Published Feb 20, 2023

274 | Tax Planning 2020 | Sean Mullaney

Tax expert Sean Mullaney shares invaluable strategies for optimizing Roth conversions, business tax planning, and charitable contributions, focusing on maximizing tax efficiency and financial independence. He delves into year-end planning for 2020, from solo 401Ks to tax gain and loss harvesting, offering advice on navigating complex tax rules for better financial health.
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  • Tax Gain Harvesting

    Tax gain harvesting offers a unique opportunity for those in the financial independence community, especially during early retirement. explains that if you're in the 12% marginal federal income tax bracket or lower, you can sell stocks like Apple, recognize a capital gain, and still pay 0% in federal taxes 1. This strategy allows you to reset your basis, potentially reducing future tax liabilities. However, it's important to consider state income taxes, as they may not be as favorable as federal rules 1.

    You might just sell that Apple stock and do one of two things. You might say, Look, I want to be more diversified. I'm going to go buy an index fund.

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    This approach can be beneficial for diversifying your portfolio or simply resetting your basis without incurring federal taxes.

       

    Tax Loss Harvesting

    Tax loss harvesting involves selling securities at a loss to offset gains, but it requires careful adherence to the wash sale rule. highlights that this rule prevents repurchasing the same or similar securities within 30 days before or after the sale, which could disallow the loss 2. It's crucial to track transactions across different accounts to avoid complications during tax season.

    Tax loss harvesting should be a tactic and not a goal. I don't believe you should set up your portfolio to tax loss harvesting.

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    Mullaney advises using tax loss harvesting selectively, focusing on total return and employing it only in years with significant losses 3.