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Hey, it’s Jeffrey — back again!
Open enrollment started November 1st. We have until November 15th to choose between HMO and PPO, figure out how much to put in our FSA, and decide if we need life insurance or disability coverage.
Last year, we just clicked "Keep Current Elections" and hoped for the best.
This year, we spent 15 minutes with ChatGPT — not because it found some huge hidden savings, but because it actually made the decision process simple instead of overwhelming.
No more staring at benefit comparison charts at 11pm wondering what "out-of-network coinsurance" means.
Here's how we used AI to get through open enrollment without the usual stress:
📬 In this email:
1️⃣ Use AI to Explain HMO vs PPO (In Plain English)
2️⃣ Use AI to Calculate Your FSA Sweet Spot
3️⃣ Use AI to Model "What's Enough?" for Life Insurance & Disability
4️⃣ Use AI to Compare Total Costs (Not Just Premiums)
💡 One Smart Read
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1️⃣ Use AI to Explain HMO vs PPO (In Plain English)
Every year, I look at the HMO vs PPO comparison and my eyes glaze over. Lower premiums vs. more flexibility. Network restrictions vs. referrals. What does any of this actually mean for us?
This year, I asked ChatGPT to break it down.
💬 Try This Prompt:
I'm trying to decide between an HMO and PPO plan. Here are the details:
[Paste your plan comparison or describe the key differences]
My fiancée and I are healthy but see specialists occasionally. We want to minimize costs for primary care while having flexibility to see specialists without hassle.
Explain the trade-offs in simple terms and help me think through which makes more sense.What ChatGPT told us:
In our case, the PPO wasn't significantly more expensive than the HMO option. For the modest premium difference, we get:
No referrals needed to see specialists
Out-of-network coverage if we need it
More flexibility when traveling
Since we both see specialists occasionally and want to minimize the friction of getting appointments, the PPO flexibility was worth it.
Our decision: PPO at $194.26 bi-weekly
💡 Pro Tip: Ask ChatGPT, "What questions should I ask myself to decide between these plans?" It'll help you think through factors you might not have considered.
2️⃣ Use AI to Calculate Your FSA Sweet Spot
FSAs are a "use it or lose it" benefit. Put in too little, you miss out on tax savings. Put in too much, you forfeit the money.
I hate this calculation — but ChatGPT made it way easier.
💬 Try This Prompt:
I'm trying to figure out how much to contribute to my FSA. Here's what I know:
- Regular prescriptions: Potentially high costs next year, could be $3,000+
- Expected doctor visits: $500
- Dental/vision expenses: $400
- Known upcoming medical expenses: [describe]
What's a reasonable FSA contribution that won't leave money on the table? The max is $3,400 for 2026.What ChatGPT told us:
We have prescriptions that could be expensive next year — potentially $3,000 or more. ChatGPT helped me think through:
Our known prescription costs
Regular doctor visits and copays
A buffer for unexpected expenses between two people
We decided to max out our FSA at $3,400 (the 2026 limit). Even if our prescription costs end up lower, we'll still use most of it between two people for medical, dental, and vision expenses.
Our decision: Maxed FSA at $3,400 annual ($130.77 bi-weekly)
💡 Pro Tip: Ask, "What happens if I overestimate? What expenses are FSA-eligible that I might not know about?" ChatGPT can explain eligible expenses beyond just prescriptions and copays.
3️⃣ Use AI to Model "What's Enough?" for Life Insurance & Disability
This is where benefits packages get overwhelming. Do we need extra life insurance? What about short-term disability? Long-term disability?
We used ChatGPT to understand what these actually do — then confirmed our decisions with our financial planner.
💬 Try This Prompt:
My employer offers:
- Free basic life insurance ($50K)
- Option to buy additional life insurance (up to multiples of salary)
- Optional AD&D
- Short-term disability (60% of salary)
- Long-term disability (66.67% of salary)
I'm engaged, planning to get married soon. Help me think through what I actually need and what's worth paying for.What ChatGPT told us:
For life insurance: My wife's employer offers free $50K coverage. ChatGPT helped us understand that she could add optional coverage at 2x her salary for just a few dollars per paycheck. Given that we just got married and I'm covered under her plan, the additional coverage made sense to protect both of us.
For AD&D: It explained that Accidental Death & Dismemberment covers specific accidents (not illness). At 2x salary for $3.69 bi-weekly, it was worth adding.
For disability: ChatGPT explained that short-term covers immediate issues (60% of salary for temporary disability) while long-term protects income if she can't work for extended periods (66.67% of salary). These felt essential.
Our decisions:
✅ Kept free $50K basic life insurance
✅ Added optional life insurance at 2x salary ($258K) - $3.69 bi-weekly
✅ Added optional AD&D at 2x salary ($258K) - $3.69 bi-weekly
✅ Added short-term disability (60% salary coverage) - $11.00 bi-weekly
✅ Added long-term disability (66.67% salary) - $31.60 bi-weekly
Our total for all insurance add-ons: $50.98 bi-weekly
⚠️ Important: We discussed these decisions with our financial planner. AI is great for understanding options, but major insurance decisions should be confirmed with a professional who knows your full financial picture.
4️⃣ Use AI to Compare Total Costs (Not Just Premiums)
The premium is just one number. The real cost is premiums + deductibles + copays + coinsurance + out-of-pocket max.
That's too much math for us.
💬 Try This Prompt:
Help me calculate the true cost of these plans:
Plan A: $X premium, $Y deductible, $Z out-of-pocket max
Plan B: $W premium, $V deductible, $U out-of-pocket max
Assuming I have [describe your typical healthcare usage], what would each plan actually cost me?What ChatGPT told us:
It walked through best-case (just routine checkups) and worst-case (hit the out-of-pocket max) scenarios for each plan. This helped me see that the PPO's higher premium was offset by lower costs when we actually use healthcare.
Even in a bad year where we hit our deductible, the PPO was only about $500 more total — and that flexibility was worth it.
💡 Pro Tip: Ask ChatGPT to create a simple comparison table. Visual comparisons make the decision way clearer.
💡 One Smart Read
OpenAI is weighing a move into consumer health apps // Business Insider
Speaking of using AI for healthcare decisions... OpenAI is exploring building consumer health tools like personal health assistants and health data aggregators. Big Tech has spent decades trying to give consumers control of their health data — and mostly failed. But OpenAI's 800 million weekly ChatGPT users are already asking health questions, and investors think the company finally has the scale and tech to succeed where Google, Microsoft, and Apple couldn't. If AI can help us make sense of open enrollment, imagine what it could do with our actual medical records.
🎯What to Do Now
✅ Don't just click "Keep Current Elections" — spend 15 minutes with ChatGPT
💬 Copy one of the prompts above and paste in your actual benefit details
📊 Compare total costs, not just premiums
🧑⚕️ For major insurance decisions, confirm with a financial planner or insurance professional
🚀 Want more prompts like this? Check out AI Playbook to level up your AI skills
📤 Know someone stressing about open enrollment? Forward this 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. Some links may be affiliate links or sponsored content for which I may receive compensation.