AI Retirement Prompts

Ready-to-Use Prompts for Every Stage

Copy these prompts, customize the bracketed sections, and use them with Claude, ChatGPT, or any capable AI assistant.

Getting Started

The "Where Do I Stand?" Prompt

Give me a brutally honest assessment of my retirement readiness.

- Age: [X]
- Annual income: [amount]
- Total retirement savings: [amount]
- Monthly savings rate: [amount or percentage]
- Debt: [list types and amounts]
- Expected retirement age: [X]
- Location: [for cost-of-living context]

Compare me to where I should be. What's the gap? 
What's the single most impactful thing I can do right now?
Don't sugarcoat it.

The "Explain It Like I'm 25" Prompt

I'm [age] and don't understand retirement accounts. Explain in plain language:
1. What's the difference between a 401(k) and an IRA?
2. What's the difference between Traditional and Roth?
3. What's an employer match and why does it matter?
4. What should I invest in inside these accounts?
5. How much should I be saving?

Assume I know nothing. Use concrete dollar examples.

Scenario Modeling

The "What If" Prompt

Run these retirement scenarios for me:

Base info:
- Age: [X], retirement age: [X]
- Current savings: [amount]
- Monthly contribution: [amount]
- Expected return: 7% nominal

Scenarios:
A) I keep everything as is
B) I increase contributions by $[X]/month
C) I delay retirement by [X] years
D) I do both B and C
E) A market crash drops my portfolio 40% in year [X]

For each, show: projected savings at retirement, annual income 
using 4% rule, and probability of money lasting to age 90.

The "Retirement Date Calculator" Prompt

When can I realistically retire?

- Age: [X]
- Current savings: [amount]
- Monthly contribution: [amount]
- Annual spending need in retirement: [amount] (today's dollars)
- Expected Social Security at FRA: [amount/month or "not sure"]
- Pension: [amount or "none"]
- Debt: [list]
- Other income in retirement: [if any]

Calculate the earliest age I can retire at three 
confidence levels: conservative (90% success), 
moderate (80%), and aggressive (70%).

Tax Strategy

The "Roth Conversion" Prompt

Should I do Roth conversions? Help me evaluate.

- Age: [X], retirement age: [X]
- Traditional IRA/401(k) balance: [amount]
- Roth IRA balance: [amount]
- Current tax bracket: [percentage]
- Expected tax bracket in retirement: [higher/lower/similar/unsure]
- Years until RMDs begin: [X]
- Current year income: [amount]
- Room in current tax bracket: [amount before next bracket]

Calculate:
1. How much I could convert this year without jumping a bracket
2. Total tax savings over retirement from converting vs. not
3. A multi-year conversion schedule that minimizes total lifetime taxes
4. Impact on Medicare premiums (IRMAA)

The "Tax-Efficient Withdrawal" Prompt

Create a year-by-year withdrawal plan for my first 10 years of retirement.

My accounts:
- Traditional 401(k): [amount]
- Roth IRA: [amount]
- Taxable brokerage: [amount] (cost basis: [amount])
- Social Security: [amount/month], starting at age [X]
- Pension: [amount/month or "none"]

Annual spending need: [amount]
Filing status: [single/married]
State: [for state tax]

Optimize for: minimum lifetime taxes.
Show: which account to withdraw from each year, 
tax impact, and how balances change over time.

Social Security

The "When to Claim" Prompt

Optimize my Social Security claiming strategy.

Me:
- Age: [X], health: [excellent/good/fair/poor]
- FRA benefit: [amount/month]
- Other retirement income: [sources and amounts]
- Retirement savings: [total]

Spouse (if applicable):
- Age: [X], health: [excellent/good/fair/poor]
- FRA benefit: [amount/month]

Show me total lifetime benefits for claiming at 62, 65, FRA, and 70.
Account for survivor benefits if applicable.
What's the break-even age for each scenario?
What do you recommend and why?

Healthcare

The "Healthcare Bridge" Prompt

I'm retiring at [age], before Medicare at 65. 
Help me plan health coverage for the gap.

- Current employer plan cost: [amount/month, employer portion + mine]
- Spouse's employer plan available: [yes/no]
- Expected retirement income: [amount] (for ACA subsidy calculation)
- Health conditions: [list]
- Regular medications: [list]
- State: [X]

Compare options: COBRA, ACA marketplace, spouse's plan.
Calculate estimated premiums and out-of-pocket costs for each.
Show how managing my income could maximize ACA subsidies.

Estate Planning

The "Estate Documents Checklist" Prompt

What estate planning documents do I need? Help me create a checklist.

- Age: [X]
- Marital status: [X]
- Children: [ages]
- State: [X]
- Approximate net worth: [range]
- Retirement accounts: [types]
- Real estate: [properties]
- Business ownership: [if any]
- Existing documents: [list any you already have]

Give me:
1. Documents I need and what each does
2. Priority order for getting them done
3. Whether I need an attorney or can use online services
4. Beneficiary designations to check/update
5. Common mistakes to avoid

Ongoing Monitoring

The "Portfolio Health Check" Prompt

Review my retirement portfolio allocation.

My investments:
[List each fund/holding, amount, and percentage of total]

My details:
- Age: [X], retirement age: [X]
- Risk tolerance: [conservative/moderate/aggressive]
- Total portfolio value: [amount]

Evaluate:
1. Is my allocation appropriate for my age and timeline?
2. Am I too concentrated in any one area?
3. What are my total fees?
4. Do I need to rebalance?
5. Simplification opportunities?

The "Inflation Impact" Prompt

Show me how inflation will affect my retirement.

Planned annual spending: [amount] in today's dollars
Years to retirement: [X]
Years in retirement: [X]
Assumed inflation rate: 3%

Calculate:
1. What my spending will actually need to be in year 1 of retirement
2. What it'll be in year 10, 20, and 30
3. Total spending over retirement in nominal dollars
4. How much more I need saved to account for inflation