Most people don’t actually know if they can retire when they want—they’re guessing. This is the exact prompt you can use to start getting real answers.
I recently created this for my husband and me, and it was incredibly helpful as we’ve entered a new phase of life. I retired from the federal government and now work in the private sector, and our son is halfway through college.
We’ve worked with a financial advisor for over 10 years, but we wanted an additional perspective on our scenarios—and this helped us pressure-test our thinking.
Now before you tell me ChatGPT isn’t a real financial advisor—relax, friends! This is just a tool for your toolbox. A useful one.
I will always recommend having a real financial advisor in your corner to help you think through the big decisions. This just helps you get organized and ask better questions.
Bonus: Here’s a longevity estimator to figure out when you may 🐸 croak/how far to plan your money to last. Fun!
First, do NOT put any personally identifiable information (PII) in the prompt such as your Social Security Number, bank/investment account numbers, even the name of the banks/institutions holding your accounts. Keep it all about the data.
If you’re Single:
Can you perform a retirement analysis for me?
I am planning to retire at age [insert age]. I am currently [current age].
Current Assets
- Traditional IRA: $
- Roth IRA: $
- 401(k): $
- High-yield savings (emergency fund): $
- Checking and savings: $
Annual Contributions
- 401(k) contributions (employee): $/year or %
- Employer match: $/year or %
- Other savings/investments: $/year
Income & Benefits
- Expected Social Security:
- Age 62: $X,XXX/month
- Age 67: $X,XXX/month
- Age 70: $X,XXX/month
- Pension or other fixed income: $/month (if applicable)
(Note: I am still working and expect these numbers to change over time.)
Spending
- Current monthly expenses: $X,XXX
- Expected retirement spending: $X,XXX/month
(If unsure, assume similar to current or slightly reduced/increased based on lifestyle plans.)
Assumptions / Preferences
- Desired lifestyle in retirement: (e.g., maintain current lifestyle, travel more, downsize, etc.)
- Risk tolerance: (conservative / moderate / aggressive)
- Life expectancy assumption: (e.g., plan to age 90 or 95)
What I’m Looking For
- Probability of successfully funding retirement
- Recommended retirement age (if different from my target)
- Withdrawal strategy (which accounts to draw from and when)
- Tax optimization opportunities
- Risks I should be aware of (market, longevity, inflation, etc.)
If You’re Consciously Coupled:
Can you perform a retirement analysis for us?
We are planning to retire at age [insert age] for both of us.
I am currently [age], and my partner/spouse is [age].
Current Assets
- My Traditional IRA: $
- My Roth IRA: $
- My 401(k): $
- Spouse’s Traditional IRA: $
- Spouse’s Roth IRA: $
- Spouse’s 401(k): $
- Joint high-yield savings (emergency fund): $
- My checking and savings: $
- Spouse’s checking and savings: $
Annual Contributions
- My 401(k) contributions (employee): $/year or %
- My employer match: $/year or %
- Spouse’s 401(k) contributions (employee): $/year or %
- Spouse’s employer match: $/year or %
- Other joint or individual savings/investments: $/year
Income & Benefits
My Social Security:
- Age 62: $X,XXX/month
- Age 67: $X,XXX/month
- Age 70: $X,XXX/month
Spouse’s Social Security:
- Age 62: $X,XXX/month
- Age 67: $X,XXX/month
- Age 70: $X,XXX/month
- Pension or other fixed income (identify whose): $/month
(Note: We are both still working and expect these numbers to change over time.)
Spending
- Current combined monthly expenses: $X,XXX
- Expected retirement spending: $X,XXX/month
(If unsure, estimate by taking total household expenses over the last 12 months and dividing by 12.)
Assumptions / Preferences
- Desired lifestyle in retirement: (maintain current lifestyle, increase travel, downsize, etc.)
- Risk tolerance: (conservative / moderate / aggressive)
- Life expectancy assumption: (e.g., plan to age 90 or 95)
What We’re Looking For
- Probability of successfully funding retirement
- Recommended retirement age (if different from our target)
- Withdrawal strategy (which accounts to draw from and when)
- Tax optimization opportunities
- Risks to consider (market volatility, longevity, inflation, sequence of returns, etc.)
Once you’ve filled this out, you have two options:
- Run your own projections (I’ll be sharing how soon), or
- Take this directly to a financial advisor and skip the vague conversations
🐝 That’s the buzz for today – go forth and make great money decisions!