December 31 is the single most important deadline in personal finance.

Almost every single tax saving strategy that can save you a meaningful amount of money needs to be implemented by this date.

Once the clock strikes midnight, most of your best planning moves are gone for the year.

In this post, I decided to break down the seven most important things for you to look into that have a December 31 deadline.

This is not a list of every single tax planning move (for that, you should download my guide)… but, the specific things you need to look into and implement by the end of the year.

Save this post. Share it with your tax professional. And let’s save some money.

I just launched a new online course called The Tax Strategy Masterclass for High Earners.

This 4-hour video course is a culmination of my best tax advice for W-2 professionals and business owners that make more than $200Ka year.

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It is currently available for a special launch price of only $299 (until Friday at midnight) and includes a bunch of special bonuses, including:

And free lifetime access to three other mini-courses I’ve created this year:

I’ll send you more information about the course tomorrow… but the cart closes on Friday, November 21 at midnight ET.

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There’s also a 30-day money back guarantee if you take the time to actually go through the lessons and find it to NOT be helpful.

More information on the course tomorrow…

If you’ve sold any investments for a profit this year, now is the time to see whether you can harvest losses elsewhere to offset those gains.

Remember: When you sell an investment for a profit, the IRS considers that a capital gain and you will owe taxes on that gain.

But the tax code has a significant tax benefit for investors built into it: If you sell another investment at a loss, that loss can cancel out the gain (dollar for dollar).

This is one of the simplest and most reliable ways to cut your tax bill:

If you employ a direct indexing strategy to index the market (I’ve written about my experience before), this strategy is implemented for you on autopilot.

My direct indexing software has generated six-figures in usable capital losses for me this year alone:

These losses are more than enough to offset my capital gains elsewhere, leading to no capital gains taxes for 2025.

You can gift up to $19,000 to anyone this year without touching your lifetime gift tax exemption.

For married couples, you can combine your limits for $38,000 per recipient.

Here are a few ways to get the biggest benefit from these gifts:

But remember: the transfer has to be completed by December 31.

And then on January 1, your limit will fully reset for 2026!

When you file your taxes, you can choose between taking the Standard Deduction or itemizing your deductions.

If you choose to itemize your deductions, you can deduct a lot of things you wouldn’t be otherwise able to, like:

This can be very significant, particularly if you hit the $40K in state and local taxes.

If you are going to itemize your deductions, it could be worth reviewing if it makes sense to “bunch deductions”.

Bunching deductions refers to trying to squeeze in a few more deductions that you can itemize this year (incase you reset back to the standard deduction the next year)

This could include strategies like:

The goal of this strategy is to get the maximum bang from your buck from the years that you itemize.

If you are charitably minded, you need to complete all charitable gift giving by December 31 to qualify for a 2025 tax deduction.

Here are two important strategies to make the most of charitable gift giving:

You don’t just have to donate cash to charity. You can instead donate appreciated assets (like public stocks) and get an even bigger tax deduction.

If you donate stock with a low cost basis, you can avoid the long-term capital gains taxes you would have to pay. The charity wins by getting a larger gift and you get a bigger tax deduction.

Ideally, you want to start this process soon since it can take a couple of weeks to complete and you don’t want to be stressing over share transfer timelines in the last week of December.

A Donor-Advised Fund (DAF) is a phenomenal tool for tax planning.

A DAF lets you front-load a big donation to charity upfront — you get the tax deduction immediately.

You can then donate money from the DAF to charity on your own timeline… even many years later!

Meanwhile, the assets in the DAF are invested so the money you can eventually donate to charity keeps growing.

You want to ensure you complete your gift into the DAF by December 31. Most DAF software providers allow you to donate both stock and cash.

This is my favorite tax planning move for anyone who may temporarily find themselves in a lower tax bracket than usual.

Maybe you lost your job, or went to graduate school this year, or are temporarily a resident of a state with low or no state income taxes.

This could be a good time to consider doing a taxable conversion of some of your pre-tax retirement funds to Roth.

The amount converted is taxed as income for the year… but if you are in a lower tax bracket this year, it could be well worth paying those taxes at a much lower rate than usual.

There are two big benefits to a taxable Roth conversion:

The conversion needs to be fully completed by December 31 so try and get started on it soon.

December is your tax planning Super Bowl as a business owner or an individual with any kind of self-employment income.

Here’s my quick checklist of things to look into:

If you are going to be very profitable this year, it could be a good idea to prepay large business expenses for next year upfront.

Ask vendors that you are likely to keep using if they offer a discount for annual plan prepayments to knock down your 2025 taxes.

If you have any self-employment income, you may qualify for potentially the most powerful retirement plan in America.

Set up a Solo 401k by the end of the year, and make an election for how much you want to contribute. You can then contribute the dollars anytime before filing your taxes.

If you are an S-Corp, ensure you run your W-2 payroll by end of year.

Make sure your tax professional has helped calculate the optimal salary number to fully maximize your QBI exemption and you have factored in your retirement plan contributions.

If you are confused by what that means, read my self-employed tax saving handbook.

HSAs roll over. FSAs do not.

Most Flexible Spending Accounts are “use it or lose it,” meaning unused funds evaporate at year-end unless your plan has a small grace period.

Don’t leave free money on the table:

For HSAs, you have until April 15, 2026 to make 2025 contributions but FSAs are a December 31 sprint.

OK, that was a lot to digest.

If you still have questions about any of these strategies to save money on your taxes this year, I’m hosting a free workshop on Thursday on How to Pay Less in Taxes in 2025:

Join me for an hour-long workshop where I break down:

Sign up here (I’ll also send a replay afterwards)

And keep an eye out for an email for me tomorrow sharing more information about my new tax course…

Full Disclosure: I'm writing this as myself, not as some investment adviser or broker-dealer. Purely educational or my personal thoughts - not investment, legal, tax, or professional advice. While my startup Carry owns an investment adviser and broker dealer, this is not meant to be an advertisement and nothing here represents them. Financial decisions involve risk, including losing money. Taxes are complex. Please do your own research or talk to a licensed pro before acting on anything you read here.