Avoid These Retirement Tax Mistakes

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It's the One of a Kind Financial Show Daily, and I'm your host, Mike Milligan. It's Thursday, April 23rd. The hidden cost of doing nothing after tax season is tremendous. Filing your taxes might feel like you've hit the finish line, but what if doing nothing afterwards is actually costing you more than you realize? Gary and I had a freestyle conversation on this over the— over this weekend on the One of a Kind Financial Show that I think you'll find mentally stimulating and fiscally appropriate at this time. And so enjoy this conversation. And at the end of this, I want to give you a few opportunities to connect with us.

So Mike, we use the term tax strategy quite a bit today. And I think for a lot of people, it sounds a little abstract. It sounds important, but also a little unclear. So, Mike, let's simplify this. When you say tax strategy, what does it actually look like in practice?

Well, it's a great question because you're right, Gary. Tax strategy can sound complex, but at its core, it's really about being intentional with how and when income is recognized over time. And typically, it starts with understanding 3 key areas. your current income and tax bracket, where your assets are held, such as are they in taxable, tax-deferred, or tax-free accounts, and how those pieces interact over time. From there, you can begin building a strategy that's coordinated, not just reactive.

So instead of just looking at this year, you're looking at the big picture, the bigger picture, aren't you, Mike?

Yeah, because focusing only on one year can sometimes lead to decisions that look good in the short term, but may not be as effective over the long term. A strategy looks at this year, next year, and several years down the road and asks, how do we manage income across that timeline as efficiently as possible?

So let's break this down step by step. What would the process actually look like, Mike?

So a simple way to think about it is in a 4-step system. So step 1 is to understand your current position. This includes the income sources that you have, the tax bracket you're in, and the deductions and credits that you qualify for. This is where your tax return becomes valuable because it provides that data. Step 2 is to identify opportunities within your current tax bracket. So we talked about filling up the bucket in an earlier segment, but most people fall within the top and the lower ends of a bracket. And they don't ever realize that maybe they just accidentally went over the bracket or they have a lot of room to get to the top. So, this is where this strategy brings things like partial Roth conversions, capital gain management, or income adjustments into play, depending on the individual situation. The goal here isn't to eliminate taxes entirely, but to be thoughtful about when they're paid. So after we— step 1, understand your current position. Step 2, identify opportunities within your current bracket. Step 3 is about coordinate your income sources. Uh, before I go on to step 3 and 4, Gary, do you want to tell everybody how they can reach out and contact us?

Yeah, absolutely, Mike. This sounds like a plan. Let's do it right now. You want to pick up the phone, you want to dial this number: 800-748-1838. 800-748-1838. Or text the word ideas to 600-700- The show is the One of a Kind Financial Show with Mike Milligan. Mike is with One Oak Financial. One more time on the phone number, get ahold of Mike and the team that can help you through all these tax strategies that we've been talking about this entire show. 800-748-1838 or text the word ideas to 600-700. What's step 3, Mike?

That's coordinating your income sources. Thanks for giving that phone number, Gary, by the way. It allowed me to wet my throat a little bit. So step 3 is to coordinate income sources. This is where planning becomes more dynamic. For example, which accounts are being used for withdrawals? How do those withdrawals impact taxation on Social Security, and could they affect your Medicare premiums? See, these decisions don't exist in isolation. They interact. And then step 4 is to revisit and adjust annually because things change. Tax laws evolve, just like the one big beautiful bill in 2025. Incomes fluctuate and goals shift. A strategy isn't something you set once. It's something you refine over time.

So it actually makes us feel, you know, more approachable. It's not just one big complicated move. It's kind of a whole process, isn't it, Mike?

It's important to emphasize this isn't about finding a perfect strategy or predicting future tax rate increases. It's about making informed decisions based on what we know today while staying flexible for what may change. Because ultimately, tax planning is just one piece of a broader financial plan.

And I think that's where people get stuck. They hear these different strategies, and they aren't sure if it applies to them, Mike.

Well, that's very common, because not every strategy is appropriate for every person. What matters is your goals, your timeline, your income needs. That's what determines how these pieces come together. So instead of asking, what's the best strategy, the better question is, what strategy fits my situation?

And that's really where it comes down to, and to understand how these concepts apply to your specific situation, not just in theory, Mike.

And for, yeah, for those listening today, this is where a thoughtful conversation can bring clarity. Not to implement anything immediately, but to walk you through like what your current tax picture looks like, what opportunities may exist, and how those decisions align with your overall plan. Because when you understand the structure behind a strategy, It becomes much easier to make confident, informed decisions over time.

Yep. Uncle Sam, the biggest partner that you have. Am I right, Mike?

And it's why I get the opportunity to write another book called The Partner You Never Knew You Had. And so, I'm looking forward to talking more about that on the show in the coming weeks. But Gary, I'd love to tell everybody about the One of a Kind Financial Plan.

Yeah. Why don't you do that, Mike? We have a minute or two left. Tell everybody about that. Yeah.

The One of a Kind Financial Plan addresses these tax Tax strategies that we have described in a step-by-step process. Because you guys probably believe that taxes are complicated. You've been made to feel that way. But one of the things that One Oak Financial and I do is we make the complicated simple. And we're going to create step-by-step processes, just like I've outlined here for tax strategy, that You know, over your lifetime, over the rest of your life and into your beneficiary's life, we pay Uncle Sam and the state where you live less income tax than you would have without a tax strategy. We're going to create a retirement income plan to give you more money to live on that's adjusted for inflation as things get more expensive, an investment plan that helps you sleep at night. Where you don't worry about the next conflict or the next crisis that comes. A long-term care plan that takes care of you when you're at your most fragile. And a legacy plan that says, I love you, to the next generation. So, we build the one-of-a-kind financial plan for our listeners, for those who trust us to manage their finances, because you are unique, you are one of a kind, and a one-of-a-kind life deserves a one-of-a-kind financial plan.

And that's why we want to give our listeners the opportunity to review their individual plans for retirement. Folks, you could find out if there's any potential red flags that could cause problems for you down the line with your current plan or advisor. Now here's the deal. We want to make this accessible for you. So we're offering this consultation at no cost or no obligation. That phone number is 800-748-1838, 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. I promised you that 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, 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 before you execute any strategies, either reach out to our firm or meet with a licensed fiduciary financial Uh, profession. Until next time, be one of a kind.

Be one of a kind with Mike's plan. In a face shot growth, take a stand. Visibility, strategy, take that lead. Transformation's yours, fulfill the need. Mike's got the way to help you rise and stay. Leadership impact you'll find in your one of a kind mind. Be one of a kind. Take the flight. Ooh, ooh, ooh. Mike's the guide. You'll shine bright.