In this episode of the One of a Kind Financial Show Daily, host Mike Milligan and co‑host Gary Nolan discuss the evolving financial landscape for seniors heading into 2026. They begin by highlighting increased life expectancy—today’s 65‑year‑olds can expect to live to 85 or beyond—requiring retirement portfolios to sustain 25‑30 years of income. The duo explains that Social Security, which on average replaces about 40% of pre‑retirement earnings, is not designed to be the primary income source and faces solvency challenges, with trustees projecting trust‑fund depletion by 2034 unless Congress intervenes. They then turn to Medicare, noting its premiums, deductibles, copays, and lack of coverage for dental, vision, hearing, and long‑term care, and cite Fidelity’s estimate that a typical 65‑year‑old couple will need $315,000 (in today’s dollars) for healthcare in retirement. Inflation is addressed both as CPI‑driven cost‑of‑living adjustments and as lifestyle inflation affecting travel, utilities, insurance, and tuition. The hosts identify commonly overlooked retirement components for high‑net‑worth individuals: tax drag, required minimum distributions, Roth conversion windows, and long‑term‑care contingencies. They introduce the “One of a Kind Financial Plan,” a comprehensive framework that includes vision setting, tax management, guaranteed lifetime income, fee‑aware investment strategy, long‑term‑care planning, and legacy planning. Throughout the segment, listeners are invited to obtain a recorded webinar on Social Security maximization, purchase Milligan’s bestselling book, enroll in a personal‑financial‑planning course offered through Old Dominion University, and contact One Oak Financial via phone or text. The episode concludes with a standard disclaimer that Milligan’s remarks are personal opinions, not investment advice, and advises consulting a licensed professional.
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Welcome to the One of a Kind Financial Show Daily with your host, Mike Milligan. It is Tuesday, November 18th. This past weekend on the One of a Kind Financial Show, Gary and I talked about Social Security, Medicare, and changes that seniors need to know heading into the, into 2026. We spoke about 4 or 5 of those changes that are coming down the road, but we also want to offer you something. We have a webinar presentation called Social Security Maximization that we typically do live, but I recorded it a couple weeks ago, a studio in Houston, Texas, because I think it's valuable that we get this information out before these changes occur so people know what to expect. So if you want a copy of that webinar, all you have to do is text the word NEWS, N-E-W-S, to 600-700 or follow the prompts that Gary mentions in, in the segment that comes next. Enjoy this segment from the One of a Kind Financial Show.
And as I'll Let's start with the big assumption. How many years of income are really planned for retirement? Some people are still working in a 15-year horizon, but today's retirees are living longer than ever. So how do you shape that plan? How do you reshape that plan?
Well, life expectancy has climbed tremendously. Over the last couple of years. I mean, like really over the last decades to nearly 85 years old for today's 65-year-olds. For many, 90+ is well within reach. That means your portfolio should be on the hook for providing 25 to 30 years of income. I mean, that's insane when you think about only having worked 30 or 40 years. So if you're only planning for 10 to 20 years, you might run short, not because you overspent, but because you just outlived your math.
Yeah, absolutely. Many folks, I don't know why this is true, think they can rely on Social Security. May not be wise. So how should people rethink the role of Social Security in their retirement income plan?
Well, Social Security was never meant to carry your entire retirement. On average, it replaces about 40% of your pre-retirement earnings. And the replacement rate is lower for high earners. And the program's own trustees project the combined trust funds could be exhausted by 2034. At which point continuing payroll income, the amount that workers pay into the plan, will only cover about 81% of scheduled benefits unless Congress acts. That's why Social Security should be treated as a supplement, not the foundation of your retirement plan.
What do you think is going to happen if you had a crystal ball, Mike, and looking ahead to 2034, what do you think is going to happen?
I think the— I think Congress will create new tax revenue to be able to to fund Social Security. The voting bloc, which is senior citizens, are some of the most loyal voters, and they're the ones who show up for the issues. If they're in a nursing home or even an assisted living, they'll get bussed down to the voting precinct. And even now, senior voting has been made so much easier because many states allow for seniors to come early.
