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Hey, it’s Jeffrey — back again!
Every year I tell myself I'll be smart about holiday spending. Set money aside. Stick to a budget.
And every year? The costs sneak up anyway.
It's not just gifts — it's your partner's gift, office parties, tips for service providers, hosting costs, and charitable donations. Before you know it, December hits your budget like a freight train.
So this year, I asked ChatGPT to help me figure out what I was actually going to spend — including all the stuff I was going to forget about.
What I got: 5 different categories of December spending I had completely overlooked. Just seeing it all laid out removed about 90% of my anxiety.
This week, I'm sharing the exact 5-minute workflow to:
Find your hidden December expenses
Create a realistic spending plan (even if you didn't save ahead)
Keep the joy, remove the January regret
Let's dig in 👇
📬 In this email:
🎁 The AI Holiday Spending Plan Prompt
🔍 What ChatGPT Found (My Real Results)
💡 How to Build Your Optimized Plan
📖 One Smart Read: Why We All Overspend in December
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🎁 Step 1: The AI Holiday Spending Plan Prompt
I opened ChatGPT and pasted this:
I want to optimize my holiday spending without stress. Help me:
1. List everyone I'm buying gifts for
2. Identify December expenses I might be forgetting (travel, tips, donations, events, hosting, etc.)
3. Decide on a total budget that feels both responsible AND joyful
4. Create a simple one-page plan I can actually stick to
Ask me questions one at a time, then give me a clear plan. No spreadsheets. No tracking every purchase.It really tried to make sure I remembered everyone
💡 Pro Tip: Keep this chat open all month. Just type "update my plan" whenever something changes.
🔍 Step 2: What ChatGPT Actually Found
Here's where it got interesting.
I thought I'd spend about $1,000 this December.
ChatGPT started with the obvious stuff — gifts for family, friends, maybe some coworkers. But then it asked: "What about your partner?"
Right. That's another $200 minimum if I want to get something thoughtful. How did I almost forget that? And since we combine our budgets, that's actually $400 total.
Then it kept going — asking about things I'd completely forgotten:
My Hidden December Expenses:
Partner gifts ($400)
Extra tip/gratuity for hair stylists, cleaners, etc. ($150)
Food and drinks to bring to parties ($100)
Incidentals for travel to Las Vegas ($400)
Total hidden expenses: $1,050
This is the stuff that makes January credit card statements feel shocking.
💡 Step 3: How to Actually Use Your Plan (Without Tracking Everything)
After ChatGPT gives you your plan, here's how I'm using it:
Keep the chat open on your phone. When you make a purchase, open the chat and type something like:
"I just spent $[AMOUNT] on [CATEGORY]. What do I have left in that category?"
ChatGPT remembers your plan and does the math for you.
Check in once a week. Instead of tracking every transaction, just ask:
"I've spent about $[X] on gifts so far. Am I on track? What do I have left?"
Handle surprises without stress. Got invited to another holiday party? Need a last-minute host gift?
Ask: "I just got invited to another party and need a $30 host gift. How does this affect my plan?"
The plan adjusts. You stay calm. No spreadsheet required.
The whole point is clarity, not restriction.
💰 Bonus: Use Last Year's Data
If you want to get even more accurate, export your December spending from last year.
You can download transactions from:
Your credit card/bank website
YNAB
Monarch Money
Quicken
Then try this:
📋 Advanced Prompt:
I'm uploading my December [YEAR] spending data. Analyze it and tell me:
1. What categories did I spend the most in?
2. What expenses show up every December that I might forget about this year?
3. Based on this data, what should I plan for this December?This turns your past spending into future clarity.
💡 One Smart Read
AI helps drive record $11.8 billion in Black Friday online spending // Reuters
While the last edition of MMAI noted “You won’t be able to offload your holiday shopping to AI agents anytime soon,” AI-driven traffic to retail sites jumped 805% this year as shoppers used tools like Amazon's Rufus and Walmart's Sparky to find deals. The interesting part? People spent more overall but bought fewer items per transaction — meaning AI is helping shoppers be more intentional, not just impulse buying.
Worth remembering: AI works both ways. It helps you plan your spending, but retailers are using it to drive sales too.
🎯What to Do Now
✅ Copy the prompt above
✅ Open ChatGPT and run it (takes 5 minutes)
✅ Reply and tell me the most surprising hidden expense you found
How did you like today's newsletter?
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. Some links may be affiliate links or sponsored content for which I may receive compensation.