Eight modules — the catch-up window math, the Roth conversion year, the Social Security claim-age decision, second-act career economics, healthcare cost planning, estate basics, the inflation-resilient portfolio, and the one-page financial dashboard.
Module 1 of 8 · Preview
The catch-up window — what the IRS hands you at 50.
At age 50, the IRS lets you contribute extra to retirement accounts on top of the normal limit. For 2025: $7,500 extra to 401(k)s (total $30,500), $1,000 extra to IRAs (total $8,000), and the new SECURE 2.0 "super catch-up" at age 60-63 is $11,250 extra to 401(k)s.
The window math
$30,500/year for 10 years at 7% return = $421,000. At 8% (S&P historical) = $441,000. These are not small numbers.
The catch: only 14% of eligible women use the catch-up (vs 19% of men, per Vanguard's How America Saves 2024). The gap costs the median woman roughly $180K by age 65.
Module 1 covers the framework. Modules 2-8 are member-only and cover the implementation — the year-by-year tax plan, the Roth conversion year identification, the Social Security claim-age optimization for your specific situation, and the dashboard you maintain monthly.
Module 2 of 8
The Roth conversion year — finding yours.
Somewhere in the 45-65 window, most people have exactly one year where their marginal tax bracket is unusually low. Converting traditional IRA to Roth during that year is worth $40-$200K over a lifetime.
What makes a year "your" Roth conversion year
Look for any year where your income drops temporarily: job transition, sabbatical, spouse retires earlier than you, you retire but haven't started Social Security, large charitable deduction year, year you sell a business (or year after), year you exercise options that hit AMT.
The 4-year retirement window most people miss
Most common Roth window: the 4-year stretch between stopping work (62-66) and starting RMDs (73). No paycheck, possibly no Social Security yet (if delaying to 70), no RMDs. Artificially low marginal bracket. Converting $40-$80K/year during this window — over 4 years — moves $160-$320K into Roth at the lowest possible tax rate.
The math for your specific case
- Pull last 5 years of marginal brackets (1040 line 16 / line 15).
- Project next 5 years.
- Identify the dip. That's your candidate year.
- Run the conversion math: tax now at low bracket vs. avoided tax later at high bracket.
- Talk to a CPA who does Roth conversion planning specifically.
Module 3 of 8
Social Security claim-age math.
Social Security lets you claim anywhere from 62 to 70. The decision matters because claiming early reduces benefit 30% (62 vs 67), delaying to 70 increases it 24% — permanent and inflation-indexed.
The survivor benefit nobody runs correctly
When one spouse dies, the survivor keeps the higher of the two benefits, not both. The lower benefit goes away. If the higher-earning spouse delays to 70, that delay benefit becomes the survivor benefit. Both spouses protected by the delay.
The optimal pattern for most couples
- Lower earner claims at 62-66 for current cash flow
- Higher earner delays to 70 to maximize survivor benefit
- Breakeven against simply claiming at 67: roughly age 80
- If the higher-earning spouse lives past 80, delay-to-70 strategy wins
- Median life expectancy of 65yo woman in US: 87
The 2025 Social Security Fairness Act
Important for people who paid into Social Security AND a public pension (teachers, firefighters, federal employees): WEP and GPO were repealed January 2025. ~3 million retirees got benefit increases averaging $360/month. Check if you're affected.
Tools
Use Open Social Security — free, intelligent, runs married-couple optimization. Better than 95% of professional advice.
Module 4 of 8
Second-act career economics.
You likely have 20-25 productive years ahead, not 10. The pivot at 52 has time to pay off — but only if the math is run honestly.
The pivot math
A meaningful career pivot usually means 2-4 years of lower income while you build the new thing, followed by income that meets or exceeds the original.
Example: current income $180K, spending $120K, savings $60K/year. Pivot year 1: income $90K, drawdown $30K from savings. Year 2: $130K, save $10K. Year 3: $180K, back to baseline. Total cost of pivot: $40-60K from savings over 3 years.
Three pivot types ranked by risk
- Adjacent pivot — same industry, different role. 75% success rate (Stanford DCI longitudinal data). Time: 3-9 months. Lowest risk.
- Adjacent expertise pivot — different industry, same skill. 75% success rate. Time: 9-18 months.
- Fresh start — different industry, different skill. 35% success rate. Time: 18-36 months. Highest risk.
Two-thirds of fresh starts don't pencil. Most people are better served by an adjacent pivot to work they actually want.
Module 5 of 8
Healthcare cost planning — the gap years.
If you retire before 65 (Medicare eligibility), you have a healthcare insurance gap. This is one of the biggest under-planned items in pre-retirement budgets.
Options for the gap years (typically 55-65)
- COBRA — extends employer plan up to 18 months. Expensive (full premium + 2%). Useful as bridge.
