Reduce Taxes
Legal strategies to keep more of what you earn — optimized accounts, timing decisions, and overlooked deductions.
Most people overpay taxes by thousands of dollars per year through missed deductions, wrong account types, poor timing of investment sales, and underused pre-tax vehicles. This is not about complex strategies — it's about using the tools the tax code already provides.
Key leverage points: maximizing pre-tax retirement contributions, using an HSA (triple tax-advantaged), timing capital gains to stay in the 0% or 15% bracket, correct Roth vs. Traditional account allocation, and self-employment deductions if applicable.
Action checklist
Work through the steps in order. Progress saves in this browser, without an account.
Audit what you owe
This month
Surfaces every missed opportunity and its dollar value.
Tool: Tax Health ScoreEvery dollar deferred lowers your taxable income now.
Triple tax-advantaged and a stealth retirement account.
Article: HSA: the triple tax advantage
Optimize this year
Before year-end
Avoid a surprise bill — or an interest-free loan to the IRS.
Tool: W-2 Tax OptimizerVesting and disposition timing change what you owe.
Tool: RSU & ESPP CalculatorSelling in the right year can erase the tax entirely.
Tool: Capital Gains Calculator
Plan multi-year
Ongoing
Convert cheaply now to cut future RMDs and lifetime tax.
Tool: Roth Conversion AnalyzerArticle: Roth conversion strategy guideOffset gains and up to $3,000 of ordinary income.
Tools to reduce taxes
Free calculators and assessments selected for this goal.
- 1W-2 Tax OptimizerPre-tax benefit headroom, withholding accuracy, and W-4 recommendations for salaried employees
- 2RSU & ESPP CalculatorUnderstand your RSU vesting tax gap and optimal ESPP disposition strategy
- 3Roth Conversion AnalyzerModel partial Roth conversions by bracket — lower lifetime tax exposure
- 4Tax Health ScoreIdentify every missed tax opportunity and estimate the dollar savings
- 5Capital Gains CalculatorModel the tax impact of investment sales — short-term vs long-term, NIIT
Recommended reading
Have a specific question?
The AI Financial Tutor gives an educational answer to a finance question in about a minute. For example: “I'm a W-2 employee earning $150,000 in California. What are the best legal ways to reduce my tax bill this year and over the next 5 years?”