In this episode of the One of a Kind Financial Show Daily, host Mike Milligan and co‑host Gary discuss how retirement is not just a financial milestone but a profound emotional transition. They explain that many boomers and older Gen Xers enter retirement with solid finances yet feel a “structure shock” when work‑based routines disappear, leading to aimlessness, identity loss, and loneliness. The conversation highlights research showing higher loneliness rates among today’s retirees and describes how community‑building (e.g., clubs, group activities) can mitigate that risk. Mike outlines his “One of a Kind Financial Plan,” which starts by asking why money matters to the client, then creates a retirement vision that incorporates health, community, and purpose, blending behavioral/transition planning with traditional investment and tax strategies. The episode ends with a strong call‑to‑action, providing phone and text contact details, and a disclaimer about the educational nature of the content. Throughout, the hosts use a conversational, empathetic tone to persuade listeners that holistic planning—addressing both money and emotional well‑being—is essential for a fulfilling retirement.
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It's the One of a Kind Financial Show Daily with your host, Mike Milligan. Most of us plan for retirement financially, but fewer plan for the emotional surprises that come with it. From loneliness to losing structure to redefining purpose, retirement isn't just a financial milestone. It's a major life transition. This past weekend on the One of a Kind Financial Show Daily, Gary and I on the radio, Walk through this, walk through this. From boomers to older Gen Xers, it's a struggle that is real. The psychological and emotional toll of going to retirement is just as big as the financial one. Yet the one-size-fits-all world of financial advising sometimes forgets that element. So enjoy this episode next, and remember, you are one of a kind, and so your financial plan should also be a one of a kind.
So here he is, sunny Puerto Rico. Hi, Mike, how are you?
I'm good, Gary. How are you today?
I'm doing good. It's beautiful in North Carolina, sunny, close to 80 today. So we're getting about the same as you, I guess, huh?
80, 84, slight breeze. The ocean is absolutely glorious. All right. But I have spoken with many people back in Norfolk this week.
Yes.
And, uh, it is, uh, many Zoom calls, many face-to-face on their computers. And people are welcoming the break in the weather.
Yes. It's nice. It's nice. Let's all enjoy it. So are you looking out at the ocean right now?
I am. It's just like, it's right here. That's the beautiful part about being in paradise. It's coming to us all. Norfolk, Virginia is right along the Chesapeake Bay.
That's right. Beautiful.
Virginia Beach is the ocean out there. My wife and I took this excursion to Puerto Rico to help the business grow, help One Oak Financial grow, but also because my wife She's half Puerto Rican and she's trying to embrace the culture that she—
Oh, no kidding. I think that's wonderful.
Yeah, she's trying to embrace the culture that she feels like she's missed her life. And it's exciting to meet new people, but the workday is still the workday. I'm still present where I am to help clients build one-of-a-kind financial plans for their one-of-a-kind life.
And that's what Mike does every single day. All right, let's get into the show. We got a lot to get to. As boomers and older Gen Xers continue to move into retirement, something notable is emerging. Many retirees are emotionally unprepared for the transition even though their finances are in order. Now, psychologists and researchers now describe retirement as a new frontier of identity shift, social isolation, and emotional adjustment that very few people can anticipate. Today, what we're gonna do, we're gonna explore these emotional surprises, connect them to real trends, and tie them back into why holistic retirement planning matters not just for your wallet but for your well-being. So the first thing I wanna ask you, Mike, is why emotional adjustments matters just as much as financial security. Why is that?
So even when retirement is financially sound, many find that the lack of structure creates a vacuum. Work provided built-in rhythms. There were meetings, deadlines, social moments, and without it, time can stretch in unfamiliar ways. One retiree described going from meticulously planned life goals to filling time around TV schedules and arbitrary rules just to make the day fill. anchored. This structure shock isn't trivial. When retirees don't replace routine with meaningful activities, they can experience aimlessness. That's why emotional transition planning, just like financial planning, deserves intentional focus before you stop working.
You talk to clients about this, Mike, from time to time?
We do, because The One of a Kind Financial Plan, the book that I wrote, even how we structure our meetings, is we start with the question, why is money important to you? And then after we allow you to wax eloquently what money can be for you, we then talk about what the vision for retirement is. And we build a vision for your retirement or a job description for retirement around what your community, your health, and your impact is going to be.
Sure.
