Retiring Single? Here's What Changes

Added: 2026-05-07

[00:00:00]Almost every retirement video that you watch assumes one thing, you're married.

[00:00:05]One of you left a comment recently that made me realize that it was time to make another video for all my single viewers out there. And that viewer wrote, "Perhaps I missed it, but I did not see anything in this video that addresses a single person. Shame on you. I hope I am wrong. Brackets are cut in half for us singles and it doesn't take much to go over 109k, especially when RMDs start." I mean, look at y'all, shaming me into making a video. Come on, man. Shame? I guess it worked though. What? Why are you yelling at me? Whatever, make me a bicycle, clown.

[00:00:41]Well, you're absolutely right. Most retirement advice is built around a married couple filing jointly. Two incomes, two social security checks, and tax brackets that are roughly double what a single filer gets. But of course, if you're retiring solo, the math changes dramatically. The tax brackets are tighter and Irma creeps up on you sooner. And some of that healthcare safety net that married couples have, well, you got to go build that yourself.

[00:01:07]And so while retiring as a single person isn't easier, it doesn't necessarily mean that you can't do it. It just means that you need a different playbook. And once you understand the rules, you might actually have more control over your financial life than some married couples do. So today I'm going to walk you through the three biggest challenges that single retirees face and how to solve each one. First, the single filer tax trap and how to keep more of your money. Second, how to make one social security check do what it needs to do for you. And third, the healthcare and housing strategy that married people don't have to think about as much as single retirees do. So first, let me show you what changes when there's only one name on the tax return. If you're single and planning to retire, tax brackets are probably already a sore subject. A married couple filing jointly can earn just under $101,000 before they hit the 22% tax bracket.

[00:02:04]Well, single filers, well, you guys cross that line at just over $50,000.

[00:02:10]Basically, half. And it gets worse from there. That 24% tax bracket tops out at just under $202,000 for singles compared to just under $404,000 for joint filers. So, you know, you get half. But here's where single retirees actually have a little bit of an advantage that not a lot of people think about. You have more control over your taxable income. You don't have the added complication of a spouse's pension, social security, or RMDs getting layered into this tax situation. Every dollar that is on your 1040 is potentially one that you do have some influence over. So let me give you a real-world example here. Let's say you're 62, single, just retired, and you've got $1.2 million in a traditional IRA. You're not collecting social security yet and your only income right now is maybe a small pension. So now you've got this beautiful window where your taxable income is lower than it may ever be again. These are your gap years between retirement and RMDs where you have the opportunity to do some of these tax strategies like strategic Roth IRA conversions. Unlike a married person who might have a spouse's income that complicates their tax return, you've got more of a clean slate. You could convert, let's say, $48,000 a year from your traditional IRA to a Roth IRA and every single dollar of that conversion could stay inside that 12% tax bracket after your standard deduction. For married couples, it's a little bit tougher for them to get that kind of a clean runway for those conversions. So here's what I want you to do. Pull up your most recent tax return and look at your taxable income. Then go look at the 2026 single filer brackets. How much room do you have to jump from where you are up until the next tax bracket? That gap is your Roth conversion opportunity.

[00:04:02]But before you do, pay attention to those Irma brackets. For single filers, Irma kicks in right around $109,000 of modified adjusted gross income. One aggressive Roth conversion or an unexpected capital gain could push you over that cliff and cost you an extra $81 bucks a month in Medicare premiums, assuming you're age 63 or more. Remember those Irma penalties have a two-year lookback. That's almost another thousand dollars a year for crossing that line by just a dollar. So the strategy here is to plan your Roth conversions in the years before your RMD start, stay under those Irma thresholds, and create a pool of tax-free money that you can draw from in your 70s and 80s without it showing up on your tax return at all. And look, taxes are a big piece of this puzzle, but this next topic might be the biggest single decision that a solo retiree has to make, when to file for social security. When I'm working with a married couple and we're planning for their social security, they have a few options. One spouse can claim early while the other delays. And if one spouse passes away, the survivor keeps the higher of the two checks. There's a little bit of flexibility built into the system for them. But if you're single, none of that exists. You get one benefit, one decision, and you got to live with it for the rest of your life.

