Retire With Purpose - The Retirement Podcast 539: By the Numbers: The Real Math Behind Tax Gain Harvesting vs. Roth Conversions
Dec 19, 2025
Discover the surprising benefits of capital gains harvesting and why some retirees choose to realize gains instead of losses. Learn about the 0% capital gains bracket and the strategic timing for tax planning around Social Security and RMDs. The discussion dives into whether tax gain harvesting or Roth conversions offer better long-term savings, with insights on the implications of converting IRAs. Tune in for a fresh perspective on navigating taxes to maximize your retirement portfolio.
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Client With Big Mutual Fund Gains
- Marshall described a client with $117,000 of gains in old mutual funds needing to exit.
- The team evaluated timing and tax implications before recommending a move.
Zero‑Percent Capital Gains Opportunity
- You can harvest long-term capital gains while in the 0% bracket and pay no tax today.
- Selling and immediately rebuying raises cost basis and simplifies future rebalancing.
Exit Holdings Only When You Intend To
- Do harvest gains only when you genuinely want to exit or change an investment.
- Rebuy immediately to reset cost basis since the wash-sale rule doesn't apply to gains.