And so This structural shock from going to work to every day is a Saturday has been, and I've witnessed this now in my time in the financial services industry, I see people struggle with it. And that's why behavioral financial planning or transition planning is just as important as what stocks and bonds you own.
Right, exactly. Let's talk about loneliness, the unforeseen retirement risk.
This is one that I see even with people who have called into the show and we've said, and we build financial plans for, people will continue to work because they feel like they're part of a community. A recent analysis confirms that baby boomers are experiencing higher levels of loneliness from previous generations at similar life stages, even after accounting for health and demographic factors. Boomers today are more likely to age alone, have fewer closer family ties and experience a breakdown of traditional community structures. That's why loneliness is just not an uncomfortable feeling. It negatively impacts your health and your longevity. That's why we start in building the vision for retirement. We actually start with community.
Mm-hmm.
Community is that sense of purpose. It's the sense of belonging. And once you get A community of people that you're going to be around in retirement. And this is exactly right. People don't have the same family structure and family ties that we had 30, 40 years ago. This sense of community is different, right? We have a listener who started the Last Wives Club out in Virginia Beach. We have another listener who created a beach walking club. that gets together every Friday with a group of about 30 people. We have other people in our community who intentionally go to lunch or go to Bible studies with people. Community will help with this loneliness that people exist— that people feel when they actually get to retirement.
A couple of minutes left in the segment. I want to remind everybody of the phone number. Get on the calendar, get you all set up with that one-of-a-kind financial plan that Mike talks about. 800-748-1838. 800-748-1838. Text the word ideas to 600-700. Uh, one more question, uh, one more statement we can make here: identity loss when retirement stops being enough. When— what do you think?
Yeah, retirement isn't, uh, just a change in income, it's a change in identity. Uh, many people, like for instance, I am Mike Milligan, chairman of One Oak Financial. Yep. When I retire one day, I will just be Mike Milligan.
Yes.
That title is sometimes as much our identity as our name is. And psychology experts describe a common pattern in retirement, an early honeymoon phase followed by disenchantment, a period where the sparkle of freedom gives way to existential questions about purpose.
All right, up against the clock, Mike. Tell us about the one-of-a-kind financial plan.
Guys, we started out the show today with a very straightforward, difficult concept to talk about, but Your retirement and your life is no laughing matter. It doesn't deserve one-size-fits-all strategies, and it deserves true planning. The One of a Kind Financial Plan, if we're honest with each other, and our listeners who have, can testify to this, addresses the tax bills that are to come, the retirement income so you sleep better at night, the investment risk that is more focused on the return of your money, not the return on your money. And if you're listening today and And you face some uncertainty in your future. You face uncertainty in, and maybe you haven't spoken with your advisor in a year or two, like one of our callers last week. Maybe you haven't, maybe you don't have a clearly defined income plan for your life or a tax plan. If that's you, I'm going to tell you to pick up the phone and call now. I am answering the phones today. Gary's going to give you the number, and I cannot wait to meet you because we want to build a one-of-a-kind financial plan. for your one-of-a-kind life.
All right, let's give that phone number out right now. 800-748-1838. 800-748-1838. Or text the word ideas to 600-700. 800-748-1838. Or text the word ideas to 600-700.
This is Mike Milligan. That has been the One of a Kind Financial Show Daily for today. I appreciate the continued listenership that you, you bestow on us. By coming back daily to hear retirement investing legacy, emotional psychology tips, psychological tips when it comes to your money. If this brings value to you, I'd love for you to comment what value that brings. I'd also love for you to check out the other media that we put together, the Ideas by Mike podcast, where just this week we launched an episode with Deidre Van Nest, Our recent guests have been Casey Shoen on tax strategy, Jill Schulman on the science of being brave, and Adam Dale, how fee-based financial planning works in this, the next leg, the next quarter century from 2026 to 2050. And just as a reminder, Ideas by Mike, doing business as One Oak Financial, is an unaffiliated entity of Advisory Alpha LLC, where I am an investment advisor representative. All opinions expressed by me and Gary on the One of a Kind Financial Show and on this daily podcast, the One of a Kind Financial Show Daily, are just those. They're my opinions. This is for educational purposes only. Please do not use this to make education or to make financial or investment decisions on your own without consulting a financial professional. Thanks again for listening. And we'll see you next time. We will talk to you soon.
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