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Hey, it’s Jeffrey — back again!

$35,000 in a HYSA. Six-ish months of expenses. I've always figured that was probably fine, but I'd never actually tested it against anything specific. So I decided to find out.

I gave ChatGPT my real numbers and asked it to pick the emergencies most likely to hit someone in my situation, then run my fund through each one. Kind of like a fire drill for your savings account.

Here's the prompt:

I want to stress-test my emergency fund against multiple realistic scenarios. Here's my situation:

Monthly essential expenses: $[X]

Current emergency fund: $[X] in [HYSA/etc.] at [interest rate if known]

Employment: [salaried/self-employed/dual income] in [industry]

Job stability: [stable/somewhat stable/variable]

Health insurance: [employer-covered/self-pay/HDHP with HSA] and approximate deductible: $[X]

Known risks: [older car, health issues, etc.]

Based on my situation, choose 3-4 realistic emergency scenarios most relevant to someone like me. Run my fund through each one — tell me if it survives, how long it lasts, and where it gets stressed. Then give me my actual recommended range based on my inputs, not a generic 3-6 month rule. Finally, tell me if I'm holding more cash than I need.

What I found: Three scenarios passed comfortably: major client loss (11-14 months), appliance cascade plus income dip (10-11 months), and a medical event.

But both incomes at risk simultaneously? Perhaps not surprisingly, that one was cutting it close, with less than 6 months of runway.

The interesting part: I'm about two years away from a window where my situation changes enough that $35k goes from slightly too much to just barely enough. The prompt told me to start building toward a higher target now, not after.

It also flagged that I might not have disability insurance as a self-employed person. I do, but it was worth the check.

Run it now → ChatGPT / Claude

Keep going? Once you've got your results, try asking:

  • Now that I know my target, help me build a plan to get there in [X] months without cutting into my investments.

  • What insurance gaps should someone in my situation check for? Here's what I currently have: [list your policies].

Reply and tell me what scenarios came up for yours — curious how different they are from mine."

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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.

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