Understanding Tax-Loss Harvesting (In the USA)
Purpose: Tax-loss harvesting involves selling investments that have declined in value to realize a loss. This loss can then be used to offset capital gains from other investments that have been sold for a profit. By strategically managing these losses, investors can LOWER their taxable income and potentially REDUCE their tax bill. Using my LULU investment as an example. I have 200 shares; 100 shares were purchased (via csp assignment) on 3/25/24 at a $425 strike. Another 100 shares were purchased (via csp assignment) on 9/5/25 at a $240 strike. At Charles Schwab, they offer a feature called “Tax Lot Optimizer,” which is managed as follows: 1) Short-term (1 year and less) first, then long-term (longer than 1 year), 2) From the biggest losses to the biggest gains. I sold a covered call @$187.50 strike, which was assigned on 12/19/25. I have pre-set “Tax Lot Optimizer” methodology for my account, which I later realized was not the best approach because it applies the short-term loss first, which wasn’t my biggest loss; it only reported short-term loss of $5,250 ($187.50 - $240 = $52.50 per share x 100 shares). I spoke with the Schwab Tax Department to clarify my understanding. Consequently, it was redirected to report long-term loss of $23,750 ($187.50 - $425 = $237.50/share x 100 shares). For tax-loss harvesting, our goal is to minimize our loss (in terms of tax liability & giving up as few shares as necessary), so I need to harvest the bigger loss to offset my YTD capital gain. Ultimately, minimize my 2025 tax liability. Tip1: Remember to call your brokerage firm asap and before it settles if you have any questions or changes to be made. In the USA, it is “T+1” which means it settles 1 day after the transaction date. Once the settlement is complete, it is set for tax purposes. Tip2: Long-term capital gain has the lowest tax rate, so I always strategize in a way that will help me to yield more long-term capital gains. In this example, I have a higher probability of capital gain from the $240 than the $425 unit cost. And by 9/5/26, my $240 unit cost shares will become long-term capital gain if I sell them for more than $240.