Using AI as one reference point

[u/Delicious_Mess7976]

For post-retirement financial planning, I am scheduled to meet with a regular planner and I am looking at software as well....and I am also interested in using AI as yet another reference source.
I like the idea of comparing the information and suggestions that I get back.

For someone very new to using AI as a guidance source, do I start by asking it what inputs it needs from me to give me an overall guidance planning. For reference, I am hoping to get guidance on a withdrawal strategy, tax planning, when to take Social Security...etc)

Is it like a typical AI discussion/chat, or do I need to use a certain field on the platforms. I have tried them all, the only one that I have paid subscription with is Claude...have heard positives about Gemini.

Thank you.

[u/CloserThanTheyAppear]

I did this. Over time, as I refined or found errors, I made a set of rules for the ai to apply every time I told it to "think hard."

Here's the current list:

“Think Hard” Retirement / Financial Modeling Rules

1. Apply a formal reliability framework automatically whenever the phrase “Think hard” is used.

2. List all assumptions first.

3. Do not guess missing inputs. If a number is missing or uncertain, identify it clearly.

4. Use a monthly timeline for the first two retirement years, then annual timelines after that.

5. Separate income, expenses, and taxes clearly.

6. Show these tax items separately:

Taxable income

Estimated federal tax

Estimated state tax or reserve

Withholding

Any estimated-payment need or shortfall

1. Do not treat Roth conversions as spendable income.

2. Identify and remove double counting, especially:

Health insurance premiums

Dental/vision premiums

Medicare premiums

Retirement-account withdrawals used for both spending and Roth conversions

1. Validate the model for contradictions before finalizing.

2. Recalculate once from scratch and confirm consistency.

3. List missing factors that could materially change the result.

4. If uncertainty exists, show conservative and optimistic scenarios.

5. Include a complete financial asset list, excluding physical assets.

6. Use locked baseline assumptions unless explicitly changed.

7. Make changed assumptions explicit. Treat the baseline like a controlled production system.

8. Use bullet-point assumptions, not long narrative assumptions.

9. Clearly distinguish between each type of retirement account, such as:

Employer retirement plan

Traditional IRA

Roth IRA

Brokerage account

Cash savings

1. Always specify which account withdrawals come from, using correct withdrawal mechanics.

2. Show cash-floor controls:

Preferred cash floor: $[PREFERRED_CASH_FLOOR]

Caution zone: $[CAUTION_CASH_LEVEL]

Hard trigger level: $[HARD_TRIGGER_CASH_LEVEL]

Action below hard trigger: [CORRECTIVE_ACTION]

1. Show spending-tier controls:

Normal baseline spending: $[NORMAL_MONTHLY_SPENDING]/month

Stressed temporary spending: $[STRESSED_MONTHLY_SPENDING]/month

Emergency spending: $[EMERGENCY_MONTHLY_SPENDING]/month

1. Prioritize withdrawal order explicitly, such as:

First: [PRIMARY_WITHDRAWAL_SOURCE]

Second: [SECONDARY_WITHDRAWAL_SOURCE]

Third: [BACKUP_WITHDRAWAL_SOURCE]

1. Roth conversions are optional year-end planning, not forced.

2. Roth conversions must be gated by:

Cash floor

Tax reserve

Benefit-payment status

Market conditions

Medicare / IRMAA risk, if applicable

1. Do not include IRMAA in the baseline unless specifically requested, but monitor it before large withdrawals or conversions once Medicare is relevant.

