Early Retirement Is The Focus!
Is Health Insurance Holding You Back from Early Retirement?
You’ve worked, saved, and invested for retirement—but leaving your employer’s health insurance still feels like a major hurdle. How do you understand your options and plan for the years before Medicare?
In this episode, Matt Allen and Aaron Miller explain why Plan Shaman focuses on helping early retirees bridge the health insurance gap. We discuss the uncertainty that comes with shopping for individual coverage, the importance of accessible education, and how health insurance fits into a broader retirement plan.
You’ll learn about:
- Why leaving employer coverage can introduce unfamiliar costs, choices, and restrictions.
- How your health, income, location, and timeline to Medicare shape your options.
- Why a familiar insurance company’s individual plan may differ significantly from its employer coverage.
- How travel, moving, and splitting time between states affect your coverage needs.
- Why premiums and in-network out-of-pocket limits don’t tell the whole financial story.
- How specialized health insurance guidance can complement your financial planner’s and accountant’s work.
We also discuss how Plan Shaman gives early retirees access to free educational resources, allowing them to research independently or seek personalized help when they’re ready.
The central takeaway: make health insurance a defined part of your retirement plan. Understanding available coverage, checking provider access, and evaluating potential expenses can help you assess whether you’re ready to retire before 65.
About the hosts
Matt Allen brings over a decade of experience helping early retirees bridge the health insurance gap to Medicare. Together with Aaron Miller, he helps make the options and trade-offs easier to understand through Plan Shaman.
Planning to retire before 65?
Plan Shaman provides free health insurance education for individuals and couples preparing for early retirement. Explore your options so you can make a confident decision when the time is right.
Created 10/10/2026
Early Retirement Is The Focus Transcript
Aaron (00:08)
We got.
Matt Allen (00:09)
Welcome, welcome.
To another episode of Talking Shit. Shit of course is an acronym for straight health insurance talk. I'm Matt Allen and join with me today is Aaron Miller.
Aaron (00:21)
How do you do?
Matt Allen (00:23)
Doing just fine. Aaron? It's been a little bit. What are we talking about today?
Aaron (00:32)
Well, you know, if you look on our YouTube where we post all of these long forms, the whole podcasts, it says the retirement health insurance experts. And I want to dive in today on why that is the market that we are focused on, why those are the people we're, you know, on a mission to help bridge that gap to Medicare. Just overall talk about this, you know, subsection of people who, you know, need health insurance and why that's our focus.
Matt Allen (01:02)
Man, why is that our focus? Our focus is because these people aren't being served. They aren't being helped. And the people who are on Medicare, once they're over sixty-five, that's a very saturated market. Plenty of people are willing to help there. They'll talk you through drug plans, Medicare Advantage, Medicare supplements, some even do long term care, dental envision, all that stuff. But it's this little gap.
That these early retirees are sort of thrown to the wolves. And the majority of these people have never shopped for health insurance before. They have no idea what they're doing. They've always had a nine to five corporate job where they just click, you know, opt into the plan. Maybe they're picking between the the low deductible PPO or their HSA, but that's about it. They don't really understand the scope.
Maybe they've heard some stuff at the water cooler of people retiring early and what they did, or they've heard on the news about the marketplace or something like that. They know it's expensive, but they're they're just kind of confused. Well, we've noticed this huge lack of information out there and
I wanted to help these people. They've worked so hard to get to where they are. They've saved. They've wisely invested. And they're ready to retire. And and a lot of these people, these early retirees, they might be sixty and they're financially ready to retire, but they're letting health insurance stop them from retiring.
I want that person to understand free and clear they can just retire. We can solve the health insurance problem. If that's the only reason you're working, I want you to retire. Go enjoy your life. I don't want you still tied to that job. You worked 40 years. Go enjoy it. So that's why I like working with early retirees is they nobody's helping them. They need the help. They're responsible. They worked hard. And quite honestly, the the the little bits of information I have seen out there.
It's it's just incomplete. It's not enough. And people are getting screwed over and they don't even realize it.
