In this episode of the One of a Kind Financial Show Daily (December 23, 2025), host Mike Milligan and co‑host Gary Nolan launch a two‑part series on the seven common retirement “traps” that derail retirees, focusing on the first two: (1) assuming you can “wing it” without a written, stress‑tested plan, and (2) cashing out retirement accounts at the wrong time. They explain why informal spreadsheets or back‑of‑the‑napkin calculations miss critical risks such as market volatility, inflation, longevity, tax, and emotional decision‑making. The conversation then outlines what a true retirement plan should contain—tax strategy, retirement income strategy, investment strategy, long‑term care/healthcare plan, and legacy plan—emphasizing that a written plan improves adherence and outcomes. They discuss smart rollover tactics from 401(k) to IRA, highlighting tax‑free rollovers and penalty avoidance. Throughout, they promote the “One of a Kind Financial Plan,” a personalized, written plan designed to lower taxes, secure income, manage investments, address long‑term care, and create a legacy, with a no‑cost, no‑obligation call‑to‑action (800‑748‑1838 or text IDEAS to 600‑700). The episode ends with standard educational disclaimer and affiliation disclosures.
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Be one of a kind with Mike's Plan.
Welcome to the One of a Kind Financial Show Daily. This is Tuesday, December 23rd. Just, uh, everyone's getting excited. Hopefully the cookies are being made for Christmas Eve night. I was earlier watching Nate Barnett's— I hope I'm saying this right— comedian skit about what Christmas has become versus the birth of Jesus, Santa Claus, and snow. If you've never seen that before, I invite you to Google Nate Barnett's— if I'm pronouncing I'm pronouncing his name right. Comedian Christmas songs. It is hilarious. But one of my other favorite Christmas movies is, remember The Kid Left Home for Christmas? What a— it just, you know, he created traps for the people that were coming into his home around Christmas time. And, uh, we like to avoid traps at all points, at all times. Uh, on the One of a Kind Financial Show, uh, Gary and I talked about some retirement traps recently. See, most retirees don't lose sleep over financial disasters. They worry about the unknowns. One of the biggest threats to your retirement isn't a crash or a crisis. It's a mistake you didn't even realize you were making. We are going to address that next on this episode of the One of a Kind Financial Show Daily.
Retirement planning takes decades, but one wrong move can undo years of progress. And we're not just talking about bad luck. Most retirement derailing moments come from preventable mistakes like winging it without a plan, cashing out at the wrong time, or relying too heavily on tax-deferred accounts. Now, here's what we're going to do. Today's show, we're going to kick off a 2-part series on 7 common traps that trip up retirees, inspired by a recent Forbes article. And I'm going to break down why these mistakes happen, what to do instead, and how to bulletproof your retirement before life or inertia gets in the way. Here's the first trap, Mike: assuming you can wing it. Why so many people think they can enter retirement without a clear plan? I don't understand why they would do that.
Well, it seems counterintuitive, but even high earners and diligent savers often retire without a written, stress-tested income strategy. So many people skip this step because it's not really about winging it. It's just they think that their spreadsheet will work. And so many people either use a back of the napkin or a spreadsheet mentality for doing this. But it overlooks things like market volatility, inflation, longevity risk, mortality risk, tax risk, and so many other things that come up.
Yeah. So what does a real retirement plan include? I mean, it's not just a portfolio statement, Mike.
So often, right, most people will come into the office, Gary, or we'll talk on the phone and they'll say, well, I have a financial planner. And when I ask what the financial planner does, they'll say they manage my investments for me.
That's not the same thing.
It's not the same thing. Financial planning is, what is your tax strategy? What is your retirement income strategy? What is your investment strategy? What is your long-term care and healthcare plan? And what is your legacy strategy? See, a real retirement plan includes all of that. It's more than just return on investment. It's about forecasting expenses, modeling income, stress testing for downside markets, putting guardrails on your account. And so most people try to do this on their own, but by doing it on your own, you leave something on the table that is, that is, that is, that can derail a plan. And that what you leave on the table is emotional decision-making. See, if you have a professional on your side, we take the emotions out of it. We let the— we let the numbers dictate where we're going. We let the plan dictate it. And so, you know, a real retirement plan really is more than just investments.
