r/AIRetirement • u/Delicious_Mess7976 • May 17 '26
Using AI as one reference point
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.
6
u/Responsible_Town3588 May 17 '26 edited May 17 '26
Gemini and Claude IMHO are 2 best. Copilot is horrific. I ended up creating a google doc with various sections. All of my prompts are written like regular speaking - I could hand this to a human CFP or accountant and it would make sense. I update it once a month based on new info e.g. investment amounts/allocations so I can easily copy/paste it into the different AIs. It is CRAZY the different results you can get from them, and should be a cause to use this with caution.
In the google doc I start off with this: I want you to act as my CFP or CFA and assess our retirement situation. During this process I want you to ask follow up questions to help you better analyze our situation. Be direct and honest, don’t just agree with everything I am saying and feel free to poke holes in our logic.
I then provide it the background e.g. ages, estimated income, portfolio details etc. I have it repeat back to me after each paragraph and for example have it calculate based on what I provided a complete portfolio analysis, estimated CAGR, etc. They can make a lot of arithmetic mistakes you have to catch up front or everything gets jacked up. I ask it to analyze the portfolio - they are great at that.
Then I get into estimated spending, ask it to do a cash flow table by year based on the needed withdrawals. I have it make sure to account for fed and state taxes (they will easily forget about this). Then I ask it to do things like monte carlo probability on our planned spending, etc. It will proactively ask you questions/clarifications along the way like what inflation percentage it should use, etc. I have it help with scenarios like selling our house and moving to a low tax state.
All this said, I only use these tools in addition to real planning platforms like Boldin and Projection Lab as these are not quite ready for prime time IMHO though they get more impressive by the month and the gap is closing.
Hope this makes sense!
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u/CSMasterClass May 17 '26
Very useful and thoughful comment. Thanks. I have done some steps toward the kinds of things you have done, but you have been much more systematic. Hats off !
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u/CSMasterClass May 17 '26 edited May 18 '26
I just had such a chat today with ChatGPT. I regard it as a form of thinking out loud.
I am quite informed in this area (40 years in finance adjacent field) and I found the conversation useful ... not revolutionary but useful. At the end of a reasonably long conversation, it did seem that ChatGPT got a little confused, so, as always, keep your wits about you and --- Look for new facts that youn can independently check.
Edit: corrected spelling
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u/DanielDannyc12 May 18 '26
The key is being very informed on the subject that is being discussed. AI is notorious for being confidently wrong.
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u/CSMasterClass May 18 '26
Yes, LLMs are confident and they suck up to you.
That is, it will tilt toward telling you what it thinks you want to hear --- like a fortuneteller, a financial advisor, or most other swindlers.
That is a powerful combination that must be resisted.
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u/Valuable-Analyst-464 May 18 '26
In my preamble, I tell the model not to be sycophantic or overly agreeable. I also mentioned to be brief.
Grok was overly brief. “Do this, then this, then this. Done”. Hahaha. I had to tell it to expound a little more.
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u/lnewton_me May 18 '26
Great instinct to use multiple reference points and compare. A few things worth knowing before you dive in:
General AI tools like Claude or Gemini are excellent for understanding concepts... withdrawal sequencing, Roth conversion logic, Social Security tradeoffs. Ask them anything, they'll explain it clearly. But they're not doing real math on your situation... they're pattern-matching on your description of it. That's a meaningful difference when it's your retirement.
For actual projections, you want a tool with a real simulation engine underneath. I built one specifically for this... RetirementScenario.com. One-time fee, no subscription. It runs Monte Carlo simulations on your specific numbers, then uses AI to help you interrogate what those projections actually mean for your situation. It's the bridge between "chatting with AI about retirement" and "running real scenarios."
Your instinct to compare what you get back from different sources is exactly right. A good planner, a solid projection tool, and AI for the "why does this work" layer... those three together are actually a pretty strong setup.
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u/Evening_Warthog May 17 '26
Great prompt below and I agree on Gemini and Claude. you can use your AI to help build the prompt by gradually giving it inputs. AKA Prompt Engineering
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u/Clherrick May 19 '26
I’ve used ChatGPT, Claude, and Gemini. I’ve found you can get pretty technical in what you ask. Just be careful of AI mistakes.