Aaron (03:15)
Yeah, a hundred percent. And I know we've had this conversation before, but you know, when we help, you know, let's say someone who's twenty-six with health insurance, it's actually how we met. I was turning twenty-six. Been a while. But
Matt Allen (03:29)
Mm-hmm.
Aaron (03:31)
you know, I I you know got my health insurance figured out and frankly, yeah, sure, checked the box for me, but it didn't
change my life in any significant way. Right. It wasn't a, you know, my gosh, thank you, Matt. Like, yeah, you helped me understand my options. But with these early retirees, you know, now they get to retire, have a huge life moment because we've helped them, you know, cross that line and, you know, understand how to bridge that gap. And so, you know, the early retirees that I've helped, I've just noticed that they are
Very thankful for getting all the information and it makes our life better when we're dealing with those people too.
Matt Allen (04:16)
Yeah, it's very rewarding. And
What's great is these people are they're willing to listen, they're easy to work with, they're responsible, they show up to the meetings, they give you the information you need to do your job. It's just such a nice thing, and and our entire goal is to just bridge that gap from retirement to Medicare age. That's the scariest part where you could have a major health care expense, be undercovered, not have access to the care that you need. We fill in that entire gap. We make sure they
Get to 65 safe and sound once they go on Medicare and get a good supplement with a drug plan, they're home-free. But it's just about bridging that gap. A lot of people think Cobra's the only option, a lot of people think the Affordable Care Act's the only option. Those are two really good options, but they're not the whole scope of it. And so with Plan Shaman, the whole idea behind it was that it's a lot.
Easier for me to reach more people if we have these videos there that anybody can access at any time. If I am trying to change the world and help all these early retirees with health insurance just one at a time, the amount of people that I can help is very limited. And so what we've found is a lot of this generation, the people in their 50s and early 60s, they like to do their own research.
A lot of them do. Some of them want just want somebody to solve the problem for hold their hand, give them a presentation. We love doing that.
But some of them like to they like to get into the nuts and bolts. They like to do a little digging on their own. And they want to come up with the solution, they're DIYers. And so we wanted to give them that option as well. You can come and meet with us, you can talk with Matt, we can figure it out. Or if you want to self-educate, if you want to learn the ropes all by yourself, I don't want you know that information to be behind a paywall. I want you to be able to just go get it freely, do your own research, and maybe now that 59 year old who's absolutely hating his job, but he's got
Two million in assets and is like, I just want to retire. I don't want to be tied to this health insurance. He can now spend a couple hours going through plan shaman, understanding the situation, understanding individual health insurance, and that guy will get years back on his life for a little two-hour commitment to learn about health insurance, put in his two weeks, set up the right plan.
and go to Tahiti or something. You know, that that guy can now do
Aaron (06:45)
Yeah.
Matt Allen (06:45)
that. And if he doesn't want to meet with a salesman, because at the end of the day I am kind of a salesman, he can just do it himself. He can self serve. I wanted that to be available. So that's why we created Plant Shaman.
Aaron (06:58)
Yeah. And and these early retirees, they have all these experts in their corner. They have their financial planner, their CPA, you know, their HR, right? Who've helped them kind of get to this point of potentially retiring. But, you know, health insurance broker focused on early retirement is not, you know, someone they've ever had to use, right? So this expert doesn't exist in many circles.
And so just bringing expertise to not only, you know, the people who are actually making those decisions, those early retirees, but also to the other people who are helping them. just to know that there is an expert out there, I think has been I mean we've had good responses from the financial planners. You know, they they love having a resource for this stuff.
Matt Allen (07:49)
Absolutely. Most financial planners that I speak to have no idea a service like ours exists. And that's our that's our own marketing hill to to climb and to solve. people know that there are Medicare salespeople. I mean you could go into any office park in any major metropolitan area, throw a rock and you'll hit a mere somebody selling Medicare.
