Tax Planning vs. Tax Filing: How to Save Thousands in Retirement

Be one of a kind with Mike's Plan.

It's the One of a Kind Financial Show Daily with your host, Mike Milligan. It's Tuesday. Remember The Wolf of Wall Street? Jordan Belfort's biggest problem wasn't making money, it was keeping it. In retirement, the IRS can become your biggest silent partner unless you plan smarter. So what's changed for 2026 and how do you keep more of what you've built? In this segment from the One of a Kind Financial Show, Gary and I talked about those very things because the conversation shifted after the One Big Beautiful Bill. That's how Gary starts that segment. That's how we're going to present it back to you today. Remember, you are one of a kind, and because of that, you probably need a one-of-a-kind financial plan.

The conversation shifted after the One Big Beautiful Bill Act became law in July of 2025. Major TCJA individual provisions were expected to expire were extended, made permanent, and new deductions and income-sensitive provisions were added, meaning the best strategy in 2026 is less about guessing sunsets and more about managing brackets, Medicare costs, and future RMD pressure. So my first question to you, sir, is, are you doing tax filing or actual tax planning?

Most people spend more time planning for vacation than they do planning lifetime taxes.

Yes.

Taxes are also the biggest expense you'll ever have in your life. But retirement tax strategy isn't about April 15th. It's about how today's choices affect IRMAA, Social Security taxations, required minimum distributions, gift taxes while you're alive, and ultimately inheritance taxes. And so most people look at taxes as a winter activity to do by gathering documents, but taxes should be looked at through a 12-month, a 20— a 12-month lens. So over a year or over a 20 to 25 life expectancy. And when you look at them for a yearly basis for income and over a lifetime basis, we can actually show people how they can save tens of thousands, if not hundreds of thousands, by tax planning versus just doing tax filing.

Yeah, we're going to talk about that later in the show too. I have a whole segment on that. So do you know your IRMAA cliff edges for 2026, Mike?

So lesser-known term is the IRMAA cliff, right? IRMAA, Income in Respect of Medicare. That is like for 2026, it goes back and looks at your 2024 tax returns. That's the 2-year lookback rule on that. And so if you were a single filer in your 2024 2024 modified adjusted gross income exceeded $109,000. For married people, if it was over $218,000, and I mean just by over those numbers by a dollar, then that will trigger a higher premium tier for Medicare. That's why, you know, there's a lot of advisors, financial folks who will advise you to do Roth conversions, but they never once ask you to look at your tax return. They'll just take your word for what your taxes are. Other people will tell you to sell this or sell that, and they don't look at your tax returns. When we're doing tax planning, like especially in this new world of the one big beautiful bill, we have to look at the tax return and see what they are and then project what they'll be by the end of the year so that we could stay not only within a tax bracket you're comfortable paying taxes in, but in an IRMAA bracket. Because remember, that $1 over doesn't mean that you're getting extra benefits with Medicare. It just means you're paying more for the same benefit.

Yeah, absolutely. The show is the One of a Kind Financial Show with Mike Milligan. I want you to get on Mike's calendar. If you missed the phone number in the prior segment, here it is, 800-748-1838. Get ahold of Mike and the team, 800-748-1838, or text the word ideas to 600-700. The folks at One Oak Financial standing by this and every weekend, ready for your phone call. Get on the calendar. You deserve a more confident plan to retire. Want to be stress-free, peace of mind, sleep well at night? However you want to say it, nothing changes till you pick up the phone and dial that number, 800-748-1838, or text the word ideas to 600-700. RMD reality check. Are you building a future tax problem inside your IRA, Mike?

Required minimum distributions is your partner's distribution plan for your IRA, your partner being the IRS. And so the IRS currently says that RMDs have to begin at age 73 if you were born before 1960, if you're born 1960 or later, it's 75. If most of your wealth is in pre-tax accounts, you're basically storing up value in a tax— that's a taxable income for your future. And there's, there's plans, there are ways to avoid this. Qualified charitable distributions, qualified longevity annuity contracts, um, uh, Roth conversion strategies, whether those are micro Roth conversions or big ones to just do it one time. And the most important thing about these RMDs is they don't end when you die. They go on to your beneficiaries until that account balance is finally zero. So one of the biggest things we do in the One of a Kind Financial Plan is build an RMD plan for our clients that ultimately reduces, you know, we practice something called income smoothing. Income smoothing allows you to stay in the same tax bracket for your whole life and continues that beyond your death. It is a big part of our practice and it's something that if your current advisor is not talking to you about, if all they're talking about to you is product, And they're not talking to you about RMDs, you're just, you're delaying a problem into the future. And we all know that problems only get bigger as time moves forward.

Yeah, absolutely. Couple of minutes left. Can Roth conversions still be a win in 2026, even without a sunset deadline, Mike?

Roth conversions are awesome. Roth IRAs in general are awesome because conversions aren't only about future tax rates, they're about control. So control of What you're— what, how you take the money out without having to pay tax, control to your beneficiaries, you know, allowing money to stay and continue to defer for up to 10 years and have no tax coming out at the end. The real question is not, can you convert strategically without tripping IRA? It's why are you not converting up to those limits? Because every little, even if it's only $4,000 or $5,000 a year, um, in a properly structured, a properly structured Roth conversion, by the way, can have very little impact on your taxes, but those conversions could have huge impacts, especially if you have some longevity left in your life.

All right, up against the clock, Mike. Tell us about the One of a Kind Financial Plan one more time.

Oh, we didn't even get to in this segment, like, are you tax-deferred or accidentally tax-concentrated, which is a good question, and the estate angle of this tax bill. But guys, that's what we do when we meet. The knowledge that you hear repeatedly on the One of a Kind Financial Show, that Gary and I bring to you week in and week out is so you will take action. We want to educate on the show. We want to entertain, but more importantly, we want you to realize that you live a one-of-a-kind life. And we don't know too many other firms around the country that put you at the center of the financial plan. We do. If you would like a one-of-a-kind financial plan that clearly gives you options to retire earlier, Spend more time with your grandkids, travel more, invest more time in your community, spend more time with your lady friends or your guy friends, we could have the solution for you. It's called the One of a Kind Financial Plan. I'd love for you to call in today. I'll be answering the phone today. I'd love to get to know you. We had many call-ins on last week's show, and I'd love to talk to you about what you're doing in your life, what resonates with you, and just have that initial conversation on how we could start the process to build a One of a Kind Financial Plan.

It starts by picking up the phone and dialing this number, 800-748-1838. 800-748-1838. Or text the word IDEAS to 600-700. Your chance to benefit from the one-of-a-kind financial plan. Call right now. We have a limited number of availabilities on our calendar this week. And remember, the consultation is offered at no cost or no obligation. So what are you waiting for?

This has been the One of a Kind Financial Show Daily with your host, Mike Milligan. Gary and I are here for education purposes only. Please do not take anything we say solely as financial recommendations for you personally, because every situation is different. If you need specific financial advice, please reach out to us at Ideas by Mike, doing business as One Oak Financial. I am a registered investment advisor, investment advisor representative with Advisory Alpha LLC. Advisory LLC and Ideas by Mike doing business as One Oak Financial are separate and unrelated entities. Please consult with tax professionals before implementing tax strategies. Um, and we look forward to seeing you again on the One of a Kind Financial Show Daily.

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