Absolutely. The show is the One of a Kind Financial Show. I want you to get that one of a kind financial plan that Mike is going to talk about in just a few minutes. Let's get you on the calendar, all set up with that comprehensive plan. Here's the beauty of this whole thing: there's no cost, there's no obligation. 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 weekend during the holiday season, ready for your phone call.
800-748-1838.
Or text the word ideas to 600-700. Do it right now while you're thinking about it. The slots do fill up quickly during the show. Trap number 2, cashing out retirement accounts. Now, this one sounds simple until it's, it's too late. Then you got a real big problem on your hands, Mike.
Yeah. And this one is something that impacts retirees, but also non-retirees, people that are still in the workforce. Many people cash out old 401s when they change jobs, or they take a lump sum distribution for short-term needs. And they don't realize what the tax and the penalty implications really are. You know, a better strategy, uh, is that we coach people on is how to build an emergency fund or how to tap into things like home equity for short-term needs. And so that your long-term money can continue to grow.
And if you're under 59 and a half, you're going to pay penalties on those withdrawals too, right, Mike?
That is correct. Now, there's one exception to that. Like if you actually quit your job and you take it from your retirement plan after the age of 55, and then there's a couple of hardship provisions in there. But generally speaking, guys, a 10% penalty does occur for distributions taken from 401s before You are 59 and a half years old.
So what does a smart rollover process look like?
So it's, you know, it's not just roll it over. There's certain things you have to look like. So a smart process looks like, yes, taking that money that was— that's in that 401 that has limited investment options, fees that are often undisclosed, and rolling into an IRA where you have more options, more selections on fee, actually get the investments that will satisfy their plan needs. But when you go from that 401 to that traditional IRA or Roth IRA, if your 401 is Roth, that's a tax-free event. Most people don't realize that. They think that if I'm moving from one account to another, that it's actually, I'm going to pay some taxes. But if you do the rollover the right way, it's tax-free.
All right, up against the clock, Mike. Tell us about the One of a Kind Financial Plan.
Yeah, these have been great questions and traps here, Gary. The One of a Kind Financial Plan is a written-for-you plan that actually addresses taxes, retirement income, investments, long-term care, and legacy. Well, why do we write things down? Because statistics prove that things that are written down are more easy to follow than things that just stay in your head. Goals written down, purpose written down on sheets, Right, are easy to accomplish. And what financial, uh, the, you know, people who follow financial journals show, when you work with an advisor, you have a higher chance of success. So the One of a Kind Financial Plan is built for us, for you, to lower taxes, get the income you need to reduce fear and anxiety, investment plans that are, that have worthy fees and risk allocations for you, a long-term care plan where the younger version of you takes care of the older version of you, and finally, a legacy plan that says, I love you. Guys, we, we build these for people because we want you to have peace of mind that you're not falling into traps when it comes to your retirement. Gary, tell people how they can reach out. And by the way, guys, when Gary gives you this number today, I'm answering the calls on the other end of the line today. So I can't wait to talk to you.
All right. Mike's going to talk to you personally today. 800-748-1838. 800-748-1838. Or text the word IDEAS to 600-700.
Thank you for listening.
Thank you for listening to this episode of the One of a Kind Financial Show Daily. This is for educational purposes only. Any comments that Mike Milligan and Gary Nolan make on the One of a Kind Financial Show are those, the express thoughts of them, and should not be construed as recommendations from Advisory Alpha LLC. Mike is an investment advisory rep with Advisory Alpha LLC. Ideas by Mike, doing business as One Oak Financial, is an insurance agency educational platform and is unaffiliated with Advisory Alpha.
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