And a lot of financial planners they have the person for Medicare. But you ask the average Medicare person, Hey, my wife's sixty two, I'm sixty five, what can you do for her? And they go, I don't know
Go to the marketplace, maybe. I don't know. If you looked into short-term medical, my neighbors got one of those Christian plans, maybe that'll work. They don't have the solutions there. They don't have sort of the the walkthroughs that we do where we educate people on what all the options are and we walk them through. I mean, all of those options are viable and they all exist for different people in different situations. It's just about matching up the specific early retiree with the specific plan based
On timelines, based on health, based on income, based on travel habits, based on which state they live in, based on if they're gonna move. We we've talked to so many early retirees that you know maybe they're working in Indiana, but it's because they're moving to they're moving to North Carolina once they retire. That's where they want to retire. If they've got a vacation home in Florida or whatever it might be, there are health insurance products out there that match up to everything. And a lot of people fall into this trap because they've never bought health insurance, that they just think it's an interchange.
Changeable commodity. That well, I had Blue Cross Blue Shield at my job, so now that I'm going to individual coverage, I'm just gonna call Blue Cross Blue Shield, ask them for a gold plan. Alright, I can afford it. Let me buy it. And it's nothing like what they had at work. The networks are different, the premiums are different, the deductibles are different. The company, even though it might say blue cross blue shield, is likely a different company because there's thirty-three different blue cross blue shields across the country.
There's a lot of things that people don't realize. And to your point, they have a financial planner to help them with investments. They've got a CPA to help them with taxes. They got a real estate agent helping them put their house on the market and buy one in North Carolina. Why are they doing the health insurance on their own? Why are they asking maybe one of those people, you know, can can you help me with health insurance? What do you do? Why are they typing into Chat GPT? I need health insurance at 62. What should I buy? They should talk to somebody or
Or self educate through a program like Plan Shaman.
Aaron (10:30)
hundred percent. And yeah, I like how you say it's not just a commodity, right? It's it's it's very personalized, right? And it's not like, you know, it's unsolvable, right? Through the videos that we've made, it's it's a logic equation and it's a comfort equation for for a lot of people.
And people don't realize how much I mean you mentioned location, right? That's a huge variable that people never think to take into account when it comes to you know this health insurance decision. Because if you you are snowbirding, got a house in Ohio and a house in Florida, that ACA plan is not only just incomplete, it's not compatible with the way you're living your life.
Matt Allen (11:17)
Without a doubt, I don't think people quite realize the importance of a network.
When they are shopping for health insurance. Because they've been at this corporate health insurance for so long, all of those plans are PPOs. PPO is the best network out there. It stands for Preferred Provider Organization. And that means there is an organization of providers they prefer you use. They'll give you a lower deductible, they'll give you a lower copay, and they'll give you lower coinsurance. And you are taken care of so well inside the network. But the best part about the PPO is there's also benefits out.
Outside
of the network. You might have a higher deductible, you might have a higher copay, and you might owe more on coinsurance. But it is going to cover you no matter where you seek care in the US. That's the shining gold standard health insurance plan. That's the best thing about the PPO. When you transition to the ACA, that PPO only exists in a handful of states, and in all likelihood, the out-of-network benefits on that PPO are very poor.
The the one that always sticks out to me is there's Blue Cross Blue Shield of Illinois. I don't mean to pick on Illinois, but it's the easiest one. Blue Cross Blue Shield in the suburbs of Chicago and in Chicago, it is the gold standard. Everybody wants Blue Cross Blue Shield of Illinois. And it's the best plan out there. But when you go to the marketplace and you buy a Blue Cross Blue Shield of Illinois plan, even if you opt and pay way more money to get the PPO, because you're like, I've got to have the PPO. I need in network.
Working out in network care, make sure you look closely at your plan documents. Open up that summary of benefits and coverages. Go look at out-of-network provider deductible. You'll see it's 15,000 individual and 45,000 for the family. And then scroll down a little bit to out-of-pocket maximum. Look at out-of-network, they might call it a non-participating provider, and look at what your out-of-pocket max is. It'll say the word unlimited.
So this is simply a PPO and name only. What that means is is it going to cover you outside the network? I mean, I guess you've got a $45,000 family deductible for out-of-network care, and then it's $50-50 coinsurance with no out-of-pocket maximum.
