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Hey, it’s Jeffrey — back again!
Here's the thing: I plan my workdays with AI.
But my weekends? I used to just... wing it.
The result? Two days gone, and somehow I wasn't rested OR productive. I'd get to Sunday night feeling like I wasted the weekend — either I worked the whole time, or I did nothing and felt guilty about it.
So I created a 5-minute ChatGPT weekend workflow to help me balance fun, rest, and those little life tasks that sneak up on Sunday night.
No overwhelming to-do lists. No guilt. Just a simple plan for a weekend that feels twice as long.
Here's how to set it up:
📬 In this email:
🕒 Step 1: Create Your AI Weekend Planning Prompt
🛋️ Step 2: Run it with ChatGPT (real example)
🌅 Step 3: Use AI to Reflect on Sunday Night
💡 One Smart Read: This Week in Money + AI
Do red cars cost more to insure?
You may have heard the myth that red cars cost more to insure, often with varying reasons why. The truth is, the color of your car has nothing to do with your premium. Insurance companies are more interested in your vehicle’s make, model, age, safety features, and your driving history. What’s not a myth, though — is that people really can save a ton of money by switching insurers. Check out Money’s car insurance tool to see if you could, too.
🕒 Step 1: Create Your AI Weekend Planning Prompt
This isn't just a one-off query — it's a repeatable workflow you'll use every Friday afternoon or Saturday morning.
The goal? Plan a weekend that actually leaves you recharged — not just busy or lazy, but intentional.
Here's the full prompt to paste into ChatGPT
🧘 The AI Weekend Planning Prompt
You are a warm, supportive weekend planning assistant that helps users design a balanced, realistic weekend schedule from Friday evening through Sunday night.
Ask these questions one at a time, waiting for my response before continuing:
1. What fixed commitments or obligations do you already have this weekend?
(Include anything with specific times — appointments, events, travel, work, social plans — from Friday after work through Sunday.)
2. What's one thing you must get done this weekend (errand, appointment, or task)?
3. What's something that would make this weekend feel fun or meaningful?
4. When do you want to rest or recharge? (sleep in, nap, time offline, quiet time, etc.)
5. Is there anyone you want to see or call?
6. What's one small thing you can do Sunday night to set next week up for success?
After collecting all responses, build a realistic weekend plan that includes:
- My must-do tasks and obligations, slotted into a simple schedule
- Blocks of time for rest, fun, and connection
- A light structure for Friday evening, Saturday, and Sunday
- Sunday evening left open for a short reset and reflection
Format the plan using clear time blocks and Markdown sections like:
**Friday Evening**
- 6:00–8:00 PM: [Activity]
**Saturday**
- Morning: [Activity]
- Afternoon: [Activity]
**Sunday**
- [Time blocks]
End with a summary and on Sunday night, ask me:
"What worked this weekend, what didn't, and what do you want to remember for next time?"💡 This prompt was created using the ChatGPT prompt generator from AI Playbook, an online community I'm part of that helps you build better prompts faster.
💡 Pro Tip:
Save this ChatGPT conversation and reuse it every Friday afternoon or Saturday morning. Just say:
"Start my AI Weekend Workflow."
That's it. Your weekend begins with intention instead of just... happening.
🛋️ Step 2: Try Your AI Weekend Workflow in Action
Once you've saved your weekend workflow prompt, it's go time.
You'll go through your personalized check-in one question at a time — it only takes about 5 minutes.
Here's how mine looked last weekend:
ChatGPT asked me:
"What fixed commitments do you already have this weekend?"
Me: "Friday: Halloween party 5:30-7pm, trick-or-treating 7-9pm, then a Christmas party at 9pm. Saturday: Ice cream tasting at 11am (wedding planning!), dinner in Providence 7-9pm. Sunday: Soccer game 1-4pm, concert in Boston 8-10pm."
"What's one thing you must get done?"
Me: "Fall cleanup yard work"
"What would make this weekend feel fun or meaningful?"
Me: "It's pretty full already, but maybe getting a drink somewhere new after dinner Saturday"
"When do you want to rest?"
Me: "Sleep in both days till 9am or so"
ChatGPT responded with a balanced plan:
🗓 Your Weekend Schedule
🎃 Friday Evening
- 5:30–7:00 PM: Halloween party
- 7:00–9:00 PM: Hand out candy to trick-or-treaters
- 9:00 PM–late: Christmas party at the local bar
🍦 Saturday
- 9:00–10:00 AM: Sleep in and have a slow breakfast
- 11:00 AM–12:00 PM: Ice cream tasting (wedding dessert options)
- 12:00–2:00 PM: Yard work (fall cleanup)
- 2:00–5:00 PM: Free time — relax, maybe catch a nap
- 7:00–9:00 PM: Dinner in Providence
- 9:00 PM–??: Try a new spot for a drink
⚽️ Sunday
- 9:00–10:00 AM: Sleep in and have a calm morning
- 10:00 AM–12:00 PM: Light tasks / finish yard work
- 1:00–4:00 PM: Watch the AFC soccer game
- 4:00–6:30 PM: Drive to Boston and grab dinner
- 8:00–10:00 PM: Concert in Boston
🌙 Sunday Night Reset
- Lay out clothes for Monday morning workout
- Prep breakfast so it's easy to get up and go
Summary: This weekend balances a full social lineup with moments to rest and recharge in the mornings. You'll head into next week ready and organized.It's not rigid — it just makes the weekend feel intentional. Like having a coach who reminds you: rest is productive too.
🌅 Step 3: Reflect on Sunday Night
At the end of the weekend, ChatGPT will ask you:
"What worked this weekend, what didn't, and what do you want to remember for next time?"
This 60-second reflection helps you:
Close out the weekend feeling accomplished
Spot patterns (are you overcommitting? not resting enough?)
Make next weekend even better
💡 Pro Tip: Ask ChatGPT to summarize your last 3-4 weekends to spot trends. You might discover you're packing too many errands in, or not scheduling enough social time.
💡 One Smart Read
I Went 48 Hours Without AI // The New York Times
While I love AI, it sometimes feels like it's taking over my life. There are definitely times when I feel like I need a break. This writer tried going completely AI-free for two days — no ChatGPT, no smart assistants, no algorithm-driven feeds. What they discovered about attention, creativity, and mental space is fascinating. A good reminder that even the best tools need boundaries.
🎯What to Do Now
✅ Save the prompt to reuse each weekend
📅 Try it this Friday afternoon or Saturday morning
💬 Reflect on Sunday night
🚀 Want more prompts like this? Check out AI Playbook to get better at prompting and save time in your work
📤 Know someone who needs a better weekend routine? Forward this email
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.