Year-End Tax Planning Moves
NOVEMBER IS A GOOD time for tax planning. You still have enough time left in the year to make tax moves, but you’re close enough to December 31st to know what your income, deductions and credits might look like.
Here are some tax moves to consider:
1. Maximizing retirement contributions
Before the year ends, if you have the means, consider contributing the maximum allowed $23,500 to traditional 401(k), Roth 401(k), and similar workplace plans.
Even if you can’t max it out, increasing your contributions in November and December can still make a meaningful difference. And if your employer offers a match, make sure you’re contributing at least enough to get the full match.
2. Mega Backdoor Roth
This strategy allows high-income earners to save even more in a Roth account, if permitted by a workplace retirement plan. For example, say you contribute the entire $23,500 to a pre-tax 401(k), and receive $10,000 in employer match. You can still contribute $36,500 to after-tax account if allowed by your plan.
After contributing to the after-tax account, you can roll the funds over to a Roth IRA or Roth 401(k), shielding them from future tax.
3. Backdoor Roth
If you have a high income, you can’t contribute to a Roth IRA directly. But, there is a strategy called “Backdoor Roth”.
It involves making a non-deductible contribution (so no tax deduction) to a Traditional IRA, and then converting the amount into Roth.
Importantly, you need to ensure that you have a $0 Traditional IRA/Rollover IRA/SEP/SIMPLE by December 31, otherwise, the conversion will be partially taxable. I wrote more about the Backdoor Roth strategy in a previous issue.
4. Optimizing Charitable Contributions
If you’re planning to donate to charity before the end of the year, consider donating appreciated shares from your taxable brokerage account instead of cash. When you donate stock that has increased in value, you can deduct the full market value of the shares (up to a set AGI limit) without paying capital gains tax on the appreciation.
After the donation, you can use the cash you had originally planned to give to buy back the same shares. This effectively increases your cost basis in those shares, which reduces your future capital gains tax when you eventually sell them.
5. Tax Loss Harvesting
If you have stocks/ETFs that have a loss, consider selling them to offset gains from other investments or to claim up to a $3,000 capital loss deduction on your tax return. This strategy, known as tax loss harvesting, can reduce your taxable income and lower your overall tax bill.
A common strategy for some investors is to sell a fund that tracks the S&P 500 at a loss, and rebuy a similar fund, say the Total US Market Fund. Looking at the S&P 500, it's down ~5% from its all time highs, so it could be a decent move.
Just remember the wash sale rule: don’t buy the same or a substantially identical security within 30 days before OR after the sale, or the loss will be disallowed for tax purposes.
6. Tax Gain Harvesting
If your taxable income is below $48,350 (or $96,700 for MFJ) in 2025, consider selling appreciated securities at a gain and buying them back. This increases the cost basis of your investment and lowers future tax liability.
However, if state or local taxes apply, this strategy may not be worthwhile due to the opportunity cost of paying those taxes. This strategy is ideal for an investor in a no income tax/no capital gains tax state.
7. Maximize HSA
HSAs provide many tax benefits, including a tax deduction, tax-free growth, and tax-free withdrawals for medical expenses.
You can contribute $4,300 for individuals or $8,550 for families if you have a HDHP (minimum deductible of $1,650 for individuals and $3,300 for family coverage). Individuals age 55 and older can contribute an additional $1,000 "catch-up" contribution.
I personally maximize my HSA every year since my employer also provides a matching for it. It's a great way to save/invest for the future healthcare costs.
8. Business Entity
If you are a business owner, choosing the right business structure can have a big impact on your taxes. For individuals with net income above $100,000, electing S corporation status could be a smart move.
An S corp allows you to split your earnings between a reasonable salary and distributions. While your salary is subject to payroll taxes, distributions are not, which can reduce your self employment taxes. However, you have to analyze the payroll costs, including compliance, for maintaining that S corp status.
9. Track Expenses
Most small business owners or people with a side hustle overpay taxes because they don't keep a good track of their expenses. Some of the smaller things like entity formation or business meals could get missed. This is why it's a good practice to have a separate business bank account and connect it to various bookkeeping softwares.
Last minute bookkeeping often leads to missed opportunities and higher taxes. For self-employed individuals, tracking income and expenses consistently throughout the year can make quarterly estimated tax payments more accurate and reduce the risk of penalties.
10. Gift
In 2025, you can gift up to $19,000 ($38,000 for married couples) per person without impacting your lifetime estate and gift tax exemptions ($15M in 2026). This won't reduce your taxes now but will allow you to strategically transfer wealth to your heirs tax free. This is especially relevant for individuals living in states that have a low exemption (like Oregon with $1M)
Which ones are you going to take advantage of this year? Let me know in the comments!
Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Here are some tax moves to consider:
1. Maximizing retirement contributions
Before the year ends, if you have the means, consider contributing the maximum allowed $23,500 to traditional 401(k), Roth 401(k), and similar workplace plans.
Even if you can’t max it out, increasing your contributions in November and December can still make a meaningful difference. And if your employer offers a match, make sure you’re contributing at least enough to get the full match.
2. Mega Backdoor Roth
This strategy allows high-income earners to save even more in a Roth account, if permitted by a workplace retirement plan. For example, say you contribute the entire $23,500 to a pre-tax 401(k), and receive $10,000 in employer match. You can still contribute $36,500 to after-tax account if allowed by your plan.
After contributing to the after-tax account, you can roll the funds over to a Roth IRA or Roth 401(k), shielding them from future tax.
3. Backdoor Roth
If you have a high income, you can’t contribute to a Roth IRA directly. But, there is a strategy called “Backdoor Roth”.
It involves making a non-deductible contribution (so no tax deduction) to a Traditional IRA, and then converting the amount into Roth.
Importantly, you need to ensure that you have a $0 Traditional IRA/Rollover IRA/SEP/SIMPLE by December 31, otherwise, the conversion will be partially taxable. I wrote more about the Backdoor Roth strategy in a previous issue.
4. Optimizing Charitable Contributions
If you’re planning to donate to charity before the end of the year, consider donating appreciated shares from your taxable brokerage account instead of cash. When you donate stock that has increased in value, you can deduct the full market value of the shares (up to a set AGI limit) without paying capital gains tax on the appreciation.
After the donation, you can use the cash you had originally planned to give to buy back the same shares. This effectively increases your cost basis in those shares, which reduces your future capital gains tax when you eventually sell them.
5. Tax Loss Harvesting
If you have stocks/ETFs that have a loss, consider selling them to offset gains from other investments or to claim up to a $3,000 capital loss deduction on your tax return. This strategy, known as tax loss harvesting, can reduce your taxable income and lower your overall tax bill.
A common strategy for some investors is to sell a fund that tracks the S&P 500 at a loss, and rebuy a similar fund, say the Total US Market Fund. Looking at the S&P 500, it's down ~5% from its all time highs, so it could be a decent move.
Just remember the wash sale rule: don’t buy the same or a substantially identical security within 30 days before OR after the sale, or the loss will be disallowed for tax purposes.
6. Tax Gain Harvesting
If your taxable income is below $48,350 (or $96,700 for MFJ) in 2025, consider selling appreciated securities at a gain and buying them back. This increases the cost basis of your investment and lowers future tax liability.
However, if state or local taxes apply, this strategy may not be worthwhile due to the opportunity cost of paying those taxes. This strategy is ideal for an investor in a no income tax/no capital gains tax state.
7. Maximize HSA
HSAs provide many tax benefits, including a tax deduction, tax-free growth, and tax-free withdrawals for medical expenses.
You can contribute $4,300 for individuals or $8,550 for families if you have a HDHP (minimum deductible of $1,650 for individuals and $3,300 for family coverage). Individuals age 55 and older can contribute an additional $1,000 "catch-up" contribution.
I personally maximize my HSA every year since my employer also provides a matching for it. It's a great way to save/invest for the future healthcare costs.
8. Business Entity
If you are a business owner, choosing the right business structure can have a big impact on your taxes. For individuals with net income above $100,000, electing S corporation status could be a smart move.
An S corp allows you to split your earnings between a reasonable salary and distributions. While your salary is subject to payroll taxes, distributions are not, which can reduce your self employment taxes. However, you have to analyze the payroll costs, including compliance, for maintaining that S corp status.
9. Track Expenses
Most small business owners or people with a side hustle overpay taxes because they don't keep a good track of their expenses. Some of the smaller things like entity formation or business meals could get missed. This is why it's a good practice to have a separate business bank account and connect it to various bookkeeping softwares.
Last minute bookkeeping often leads to missed opportunities and higher taxes. For self-employed individuals, tracking income and expenses consistently throughout the year can make quarterly estimated tax payments more accurate and reduce the risk of penalties.
10. Gift
In 2025, you can gift up to $19,000 ($38,000 for married couples) per person without impacting your lifetime estate and gift tax exemptions ($15M in 2026). This won't reduce your taxes now but will allow you to strategically transfer wealth to your heirs tax free. This is especially relevant for individuals living in states that have a low exemption (like Oregon with $1M)
Which ones are you going to take advantage of this year? Let me know in the comments!
Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.The post Year-End Tax Planning Moves appeared first on HumbleDollar.
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