Concentrated Stock Retirement Planner

Tax-optimized planning for concentrated stock positions. Monte Carlo analysis with fat tails.

Work-Optional Decision Companion

Can this position make work optional?

Start with the minimum facts needed for a first answer. The planner will tell you whether the plan looks workable now, what could break it, and what to test next before you trust the answer.

  • Built for people whose life is dominated by one appreciated stock position.
  • The first answer is fast. The full builder below is where you refine housing, taxes, health costs, and advanced policy rules.
  • The math stays in the same canonical engine either way, so the quick view and the detailed view do not drift.
Ready for a first answer Fill the fields below, then get the first verdict before opening the full case builder.
First answer

Who You Are

Concentrated Position

Other Liquid Assets

What You Need

Each button jumps you to the relevant section so you do not have to guess where the answer or the detailed builder opened.

The fast answer uses your current builder defaults for growth, inflation, health insurance, Social Security, housing, and advanced tax policy until you refine them.

Full Case Builder
Refine housing, benefits, taxes, Monte Carlo, and advanced withdrawal policy
Use the detailed builder when the first answer is close, fragile, or missing important context.
Not every answer needs this. Open it when you want to audit the assumptions or test more precise scenarios.
Profile
Required (1940-2005)
Age you plan to retire

Filing Status

Single
Married Filing Jointly Soon

State of Residence

Determines state income tax brackets
Concentrated Stock Position
Optional label
Must be > 0

Expected Growth Rate

Stock Type

Lock-up Status

Freely Tradeable
Locked Until Year
Other Accounts

401(k) / Traditional IRA

Roth IRA

For Roth 5-year earnings clock

HSA

Brokerage (Taxable)

SGOV / Cash Reserve

Income & Spending

Pre-Retirement Income

Applies only before retirement age

Retirement Spending

After-tax, today's dollars
Spending floor

Social Security

62 early / 67 FRA / 70 max

Health Insurance

Pre-Medicare, unsubsidized
Housing

Home Value

Mortgage

Property Tax

Inputs changed since this answer was last run.
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Run Monte Carlo to see survival probability
Key Metrics
Decision Memo
Read This Case Three Ways
What Is Calculated vs What Needs Review

Calculated Directly

    Assumptions Driving the Answer

      Needs Outside Review

        What Actually Helped in Tests

        Single-change moves already sampled from this baseline

        How Different Access Plans Compare

        Comparing SEPP 72(t), Penalty Bridge, and Locked-to-59.5 strategies

        StrategySurvivalTypical Fail AgeBad-Case Spend FloorTotal Lifetime TaxFlexibility
        What If Spending Is Lower?

        Impact of reducing annual spending by $25k

        What If You Work Longer?

        Each additional working year adds savings and delays draw-down

        Year-by-Year Plan

        Read left to right: what the year had to fund, where cash came from, whether anything was still missing, and what you had left by year-end. Click any row for the full story.

        YearAgeSpendTax Stock SalesRoth ConvPretax Draw Roth DrawBrokerage DrawShortfall Stock LeftPretaxRothBrokerage Cash / SGOVLiquid Net Worth
        Advanced Stress-Test Settings & Rules

        Monte Carlo Settings

        Regime Switching (correlated crashes)
        Fat Tails (Student-t distribution)

        Stock Sale Strategy

        Early Access Strategy

        Conversion & Tax Caps

        Phase & SGOV Tuning

        Analysis Running
        Elapsed 0s
        Running analysis...
        Current results stay visible while this runs.