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Most contractors I work with have money in the market, maybe a brokerage account, maybe some long-term holdings, maybe stocks you bought during the slow season. With the year wrapping up, there are a few easy tax moves you can make now that can save you thousands come tax time.

Most contractors I work with have money in the market, maybe a brokerage account, maybe some long-term holdings, maybe stocks you bought during the slow season. With the year wrapping up, there are a few easy tax moves you can make now that can save you thousands come tax time.

Here are the top ones worth your attention:

1. Stop Paying 40% Taxes When You Don’t Need To

Short-term capital gains (selling stocks held <12 months) can get taxed as high as 40.8%.But long-term gains (held >1 year) max out at 23.8%.

That difference is huge—over 70% higher tax on short-term gains.

If you’re sitting on winners, this is the time to review what should be held vs. sold.

2. Use Losses to Kill High-Tax Gains

If you have losing stocks, you can harvest those losses to offset taxable gains before year-end.Losses can:

Offset capital gains

Offset up to $3,000 of regular income

Carry forward into future years

This is the simplest tax savings tool in your entire portfolio.

3. Don’t Get Hit by the Wash-Sale Rule

Unlike crypto, stocks do trigger wash-sale rules.If you sell a stock at a loss and buy the same (or “substantially identical”) one back within 30 days, the IRS disallows the deduction.

If you want the loss for 2025 taxes, you must wait 31 days before repurchasing.

Plan this carefully—contractors often forget this rule.

4. Helping Family? Use Their Lower Tax Bracket

If you support parents or kids who aren't under the kiddie tax:

Give them appreciated stock

They sell at their (lower) tax rate

You effectively shift income down a tax bracket

A simple, legal way to reduce your family’s overall tax bill.

5. Don’t Donate Stock With Losses

If you want to donate to a charity or church:

Donate appreciated stock → you deduct fair market value and avoid capital gains

But don’t donate stock that lost value → sell it first, take the loss, then donate the cash

This gives you two deductions instead of one.

These moves are easy, fast, and can save thousands off your tax bill, but only if you do them before year-end.