What?
So they can avoid the lines. So I think because seniors show up to vote no matter the weather, no matter the situation, uh, House of Reps and senators are going to take note of that and they're going to make sure they are taken care of. Which, by the way, they should be taken care of, Gary. They have funded Social Security for the last 30 or 40 years of their working. Why should they have to take a reduced benefit now?
Yeah, absolutely. No question about that. Well, healthcare is another area where assumptions go sideways. Many believe Medicare We'll cover everything. But that's— Medicare doesn't cover everything, Mike. That's not the case.
It's not even close. Medicare comes with premiums, deductibles, and copays. All of that is money out of your pocket, and it doesn't cover dental, vision, hearing aids, or long-term care. Fidelity now estimates the average 65-year-old couple will need $315,000 in today's dollars to cover healthcare expenses in retirement. That number surprises people, and it should.
Yeah, there's no question about that. That is an awful lot of money. The show is the One of a Kind Financial Show. I'm Gary Nolan. With us each week at this time is Mike Milligan. I want you to get on Mike's calendar, get you all set up with that comprehensive plan. There's no cost, there's no obligation. So what are you waiting for? The folks at Ideas by Mike and One Oak Financial standing by ready for your phone call. 800-748-1838. 800-748-1838.
800-748-1838.
Or you could text the word ideas to 600-700. So costs are going— likely to be higher and coverage lower than expected. How can retirees prepare for healthcare expenses?
Well, health savings accounts are powerful tools for those still eligible. Contributions are tax deductible, growth is tax-free, and withdrawals for medical costs are tax-free also. Even without an HSA, earmarking a portion of your IRA or 401 specifically for future medical costs can provide a buffer, buffer and peace of mind.
All right. We haven't talked about inflation yet and we're 5 minutes into the show. What's the matter with us? Okay. We're not just talking about CPI. We're talking about lifestyle inflation. How do retirees protect themselves from rising costs?
Well, CPI is what happens to like cost of living adjustments for your income. But inflation isn't just about groceries. It's about travel, utilities, Insurance, and even grandkids' tuition support all climb over time. A plan doesn't account for a 3% plus inflation rate, or one that assumes you'll spend less in retirement, will leave you constrained just when you want the most freedom.
A couple of minutes left, Mike, in segment number 1. Sometimes the problem isn't with the plan, it's what's missing. What are some commonly overlooked pieces that high net worth individuals need to factor into their retirement strategies?
Gary, that's a great Great question. Tax drag. Tax drag is the amount of money that you lose out of your income because of increase in taxes, either through income tax brackets going higher or IRMAA premiums going higher. Required minimum distributions, Roth conversion windows, missing that is a problem. Long-term care contingencies, meaning you have not saved for the costs that are sure to come if you live long enough.
Yeah, Mike's gonna put that plan together, that One of a Kind Financial Plan. Mike, tell us about that.
So the One of a Kind Financial Plan is something that I wrote the book on. That book talks about how you have to build a vision for what your retirement is going to be. Without a vision, you don't have a purpose, and the purpose then leads on to the actual plan itself. How can we manage taxes over your life to pay as little as possible? How can we create a retirement income plan that you cannot outlive? Gary, it's been proven that people who have guaranteed lifetime income live longer than those who have stress and fear from worrying about taking withdrawals from their account. Then we're going to deal with market risk by creating an investment plan that where you pay only the fees that are needed and put risk time horizon, and your tolerance at the forefront. In other words, allows you to sleep at night. We're going to put a long-term care plan in place that takes care of the older version of you, because the only person you can count on to take care of that older version of you is this version of you. And then finally, we're going to put a legacy plan in place that, yes, it is a will and trust, folks, but at the end of it, it's an I love you letter to your family saying that I have left this organized enough so you don't waste time chasing down my assets. The One of a Kind Financial Plan is built exclusively by One Oak Financial so that you can live a one of a kind life.
800-748-1838, 800-748-1838, or text the word ideas to 600-700.
Thank you again for listening to the One of a Kind Financial Show Daily. I've been your host, Mike Milligan. 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. 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, 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. 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.
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