[00:05:21]Now that doesn't necessarily mean that this decision is harder, but it does mean that it's more important that you get it right. Now the conventional wisdom is to delay as long as possible and for a lot of single retirees, that's good advice. For every year that you delay past your full retirement age, your benefit grows by 8%. So between 62 and 70, you could increase your monthly check by as much as 77%. But here's the part that really matters for single retirees. Those cost of living adjustments become a little bit more important. If you expect to live into your mid-80s or beyond, delaying means a larger inflation-adjusted check for the rest of your life. And when you're the only one paying the bills, that higher floor of guaranteed income can make a real difference late in retirement. But delaying isn't always the right call. If you've got some sort of pension or other reliable income and your investment portfolio is maybe a little on the modest side, well, claiming earlier might make more sense. Why? Because you may need the cash flow now more than you need the theoretical upside later. For example, if you're 62 with a $400,000 portfolio and a $1,500 a month pension, drawing down your portfolio for eight years while you wait to claim at 70 could put real stress on your finances.

[00:06:44]In that scenario, claiming at 63 or 64 and preserving your portfolio might give you more flexibility and more peace of mind. On the other hand, if you're 62 with $1.5 million saved up and no pension, you probably can't afford to cover your expenses from your portfolio while you wait. You draw from your portfolio now, you turn on a larger social security check later, and you reduce your sequence of returns risk in the process. The point is this, you have to run the numbers for your situation.

[00:07:18]At some point, you just got to do the math. This is not a decision to be made based on what your neighbor did or what you read in Kiplinger's. This is why we are running dynamic guardrails calculations for our clients who are approaching retirement or are in retirement. Look at your health history, your family longevity, and your other income sources here. So where for a married couple, choosing their social security timing is more of a maximization strategy, for single retirees, it's more of a hedging strategy. Okay, we've covered taxes and income, but now I want to talk about the part that a lot of people skip over entirely and it doesn't really have anything to do with money. If you've watched this video up until this point, you probably know what I'm about to say.

[00:08:02]You don't need me to sit here and tell you that not having a spouse or partner changes the equation when it comes to healthcare and aging. You get it and you've probably thought about this long before most married people ever will. So let's not belabor this point. Instead, let's talk about what you can actually do about it. Because there are real options here. And having a plan is the thing that keeps this from being one of those things that lingers in the back of your head stressing you out. So let's start with housing. If you live in a big house by yourself, at some point the question might become, is this house really serving me? And I'm not saying you got to go move tomorrow, but what I am saying is that it's worth it to start thinking about this stuff now. Okay, option one, downsize to something like a patio home. These single-level homes with an HOA that handles the yard work are popping up everywhere and they're not just for retirees. Now they're for anyone who's tired of maintaining a house that's bigger than their actual life. Hell, I got friends in their 50s who are already falling down the stairs.

[00:09:04]And personally, I've cut so much grass in my life already that paying someone else to do it isn't even a question.

[00:09:10]Something like a one-level ranch or a patio home gives you less to maintain, one level so you're not navigating stairs at 75, and a neighborhood that's usually pretty social. You keep your independence, you keep your home equity, and you haven't officially moved on to our next option, which is option number two, an active adult community. If you've spent any time in the Southeast, you've probably heard about these Sun City communities that Del Webb has been putting everywhere. These are age 55 and over communities with a clubhouse, pool, golf course, pickleball courts, and group activities. They are not care facilities. They're neighborhoods built around keeping people active and connected. For a single retiree, the built-in social network and activities are a real selling point. There are organized groups, clubs, and events designed to make it easier for everyone to socialize. Just be a little careful if you move into The Villages in Florida.

[00:10:08]We'll just leave it at that. Option three is a continuing care retirement community. CRCCs, also known as life plan communities, are maybe the most comprehensive option, even if they're maybe not the most palatable to everyone. You move in when you're healthy, you've got your own place, and if your health changes down the road, well, you can transition to assisted living or skilled nursing care without leaving the community. Entry fees can range from $100,000 to well over a million dollars, plus there are monthly fees, so they are a serious financial commitment. For most people, this isn't a decision that you need to make at 62.

[00:10:43]In fact, you might actively not want to decide to go into a CRCC, especially when you're that young. But if you have a medical history that could complicate things later, or if you simply want the peace of mind knowing that care is already arranged, it's worth looking into sooner rather than later. The healthier you are when you apply, the better your options. And now we come to option number four for housing. Stay right where you are. I ain't sitting here telling you you got to move, you stubborn old goat. If you love your home, your neighborhood, and your routine, just stay where you are. Your house is probably already paid for, and there's something to be said for staying plugged in to a community with people of all ages. I mean, you can be retired and still be young at heart. But the point is this, whatever you choose, choose it on purpose, not by default. Don't let inertia make this decision for you.