So you could owe hundreds of thousands of dollars if you need care outside the network. So these are just little nuances. That's that's a very specific use case scenario where we've we've signed up people on the Blue Cross Blue Shield PPO. Do not get me wrong. We are contracted with them, we are licensed with them, but to just immediately go, this is what I need, this is what'll work for me because it worked at my job, it's not apples to apples, it's apples to orange.
Oranges to you know sports cars to mailboxes. It's all different. They're not in the same category. They're all different things. And what we're really trying to accomplish is just protect your finances from a healthcare catastrophe. That's it. That's all we're trying to do, is just get you safely from that work job, work insurance all the way to Medicare. That's all we're trying to do.
Aaron (14:41)
Yeah. And you know, I think the other kind of hidden piece from Plan Shaman is people want to know what it's gonna cost. Right? People wanna know what it's gonna cost when they retire. And you know, they may have estimates with their financial planner, but they don't wanna talk with a quote unquote salesperson, you know, and be pressured into buying something or you know, waste that person's time even.
to get a a price, to get a quote, to plug into their financial plan. And so us building these resources, it's gonna help so many people, you know, actually understand what to plug into their financial calculator and you know how to see how far their money's gonna go. And people will see that they can retire earlier. And I I think just to your point, us providing that information is going to, you know
Spend a couple hours, get a couple of years back in your life. I mean, that's I mean, the most beautiful thing that we can offer as a health insurance broker, in my opinion. Like I don't see anything no no greater purpose in a health insurance broker than that right there. along with not going broke doing a financial catastroph or health insurance, health care catastrophe. So, yeah, I think giving people that, you know, just
transparent look into what your options are and what those cost is going to be, you know, the biggest impact we can provide. Cause frankly it doesn't exist.
Matt Allen (16:17)
Yeah. These financial planners that are putting together these retirement strategies, they've got all the software and the tools, and they're plugging in your expenses and they're doing drawdowns and distributions and there's the four percent rule and all this stuff, all these projections.
And what they typically what what we've seen is they like to err on the conservative side. They like to go a little high on a lot of these costs just to make sure the financial plan is sound and these people can retire. Because that'd be the worst thing they could possibly do is advise somebody to retire before sixty five and then that person goes broke.
Because the expenses weren't dialed in. That's what a lot of these financial planners, as part of their service, are helping these people do. And one of those line items is always going to be healthcare. It's always going to be healthcare. And so if you're 65 and over, it's a super easy calculation. You do your Part B premium, whatever your Medigap supplement costs, your drug plan if you have dental envision, there's a very clear out-of-pocket max. It's such a super simple equation. But if you're 59,
It gets a little more confusing because those financial planners, what they want to do is they want to know, okay, what's the monthly premium? And then what's the worst case scenario? What's what's if if everything goes wrong health-wise, and we have just a catastrophe, what's the most we can know? And they stress test their financial plan to make sure it can absorb that, to make sure it can handle the monthly premium and the worst case scenario. But but too often they're pushing for a lower premium.
even if it has a higher out-of-pocket max through something like the marketplace. And that's fine because they want to have the numbers fit. But what's being so overlooked is you cannot just go to the Affordable Care Act, add your monthly premium, and add the out-of-pocket maximum and go, this is our worst case annual scenario. Because it's just not true. If that Affordable Care Act plan is an HMO,
Then their liability in a worst case scenario is unlimited. It's unlimited because the HMO will not pay for health care outside of the network. So we have tons of clients in Texas, tons of early retirees. And some of them, an Affordable Care Act plan makes sense. Maybe they get a huge tax credit because of financial planning. Maybe they have a pre-existing condition and they need that pre-existing condition covered on the Affordable Care Act, whatever it might be. But all ACA Texas plans.
plans have narrow networks. They're gonna limit where you can go. So if you want to go get if you get diagnosed with cancer and you wanna go up to N.D. Anderson in Houston, well your ACA plan's not to take you there, you better have a supplement.
