In this episode of the One of a Kind Financial Show Daily, host Mike Milligan, joined by Gary Nolan, walks listeners through five common retirement pitfalls and offers concrete fixes. The first mistake, the "tax time bomb," stems from loading traditional 401(k) and IRA balances without Roth conversions, leading to large required minimum distributions (RMDs), higher Medicare premiums, and a tax shock in later years; the remedy is to start Roth conversions while tax rates are favorable. The second mistake, the "overallocator," describes retirees who chase returns by holding too many overlapping funds, especially in niche sectors like international small‑caps; the solution is a purpose‑aligned, simplified portfolio that reduces fees and risk. The third mistake, the "match ignorer," highlights the habit of neglecting employer 401(k) matching contributions, effectively leaving a guaranteed 100% return on the table; listeners are urged to set calendar reminders to increase contributions and capture the match. The fourth mistake, the "home‑equity hermit," points out retirees who are "house‑rich, cash‑poor" and avoid tapping home equity; the fix is to consider reverse mortgages, downsizing, or a well‑structured home‑equity line of credit to access funds strategically. The final mistake, the "spreadsheet Spartacus," warns against over‑reliance on complex withdrawal models that ignore personal joy and life goals; the advice is to review plans annually, prioritize happiness, and treat retirement as a life project, not just a math problem. Throughout, Milligan promotes One Oak Financial’s “one‑of‑a‑kind” planning system, his bestselling book, and a personal‑financial‑planning course offered through Old Dominion University, while providing contact information for listeners to get personalized help. The segment ends with standard disclaimer language.
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Be one of a kind with Mike's plan.
Welcome to the One of a Kind Financial Show Daily with your host, Mike Milligan. It is Thursday, November 20th, one week before Thanksgiving. Folks, I am so thankful for you listening to the One of a Kind Financial Show Daily and the One of a Kind Financial Show that airs on the radio on the weekend. I just wanted— I want you to know that today. Uh, recently on the One of a Kind Financial Show, Gary and I talked about 5 retirement mistakes nobody wants to make. Nobody wants to see their retirement go into the garbage, right? They want to know that they're going to be taken care of from all of their years of hard work. And so nobody wants a retirement plan that is not built around them. So enjoy this segment from the One of a Kind Financial Show from this past weekend. And as always, be one of a kind.
Nobody plans to mess up their retirement, but it happens. Sometimes it's a timing issue. Sometimes it's a tax thing, and sometimes because Uncle Larry says just buy dividend stocks, you'll be fine. Well, thanks, Larry. Uh, today we're having some fun. We're digging into some 5 real mistakes that trip up people on the path to and through retirement. The good news, every one of these is fixable, Mike, if you catch them in time. Here's the first one. This is a big one too, because you talk about taxes all the time. The tax time bomb.
It— most people say, I'll pay taxes later and later, and they wait And why is my Medicare premium so high? That's what happens, like, when they come into me when they're 78, 79, 84 years old. If you're stuffing every dollar into a traditional 401 or IRA with zero Roth strategy, you're basically saying, let future me deal with it. That's fine until future you hits 73 and RMDs show up with a side of tax shock. And higher Medicare costs. So how do we fix that? We need to start mixing in Roth conversions now. So you trust me, you're 8— the 80-year-old version of yourself is going to thank the 67-year-old version of you who paid some taxes. And so think of it like paying the tax toll while rates are still on sale versus just waiting and waiting and waiting. So, uh, so go ahead, think about yourself 10 years from now and just go ahead and do some conversions. Because if you do them now, that version of you is going to say, thank you.
Yep. The overallocator. What do we mean by that?
I'm 70% in international small-cap funds because, well, it sounded cool. You know, people, people often look at, look at their allocation as like somewhat of a play. Let me chase returns. And by the way, guys, if you looked at for 2025, what has been the best performing sector in the market, you'd probably go out and buy international small caps or international large caps, right?
Right.
But chasing returns has never been a successful strategy in the market. Diversification is good. Chaos is not. Some retirees are in so many mutual funds, they basically own the entire stock market. And many times, The same stock in 10, 12, 14, 18 different funds with overlapping fees, mismatch risk, and no clear strategy. So how do you fix that? Simply, you don't need 27 funds. You need a purpose-aligned allocation. Bonus, if you have a simple portfolio, it makes it easier to sleep and explain your strategy to your spouse when the market starts going down.
Yeah, we're talking about 5 real mistakes that people make and trip them up as they head into retirement or maybe in retirement already. The match ignorer.
So, yep, I never did get around to upping my 401 contributions. That's what people say. I hear that daily from 30, 40, and 50-year-olds, right, when we talk to them, because, you know, they just forget. They're busy with kids and all that. And there's so many people in retirement now that forgot to do it there too. When you leave employer matching dollars on the table, it's like saying no thank you to 100% return on your money. Have you ever, have you ever been to a restaurant, Gary, and the waiter or waitress said, hey, today I'm not accepting tips. You've never heard them say that.
No, never heard that. Never heard them.
Leaving 401 matching contributions on the calendar is like that waiter saying, no thank you on the tips today. So set a calendar reminder. If you're still working, set a calendar reminder every January. And it simply says, increase 401 contributions by 1% if budget allows. Call it your future raise or your anti- Yeah, anti-regret button.
