In today’s episode, we’re tackling these topics:
✅ January is the ideal time to reassess contributions, withdrawals & tax strategies
🔄 Retirees: map out your 2026 withdrawal strategy early
🔁 Split Roth conversions across the year for flexibility & potential tax efficiency
🎯 Use QCDs (Qualified Charitable Distributions) to lower taxable income after 70½
💸 Revisit cash positions: are they still yielding competitive returns?
📉 Consider rebalancing or realizing gains early to get ahead of tax strategy
Listen Now:
The Smart Take:
In this episode of Retire Smarter, Tyler Emrick, CFA®, CFP®, walks through a practical Retirement Planning Checklist for 2026, focused on the financial moves that matter most in the first few weeks of the year. From front-loading 401(k) and HSA contributions to planning Roth conversions, setting up Qualified Charitable Distributions, and rebalancing after a strong 2025, we break down what to do—and what mistakes to avoid.
If you want to start 2026 with confidence—and avoid scrambling at tax time—this checklist is your roadmap.
Learn more about the Retire Smarter Solution ™: https://www.truewealthdesign.com/ep-45-retire-smarter-solution/
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The Hosts:
Kevin Kroskey, CFP®, MBA – About – Contact
Tyler Emrick, CFA®, CFP® – About – Contact
Episode Transcript:
Tyler Emrick:
January sets the tone for the entire year. Decisions you make now around taxes, investments and withdrawals create options later or they take them away. In today’s episode, we’re sharing a simple January checklist to start 2026 off right.
Walter Storholt:
We’re back again on Retire Smarter, Walter Storholt always with you here alongside, of course, Tyler Emrick, a certified financial planner, chartered financial analyst, one of the wealth advisors at True Wealth Design. First show of 2026, it is here, the new year, Tyler, and I’m glad you chose checklists and not resolutions, I like a checklist better than a resolution I think.
Tyler Emrick:
Hey, some people might not, I’m a checklist person as well, probably in my planner nature. So yes, figure we’d start the year off right here and just give the listeners a little bit of a checklist that they can roll through, a quick hit, to make sure that they start the year off right. At least that’s the game plan for today. We’ll see if we can get off the rails or not.
Walter Storholt:
Yeah. We always try to get a little off the rails because there’s no fun in it otherwise. Speaking of getting off the rails, if you want to jump to our checklist conversation, just skip ahead about a minute. But we always like to play a little catch up, and the holidays just past us and we’re into the new year, so happy new year, first of all, to you. And hope you enjoyed the last couple of weeks with family and hopefully a little less work for you and some time off.
Tyler Emrick:
Yep, no, absolutely. Yeah. Well, my birthday’s in January too, so it was one of those ones that was always real close to Christmas so it was like, ah, Christmas presents, birthday presents, mixing in together. But for those other listeners, there might be January birthdays, so happy early birthday here too, yeah, should be a pretty good month.
Walter Storholt:
I know a lot of folks in my life that have just before Christmas birthdays, not many people that are early January though, so I don’t really know what that experience is like after Christmas, but close to it kind of birthday.
Tyler Emrick:
Close to it. Yeah, no, absolutely. All lumped in together. But hey, it’s all holiday cheers, all good food, hopefully visiting, a bunch of time with family so all good.
Walter Storholt:
Real quick, what was the most exciting gift the girls opened this year, what was the big hit?
Tyler Emrick:
Yeah, yeah, yeah. Most exciting gift? So my youngest would say it would have to be her dollhouse.
Walter Storholt:
Nice. Okay.
Tyler Emrick:
That she had been asking for for sure. And then my oldest was a Switch 2. Although the Switch 2 was definitely going back and forth between me and mom. Mom was like, “I don’t know if she’s ready for something like that yet.” But I think dad maybe won out a little bit. So hopefully our parenting comes through.
Walter Storholt:
You want to play a little bit on the Switch 2 with her it sounds like.
