An AI Skill for
Wills & Estate Planning.

A surprising number of the people I know will eventually die without a serious plan for what happens to their money, their house, their pets, their data, or their kids. Some will leave handwritten notes a grieving spouse cannot legally execute. Some will leave a will from 2011 that still names an ex. Some will leave nothing, and a county court will decide for them. This is not because they don't care. It's because estate planning is expensive, emotionally heavy, and the good lawyers who do it well charge five hundred dollars an hour for the parts that are basically asking you careful questions and writing down your answers.

Before I go further, a note for anyone who has not heard the word before: a skill can be thought of as a bundle of “how to” knowledge that is prepared for use by an AI agent such as Claude Code or OpenAI's Codex (yes, both names have “Code” in them; more on that in a moment). It combines reference materials, workflows, scripts, subagents, and so on, all in a way that is maximally agent-intuitive and agent-ergonomic and optimized for context efficiency (at least for a well-designed skill, which most are not). The agent loads the skill at the start of a session and then behaves like a prepared specialist for the rest of that conversation.

A quick reassurance before anyone decides this is not for them: you are the right reader for this even if you are not a programmer and have never opened a terminal. The desktop apps I recommend below (Claude Code and Codex Desktop) were originally built for software engineers, and the “Code” in those names is a legacy name; nothing you will do in them is code-specific. You chat in a text box, drop documents into a folder, and approve the occasional file read when the agent asks. You will never type a command. You will never see a black terminal window. If you can use Gmail and know how to open a folder on your computer, you can use this.

A few months ago I posted a tax-preparation skill on my paid skills site, jeffreys-skills.md. At least five readers have since told me they saved more than a thousand dollars on their taxes using it. One saved twenty thousand. That is on a twenty-dollar-a-month subscription. It got me thinking about which other expensive-specialist problems look the same shape as tax prep, where the billable hours are mostly good questions, patient listening, and a disciplined checklist. The replies kept pointing at the same one: writing a will.

So I built it. This article is the long-form explanation of what the skill is, what you need to run it, and how a smart non-technical reader with three to six hours (across a couple of sittings, not a forced marathon) can walk away with the package a real estate-planning attorney actually wants to receive.

A full estate-plan consultation with a decent attorney runs somewhere between fifteen and twenty-five thousand dollars for a household with any real complexity. Most of those hours are not the attorney drafting; they are the attorney asking you careful questions, waiting for you to find documents, and writing down your answers. The expensive part is the interviewing.

The interviewing is the part a good agent-plus-skill can do, for roughly the cost of a nice dinner, across a couple of sittings. You need four things:

Pick one of Claude Max or GPT Pro. If you have the budget, run the skill through both; the two frontier models catch different things, and the two second opinions are the cheapest quality insurance you'll buy this year. Cancel whichever ones you don't want next month. You keep every document the skill produces forever.

The other thing worth saying about a hundred-dollar-a-month frontier-model subscription: while you have it, it will also audit your tax return, review your insurance coverage, draft a business plan, compare Medicare plans, explain a confusing hospital bill, or pre-read a long contract before you send it to a lawyer. It is among the best hundred dollars per month you will spend this year even before the estate plan.

If you use AI products at all, you have probably chatted with Claude or ChatGPT on the web. Those models are very good, and they start from zero every time: fresh session, no memory, no idea whether you are asking about quantum physics or your divorce.

An agent is the same frontier model, but given permission to do things. Open files you point it at. Organize a folder on your computer. Ask you follow-up questions and remember the answers across a whole conversation. Same model, same reasoning; the difference is that it can read the documents you put in front of it and carry the thread forward instead of answering a one-shot question.

A skill is a package of domain knowledge and workflow that sits alongside the agent and bootstraps it into being an expert at exactly one thing. You can think of it as hiring an apprentice lawyer who has already read a hundred estate-planning textbooks, knows the standard interview questions, and will not forget to ask you about the 401(k) beneficiary form. When you start a session, the skill quietly loads into the agent's context and says: “for the next few hours, you are an estate-planning intake specialist; here is exactly how to do that job.”

The division of labor matters. The frontier model is clever. The skill is disciplined. Your job is just to answer good questions honestly. The skill makes sure the agent asks the right ones, cross-checks the answers, catches contradictions, and produces the specific set of documents an estate-planning attorney actually wants to receive.

