Hey, it’s Jeffrey, back again!
Paying off debt sounds simple: just throw extra cash at the highest-interest balance and you’re golden.
But in reality?
It’s hard to know where to start, how much to pay each month, and even harder to stay consistent over time.
That’s where AI and automation come in. They make the whole process faster, more flexible, and less stressful.
This week, I tested tools that:
✅ Help you choose a strategy that fits your goals
✅ Automate payments and track progress in the background
✅ Suggest simple ways to free up more cash each month
Whether you’ve got credit card or personal loan debt, it’s worth trying.
📬 In this email:
In today’s Money Meets AI edition, we look at:
📊 Step 1: Pick Your Payoff Date and Prioritize Debts
⚙️ Step 2: Automate Your Plan (So You Actually Stick to It)
📈 Step 3: Visualize Your Payoff Journey with AI
🛠️ Other Tools to Check Out
⟳ What to Do Next
THIS WEEK’S TESTED TOOLS
📊 Step 1: Pick Your Payoff Date and Prioritize Debts
Best for: Choosing a timeline and knowing where to start
Here are 3 methods to consider:
✅ Avalanche Method
Pay off debts with the highest interest rate first (e.g., credit cards), while making minimum payments on the rest.
🧠 Best for: Saving the most money in the long run
🌀 Cash Flow Method
Prioritize debts that will free up the most monthly cash fastest—like smaller loans with large payments.
💵 Best for: Boosting your monthly breathing room sooner
⚖️ Custom AI-Optimized Plan
Let ChatGPT or a tool like Bright suggest a hybrid plan based on your balances, interest rates, cash flow, and desired payoff date.
We’ll use the Avalanche Method for the sake of this example.
Before diving into tactics, I asked ChatGPT:
I have $7,000 on a credit card at 24%, $3,000 on a personal loan at 11%, and $17,000 on an auto loan at 8%. I can only afford $900/month towards my debt. How soon can I realistically be debt-free?
ChatGPT calculated that “If you start in July 2025, you’d be debt-free around January 2031.” Here are the calculations
ChatGPT also suggested that adding $100 more to my monthly payment could make a difference, so I asked it to do that. Here are the results:
It shaved 16 months off my payoff timeline, just by tweaking one number.
🔁 Step 2: Automate Your Plan (So You Actually Stick to It)
Best for: Taking the mental load off and building momentum
Once you know your monthly targets, put your plan on autopilot. Here’s how:
Set automatic payments: Use your bank or debt servicer to schedule monthly payments that align with your strategy.
Connect a budgeting app: Monarch Money lets you track spending, flag extra cash, and spot trends.
Trigger alerts + nudges: ChatGPT can generate reminders, motivational messages, or daily check-ins.
Adjust dynamically: Some tools (like Bright, Savology, or Cushion) can automatically adjust based on due dates or extra income.
💡Ask ChatGPT:
How can I automate my debt payoff plan?
ChatGPT gave me a clear breakdown of how much to send where, and how to automate it. Here’s a summary:
📈 Step 3: Visualize Your Payoff Journey with AI
Best for: Staying motivated and seeing real progress over time
Debt payoff can feel slow, especially when the numbers are big. That’s where a simple visual can help.
Ask ChatGPT to turn your plan into a clear, month-by-month payoff chart. You’ll see exactly how your balances shrink over time — and what happens if you pay just a little more each month.
💡 Example prompt to continue the conversation from above:
For my payoff plan, can you show me a monthly chart of how my debt would be paid off?
Here’s a chart to visualize the payoff:
It can also produce a Gantt Chart for the debt:
You can even get creative, too:
Build a spreadsheet formula with GPT
Ask for a “progress bar” that updates as you pay
Or ask for help based on what motivates you
What Didn’t Work So Well
I wanted to try the Bright – AI Debt Manager app to see what it could do. However, the fee felt pretty hefty. The cheapest option was $39 for 3 months, and no free trial was offered.
For me, that’s just too much without being able to test it first. I’ll see if I can get access to review for a future newsletter.
🛠️ Other Tools to Check Out
Other tools I came across but didn’t do a deep dive into for this newsletter:
Undebt.it – Compare snowball vs. avalanche visually
Qapital – Can save spare change into a “Debt Payoff” goal automatically
Rocket Money – Cancel subscriptions and track bills in one app
YNAB – For full control if you want to manually allocate every dollar
🎯What to Do Now
✅ Ask ChatGPT to build your personalized debt strategy
⚙️ Connect an app to automate payments + cash flow
📈 Ask AI to chart your progress (or build a custom tracker)
🚀 Apply any extra cash to your highest-interest debt
PS—I’d love to hear your other feedback or suggestions. Just hit reply — I read every email!
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One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.