(GoBankingRates) - After my dad died in 2018, missing documents and lack of planning turned administering his modest estate into a several-year ordeal. Hoping to avoid making the same mistakes, I asked ChatGPT for a road map to drama-proof my own estate.
It produced a 12-month checklist to follow to get affairs in order. Keep reading to discover ChatGPT’s plan that can help anyone get their money and estate in order in just a year.
January: Build the ‘Estate Map’
ChatGPT noted that most estate messes start because of missing, incorrect or incomplete information. The goal for January, then, is to organize vital information
The first step is to inventory every asset and debt, including account numbers, on paper or in a spreadsheet to serve as a master estate file. The file should contain the following information for each item:
- Where it’s held
- Whose name is listed on it
- The beneficiary’s name
- Approximate value and cost basis, if applicable.
The next suggestion was to create digital and print versions of an “In Case of Emergency” file with information heirs might need.
February: Review Titles and Beneficiaries
Some assets transfer outside of a will, and the chatbot said these items often override everything else. The goal this month is to “lock them down” by completing the following tasks.
- Review and update beneficiaries and paid-on-death/transfer-on-death designations for retirement accounts, life insurance, and bank and brokerage accounts.
- Check ownership and titling on major assets, such as real estate and business interests.
- Consider whether each account should name beneficiaries directly or go into a trust.
March: Designate Agents and Decisionmakers
Selecting people who can act on your behalf keeps family members from having to improvise during a crisis.
The artificial intelligence (AI) chatbot said to choose the following:
- Financial power of attorney
- Healthcare proxy
- Executor or personal representative to manage the estate.
ChatGPT said to check with these individuals to make sure they’re willing, and to appoint backups just in case. The representatives’ contact information should go into the “In Case of Emergency” file.
April: Meet With Estate Planning Professionals
The chatbot recommended meeting with an attorney, CPA and/or financial advisor to go over the estate file and work out the best structure for assets, family dynamics and state laws.
The next step is to create a to-do list of documents to draft or update.
May: Draft or Update Legal Documents
This month’s goal is to finalize legal documents pertaining to the estate. For example, take a look at these documents:
- Healthcare directive/HIPAA authorization
- Financial power of attorney
- Revocable trust, if recommended
- Will.
Be sure to account for any changes you’d want to see in the event a beneficiary dies before you, divorces, or becomes incapacitated or unreachable.
June: Sign, Notarize and Store the Documents
Documents are enforceable only if they’re properly signed and notarized. And in the case of a trust, title to the assets that will fund the trust need to be transferred.
Digital copies should be securely stored online and paper copies added to the master file.
July: Create an ‘Incapacity Playbook’
An incapacity playbook contains everything caregivers need to know if you become unable to tend to your own affairs. The AI suggested these things be included:
- Monthly bills
- Insurance policies
- Property maintenance contracts
- Preferred professionals, including CPA, attorney and real estate agent
- Emergency contacts.
ChatGPT also recommended digitizing the playbook and storing it in an online document “vault” accessible by someone you trust.
August: Organize Your Digital Life
Caregivers and/or decision makers need quick access to accounts. A list of PINs and passwords, including for cellphones, banking and investing, email, cloud storage, social media and bills, will ensure that they have what they need — as long as the accounts don’t require biometric authentication as opposed to two-factor authentication methods like text and email.
Instructions on whether social media accounts should be deleted, memorialized or left as is should also be part of this process.
September: Stress-Test the Plan
Family structures and dynamics can be complicated. The task for this month is to run the estate plan through challenging family situations to see how it holds up. Those situations might include disabled heirs, heirs with credit or substance abuse issues, heirs at high risk of divorce, and bequests to members of blended families.
The documents might need updating after the stress-test.
October: Create a Tax Strategy
Tax liabilities can cause major headaches for heirs. The right strategy reduces taxes and makes things easier for survivors. A tax professional can provide guidance on the following:
- Gifting plan
- Roth conversion/tax-bracket management
- Charitable giving
- Life insurance review.
November: Talk To Heirs About the Estate
Estate discussions are never easy, but they’re instrumental in avoiding unpleasant surprises and conflict. Points to cover include:
- Who’ll serve as the agents and executor
- Where the documents are stored
- The general state of the estate
- The values and priorities that influenced decisions.
December: Annual Review
The AI recommended an annual review to ensure that the estate plan still reflects your wishes, and that the agents and executor you’ve selected can still perform those duties.
This also is the time to update documents to reflect births and deaths, marriages and divorces, and any major changes in assets or debt.
How Successful Was ChatGPT in Drama-Proofing an Estate?
There’s no surefire way gauge success until the real-life test, but the AI’s checklist provided a useful framework that would help any family navigate the administrative challenges they might face before and after the death of a loved one.
Just as importantly, it also called attention to its shortcomings. ChatGPT noted that its “clean logic” might underestimate real family dynamics, for example, and it acknowledged that it can’t reliably tailor an estate plan to a particular family — all of which highlights the need for professional guidance to fully drama-proof your estate.
By Daria Uhlig
Edited by Jenna Klaverweiden
January 13, 2026
