In this episode of the One of a Kind Financial Show, host Mike Milligan (joined by co‑host Gary Nolan) breaks down practical tax‑planning concepts for listeners. The conversation starts with a listener’s question about filing a tax extension, emphasizing that an extension is a tool for timing, not a pause on planning, and that getting the return right (including K‑1s and tuition statements) is crucial. They discuss how unexpected tax liabilities signal a lack of coordination between income withdrawals and tax strategy, and they urge listeners to use the extension period to adjust their plans. The hosts then move to Roth conversions, advising that many retirees could benefit but should consider income level, tax bracket, and long‑term goals, and that conversions should be done strategically rather than all at once. They stress that tax planning is an ongoing process that can still make a difference for the 2025 and 2026 tax years. Throughout, they repeatedly promote One Oak Financial’s “One‑of‑a‑Kind Financial Plan,” a two‑meeting, customized plan that maps assets, creates a comparative report, and evolves with the client’s life. Mike announces a joint venture with Tax Reduction Strategies (led by Joshua Stroud) to provide defensible, code‑based tax solutions for 2026, and provides multiple calls‑to‑action: call 800‑748‑1838, text “ideas” to 600‑700, visit oneoakfinancial.com, or comment “taxes” on the podcast. The episode ends with standard disclosures about advisory status and the informational nature of the content.
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It's the One of a Kind Financial Show Daily. I'm your host, Mike Milligan, and it's Friday. Everyone talks about tax strategy, but what does that actually mean? Today we're going to break down what a real tax plan looks like, and we're going to take the words or the theory of tax strategy and just tell you what it really means. In a simple, easy-to-understand format. Enjoy this conversation from me and Gary that we had on the One of a Kind Financial Show over this past weekend.
So, here's our first question. This person filed an extension, Mike. So, I'm about to file. Should I get it done and worry about planning later?
You know, this is an interesting question because, you know, Gary, my family still lives all in Virginia. And right now, in my family, I have— and I count my family as both my mother who's still living and my kids and even my ex-spouse is that we're all family because we're all part of raising a generation of kids. But I actually got a text very similar to this from my ex, and it basically said, I need to file an extension. How do I do it?
Yeah.
Well, filing the return is important, but getting the return right is just as important. So because there are some things that drag, right? So like K-1s, Because of corporations maybe extending their tax returns, you don't get a K-1 on time. Maybe, like in the case of my family, we were missing a 1098-T, which is the tuition statement for my daughter who's in college. But getting it right is more important. That's why the federal government put in extension timelines. You know, like an extension, and you can file an extension many ways, like this person did. But that extension can be done by paper form, it can be done electronically, but now is the time to start planning with that extension, because the best time to finish this up and get it to the finish line is when the numbers are fresh. That extension doesn't give you a 5-month respite just to then build the stress back up again. So now, instead of moving on and putting it aside, you should just go on, lean in, and finish it up.
Yeah, let's do it now while you got the opportunity. You're fortunate enough to get the extension, but let's take advantage of it. Let's not wait another 4 and a half months to get started. I owed more than I expected. What does that tell me, Mike?
It usually signals a lack of coordination between income withdrawals and tax strategy. It's not just about what happened. It's about what can be adjusted moving forward. See, that's— that surprise is actually useful. Because isn't the real question, or shouldn't our question be, how do we prevent this from happening again? And so this is where we look and we talk about, come on in, schedule a time with us. And by scheduling a time with us, we can make sure you're taken care of where the surprise doesn't come back at you.
Yeah, you don't want this to happen. I mean, one time is okay, but you don't want to repeat the same thing over and over again, Mike. Am I right?
That's correct.
Yeah, absolutely. The show is the One of a Kind Financial Show with Mike Milligan. I'm Gary Nolan, your host. That phone number is 800-748-1838, 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. Let's get you 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, the fact of the matter is that Mike and the team cannot help you Unless you pick up the phone and dial that number, 800-748-1838, or text the word ideas to 600-700. Should I be thinking about Roth conversions this year? What do you think?