Tyler Emrick:
I think that might be her secret, yeah, that’s probably the crux of why she says no, she doesn’t want me to be on it, but yeah, we’ll see.
Walter Storholt:
Too funny, too funny. All right, well, let’s get down to serious business, checklist time for folks. So January, obviously just a logical month to do these kinds of things.
Tyler Emrick:
Absolutely. Well, it’s the compounding effect. I mean, we have an entire year coming up. Some of the changes that you make now will just slowly compound over the year. So there’s a handful items, we think it’s always good for families to just take a look at and review and just make sure that you start the year off on the right foot. So we’ll have a mix of good stuff for retirees, maybe individuals heading into retirement this year and individuals still working. So we’ll try to cover the whole spectrum here. But yeah.
So the big levers I’m going to start out with is really starting to think about just your retirement accounts and that retirement account usage, think 401ks, 403Bs, HSA accounts, things like that. And taking a look at how much you’re contributing to those accounts. This is especially important for individuals that are potentially looking to retire this year. You might only be working part of the year. The question becomes is, do you need to ramp up and increase those contributions to the plans to make sure that you hit your goals if you’re not going to be working throughout the entirety of the year?
The other thing is is you’re getting ready here in about a month or so to start getting those tax documents. So you can take a look at those tax documents, your W-2s and say, “Well, hey, how much did I contribute to my retirement plan last year? Do I need to adjust that up? Do I have room to adjust it?” Same thing for your HSA accounts, I mean, these are wonderful accounts. Walt and I talk about them all the time here on the podcast. But they’re great. So if you’re using those, that’ll come on your tax forms as well. And you’ll be able to take a look and say, “How much did I contribute? Is there still room for me to contribute for the prior year?” Because that is one of those quirky ones where you can still contribute into January and February for the prior year. Same thing for your IRA accounts for the prior year for that matter.
So just taking a look at how you’re saving in these accounts, I think January is a good time to do it. One thing we do need to be mindful of though, for those individuals that are maxing out in their retirement accounts, so the 401ks, 403Bs, some employers do their match a little bit differently. So for those individuals that are maybe maxing out their retirement plan early in the year, you do need to make sure that your retirement plan will though catch up and give you the matching contribution that you should get throughout the entirety of the year because sometimes that does get shut off, of course, if you’re not making contributions. So we do want to be a little bit leery of that.
But outside of that, making sure that you’re utilizing those retirement accounts, you’re putting what you want to in it, I think is an important good first checklist here as we start January off. Along those lines-
Walter Storholt:
Yeah. I’ve always tried to do that, Tyler, over fund plans at the beginning of the year, just to make sure that you’re ahead of the curve. And that you’re just like, “All right.” I also, I don’t know if this is how you’re supposed to do things, Tyler, but this is in Walter’s world, what I like to do, I try to fully fund everything before December hits. So those last couple paychecks at the end of the year are a little bit bigger because you’re not having anything come out of them. So that’s my dollar cost averaging with a twist.
Tyler Emrick:
Yeah, no, that’s good, that’s good, that’s good. But you do got to be careful, got to make sure you get that free money, that match, and make sure that doesn’t cause any problem with it. Same thing for those after tax contributions, for those of you that have that as an option inside of your plans, it’s another good contribution way to get money inside of those retirement plans for sure.
Now, for those individuals that maybe aren’t working and are retired, I think it’s mapping out your distributions for the year. If you haven’t done it in the last couple months, generally here at True Wealth Design we’re looking at that at the end of the year, we’re looking at in October and November and the year ahead, but if you haven’t done that, taking a look at where your money is going to be coming from throughout the year I think is going to be important.
If you have a Roth conversion that you want to take care of that year, do you want to do some of it early in the year and then some of it later in the year and split that up, I think is another good thing to consider as you’re, “Hey, do I want to have those conversions done.” So that timing. Since the laws changed a number of years ago where we can’t do what we call a Roth recharacterization, a lot of times we wait till the end of the year to do our Roth conversion.
