The tax due date of the current year is in April of the following year. However, when it comes to tax planning, you should not wait until then. Tax planning is different than tax preparation which I covered in my previous blog post here. There are some tax planning opportunities you can only take advantage of before December 31. This week I will only cover individuals. Business owners will be covered in a different post.

Before we get into different strategies, there are three key numbers you need to know when it comes to tax planning: your estimated itemized deduction amount, your estimated marginal tax rate, and your estimated long-term capital gain tax rate. Some strategies only apply to people whose itemized deduction is higher than the standard deduction ($12,400 for single and $24,800 for a married couple in 2020). Your marginal tax rate and long-term capital gain tax rate will help determine approximately how much taxes you could save by implementing certain strategies.

Now let's take a look at some of the common tax planning opportunities you should consider before December 31.

1. Pay part or all of the second installment of your property tax before December 31.

The due date of the second installment of your property tax is usually in the following year. It makes sense to pay it later from the cash flow perspective. However, if your itemized deduction is higher than the standard deduction and the lump sum of your state income, sales, and property tax is lower than the maximum deduction allowed ($10,000 in 2020), it can be beneficial to pay it now to maximize your deduction for the current year.

2. Manage the timing of your charitable contributions.

Qualified charitable contributions are tax-deductible as an itemized deduction. If your itemized deduction is lower than the standard deduction, you could consider delaying your current year charitable contributions to a later year when your itemized deduction is higher, and vice versa.

3. Donate appreciated property instead of cash.

For people who are making charitable contributions, from the tax perspective, it's usually better to donate appreciated property like stocks instead of cash as you don't have to pay taxes on the capital gains.

4. Convert Traditional IRAs to Roth IRAs.

For people who have pre-tax money in your IRAs, if you expect your marginal tax rate will be higher when you take out the money, you could convert some or all of your money in traditional IRAs to Roth IRAs, and pay income taxes now under your current tax rate. There are two things to watch out though. First of all, if you have after-tax money in addition to pre-tax money in your traditional IRAs, you cannot only convert pre-tax money. It has to be pro-rated based on the total value of all your IRAs. Second of all, converting too much money to Roth IRAs may push you into a higher tax bracket. If that's the case, it may be beneficial only to convert some of them and convert the rest in later years.

5. Manage the timing of your bonuses, stock compensations, and other income if possible.

If your marginal tax rate for the current year is higher than usual or you expect to fall into a lower tax bracket next year, it can be beneficial to defer your current year bonus and other income, such as stock options and ESPPs, and vice versa. You could learn more about different tax treatments on ESPPs and NQSQs from my previous blog posts here and here.

6. Increase contributions to your retirement plan at work.

If you haven't maxed out your retirement plan contributions at work and expect to have a lower marginal tax rate when you take out the money, you could increase your pre-tax contributions and save taxes now. If you think your tax rate will be higher after retirement, you could increase your Roth or even after-tax contributions rather than pre-tax contributions to save tax in the long run. You could learn more about after-tax 401(k) contributions in my previous blog post here.

7. Sell investments with long-term capital gains.

If your long-term capital gain tax rate is zero or you expect to have a higher tax rate later when you need the money, you could sell some of those investments, realize long-term capital gains, offset any capital losses you have if any, and pay no or little taxes for the current year.

8. Sell investments at a loss.

No one likes to turn a paper loss into a real loss. However, under certain circumstances, it actually can be a good thing from the tax perspective.

One of which is that if you can find some investments similar to your current ones, you could take advantage of a strategy called tax-loss harvesting by selling your current investment at a loss, offsetting your capital gains from other investments or your ordinary income up to $3,000 per year, and using the selling proceeds to buy investments similar to the one you just sold. The biggest caveat here is that you won't get this tax benefit if you buy back the same investment within 30 days before or after the sale. It falls under the wash-sale rule which you could learn more about it here. The key to making this strategy work is to find similar but not the same investment.

Tax-loss harvesting is also helpful when you are subject to the additional 3.8% Net Investment Income Tax (NIIT) which you could learn more about it directly from the IRS here. Selling some investments at a loss could offset some of your investment gains and then reduce or even avoid the NIIT.

9. Become eligible for Health Savings Accounts(HSAs) on December 1st.

If you plan to start taking advantage of HSAs which you could learn more about it from my previous post here, you don't have to wait for next year. Based on the last-month rule which I also covered in that blog post, as long as you are eligible on December 1st in the current year and remain eligible for the following 12 months, you can contribute up to the maximum contribution allowed ($3,550 for individual coverage and $7,100 for family coverage in 2020) for the current tax year.

10. Take advantage of the annual exclusion amount($15,000 in 2020) when giving gifts to people other than your spouse.

Most people are not subject to the gift tax in 2020 due to the lifetime applicable exclusion amount($11,580,000 per person in 2020). However, you still need to file a gift tax return, Form 709, to report any gifts you make over the annual exclusion amount($15,000 per donee in 2020). In other words, proper management of your annual gift amount will save your time and avoid the hassle of filing a gift tax return.

Non-U.S. residents and non-US citizens are subject to different rules when it comes to gift and estate taxes which you could learn more about it from my previous blog post here.

Also, you could supercharge your 529 plans by contributing a lump sum of the maximum worth of five years’ annual exclusion amount to it without using your lifetime applicable exclusion amount. You do need to file Form 709 and make a special election on it though which I covered in one of my previous blog posts here.

There are many tax planning opportunities. I've only covered some of them in this post. I understand that most people only think about taxes at the end of the year or around the tax due date in the following year. However, just like financial planning, tax planning is also an on-going process. It works best with timely review and adjustments. As always, I recommend you consult with a qualified tax and financial professional based on your specific situation.

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