Retirement Preparedness Checklist
62-question gap analysis with Pre/Post-retirement filters and a readiness score.
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Hindsight Is Money
Leveraging my hindsight to help you shorten your path to financial independence.
Free retirement planning spreadsheets, videos, and the resources I actually use — before and after retirement.
Watch on YouTube
Money lessons I learned the hard way, so you don't have to. New videos walk through each tool with real examples.
Free Retirement Tools
🔒 Free Tools are for YouTube subscribers of Hindsight Is Money.▶ Subscribe
Google Sheets templates — Coming soon. Links are paused while I finish sharing the public copies. Yellow cells will be your inputs.
Planning & Readiness
Weeks of Our Lives
See your life in weeks and put the time you have left in perspective.
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Retirement & Cash Reserve Countdown
Count down to retirement day and track your cash reserve target.
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Boldin AI Prompts
Ready-to-use AI prompts for getting more out of Boldin planning.
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Income, Tax & Withdrawals
Income, Tax & ACA Planner
Plan retirement income against tax brackets and ACA subsidy limits.
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Roth Conversion Strategy
Model Roth conversions year by year and their tax impact.
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Withdrawal Plan Timeline
Map which accounts you draw from, and when.
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Guardrails Strategy
Set spending guardrails that adjust with your portfolio.
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Pay Contributions Tracker
Track paycheck contributions to retirement accounts against limits.
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Investing Buckets
Bucket Strategy & Allocations
Set up a bucket strategy and target allocations for each bucket.
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Bucket 1 Treasuries & Bonds Screener
Compare Treasuries and bond funds for your short-term safety bucket.
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Bucket 2 Dividend Funds & Equities Screener
Screen dividend funds and equities for your growth-and-income bucket.
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Spending & Healthcare
Median Monthly Spend
Find your real median monthly spending from tracked expenses.
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Healthcare Retirement Estimation
Estimate healthcare costs from retirement through Medicare.
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Creators & Sites I Learn From
My own "YouTube University": the channels and sites that taught me the most. More picks from my subscriptions are on the way.
Retirement Planning
Big-picture retirement shows: when you can retire, how much you can spend, and how to make it last.
- James Conole – Root Financial (YouTube)Practical retirement planning walkthroughs from a CFP®.
- Root Financial (YouTube)Weekly retirement show with real-world scenarios.
- Root Financial (website)The firm behind the show, plus retirement education.
More coming soon
Investing
Building wealth step by step: savings order of operations, investing basics, and avoiding costly mistakes.
- The Money Guy Show (YouTube)The Financial Order of Operations and wealth-building basics.
- Money Guy (website)Free resources, guides and show notes.
More coming soon
Budgeting & Debt
Getting the foundation right: a budget, an emergency fund, and getting rid of debt.
- The Ramsey Show (YouTube)Live call-in show on debt, budgeting and money habits.
- Ramsey Solutions (website)The Baby Steps, budgeting tools and articles.
More coming soon
Taxes
Keeping more of what you've saved: Roth conversions, tax brackets, and withdrawal order.
More coming soon
Other
Everything else that makes a rich life, beyond the spreadsheets.
More coming soon
Helpful Resources
Government
Official sources for benefits, taxes and coverage. Start here before anywhere else.
- my Social SecurityCheck your earnings record and benefit estimates.
- Medicare.govOfficial Medicare coverage, costs and enrollment.
- IRS.govTax rules, forms and retirement plan limits.
- IRS Publication 969 (HSAs)Official rules for HSAs and other tax-favored health plans.
- Investor.govSEC investor education and adviser lookup.
- TreasuryDirectBuy Treasury bills, notes, bonds and I bonds directly.
- HealthCare.govACA Marketplace coverage and subsidy estimates before Medicare.
Calculators
Run the numbers yourself and stress-test your plan.
- SSA Benefit CalculatorsOfficial Social Security benefit estimators.
- Compound Interest CalculatorInvestor.gov growth calculator.
- FIRECalcHistorical-returns retirement success tester.
- cFIREsimFlexible retirement simulator with spending models.
- BoldinFull retirement planning software (free and paid tiers).
- Boldin Help CenterHow-to articles for building your plan in Boldin.
Longevity / Life Expectancy
How long should your money last? Plan for a long life, not an average one.
- SSA Life Expectancy CalculatorAverage life expectancy by birth date and sex.
- Actuaries Longevity IllustratorFrom the SOA and American Academy of Actuaries: odds of reaching each age, for singles and couples.
- Living to 100Lifestyle-based life expectancy quiz with health tips.
Healthcare Cost Estimators
Healthcare is one of retirement's biggest wildcards. Estimate it across Medicare, Medicaid and private coverage.
- Medicare Plan FinderCompare Medicare Advantage and Part D plans and costs.
- Medicare CostsCurrent Part A/B premiums, deductibles and coinsurance.
- KFF Marketplace CalculatorEstimate ACA premiums and subsidies by income, age and ZIP.
- Medicaid & CHIP (HealthCare.gov)Check if you may qualify for Medicaid.
- Fidelity Retiree Health Care CostsFidelity's estimate of lifetime retiree health costs.
- eHealthPrivate quotes: individual, short-term, Medigap, dental and vision.
Investing Research
Look up funds and companies before you buy.
- Yahoo FinancePrices, charts and fund data.
- SEC EDGAR Full-Text SearchSearch company filings straight from the source.
Contact
Send me a note. Pick a topic so I can route it, and keep it under 1,000 characters.