The whole complexity lives inside the skill. You do not have to understand revocable trusts, POAs, or the 2026 OBBBA exemption to use it. You have to know the names of your family members, roughly what you own, and where the important documents live. The skill handles the rest, and flags anything it is genuinely unsure about for the attorney who signs the final papers.

This skill is educational planning support, not legal advice. A licensed estate-planning attorney in your state still needs to review and sign the final documents. Nothing on this page creates an attorney-client relationship.

Four things, in order. Each one takes two to five minutes. Twenty minutes total, and you only pay for things you are going to keep anyway.

1. 1. A frontier-model subscription.

   Go to claude.ai → Settings → Upgrade → Max 5x ($100/mo). Or chatgpt.com → Upgrade → Pro ($200/mo). Either works. Claude Max is the cheaper starting point for this skill; pick GPT Pro if you prefer OpenAI's model. Pay by card. Cancel next month if you want to. No long-term contract.

2. 2. The desktop app (free).

   For Claude, download Claude Code Desktop (Mac or Windows). For OpenAI, download Codex Desktop. Sign in with the same account from step 1. This is the app the agent lives in. It can open folders on your computer and read the documents you drop into them.

3. 3. A jeffreys-skills.md account ($20/mo).

   Go to jeffreys-skills.md → Sign up → pay with Stripe or PayPal. Same cancel-anytime rules. Same “you keep the documents” rules.

4. 4. Install the skill.

   From the jeffreys-skills.md dashboard, open the wills-and-estate-planning skill page. Click Generate install prompt. Copy the block of text it gives you. Paste that block into your desktop app's chat box. Press enter. The agent reads it, asks you to approve one download, installs itself, and reloads. Ninety seconds.

Comfortable in a terminal? You can install via the jsm CLI instead: jsm install wills-and-estate-planning-skill after jsm login. Same signed bundle, same outcome. Everyone else should stick with the desktop-app flow above.

Once the skill is installed, the whole workflow is: one folder, one conversation, as many sittings as you need. The agent remembers what you told it between sessions because everything it writes lands in that folder.

1. 1. Make a new folder on your computer.

   Anywhere is fine. Your desktop, your Documents folder, wherever. Call it something you will recognize later. my-estate-plan is a reasonable default. This is where everything will live: your input documents, the drafts the skill produces, and the final packet for your attorney.

2. 2. Drop every document that matters into the folder.

   Messy is fine. The skill will organize it. What you want in there: last year's tax return, a statement from each brokerage / 401(k) / IRA / bank account, current beneficiary designations on retirement accounts and life insurance, any existing will or trust (even if it is old or wrong), deeds, titles, and vehicle registrations, your passport for identity reference, and a short list of the bank and crypto accounts you have. Do not put your crypto seed phrase itself in the folder; a pointer to where it is stored is enough.

3. 3. Open the folder in Claude Code or Codex Desktop.

   Launch the desktop app. File → Open Folder → pick the folder you just made. The agent is now pointed at it and can read any document you drop in.

4. 4. Start the conversation.

   In the chat box, type: “please use the wills-and-estate-planning skill to help me draft an estate plan” and press enter. The skill loads. The agent asks its first question. Answer honestly.

5. 5. Answer its questions.

   It will ask about the people in your life, what you own, what you owe, who is currently named on each beneficiary form, what you actually want to happen, and what keeps you up at night. Take breaks whenever you need to; close the app and come back tomorrow if you want. The agent remembers the state of the conversation because the files it is writing are all in your folder.

Short list. These are the tips that separate a good first pass from a great attorney-ready one.

• Run the skill at least twice. Treat the first session as the rough draft. Start a second session in the same folder a day later and say “audit the estate-planning packet you produced last time.” The skill will review its own work, catch missing facts, and flag weak spots. Almost everyone finds something important on the second pass.
• If you have both Claude Max and GPT Pro, use both. Open the folder in Claude Code, run through the skill there. Then open the same folder in Codex Desktop and run it again. The two frontier models do not overlap perfectly: Claude often surfaces family-dynamics and emotional-coordination issues earlier; GPT often surfaces cold tax and structural issues earlier. Compare the two packets. Merge the best of each.
• When it asks something you don't know, say so. “I don't know” and “I need to check with my spouse” and “I need to look that up” are good answers. The skill will explain the question, tell you why it matters, and re-ask once you have the information. Pretending to be certain when you are not is how mistakes get baked into estate plans.
• It is fine to not have every document ready. When the skill asks for something you cannot put your hands on in the next ten minutes, tell it “I don't have that right now.” The session continues. When you find the document a day later, drop it into the folder, open a new sitting, and say something like “I found the 401(k) statement; please re-check whatever you flagged about beneficiaries.” Nothing is blocked by a single missing document; the skill notes what is still unanswered and will revisit it when you come back.
• Save the final packet in your folder. It is yours. Email the Attorney Engagement Brief plus whichever supporting documents your attorney asks for. Keep the folder itself backed up somewhere sane, the same way you would keep your tax returns.

