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Hey, it’s Jeffrey — back again!
Every year, the same advice shows up everywhere: cancel subscriptions, skip the latte, meal prep on Sundays. And sure, maybe you save $200 a month if you're aggressive about it.
Meanwhile, you're leaving thousands on the table somewhere else, and you don't even know it — because nobody's ever helped you figure out which big moves actually apply to your specific situation.
That's the real problem. It's not that people don't know they should "optimize their finances." It's that the high-impact stuff, like maxing out the right retirement accounts, reshuffling insurance, fixing tax withholding, is different for everyone, and figuring out your list is the tedious part nobody wants to do.
So I asked Claude (my current LLM of choice) to do it for me. Here's the prompt:
I want you to help me find the biggest financial wins I'm leaving on the table — not small optimizations like canceling subscriptions, but changes worth $500+ each.
Ask me the following questions one at a time, waiting for my response before continuing:
What's your approximate household income range?
Do you own or rent? If own, when did you last refinance or shop your mortgage rate?
What types of retirement accounts do you have, and are you maxing any of them? Is there an employer match you might not be fully capturing?
When's the last time you shopped your insurance — auto, home/renters, life, umbrella?
What credit cards do you use most, and do you know roughly how much you spend per month on them?
Do you have any stock compensation (RSUs, options) or equity from your employer?
When's the last time you checked your tax withholding — did you owe a lot or get a big refund last year?
Any big purchases or financial decisions coming up in the next 12 months?
Do you have a high-deductible health plan with access to an HSA?
Is there anything you've been meaning to do with your money but keep putting off?
After I answer all 10 questions, give me a ranked list of my top 5 highest-impact financial moves. For each one, include: what to do, an estimated dollar impact per year, how long it would take to do, and why it matters more than the small stuff people usually focus on.
What I got: A ranked list of 5 moves totaling roughly $6,000-12,000 in year one. Some highlights from mine:
Max out my solo 401k: In the scenario I gave, I was leaving thousands in contributions on the table. At my tax bracket, that's thousands in unnecessary taxes. This one move is worth more than canceling every subscription I have — forever.
Credit card strategy overhaul: I'm spending $72K/year on cards and averaging about 2.4% back. The right card setup could get me closer to 3.5-4%, which is an extra $800+/year for basically no effort beyond the initial switch.
Get umbrella insurance: Not a "savings" win, but at my income level, going without $1-2M in umbrella coverage is a risk I shouldn't be taking. Costs about $250/year.
Was all of it useful? Honestly, I'd already done a lot of this as I'm pretty financially dialed in. But #1 alone would've been worth $5,000+/year if I hadn't already known about it. And one recommendation was flat-out wrong — it suggested tax credits from the Inflation Reduction Act that were outdated. So verify anything time-sensitive.
The point isn't that AI gives you perfect advice. It's that in 10 minutes of answering questions, you get a prioritized list of what to focus on for your situation, instead of reading another article that tells you to cut the gym membership.
Keep going? Once you've got your top 5, try asking:
"Walk me through exactly how to execute #1 — step by step, in plain English."
"What's the single highest-ROI move on this list if I can only do one thing this month?"
"Are there any tax deadlines I need to be aware of for these moves?"
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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.