And so these people who are looking at, okay, my my ACA plan's nine hundred dollars a month and I got a ten thousand out of pocket max, my worst case scenario then is what, ten thousand eight hundred plus ten thousand it's twenty thousand eight hundred on the year. That's the most I can owe. Well, not so fast, is it an HMO?
Okay, what if you need care outside the network? What if you want to go somewhere outside the network? What if you get a terrible diagnosis and the only surgeon that you feel comfortable with doesn't accept your ACA plan? Well, now your max for that year isn't $20,800. It's unlimited. It's whatever the surgery costs, plus your premium.
So, what they need to more so factor in is how do we make sure we actually have a true maximum out of pocket? So you can add supplements to these ACA plans that extend the network. You could just completely forego an ACA plan and just get a private, unlimited network health insurance plan for these people in early retirement. But it's not this simple of saying premium plus out-of-pocket max when you have a narrow network plan. Your actual exposure is unlimited. And so these are the conversations we need to be.
having with these early retirees because if you pointed that out and you showed that to them, they might say, well, gee, we're not comfortable with that. But we are comfortable paying a couple hundred bucks a month extra to then have that out-of-network care addressed with one of these supplements. And now we do have a true out-of-pocket max. Now we can retire early. Now we are safe and sound in this gap for a health care catastrophe because now
We've plugged all the holes in these ACA plans, or we've completely foregone an ACA plan and we just have a private plan with a max out-of-pocket. There are so many additional factors than just premium plus out-of-pocket max. And that's just some of the expertise that we bring to the table. We are only dealing with health insurance for early retirees. That's all Plan Shaman does. We are so staying in our lane. We're not going to talk about disability, long-term care. We're not doing anything with life insurance. We are
completely staying in our lane so we can be the experts in the 29 different states that we're going to be doing business in. Please use us. Please make sure that your financial plan is sound. Don't just do the premium plus out-of-pocket max calculation. We can help walk you through that so it gets properly plugged into the financial plan. Then you can stress test it then your person can retire safely.
Aaron (21:39)
I love it. I love it. These are the people who need help. These are the people who need the information. And that's why we're doing it.
Matt Allen (21:48)
Absolutely.
Aaron (21:52)
That's what we got today.
Matt Allen (21:54)
That was good one. it helps to clarify and solidify in my mind, hey, why I'm working with early retirees. It's good to revisit that and really allowing somebody to retire early and actually enjoy the fruits of their labor years earlier than maybe they could have imagined by asking them to commit two hours of their time.
is an incredible bargain. And so if you're on the fence about it, if you want to learn more about it, reach out, watch some videos, spend two hours of your time. Maybe you're not ready yet. Maybe you're ready earlier than you think though. And a couple hours could give you back years of your life. This has been another episode of Talking Shit. Shit, of course, is an acronym for straight health insurance talk. I am Matt Allen.
Aaron (22:47)
And I am Aaron Miller.
See next time.
Matt Allen (22:54)
See ya.
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Frequently Asked Questions (FAQs)
Why does PlanShaman focus only on early retirees? People retiring before 65 fall into a gap. Medicare shoppers have plenty of help, but early retirees often buy individual coverage for the first time with little guidance. We focus only on getting them safely from employer coverage to Medicare.
If I had Blue Cross Blue Shield at work, can I just buy the same plan individually? Usually not. Individual plans from the same brand often have different networks, deductibles, and premiums. There are dozens of separate Blue Cross Blue Shield companies across the country, so the name alone tells you little.
Is premium plus out-of-pocket maximum my true worst-case cost? Only for in-network care. On an HMO or EPO, care outside the network may not be covered at all, so your real exposure can be unlimited. Adding a supplement or choosing a plan with no network restrictions creates a true ceiling.
I split time between two states. What should I look for? Check where your plan's network actually works. Many ACA plans only cover in-network care within one state or region. Snowbirds and frequent travelers often need a supplement or a private plan with nationwide access.
How does PlanShaman work with my financial planner? We give your planner realistic numbers for premiums and worst-case costs, including network risk. That way your retirement plan is stress-tested with real health insurance figures, not a rough estimate. We handle health insurance only; your planner and CPA handle the rest.