After You File: 2026 Tax Planning Moves Most Retirees Miss

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It's the One of a Kind Financial Show Daily with your host, Mike Milligan. The biggest tax mistakes don't happen before April 15th. They happen right after it. What do I mean by that? I mean that many people finish their tax returns. They feel like they're done and they check out for taxes until, let's say, maybe December of this year. Maybe they'll go in and try to do some Roth conversions, do something late. But while the ink is still wet on your tax return, now's the time. This period right now is the time where planning should start. Planning requires more than reactions at the end of the year. It requires thoughtful analysis of what's important to you, what your vision for retirement or your life is, and even powerful concepts that you can implement now in April. Of 2026 to make the bill in 2027 less or appropriate for you. Enjoy this segment from the One of a Kind Financial Show for this past weekend. And remember, you are one of a kind.

All right, once taxes are filed, most people mentally checked out, and that's exactly where the planning should begin. So here's the pattern. Every year, people file their taxes, they feel relief, they go, ah, and they move on. But for retirees, the most single biggest missed opportunity of the entire year is right now, because once you know the numbers, you finally have clarity, and clarity creates opportunities. So why is the period right after tax season so important for planning, Mike?

Well, you know, now you're working with real data, and we, we all know that when we're not working with estimates but we're working with actual numbers, the outcome is going to be Easier to determine. So you know the income, you know the tax bracket, you know your deductions and your exposure. This allows for proactive decisions now in 2026 for things like Roth conversions or income adjustments or capital gain strategies. So waiting till next year, waiting till 11 months from now to start doing tax planning means that you lose months of opportunity. And so isn't the best time now? Isn't it the best time now to plan versus when you're filing next year?

Yeah, absolutely. And folks should take advantage of this opportunity right now. Again, I'm going to give the number and Mike's calendar so you get on Mike's calendar again in just a couple of minutes. This— I'm not familiar. What is tax bracket fill strategy and why is it so powerful? What does that mean?

So this is one of those lesser discussed strategies that can make a huge difference over time. It involves intentionally Realizing income like Roth conversions up to the top of your current tax bracket without spilling into the next bracket. So imagine, you know, let me, let me paint this picture another way. Imagine you have like a water bucket, a water jug, a jar even, and, you know, you have enough in that jar where there's maybe 2 or 3 inches until the top. So you can add more water in until it doesn't spill up. And by doing that, you know, maybe it makes the pail that is holding the water not as heavy for you to carry because you've dispersed some of that water around. Filling up the tax bucket strategy is going to prevent you in the future from having a pail that overflows or a jar that overflows where your taxation actually goes up because you've deferred, deferred, deferred, deferred income forever. See, the tax man's coming. Because if we do this correctly, it can reduce future RMDs and lifetime tax liability.

Reminds me of the song, I think it was 1967, Taxman by the Beatles, by the way. Check it out.

I've never— I am going to check that out because I feel like that's a song I should know. I mean, I know the song Money, Money, Money, right? But I don't know the song Taxman. I'm going to go look that one up.

Taxman by the Beatles. Yes. So how do Roth conversions fit in the conversation right now?

Well, with ongoing uncertainty around future tax rates and rising federal debt, many retirees are reconsidering tax diversification. Folks, if you're not driving right now, or if you're driving, remember this. I'd love for you to go look up a website. It's www.usdebtclock.org.

usdebtclock.org.

It shows you not only the federal deficit that we run and the amount of debt we're in, but it also shows you the debt per citizen and the debt per taxpayer. Right now, the debt per taxpayer is a whopping number. It is a huge number. It's over $300,000 per taxpayer. And I could tell you, folks, if you— If you think tax rates are going to stay low like this forever, you've got a major shock coming for you in the future. That's why doing— filling up the bucket to the top and looking at things like Roth conversions while rates are high is going to prevent you from being a victim to the U.S.'s overspending that we have done for generation upon generation.

Yeah, and that's why you need Mike in your corner. Mike can help you all through that. That phone number is 800-748-1838, 800-748-1838, or text the word Ideas to 600-700. Folks at Warnock Financial standing by ready for your phone call. If you're just joining us, this is the One of a Kind Financial Show with Mike Milligan. I'm Gary Nolan, your host. One more time on the phone number, 800-748-1838. Text the word ideas to 600-700. What role does IRMAA play in tax planning that most people overlook, Mike? We've got about a minute or two.

Yes, so IRMAA, Income-Related Monthly Adjustment Amount, can increase Medicare premiums based on the income levels from Taxes you filed 2 years ago. Many retirees trigger it without realizing it, especially when doing large withdrawals or conversions. It's essentially a hidden tax tied to your income. So when you're making tax decisions with a financial professional like me, we're going to make sure that you're not— that you're staying below or staying in the current tax bracket for income, but we're also going to make sure that you understand any IRMAA related activities that's going to come that can adjust your Medicare premiums.

So why do retirees need coordination between their advisor and CPAs? So many CPAs and advisors don't even talk, Mike.

Well, yeah, I mean, there's a lot of great CPAs around Hampton Roads and around the country, but they're just some of the busiest people I know. They're not the people we see out this time of year. They're not the people we see out to dinner at 6:30 with your family or out of the soccer match because they're busy, busy, busy, busy. See, tax strategy doesn't exist in isolation. Investment decisions, withdrawal strategies, and tax planning all interact and intersect with each other. Without coordination, opportunities are missed and mistakes can compound. See, the CPA reports the past, but the advisor helps shape the future. So, these conversations should happen together because you are unique, you are one of a kind, and a one-of-a-kind financial plan is what you need to make sure taxes are reduced in your lifetime.

Yeah. Thanks, Mike. Tell us about the one-of-a-kind financial plan. We got a minute or 2 left.

I wrote the book, The One-of-a-Kind Financial Plan. It's available on Amazon. For those who are listening, by the way, if you want to come into our office and get a copy of the book and go through a workshop on how to build the one-of-a-kind financial plan, You can call in today and we'll make sure you know when those dates are. But what I'd also tell you is that the One of a Kind Financial Plan centers around taxes because it is the biggest expense you'll ever have in your life. We're going to get your taxes correct. We're going to create a plan that addresses that biggest expense and also create retirement income you can't outlive investment strategy that makes sure that the risk is adjusted for your lifestyle so you could sleep at night. A long-term care plan so you end life with dignity and a legacy plan that says, I love you. That's the one-of-a-kind financial plan. We build it because we know, you know, you are living a one-of-a-kind life.

Absolutely. Get the one-of-a-kind financial plan from Mike Milligan. Mike's with One Oak Financial.

That phone number is 800-748-1838, 800-748-1838, or text the word ideas to 600-700- This has been the One of a Kind Financial Show Daily with your host, Mike Milligan. I am an investment advisory representative with Advisory Alpha LLC, a registered investment advisory firm with the Securities and Exchange Commission. Ideas by Mike, doing business as One Oak Financial, is an unaffiliated entity of Advisory Alpha LLC. All opinions expressed on this, the One of a Kind Financial Show Daily, are those of me and Gary Nolan. My co-host. This is for educational purposes only. Before executing any investment or tax strategy, please consult with the appropriate professionals for both, ones that are licensed and credentialed and capable of working with you as a fiduciary. If you have additional questions from this show, you can reach out to us at One Oak Financial. That's the number oneoakfinancial.com. Or if you wanted to connect with me, Mike Milligan, personally, you could do so on my website, mikemilligan.com. As always, you are one of a kind.

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