For many retirees, that answer is yes, but it depends on your income, tax bracket, and long-term goals. The key is doing it strategically, not all at once. And so this is where planning really becomes essential.
All right, final question, Mike. We got about 3, 4 minutes left. Is it too late to make a difference this year?
And this year being 2025, if you're talking about tax year '25, yes. But if you're talking about 2026, the answer is no, because tax strategy is one that we can really dive into right now. Like, if you've listened to the show, maybe tuned us out, I would invite you now to listen To the next minute or so, 90 seconds. You pay too much in tax. You have let taxes happen to you versus planning them out. There's some number, and I could show you on your tax return where if you were to schedule a time with me, you bring it in. I could show you on your tax return where you had a miss strategy.
Where?
It's not perfect. And by the way, if somebody were to look at my clients' tax returns, they could see some possible myths, but not many. Because if you were to bring your tax return in, bring in your statements, and let's create the one-of-a-kind financial plan, we're going to take care of the biggest expense you have in your life, and that is taxes. And if we can help reduce those by 4% to 12%, isn't that worth working with a firm that helps you reduce real numbers? So if your tax liability was $15,000 this year and we could get it down to $10,000, isn't that a powerful testament to what tax planning can do? And so yes, we have a chance to make a difference this year in the 2026 tax returns. And Gary, I'd love to be able to get people into the office to do that. Do you know any way that they can get to our office?
Yeah. Absolutely. They can pick up the phone, they can call this number, 800-748-1838, 800-748-1838, or text the word ideas to 600-700. That's ideas to 600-700. Mike, we've got about a minute left. Tell us a little bit more about the one-of-a-kind financial plan.
Uh, we can do, like, uh, for you, our listeners, uh, we can build a one-of-a-kind financial plan in about 2 meetings. Together. And so, most people, whenever you think of one of a kind, they think about like the pyramids or maybe the Taj Mahal that was built over centuries and centuries of time. The thing about the one of a kind financial plan is we can build it in about 2 meetings together, because it's not complicated if you have a clear vision for what your life is. Because we take your statements, maybe their statements are in a shoebox or stored electronically behind a password. On your phone or computer. We could take those statements, we can analyze them behind the scenes by building an asset map and creating a comparative report on your analysis. And when we bring it together, when we have your vision, when we have your resources, we can put a plan together that's the beginning of that one-of-a-kind life. Because that plan, when done, it evolves, it's dynamic, it's living.
Yeah.
just like you are, because we want you to be able to take those one-of-a-kind trips. We want you to spend those magical moments with your grandkids. We want you to be able to take care of those you love the most. And so the One of a Kind Financial Plan is built for you, those who are living a one-of-a-kind life. And that's what we do every day. We build those at One Oak Financial for our clients.
All right. One more time on the phone number before we wrap up today's show. 800-748-1838, or text the word ideas to 600-700.
That has been a segment from the One of a Kind Financial Show with Gary and I. Um, I promised you that, um, for your taxes, One Oak Financial and me, Mike Milligan, wanted to offer you something. We have recently partnered with Tax Reduction Strategies, an independent tax planning firm that we are joint venturing with based out of Oregon. Joshua Stroud and his team have helped dozens of our clients already, and we have a goal of helping hundreds, if not 1,000 clients in our partnership bring real tax solutions from the tax code that's defensible with I's dotted and T's crossed in the year 2026. If taxes are a struggle for you, I, um, because you've listened to us and you realize taxes are the biggest expense you have in your life, I encourage you to reach out to us at One Oak Financial, www.oneoakfinancial.com. That's the number one, oakfinancial.com. Or comment in this podcast with the simple word taxes, and we will find a way to reach out to you. This has been Mike Milligan for the One of a Kind Financial Show Daily. 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 based in Norfolk, Virginia.
We are an unaffiliated entity of Advisory Alpha LLC. This podcast is done for informational purposes only. And, um, before you execute any strategies, either reach out to our firm Or meet with a licensed fiduciary financial professional. Until next time, be one of a kind.
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