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Hey, it’s Jeffrey — back again!

There's a category of money stuff that never feels urgent.

Not because it isn't important — it's actually really important — but because nothing bad has happened yet. So it stays on the list. Month after month. Year after year.

Beneficiary designations are the best example I can think of.

You named someone when you opened the account. Maybe it was your parents. Maybe it was an old girlfriend. Maybe it was before you got married. And then you moved on with your life and never looked at it again.

Here's why this one is worth doing now: in most cases, beneficiary designations override your will — regardless of what it says. Whoever is named on the form typically gets the money. Courts don't care what you intended. The form wins.

Which means spending 20 minutes checking these is probably the highest-value-per-minute financial task most people never get around to.

So this week, I built a prompt that actually makes it easy.

Instead of handing you a checklist and wishing you luck, it walks you through your accounts one question at a time — like a quiz. You answer, it builds a picture of everywhere you have money, and then it gives you a prioritized list of the accounts most likely to be outdated or overlooked.

The whole conversation took about 10 minutes. It reminded me of a few accounts I hadn't thought about in years, including one I genuinely hadn't considered at all.

I want to audit my beneficiary designations but I'm not sure I know all the accounts where I've named one. Can you walk me through this one question at a time? Ask me about each account type, whether I have it, and any relevant details about when I opened it or if my life situation has changed since then. Make sure to cover all common account types, including ones people frequently overlook. Once we've gone through everything, give me a prioritized list of the accounts I should go verify, starting with the ones most likely to be outdated or overlooked. Start with the first question.

Run it now → Claude

Here's what came up when I ran it on my own accounts 👇

The prompt walked me through every account type, one at a time: current 401(k), IRAs, HSAs, life insurance, brokerage, and bank accounts. A few things I expected to come up did: my investment accounts and life insurance policy were flagged for verification since they were set up before I got engaged.

But the one I wasn't thinking about at all was my business checking account. I hadn't thought of this one, and what happens to it. It's a bit more complicated since it's under my LLC, but I've added it to my to-do list to sort it out.

The AI organized everything into a prioritized verification list at the end, sorted by the likelihood that each account would be outdated or overlooked. I walked away with a clear action plan, rather than a vague sense that I should probably look into this someday.

Keep going? Ran the main prompt? Here are three ways to go deeper:

1. The "what would actually happen" scenario

Based on the accounts we just went through and who I have listed as beneficiaries, walk me through what would actually happen if I died today. Who gets what, in what order, and is there anything that looks inconsistent or potentially problematic?

2. The contingent beneficiary check

I've been focused on my primary beneficiaries, but I haven't thought about contingent beneficiaries — the backup if my primary beneficiary dies before me or at the same time. Which of my accounts should have a contingent beneficiary listed, and what should I think about when choosing one?

3. The life event follow-up

I recently [got married / had a child / lost a spouse]. Which beneficiary designations should I update first, and is there anything that changes legally after this kind of life event?

AI tip worth trying this week: Ditching FAQs

I have almost no patience for FAQ pages anymore. They're long, they never answer the exact thing you're asking, and you end up reading through 15 questions that don't apply to you before finding the one that does.

I've started just asking Claude instead. I've been pleasantly surprised how well it can do with these types of questions that feel niche. This week, I had a pretty specific question about how to handle an irregular reimbursement situation in YNAB.

Not a basic "how does YNAB work" question, but something specific enough that I'd have been scrolling through help docs for 20 minutes. I just described my situation and got a direct answer in about 30 seconds. I had a few follow-up questions too, and Claude easily handled that as well.

Works for any software you're trying to figure out. Describe what you're trying to do, not what you're searching for.

AI agents now read your docs almost as much as humans do.

Mintlify analyzed 790 million requests across its documentation platform. The finding: AI coding agents account for 45.3% of all traffic, nearly tied with traditional browsers at 45.8%.

Two tools are driving almost all of it:

  • Claude Code: 25.2% of total traffic, more requests than Chrome on Windows

  • Cursor: 18% of total traffic

  • Together they account for 95.6% of all identified AI agent traffic

The rest of the field, OpenCode, Trae, ChatGPT, and NotebookLM, is showing up but nowhere close.

One caveat: OpenAI's Codex doesn't send an identifiable user-agent header, so the real agent percentage is likely even higher.

The takeaway for anyone maintaining developer docs: your documentation now serves two audiences. Structure and machine-readability matter as much as clarity for human readers.

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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