Retirement Prompts for Every Decade of Planning

Compare retirement accounts for my situation. Income: [amount]. Employer: [401k match details]. Current age: [X]. Include: 401k (match first!), Roth IRA vs Traditional IRA logic, HSA as stealth retirement account, backdoor Roth if high income, Mega Backdoor Roth if offered, taxable brokerage after maxing tax-advantaged.

Should I choose Roth or Traditional? Current tax bracket: [X%]. Expected retirement bracket: [describe]. Include: tax arbitrage math, current vs future tax policy risk, diversification benefit (tax-free vs tax-deferred buckets), Roth's no-RMD advantage, conversion opportunities in low-income years.

Optimize my 401k. Employer: [match details, fund options]. Current contribution: [%]. Include: getting full match first, fund selection from options (index funds preferred), expense ratio analysis, target date fund reasonableness, rebalancing schedule, increasing 1% annually.

Use HSA as retirement account. Current HSA: [amount]. Family or individual plan: [X]. Include: max contribution this year, invest (not spend) strategy, pay medical out-of-pocket, save receipts for tax-free withdrawal 30+ years later, triple-tax advantage explanation.

Calculate my retirement number. Desired annual spending: [amount]. Social Security estimate: [amount]. Include: 25x rule (4% SWR), healthcare costs pre-Medicare, inflation adjustment (3%), longevity assumptions (30+ years), part-time income offset, conservative vs aggressive scenarios.

Build FIRE plan. Current age: [X]. Target FIRE age: [Y]. Income: [amount]. Savings rate target: [%]. Include: years-to-FI calculation (savings rate → years), required accumulation, barista-FIRE vs full FIRE vs fat-FIRE distinction, lifestyle design during + after.

I'm [X years old] behind on retirement. Catch-up plan. Current savings: [amount]. Target retirement age: [Y]. Include: 401k catch-up after 50 ($7500), IRA catch-up ($1000), aggressive savings rate, delayed retirement impact, part-time work plan, downsizing considerations, Social Security optimization.

Visualize compound growth for retirement. Monthly contribution: [amount]. Years: [X]. Assumed return: [7-10%]. Show: total contributions vs investment growth, decade-by-decade breakdown, impact of +1% return, impact of +$100/month, impact of 5 extra years. Motivate consistency.

Optimize Social Security claiming. Full retirement age (FRA): [X]. Expected benefit at FRA: [amount]. Include: claim at 62 vs FRA vs 70 tradeoffs, spousal benefits coordination, break-even analysis, longevity assumptions, lump-sum-from-delay psychological math.

Build retirement bucket strategy. Retirement start: [year]. Buckets: 1 (cash, 1-2 yrs), 2 (bonds, 3-7 yrs), 3 (stocks, 8+ yrs). Include: initial allocation, refill rules, tax-ordering (taxable → traditional → Roth), RMDs at 73.

Explain + mitigate sequence risk. Current portfolio: [stocks/bonds]. Retirement date: [year]. Include: how bad early returns devastate 30-year retirement, glide path (bonds increase pre-retirement, decrease after), bond tent concept, delay expenses if possible first 5 years.

Order withdrawals tax-efficiently. Accounts: taxable brokerage [amount], Traditional IRA [amount], Roth IRA [amount]. Annual need: [amount]. Include: taxable first (capital gains, often 0% bracket), then Traditional (fill lower brackets), Roth last. Adjust for RMDs at 73.

Build 5-year pre-retirement checklist. Retirement date: [year]. Include: healthcare transition plan (COBRA, ACA, Medicare at 65), debt elimination (mortgage if possible), emergency fund bulk-up (1-2 years expenses), test-drive budget, portfolio glide path shift, estate documents update.

Plan healthcare costs in retirement. Retiring before 65: [years]. Include: COBRA (18 months max), ACA subsidies (income-based — Roth withdrawals advantage), part-time work for benefits, Medicare at 65, Medigap, long-term care insurance analysis (self-insure vs buy).

Legacy planning checklist. Include: will + trust (avoid probate), beneficiary designations review (overrides will!), power of attorney (financial + medical), charitable giving strategy, intended inheritance, communicating wishes to family, revisit every 5 years.