RSU/ESPP diversification
Selling vested concentration to diversify equity-comp exposure.
High Fit Concentrated single-employer exposure carries idiosyncratic risk on top of your job risk; diversifying is a category-level priority.
- Liquidity:
- Days
- Risk:
- Low
- Tax:
- Taxable
- Horizon:
- Any
What changes this: Reducing concentration to your target percentage of net worth.
Donor-advised fund (education)
Bunch charitable deductions; donate appreciated assets to skip cap-gains.
Medium Fit For high-income or legacy-stage households, DAFs allow bunching deductions and donating appreciated assets.
- Liquidity:
- Years
- Risk:
- None
- Tax:
- Taxable
- Horizon:
- Any
What changes this: Charitable intent and bunching opportunities raise priority.
Municipal bonds (education)
For high-bracket investors; coupon may be federally tax-exempt.
Medium Fit At higher tax brackets, federally tax-exempt muni interest can beat taxable bond yields after-tax.
- Liquidity:
- Months
- Risk:
- Low
- Tax:
- Federally tax-exempt (munis)
- Horizon:
- 1+ years
What changes this: Crossing into a higher bracket raises this option's relevance.
Rental real estate analysis
Direct-ownership rental property — illiquid, leverage, active management.
Medium Fit A category-level option for diversifying beyond market assets — accept illiquidity, leverage, and active management as tradeoffs.
- Liquidity:
- Years
- Risk:
- High
- Tax:
- Taxable
- Horizon:
- 5+ years
What changes this: Lifestyle, time, and liquidity preferences drive whether this fits.
Backdoor Roth (education)
Non-deductible IRA contribution converted to Roth IRA; pro-rata rule applies.
Low Fit Most useful for high-income filers who are already maxing other tax-advantaged room.
- Liquidity:
- Years
- Risk:
- None
- Tax:
- Tax-free (qualified)
- Horizon:
- 10+ years
What changes this: Crossing the Roth IRA income phase-out and filling other accounts raises priority.
Related tool → Bond ladder
Staggered bond maturities to manage rate and reinvestment risk.
Low Fit Useful for known-date goals or retirement; less central during accumulation.
- Liquidity:
- Months
- Risk:
- Low
- Tax:
- Taxable
- Horizon:
- 1–20 years
What changes this: Approaching retirement raises priority.
Mega backdoor Roth (education)
After-tax 401(k) contributions converted to Roth — only if the plan allows.
Low Fit Plan-dependent; useful only after exhausting standard tax-advantaged room.
- Liquidity:
- Locked
- Risk:
- None
- Tax:
- Tax-free (qualified)
- Horizon:
- 10+ years
What changes this: Confirming plan support and filling standard space raises priority.
Tax-efficient taxable funds
Low-turnover index funds in taxable accounts to minimize realized gains.
Low Fit Tax-advantaged room is unused — fill it before adding to taxable.
- Liquidity:
- Days
- Risk:
- Medium
- Tax:
- Taxable
- Horizon:
- 3+ years
What changes this: Once HSA/IRA/401(k) are full for the year, taxable becomes the next stop.
Taxable brokerage
Flexible non-retirement investing; long-term capital-gains and step-up basis.
Low Fit Tax-advantaged room is unused — fill it before adding to taxable.
- Liquidity:
- Days
- Risk:
- Medium
- Tax:
- Taxable
- Horizon:
- 3+ years
What changes this: Once HSA/IRA/401(k) are full for the year, taxable becomes the next stop.
Treasury ladder
Staggered Treasury maturities for predictable cash flow and reinvestment.
Low Fit Useful for known-date goals or retirement; less central during accumulation.
- Liquidity:
- Months
- Risk:
- Very low
- Tax:
- Taxable
- Horizon:
- 0–10 years
What changes this: Approaching retirement raises priority.
Related tool →