But for those listeners that do big Roth conversions throughout the year, it might make sense to split it up and do part of it in January and part towards the end of the year. You get all that year of hopefully growth as long as you’re investing it appropriately. You could have some growth inside of that Roth. And we certainly would rather have that inside the Roth than we would inside of the IRA. So being mindful of, hey, if you do those Roth conversions early in the year, well, what type of investments are you going to be putting them into? Do you want market risk? Do you not? That type of thing I think is important.
So really that first big lever, Walt, is how are you using your retirement accounts? How much are you putting into them or how much are you distributing from them? For our retirees I think are a big thing to consider. Which leads me to my next point is that distribution planning for retirees. I want to double down on this a little bit. And understanding where your money is going to be coming from and which accounts you want to be pulling from I think are extremely important for retirees.
Are you going to do IRA? Are you going to do Roth? Are you going to pull from your taxable account? Are you pulling from your savings? These are all things that you want to know. And if you don’t know them, January is a wonderful place to put it.
For those individuals that are gifting, we have those qualified charitable distributions that we’re pulling from accounts as well, for those that aren’t familiar, these are these distributions where you can pull money out of your retirement accounts, your IRAs, and as long as you gift them to a qualified church or charity, they do not actually hit your tax return. These are going to be available for individuals once they hit 70 and a half. So if we are doing our qualified charitable distributions and you’re doing it to actually lower your required minimum distribution, well, how are those coordinating? And what is your RMD for the year and what is the QCD that you’re wanting to do? And just making sure that, hey, do I want that qualified charitable distribution to come out monthly from my accounts? Am I going to be doing that at the end of the year? Am I going to be doing my RMD at the end of the year? These are all those timing considerations, Walt, that we definitely want to be mindful of. And getting an understanding of what you want to accomplish early in the year I think sets you up and sets you up well for the remainder of the year.
The final thing I’ll say about distribution planning, I would also urge you to think through your tax withholding and how you’re doing your tax pay-ins for the upcoming year as well. This is a big one for our retirees.
A lot of individuals might set up monthly distributions from their IRA account, and those distributions might have some tax withholding off of them. Well, if it’s a big chunk of tax withholding, the question becomes is, do we really want to be doing that tax withholding on a month in, a month out basis? Or do we maybe want to leave that money invested inside of our IRA accounts and then do that tax withholding on a big distribution at the end of the year?
So these are some of those minutia, some of the details that I think is always good to take a look at as we’re heading into a new year.
Speaker 3:
What would your life look like if you designed it around your true wealth? It’s a powerful question. And one that True Wealth Design helps individuals, families, and business owners answer every day. With a fully integrated approach to financial planning, tax strategy, investments, and business advisory, their team can bring clarity and confidence to every part of your financial life. Take the first step toward a stronger financial future with a no cost, no obligation discovery meeting. Just click the link in today’s show description to get started.
Walter Storholt:
And that big reason is just because we get the whole year to work with. So if you wait till July to start thinking about things, well, now you only have a couple of months to make moves and you may miss some opportunities that way. So makes total sense to have January be this … it’s not arbitrary. Like new year’s resolutions actually arbitrary in the grand scheme of things, you’re talking about a life change, January is just a convenient time to [inaudible 00:11:12].
Tyler Emrick:
Working out a little more.
Walter Storholt:
All those-
Tyler Emrick:
I’m the typical one that needs to [inaudible 00:11:16]
Walter Storholt:
But no real big difference if you do it in July or if you had done it in December. These are actually some legitimate reasons to treat January a little bit special because of this additional time that you get.
Tyler Emrick:
Sure. They give you more flexibility. If you’re heading into the year planning for it, I think it really does provide quite a bit of flexibility towards the end of the year as you’re recapping saying, “All right, hey, how did the year turn out? Is it what I expected and what do we need to get in and done before the end of the year?”
Walter Storholt:
Well, you bring up a great point because yes, you have now a full year to plan, but you also just wrapped up 2025 and the dust is still settling from the prior year financially in a lot of ways, so I think that brings up a few to-do items as well.
