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Year-End Retirement Tax Planning: What You Should Be Doing Before December 31st

Couple doing retirement tax planning

As we head into the final weeks of the year, it’s easy to focus on the holidays, family time, and wrapping up projects at work. But if you’re approaching or already in retirement, this is one of the most important windows for smart financial planning—especially when it comes to retirement tax planning.

At A Better Way Financial, we often say: You’ve worked hard to save and invest—now it’s time to make your money work hard for you. And one of the best ways to do that is by strategically lowering your tax obligation before the clock strikes midnight on December 31st.

Here’s what we’re helping our clients in the Lehigh Valley focus on right now—and what you should consider as part of your own retirement checklist.

Putting Investment Losses to Work: Tax Loss Harvesting

If you have a non-qualified investment account, some of your holdings may be down this year while others are up. While that may seem like a mixed bag on the surface, it can actually present a valuable opportunity through tax loss harvesting.

By selling investments that are currently at a loss, you can offset gains in other parts of your portfolio—effectively reducing your taxable income. This is a smart, proactive move to help rebalance your portfolio and reduce what you owe to the IRS.

If you’re not sure whether this applies to you, we can help you review your positions and determine if tax loss harvesting makes sense as part of your retirement tax plan.

Don’t Overlook the Power of HSAs

For those with high-deductible health plans, the Health Savings Account (HSA) remains one of the most powerful tools in the tax planning toolbox.

Contributions are tax-deductible, the money grows tax-deferred, and as long as you use it for qualified medical expenses, withdrawals are tax-free. That’s a triple win—and it’s all completely legal and IRS-approved.

Over the course of a typical retirement, many individuals will face hundreds of thousands of dollars in healthcare costs. By consistently contributing to and investing within an HSA, you can build a tax-free reserve to cover those expenses and reduce your reliance on taxable income.

Want to know if you’re eligible for an HSA or how to best use one? Let’s review your plan together.

Max Out Your Roth IRA Contributions

If you’re eligible to contribute to a Roth IRA, the deadline to do so for the 2025 tax year is April 15th—but acting now gives your money more time to grow.

The IRS recently increased contribution limits:

  • Up to $8,500 annually if you’re over age 50
  • Couples filing jointly can contribute up to $15,000 combined

Roth IRAs grow tax-free and allow for tax-free withdrawals in retirement, making them an essential part of any retirement tax planning strategy.

Rethinking Your 401(k) Strategy

Whether you’re still working or nearing retirement, your 401(k) plays a critical role in your financial future. But are you making the most of it?

Many plans now offer both traditional (pre-tax) and Roth (after-tax) contribution options. Choosing the right one depends on your income now vs. what you expect it to be in retirement. There may also be an option to make after-tax contributions, which opens the door to the “mega backdoor Roth” strategy—allowing you to potentially invest up to $70,000/year in tax-advantaged retirement accounts.

Not sure what your plan allows? We’ll help you decode it.

Roth Conversions: Are They Right for You Retirement Tax Plan?

The end of the year is also the deadline for completing Roth conversions. This strategy lets you move money from a Traditional IRA or 401(k) to a Roth account—paying taxes now so you can enjoy tax-free withdrawals later.

Done strategically, Roth conversions can help:

  • Reduce Required Minimum Distributions (RMDs)
  • Minimize lifetime tax exposure
  • Create more flexibility in retirement income planning

We’re actively helping many of our clients complete their Roth conversions before the year ends. If you’re wondering whether it makes sense for your situation, request your complimentary Retirement Tax Plan today.

The Real Impact of Retirement Tax Planning: A Case Study

Recently, we met with a couple referred by one of our long-time clients. He was 63, she was 57. They had saved $1.9 million for retirement and wanted to generate $120,000 a year in retirement income, starting in just a couple of years.

After analyzing their current tax and investment structure, we found that their brokerage account was being actively traded by a large investment firm—triggering unnecessary short-term capital gains. We shifted the strategy toward long-term passive management, reducing their tax rate from 22% to 15% on gains.

We also implemented a Roth conversion strategy, moving up to $100,000 annually over the next eight years. This single move projected over $800,000 in tax savings throughout their retirement.

Let’s get to work developing a retirement tax strategy that helps you minimize taxes and maximize your income in retirement. To get started, click below to book your complimentary 15-minute Discovery Call today!

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