I like that a lot. The show is the One of a Kind Financial Show with Mike Milligan. I'm Gary Nolan, your consumer advocate. Let's get you on the calendar all set up with that comprehensive plan, with that one of a kind financial plan that Mike talks about. It starts by picking up the phone and dial this number: 800-748-1838. 800-748-1838. Or text the word IDEAS to 600-700. Let's see, uh, we got through the overallocator, we got through the time Tax bomb, the match ignorer. How about the home equity hermit?
I'm house rich, cash poor, and the eating tuna out of a can to avoid touching my equity person, right? There's nothing wrong. There's nothing wrong, guys, with eating tuna out of a can. I like it. It's high in protein.
Yes.
But listen, your home can be a powerful asset in retirement, but too many people treat it like a financial museum. It's nice to look at, but never to touch. How do you fix it? Guys, do not stop listening to the show when I say this. You fix it with a reverse mortgage or downsizing or a well-structured home equity line of credit where you can ask— access your equity smartly. Could you imagine when the stock market was down this year by 20% in March, if you had a home equity line where you could have put $50,000 back into that Market down 20%, and from now it's up 30% from then. That $50,000 would've become $65,000. That's how you be— that's how you can be smart about the equity in your home. We encourage all retired people that are heading to retirees, get a home equity line of credit before you retire. While you still have income, qualify. And if you never use it, you'll still be thankful that it's there.
I bet you have guys that come in the office with this, the spreadsheet Spartacus. They have a 37-tab Excel sheet, right?
And 14-point withdrawal strategy and absolutely no idea what brings them joy. Spreadsheets, guys, it is so hard to put happiness on a spreadsheet, right? It's impossible. Now, spreadsheets can bring you comfort by knowing there's money there. But I would love to see a spreadsheet 5 years from now that's 100% accurate to reality. Planning is critical, but your retirement is not a math project. It's your life. The goal is not to optimize every dollar. It's to live well. It's to give well in each— and at the end of each year, feeling like you stewarded your time, money, and purpose wisely. So once a year, revisit your plan and ask, Is this helping me live the life I want? If not, adjust. Even the best spreadsheet can't tell you what matters most.
Mm-hmm. Yeah.
And Mike and the team will help you with year-end reviews, and they review your accounts as often as you'd like to. All right. We're up against the clock, Mike. Final thoughts?
Well, retirement planning doesn't have to be perfect, just intentional. If any of these mistakes made you laugh, and I hope they did, or even wince, it might be time to reach out to us. One Oak Financial exists to build one-of-a-kind financial plans. Our system is unique in the market because it addresses the 5 things that are most important: taxes, retirement income, investments, long-term care, and legacy. And guys, I'll just leave you with this. The plans of the diligent lead surely to abundance. This doesn't mean that the plan has to be fancy. It just needs to be faithful. Let's build your one-of-a-kind financial plan together.
All right, let's do it. Let's do it right now. Let's get you on the phone, get you all set up with that comprehensive plan. With the one-of-a-kind financial plan, starts by dialing this number: 800-748-1838. 800-748-1838. Or text the word IDEAS to 600-700. Do it right now. The folks at One Oak Financial and Ideas by Mike standing by, ready for your phone call.
Thank you again for listening to the One of a Kind Financial Show Daily. I've been your host, Mike Milligan. If you If you enjoyed the segment that you just listened to, I invite you to connect with us on Amazon. Google The One of a Kind Financial Plan. It's a bestselling book in the personal tax category, and I invite you to do that. Number 2, if you feel like you need more education when it comes to your own personal financial planning, we have a course that's offered through Old Dominion University in Norfolk, Virginia. It's offered virtually, and it's a self-paced course called Personal Financial Planning that I helped develop and I teach. It is 6 sessions, 90 minutes each, and full of recordings for you that you can start and stop based on what you need. It goes through the psychology and philosophy of money, the cash management, budgeting, and debt management. We talk about insurance, whether it's property and casualty, like your homeowners, autos, renters, to the type of insurances you work on at, or you need to replace the biggest asset you have, which is your income. Then we move over and talk about— do a real big investment dive into the difference between mutual funds and ETFs. We go all the way from crypto down to individual stocks and bonds from an academic standpoint.
Then we look at retirement planning, Tax planning, long-term care, and legacy.
Ultimately, with the idea that you can build a one-of-a-kind financial plan for yourself. Ultimately though, what it does is it equips you with knowledge that if you're ever in a conversation with a financial advisor or a financial planner, you know the questions to ask. So I invite you to reach out to us. You can go to mikemilligan.com under the Educate tab and see how to register for that. We also put some resources behind that on school.com in our private closed group where you can ask questions and learn more. As always, just remember that I am an investment advisory rep, not only with One Oak Financial, but also Advisory Alpha LLC. Ideas by Mike, doing business as One Oak Financial, Mike Milligan LLC, and Advisory Alpha LLC are unaffiliated entities. And thus, all opinions expressed by me and Gary on the One of a Kind Financial Show and me on the One of a Kind Financial Show Daily are purely my opinions and does not reflect investment advice. Please consult with a licensed financial professional before making any decisions. Till next time, this has been Mike Milligan.
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. Mike's the guide. You'll shine bright.