Tyler Emrick:
It does, in the year-end stuff, a lot of the things we talk about is like harvesting losses in your taxable brokerage accounts. I have that down as a January thing to take a look at as well. You might have done your tax planning at the end of last year and maybe not rebalanced your investments because you didn’t want to take the tax hit or you didn’t have room inside of a particular income bracket to do that.
I think January is a good time to take a look at your investments too and decide, hey, am I allocated appropriately? Do I need to maybe take some gains to lower a concentrated stock position or whatever the case may be? We got a whole new tax year ahead of us now and we want to take advantage of it.
So obviously you got to have some insight into how much gains you want to take for the year to be able to do that. So that goes back to that planning aspect of things. But I think taking a look at your investments and, hey, how am I allocated? Do I need to make any changes? Do I want to maybe make some sales and harvest some gains early on this year to get better positioned for the year ahead?
I think that goes with your investments, but it also goes with some of your cash positions as well. Over the last year, we’ve seen money market accounts and savings accounts slowly start to pay a little bit less in interest over the year. It looks like that might continue over the course of 2026. So it’s always a good time to take a look at your cash levels and say, “Hey, am I still getting market rates on the cash that I have? Do I need to maybe switch that? Should I look at changing my cash position and putting it in something that’s maybe a little bit more tax efficient?”
Some individuals inevitably will get a tax document with that interest for the prior year and it’s going to impact your 2024 taxes. Now would be the time to plan for that for 2025 and say, “Hey, do I want to maybe take that cash and move it to something that’s a little bit more tax efficient? Or if I’m not getting interest on my cash, do I want to maybe take a look and moving it to somewhere else?”
Walter Storholt:
Well, great stuff, Tyler. That’s a fantastic beginning list for 2025. And it’s a great reminder that if you’re hearing this and you’re like, “Yeah, I need to go through all of this, but I don’t know how to do that, I don’t know how to rebalance, I don’t know how to figure that stuff out, I don’t know how to look at the big picture.” Totally legitimate answer. Even if you’re smart about saving and investing and building your wealth for retirement, it can be very difficult when you try to start figuring out all the tax efficient moves and the best places to take your money and all these right steps to take. How can I be proactive?
Sometimes you don’t know until you’ve got this years of experience that Tyler and the team at True Wealth Design have. So what we offer is a chance to have a 20-minute discovery call with a member of the team. And all you have to do is go to truewealthdesign.com and all you’re going to do is click the ‘let’s talk’ button. It is the ‘let’s talk’ button, right, Tyler?
Tyler Emrick:
Yeah, it is the ‘let’s talk’ button, yeah, let’s go that way.
Walter Storholt:
Wait, what did it used to be? I finally have gotten to where that’s in my mind now. I was questioning it because I used to think it was something else.
Tyler Emrick:
Something else. Yeah, I think it was just schedule a call, I think it was something pretty basic.
Walter Storholt:
Something like that.
Tyler Emrick:
It’s definitely ‘let’s talk’, almost a neon green on the website now.
Walter Storholt:
Okay. There we go. So click the ‘let’s talk’ button and schedule your time to visit. It’s a 20-minute discovery call with a member of the team. You’ll see if you’re a good fit to work with one another, where some of those areas of improvement are in your own financial plan and it gets the conversation started. So low pressure, easy to engage that way. Click the link in the description of today’s show to access that or, again, go to truewealthdesign.com.
And come back for next week’s episode, we’re going to continue this theme of beginning of the year, things that we need to be working on and thinking about. We’re going to dive a little bit deeper into the investment side, and in particular talk about some of those tax efficiency options that you can plan for here at the beginning of the year, could save you thousands of dollars in taxes over the course of the year. So Tyler’s going to detail all of that for us next time around.
In the meantime, Tyler, thank you. We’ll see you again on Retire Smarter.
Speaker 4:
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