- ACA marketplace — subsidies up to ~400% of poverty level. Often $0-$500/mo depending on AGI.
- Spouse's employer plan — if available, usually best.
- Health-sharing ministries — cheap but not insurance, risk-on-you for major events.
- Direct primary care + catastrophic plan — $100-200/mo primary + cheap high-deductible plan.
The ACA subsidy strategy
ACA subsidies are based on Modified AGI. In the gap years, controlling MAGI deliberately (by using Roth dollars instead of traditional, or living off non-qualified accounts) can put you in subsidy zones that save $10-20K/year in premiums.
Medicare planning
At 65, the Medicare decision tree matters. Original Medicare vs Medicare Advantage. Part D drug plan timing. Medigap supplement timing (one-time underwriting window).
Detailed Medicare guide updates annually in this course. The decisions at 64-65 have multi-decade consequences.
Module 6 of 8
Estate basics — what every 50+ adult needs.
You don't need a complicated estate plan. You need the basics done correctly.
The 5 documents
- Will — names guardian for minor children if applicable, names executor, distributes assets.
- Durable power of attorney — names someone to handle finances if you can't.
- Healthcare proxy / medical POA — names someone to make medical decisions if you can't.
- Living will / advance directive — specifies your wishes for end-of-life care.
- HIPAA release — lets named people access your medical info.
For most middle-class families, these 5 documents are sufficient. Cost: $500-$2,000 with a real attorney. The DIY services (LegalZoom, etc) are okay but a real attorney is worth it for complications (blended families, business interests, large estates).
Beneficiary designations — the silent override
Beneficiary designations on retirement accounts and life insurance OVERRIDE your will. If your 401(k) beneficiary is still your ex-spouse from 2008, they get it — regardless of what your will says.
Action: pull every retirement account, life insurance policy, and HSA. Verify the beneficiary. Update if needed. 30-minute exercise; can prevent the worst-case estate outcome.
The 2025 estate tax landscape
Federal estate tax exemption for 2025 is $13.61M per person ($27.22M per couple). Below that, no federal estate tax. Some states have lower thresholds. If your total estate (including life insurance face value) approaches your state's threshold, talk to an estate attorney.
Module 7 of 8
The inflation-resilient portfolio at 55.
The portfolio that worked in your 30s is not the portfolio that works in your 50s. Asset allocation in midlife has different optimization criteria.
The reframe: time horizon vs. drawdown sensitivity
The "100 minus age" rule for stock allocation is wrong by about 15 percentage points for most modern 55-year-olds with 30+ years of life expectancy. The correct framework is:
- Money you need in the next 3 years: cash equivalents (HYSA, T-bills, short-duration TIPS)
- Money you need in years 3-10: bond ladder + dividend equities
- Money you need beyond year 10: equity-heavy, broadly diversified
This frames the question as "how long until I need this specific dollar" rather than "what's my age." A 55-year-old with adequate cash buffer can still hold 70-80% equities in the long-horizon bucket.
Inflation-aware allocations
- I-bonds and TIPS in the medium-horizon bucket
- Equity heavy in the long-horizon bucket (equities historically outpace inflation over 10+ year horizons)
- Real estate exposure (REITs or owned home) provides inflation hedge
- Avoid long-duration bonds in inflationary environments (the 60/40 disaster of 2022 was driven by this)
The annual rebalance
Once a year (December usually), rebalance to your target allocation. Sell what's gone up, buy what's gone down. Mechanical, not discretionary. Single highest-yield "do nothing else" portfolio intervention.
Module 8 of 8
The one-page financial dashboard.
Most people don't have a financial dashboard. They have account statements they look at quarterly. The dashboard is different.
The one-page format
A single sheet (spreadsheet, paper, app — doesn't matter) that shows:
- Net worth (assets minus liabilities)
- Annual spending (rolling 12-month total)
- Savings rate (savings / income)
- Years of expenses in savings/investments (FI ratio)
- Asset allocation percent (cash / bonds / equities / real estate / other)
- Account-by-account balances (one line per account, no detail)
- Upcoming financial events (tax estimated payments, RMD year, Roth conversion year, kid's college tuition, etc.)
Update cadence
Monthly review (15 minutes). Annual deeper review (2 hours, usually December).
What the dashboard catches
- Lifestyle inflation creeping up
- Asset allocation drift from target
- Forgotten accounts
- Beneficiary designation issues
- Tax planning opportunities (Roth windows, charitable bunching, etc.)
- Insurance gaps
The dashboard does what "checking accounts" does not. It surfaces the strategic picture, not the operational picture.
Template
Course members get the editable Google Sheets / Excel template via email after enrollment. Reply to the welcome email to receive.
Annual updates
This course updates each January with the new year's IRS limits, Social Security adjustments, ACA subsidy thresholds, estate tax exemption, and any major tax law changes. Members get all updates automatically for life.