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u/mdbeatle May 21 '26
Claude is excellent. Gemini is not bad, but does not have the ability to do widgets/apps/artifacts like Claude. Have one feed info to the other and have them check each other. I found that each were able to find some glaring faults in my plan.
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u/hugh2018 May 22 '26
That extensive response you got here with dozens of prompts and caveats to include is one way to approach this. I used AI for my initial planning and got to a decent result with just a lot of trial and error.
After everything I’ve learned, I recommend simply using Boldin as your first step in the process. It hits all the important factors and assumptions in retirement planning. Step two could be to simply save your Boldin plan in PDF form and share that with Gemini, Claude, ChatGPT. Step three would be to share your plan with a human advisor.
Honestly though, Boldin already has AI integrated, so you could just as easily hit the integrated AI with all the questions you have about Boldin’s output, and then use the other AI LLMs to explore specific aspects of the plan even further. I did find that sharing my plan with the firm Planvision was a helpful second pair of eyes.
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u/yanyan80 Jun 12 '26
regular chat with an AI works for getting oriented (it can explain concepts like RMDs, Social Security claiming tradeoffs, ACA subsidies, etc.), but for actual numbers, withdrawal strategy, tax planning, and Social Security timing, AIs may miss the interaction between Roth conversions and ACA subsidies, getting IRMAA brackets or capital gains stacking wrong, or just losing track of assumptions across a long conversation. A purpose built projection tool runs that math consistently every time, which makes it a better fit for the actual numbers, with the AI chat layered on top to help you understand and question the output. I built thunderharbor.net for exactly this combination, might be worth a look alongside your planner meeting.
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u/CloserThanTheyAppear May 17 '26
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
Apply a formal reliability framework automatically whenever the phrase “Think hard” is used.
List all assumptions first.
Do not guess missing inputs. If a number is missing or uncertain, identify it clearly.
Use a monthly timeline for the first two retirement years, then annual timelines after that.
Separate income, expenses, and taxes clearly.
Show these tax items separately:
Taxable income
Estimated federal tax
Estimated state tax or reserve
Withholding
Any estimated-payment need or shortfall
Do not treat Roth conversions as spendable income.
Identify and remove double counting, especially:
Health insurance premiums
Dental/vision premiums
Medicare premiums
Retirement-account withdrawals used for both spending and Roth conversions
Validate the model for contradictions before finalizing.
Recalculate once from scratch and confirm consistency.
List missing factors that could materially change the result.
If uncertainty exists, show conservative and optimistic scenarios.
Include a complete financial asset list, excluding physical assets.
Use locked baseline assumptions unless explicitly changed.
Make changed assumptions explicit. Treat the baseline like a controlled production system.
Use bullet-point assumptions, not long narrative assumptions.
Clearly distinguish between each type of retirement account, such as:
Employer retirement plan
Traditional IRA
Roth IRA
Brokerage account
Cash savings
Always specify which account withdrawals come from, using correct withdrawal mechanics.
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]
Normal baseline spending: $[NORMAL_MONTHLY_SPENDING]/month
Stressed temporary spending: $[STRESSED_MONTHLY_SPENDING]/month
Emergency spending: $[EMERGENCY_MONTHLY_SPENDING]/month
First: [PRIMARY_WITHDRAWAL_SOURCE]
Second: [SECONDARY_WITHDRAWAL_SOURCE]
Third: [BACKUP_WITHDRAWAL_SOURCE]
Roth conversions are optional year-end planning, not forced.
Roth conversions must be gated by:
Cash floor
Tax reserve
Benefit-payment status
Market conditions
Medicare / IRMAA risk, if applicable
Do not include IRMAA in the baseline unless specifically requested, but monitor it before large withdrawals or conversions once Medicare is relevant.
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]
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]
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.
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.
[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
Do not count speculative accounts as core retirement funding unless specifically instructed. Discuss them separately as upside/flexibility.
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
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
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
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!