Checklist #24 · Tax
Capital Gains Tax Planning
Guide your approach to timing investment sales, managing capital gains exposure, and legally minimizing tax impact on portfolio growth.
20 action items~15 min to complete3 sections
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Assess Your Capital Gains Situation
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Identify all positions with significant unrealized gains in taxable accountsKey
Calculate estimated total net capital gains expected this year
Determine your capital gains tax rate based on taxable incomeKey
Check for any capital loss carryforwards from prior yearsAction
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Long-term capital gains tax rate for most middle-income earners (2024)
37%
Ordinary income rate that applies to short-term gains for high earners
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Apply the Right Strategies
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Harvest losses to offset gains before year-endKey
Evaluate the 0% long-term capital gains bracket
Consider bunching gains or losses into a single tax year
Delay year-end sales into January to defer the tax bill by 12+ monthsAction
Avoid taking short-term gains except when the business case is overwhelmingWatch out
Use specific lot identification methodAction
Consider LTCG bunching with deductionsKey
Review state and local tax implicationsWatch out
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Advanced Strategies
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Donate appreciated assets directly to charity instead of cashKey
Evaluate a Qualified Opportunity Zone investment for very large gains
Consider installment sales for business or real estate proceeds
Review primary home exclusion eligibility if selling your residenceKey
Coordinate gains recognition with Roth conversion planning
Work with a CPA before any large liquidity event (business sale, stock option exercise, real estate sale)Action