Four things the skill handles automatically, without your having to think about them or understand the mechanics.

1. It auto-adjusts to your complexity.

The skill scales from a twenty-six-year-old renter with a first 401(k) through to a hundred-million-dollar industrialist with four generations to plan for. Same interview; different depth. Tap a rung below to see which tier matches your facts. A blended family, a business stake, self-custodied crypto, or a second-state property bumps you a tier regardless of net worth.

2. It catches the mistakes that wreck most plans.

Most estate-plan disasters are not exotic. They are a handful of patterns the skill runs every plan through before it hands you anything: the 401(k) that still names an ex-spouse, the trust that was drafted but never funded, the springing POA that does not trigger when you need it, the pet with a longer life expectancy than yours. Tap a card to see what actually goes wrong and which subagent catches it.

3. You walk away with a real document package.

A serious session produces a structured project directory with forty-five files organized so a lawyer, a spouse, or a future version of you can pick up where you left off. Intake files, analyses, draft documents, and an Attorney Engagement Brief structured the way an estates attorney actually wants to read a new client.

4. The math versus a cold-start attorney consult.

Attorney rates and timelines vary. The point is the order of magnitude. Slide the net-worth bar and toggle the complexity overlays to see a rough estimate of what an attorney would quote for a comparable cold-start consultation versus what this skill costs you in a month.

The comparison is a rough guide, not a legal fee quote. Exact quotes vary by state, firm, and facts. The skill subscription is the real number. The attorney number is the rough order of magnitude you are skipping past by showing up already prepared.

Estate-planning law is a moving target. The federal exemption changed in 2018, changed again in 2026 under the OBBBA, and will likely change again. State thresholds drift. Execution formalities vary across fifty jurisdictions. The skill separates the evergreen methodology it trusts in full from the volatile law it has to re-verify at session time; every live-law lookup is logged in official-source-log.md with source URL and date, so your attorney can audit what the skill relied on and your future self can see what needs rechecking.

The output handed to your attorney is, at minimum, four documents: an Attorney Engagement Brief of about four pages, a set of Interview Questions you can ask them on the first call, a Handoff Readiness scorecard the skill runs on its own output before it ever leaves your laptop, and a Document Package Index so nothing is lost in email. The skill does not sign, notarize, or file anything. It cannot practice law. What it can do is make sure the lawyer who does is starting from a prepared client instead of a cold start.

The whole thing: your attorney still signs. The skill gives them the best first meeting they have ever had from a new client.

A pattern, not a product.

Estate planning is one of a handful of expensive-by-default life admin domains where the professional is plentiful and well-trained, and most of the hours they bill for are actually just asking you careful questions and writing your answers down. Tax preparation is another. Medicare plan selection. Social Security claiming strategy. College financial aid. Divorce financial planning. Medical bill auditing. Long-term-care insurance. In every one of these, you pay an expert for a long initial intake before they can do the part only they can do.

That shape of problem is exactly what an agent-plus-skill can compress: the preparation, not the judgment. Your attorney still signs. Your CPA still files. Your Medicare broker still enrolls you. What changes is that a large share of the preparation can happen across a couple of evenings or a weekend morning at your kitchen table, for roughly a hundred and twenty dollars, instead of entirely inside the specialist's billable hour.

This is the shape of a lot of what is coming. The model is not that AI replaces the professional. The model is that the professional gets to spend their time on what they are actually expert at, because the intake work no longer has to run through their clock. You get the packet. They get the signature.

If you want the other concrete proof point, the tax-preparation article is the first place this pattern became obvious to me. Estate planning is the second. If you have a frontier-model subscription already, the only real barrier to trying this one yourself is the twenty minutes of setup above.