Tax planning done only in April is tax reporting, not tax planning. The decisions that determine your tax bill happen throughout the year. Here's the calendar that keeps more money in your pocket.
January–March: the contribution window
- Make prior-year IRA contribution (deadline: April 15): You can contribute to a Roth or traditional IRA for the prior tax year until April 15. If you haven't maxed last year's IRA, do it now.
- Max HSA for prior year (deadline: April 15): Same window as IRA. An often-missed opportunity for the triple tax advantage.
- Estimate your tax return: If you'll owe significantly, adjust W-4 withholding now rather than writing a check in April.
April–June: midyear adjustments
- Review year-to-date income vs projected — are you on track for your expected bracket?
- Make Q2 estimated tax payment (June deadline for freelancers)
- Review investment portfolio for tax-loss harvesting opportunities
July–September: planning season
- Begin projecting year-end income accurately
- If you'll have unusually low income this year: consider Roth conversion to fill bracket
- If stock holdings have unrealized gains held 12+ months: plan sale timing
October–December: the action quarter
- Tax-loss harvesting (before Dec 31): Identify and sell losing positions. Buy similar replacement to maintain exposure.
- Charitable bunching: Give 2 years of donations in one year to exceed standard deduction threshold
- Max 401(k) contributions: Verify you'll hit $23,500 by December 31 — increase paycheck percentage if needed
- Roth conversions: Execute conversions before year-end to apply to this tax year
- Review RMDs if applicable: Must take by December 31 or face penalty
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