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Year-End Planning Checklist

Ways to finish 2023 on a strong note.


  • Don't forget to use your Flexible Spending Account (FSA) funds.

  • Required Minimum Distributions (RMD) must be taken by 12/31.

  • Feeling generous? Consider donating stock and using a Donor-Advised Fund.

  • Prepare for taxes on your equity compensation.

  • Build out tax-free balances with Roth and HSA opportunities in 2023.


Year-end can be very busy, but it's crucial to carve out some time to make sure that you end 2023 on a high note and position yourself in the best way possible for 2024.

While we can't cover every potential planning item, here few items to have on your radar.

Flexible Spending Account (FSA)

The vast majority of FSA plans do not allow you to roll balances into the following plan year. Because it’s often a use-it-or-lose-it scenario, make sure you use your balance on qualified expenses.

Generally, you have until December 31st to incur the expenses and until April of the following year to submit reimbursement requests. Check with your provider to confirm plan-specific features and dates.

Required Minimum Distribution (RMD)

If you are age 72 and older, you are required to satisfy 2023 RMDs from pre-tax retirement accounts by December 31st. DO NOT wait until the last week of the year to process your distribution, as custodians can get backed up with several year-end processing requests. If you are working with an advisor, this is something they should be tracking and processing for you.

Also, if inherited a pre-tax IRA from someone who passed away before December 31, 2019, RMDs also apply to you.

If you don't need your RMD to support your spending needs, then you may want to consider a qualified charitable distribution (QCD) to manage your tax exposure.

Gifts & Donations

If you’re looking back on the year and feeling extra generous with family and loved ones, you can gift up to $17,000 per person in 2023 without impacting your estate tax exemption.

With the higher standard deductions in place since 2018, most taxpayers find it helpful to bunch their donations into a single year to maximize the tax benefits.

Did you know that donating highly appreciated stock is a very tax-efficient way to make donations? A Donor-Advised Fund (DAF) is a great way to turn your lump-sum donation into a multi-year donation strategy.

Equity Compensation

December is a great time for executives and key employees to review their equity compensation. Keep tabs on what you’ve accumulated this year and anticipate what will be coming next year.

From a tax standpoint, consider that the value of restricted stock and exercised non-qualified stock options (NSOs) are taxed as ordinary income. If you exercise incentive stock options (ISOs) but don’t sell the stock in the same year, then you may be subject to alternative minimum tax (AMT).

As far as your investment strategy goes, determine whether to keep your accumulated shares or sell them. A strong consideration in your strategy is how much you are invested in your current employer. Between your income, options, and grants, you don’t want too much of your security tied solely to your employer.

Portfolio Review

Year-end is a perfect time to assess your household investment strategy, with extra emphasis on the household. Each account should be playing a role and complementing all of your accounts – even the 401(k) from three employers ago that you haven’t done anything with.

Evaluate the need to rebalance and any opportunities for tax loss harvesting. If you are retired, start thinking about your cash needs for 2024. Depending on the investments you own, it can make sense to free up the cash a few months in advance or closer to when you'll need it.

Roth Conversions

It's very common for people to have the majority (if not all) of their retirement savings in pre-tax dollars, meaning those dollars have never been taxed. This creates a potential tax risk in the future because we don’t know what your marginal tax rate will be in six months, let alone in 10 to 30 years. We do know that if tax rates go up, more of your money will go towards paying taxes than supporting your lifestyle.

To help you navigate any potential high-tax environments in the future, consider Roth conversions. Anyone who finds themselves in a much lower income tax situation this year should see if converting a portion of their pre-tax savings to Roth makes sense. While you will be paying taxes today, the Roth dollars will now grow tax-free for the rest of your life and for the next generation.

Roth conversions require thorough and careful tax planning and cannot be reversed, so be sure to work with your advisor and CPA.

Identify Opportunities for 2024

Did you max out your 401(k) and still have money to save? Find out if your 401(k) plan offers an “after-tax” contribution option. No, this is not the same as Roth. If so, you might be able to take advantage of a Mega Backdoor Roth strategy.

If you’re an executive, your company may offer a 457 or deferred compensation plan that will allow you to save above and beyond the 401(k) limits. While tax-deductible contributions are nice to have, be aware of the credit risks that come with a deferred compensation plan before participating.

Interested in contributing to a Roth IRA? Be mindful of income and contribution limits. If you’re not eligible for direct contributions, then talk to your advisor about a Backdoor Roth IRA.

If you’re in a high deductible health insurance plan, see if you’re eligible for arguably the strongest savings vehicle out there – a Health Savings Account (HSA). HSAs offer triple-tax savings potential.

  • Tax-deductible contributions

  • Tax-deferred growth (if invested)

  • Tax-free distributions for qualified health expenses

On top of the tax benefits, some employers will even make a match contribution to your HSA. With health issues that can arise later in life, HSAs are perfect for long-term care planning. And, unlike a Flexible Spending Account (FSA), an HSA is a savings account, so your balance stays with you.


Your checklist may be different from another person’s, and your own list may change from year to year. Take this time to reflect on what you're truly working towards to know which planning items should be on the top of your list for the rest of 2023 and in 2024.

Your GPS won’t give you directions until you tell it where you want to go. The same applies to your money. Identifying your goals will allow you to have a real strategy in place and prevent you from going off course when markets don't go your way.

Frank Iozzo, CPWA®

President, Private Wealth Advisor


Want to make the most of your 2024?

Click here to schedule a free, 30-minute consultation to learn how we can help.


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