[00:11:34]Think about what your life looks like at 70, at 80, and ask yourself whether your housing supports that life or makes it harder. And look, don't shame me in the comments for bringing all this up. Hey, look, maybe some of y'all do need to move to The Villages. Geez. Okay, now let's talk about long-term care insurance. Wah wah wah. Everybody's favorite subject. So, the number of insurance companies that are still selling traditional stand-alone long-term care policies has shrunk dramatically. I think Mutual of Omaha is the biggest name that's still standing here. There are a few others like National Guardian Life and Northwestern Mutual that are still on the market, but the options are pretty thin compared to what they used to be 10 or 20 years ago. But does that mean that you need to go run out and buy one? Not necessarily. For single retirees, long-term care planning is something that you need to think about a little bit more carefully than a married couple would. About 70% of people turning 65 today will need some form of long-term care. When someone who's married reaches the point where they'll need some type of long-term care, their spouse is often that person for some time before they bring in professional help. But without a spouse, the cost of that kind of care can really add up. And if you need help with your daily activities, you're hiring someone from day one. So, the risks of having to pay for all of this is real, but the question is, how do you want to cover it? You've basically got three paths here. The first is to buy a stand-alone long-term care policy from one of the few carriers that I mentioned earlier. They're expensive, they're hard to get, and the premiums have tended to increase over time. Option two is to look at one of these hybrid universal life policies with a long-term care rider. These are complicated insurance products that are more expensive up front, but they will pay out either way.

[00:13:23]With these kind of policies, if you need care, they cover it. If you don't, you should have some sort of death benefit for your beneficiaries. And then we come to option three, which is to self-insure. If you've paid off the house, the equity can absolutely be part of your plan. When the time comes, you could use the proceeds from the sale of the house to fund moving into an assisted living facility, or use a reverse mortgage to pay for in-home care. It's not as clean as some sort of long-term care policy, but it is an option. And if none of those options feel right, well, there's always a fourth option. Start spoiling your nieces and nephews now and hope that one of them has a guest suite for you to crash in. And so, housing and health is a big part of this, but I've got one more thing for you to think about.

[00:14:10]Retirement planning for one isn't just about money. It's about what you do with your time and who you spend it with.

[00:14:16]There's real research that shows that social isolation carries health risks comparable to smoking. And for single retirees, that risk increases when you stop going into the office and your daily social circle shrinks. Now, a lot of single retirees get ahead of this intentionally. They might relocate to a more walkable neighborhood where they can go to a coffee shop, the gym, and restaurants without getting in a car.

[00:14:42]Others are moving closer to friends and family. Now, the specifics matter less than the mindset. Retirement for one doesn't have to mean retirement alone.

[00:14:51]But look, this doesn't happen by accident. You've got to build this into your plan just like you would your Roth conversions and your social security strategy. Okay, let me tie all of this together. Honestly, a lot of my videos and a lot of videos on YouTube are built around married couples because that's what the financial planning world defaults to. And so, to my commenters who shamed me into making this video, you're right. Single retirees absolutely have a different playbook. Okay, so here's your short list here. Number one is to map your Roth conversion window.

[00:15:23]Find that gap between what you expect your retirement income to be and the next tax bracket or Irma threshold and use it every year before RMDs start.

[00:15:33]Number two is to get serious about your social security decision. Run the numbers, hire a planner to calculate your retirement guardrails. Don't forget to consider your health, your other income, and how long your portfolio needs to last. You only get one shot to do this social security thing, so make it the right decision. Number three is to make a housing and care plan. Now, that might look like buying a hybrid universal life policy with a long-term care rider. Might mean moving to The Villages. It might mean self-insuring with your home equity, or just being intentional about staying in your home.

[00:16:07]Having a plan beats having to worry.

[00:16:10]Hey, if this video was helpful, please hit that subscribe button. I try to put out videos every week to help you retire with less stress and more confidence without scaring the out of you.

[00:16:21]I've been making these videos on YouTube for nine years now, and I would love your help getting to 100,000 subscribers. And hey, if you need help with all this retirement planning stuff, check out my firm. There's a link in the description below. Hey, I want your retirement and your life to be an amazing one. Thank you so much for watching, and I'll see you in the next video.

[00:16:40]Okay, damn. Well, here's your video.