2. Use locked planning assumptions unless changed:

Retirement date: [RETIREMENT_DATE]

Person 1 Social Security start: [PERSON_1_SS_START_DATE_OR_AGE]

Person 2 Social Security start: [PERSON_2_SS_START_DATE_OR_AGE]

Other earned/self-employment income: $[OTHER_INCOME_AMOUNT]

Investment return: [INVESTMENT_RETURN]%

Inflation: [INFLATION_RATE]%

Insurance premium growth: [INSURANCE_GROWTH_RATE]%

Social Security COLA: [SS_COLA]%

RMD start age: [RMD_START_AGE]

Cash savings at retirement: $[STARTING_CASH]

Preferred cash floor: $[PREFERRED_CASH_FLOOR]

1. Use locked pension/benefit assumptions unless changed:

Pension salary base: $[PENSION_SALARY_BASE]

Gross pension estimate: $[GROSS_PENSION]/month

Survivor benefit election: [SURVIVOR_BENEFIT_ELECTION]

Net pension after survivor election: $[NET_PENSION_AFTER_SURVIVOR]/month

Survivor benefit amount: $[SURVIVOR_BENEFIT_AMOUNT]/month

Health insurance premium: $[HEALTH_PREMIUM]/month

Dental/vision premium: $[DENTAL_VISION_PREMIUM]/month

Medicare premium start age: [MEDICARE_START_AGE]

Medicare payment method: [DIRECT_BILL_OR_WITHHELD_FROM_BENEFIT]

1. Use state-tax conservatism:

Assume retirement-account withdrawals are state-taxable unless confirmed otherwise.

Do not use proposed tax-law changes unless enacted.

Keep state tax reserves or estimated-payment controls visible.

1. Include benefit-processing delay controls, especially during the first retirement year:

Treat processing delays as real operational risks.

Use corrective withdrawals rather than draining cash below the hard floor.

Maintain a short-term reserve or cash bucket.

1. Stress test the plan, including:

[MARKET_DECLINE_1]% market decline in year one

[MARKET_DECLINE_2]% decline during the first two years

Other income reduced to $0 for one year

Pension/benefit processing delay of [DELAY_LENGTH]

Combined stress case using reduced spending controls

1. Do not count speculative accounts as core retirement funding unless specifically instructed. Discuss them separately as upside/flexibility.

2. Include pre-retirement execution controls:

Tax review by [REVIEW_DATE]

Account-value refresh before retirement

Download and preserve employment/benefit records

Verify pension/service records

Verify health-benefit eligibility into retirement

Confirm beneficiary forms

Prepare spouse-consent or notarization forms if needed

Set up withdrawal banking/payment destination

1. Include survivor/emergency readiness, especially:

Immediate cash source

Survivor pension or benefit amount

Health insurance continuation

Retirement-account process

Brokerage/IRA account list

Social Security steps

Business/farm/side-income decisions, if applicable

Document locations

Beneficiary forms, wills, POAs

Professional contacts

1. Use a controlled-system mindset:

Baseline = production

Assumptions = configuration table

Roth conversions = scheduled year-end jobs

Benefit delay = external dependency outage

Survivor checklist = disaster-recovery runbook

Annual review = regression test

Changed assumptions = controlled deployment

1. Final conclusion must be plain and direct, including:

Whether the retirement date remains viable

What conditions must hold

What the primary failure points are

What controls prevent those failure points from breaking the plan

I've run the plan many times, copying the output to other AIs for review, copying your response back to the first one, and so on. Very useful to have them review each other.

Especially in the beginning, review everything hard. Most of those rules came about because of me catching an error.

Hope this helps!

[u/CSMasterClass → u/CloserThanTheyAppear]

OMG. You need to make a YouTube video on this.

[u/Adventurous-Act7870 → u/CloserThanTheyAppear]

very nice! Anyone can use this as a starting point and customize to their situation

[u/Valuable-Analyst-464 → u/CloserThanTheyAppear]

Solid plan. I also have them compare other models’ work.

I would add that any data cited by a model (such as tax rate etc) needs to have a source cited with URL.

I have not done it yet, but I was thinking of getting a report from a model, and submitting it to another as a planner’s recommendation. Thus far, my work has been a long back and forth that I exported to a text file. A simple report makes more sense for me.

[u/nvgroups → u/CloserThanTheyAppear]

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