Read The Transcript Here:

Steven Jarvis, CPA (00:53)
Hello everyone, and welcome to the next episode of the Retirement Tax Services Podcast, Financial Professionals Edition. I’m your host, Steven Jarvis, CPA, and helping me help all of you get ready for the end of the year and the upcoming tax filing season, I’m once again joined by a good friend from Belay, Brooke Cecil. Brooke, welcome to the show.

Brooke Cecil (01:11)
Hey, thanks for having me, Steven.

Steven Jarvis, CPA (01:13)
Brooke, before we dive in and talk about these important dates that really we all need to be keeping in mind as we get towards the end of the year and into the next year, just remind our audience a little bit of your background and what it is you do with Belay.

Brooke Cecil (01:25)
Yeah, so I, as Steven said, I’m Brooke Cecil. I am the VP of Financial Solutions here at Belay.. I’ve been with the team for 12 years. So one of my roles is just really helping our clients in the way of bookkeeping, accounting clerk services, CFO and controller services, really just trying to free up folks, much like your listeners, to take over those bookkeeping items, those daily tasks that we often can do, but we probably shouldn’t do. It’s not necessarily the best usage of our time. So we provide those solutions to our clients as well as executive assistants. So that’s a little bit about what we do here at Belay.

Steven Jarvis, CPA (02:06)
Yeah, so for anyone listening, if you don’t have clients who pay taxes, if you don’t pay taxes, if you don’t work with business owners, like you don’t have to listen to this episode, but if none of your clients do any of those things, you’ve probably got bigger problems. So we’re gonna go through some really important reminders and provide some great resources here. So there’s definitely one worth listening to. So, Brooke, we’re recording this in November. It’ll get released here in November. And so this is really what we want to focus on, are these key things that people want to be thinking about as we get into the end of the year and into the next tax filing season. anything top of mind for you that’s like, hey, like if you don’t remember anything else, here’s the thing to remember before we start going through our list of dates.

Brooke Cecil (02:40)
Yeah, I mean, I would say, you know, this is an ideal time that everybody should be talking with their CPAs, right? And their financial advisors to make sure that we are maximizing as much as we can as we close out 2025. So I would say that is one of like the heavy hitters that everybody should be focusing on if they have not already done so. And then I would say additionally, you know, much like we see in our business is making sure that their books are up to date and ready to go. You will be your CPA’s best friend if you do that as we step into the beginning of the year.

Steven Jarvis, CPA (03:15)
Yeah, such a great framework to start on because when we talk about taxes, it can be easy to get really focused on kind of like the really extreme examples of someone saving taxes or putting $5 billion into a Roth account or whatever that might be. But for most of us in most years, it’s really about doing the simple things consistently over time. And so even as we talk about key dates here, like we’re not, we’re not just focused on, Hey, how does this save my client taxes right now? Maybe it does, maybe it doesn’t, but taxes tend to taxes, bookkeeping, accounting, even though this is something I spend all my time and Brooke, you spend your time here. This isn’t most people’s favorite topic. And so if we can find ways as financial advisors to make this less painful, to make it less unexpected, to take some of the surprises and shocks out of it, we’re delivering massive value by creating better experiences and better outcomes. So it is really important to keep this stuff in mind and then to help our clients through these key dates. And we’re gonna go through quite a few dates here. And Belay has been kind enough to organize this into essentially a reference guide that everyone can download so if you text RTS to five five one two three Belay will have a download for you of all these dates we’re gonna talk about so if you’re driving in the car or even sitting at your desk, you don’t feel like you need to commit all these to memory or write them all down as you go You can text RTS to five five one two three. We’ll get you a list of all of these, so Brooke I’ll let you go first. Let’s start getting into key dates that we need to remember.

Brooke Cecil (04:33)
Yeah, absolutely. And I will say the beginning of the year, there are some big dates. So it’s a rather robust Q1, early Q2, and the first being January 15th. So that is when we want our final quarterly estimated tax payments. And one thing that we encourage folks to do is really connect with their CPA just to kind of look at the year as a whole to make sure that we haven’t underpaid for 2025 because come either March or April, we really wanna make sure that we’ve got those payments in accurately to kind of help us as we get further into the quarter. So that would be the first one. And then January 31st, you know, kind of rounding out the month, two big things that we’re gonna be looking at. So first are those 1099s that’ll be due at the end of the year or end of the month, of January. And that’s for retirement distributions, interest and dividends. And then also the IRS opens it up. It’s like, you know, the opening of deer season almost as we look at it right now in the month of November. But that’s really when tax season will start. One of the things that I always encourage folks, though is that if they’re anything like me and they’re type A and they want to get things moving. You know, my husband’s a business owner and so it never fails those forms even though they are due on the 31st. They seem to trickle in so, you know the power of the pause. Let’s give it a moment and make sure we have all of our information in before we’re handing it over to our CPA.

Steven Jarvis, CPA (05:597)
Yeah, Burke, I love that reminder there because if you watch Super Bowl ads and you hear from TurboTax and H&R Block, they’re really pushing everybody to get giant refunds every year and to file their taxes as quickly as possible. For most of us normal humans, it’s more important to take a little time to have that pause and make sure we get it right. And so this is a great area for financial advisors to step in with things like a year-in-tax-planning letter, a 1099 letter. These are great areas for delegation to team members. But to be able to remind clients of here’s the tax documents you’re expecting, some of those do at the end of January, that you can remind them of when they should expect those documents, so that on January 21st, they’re not like, hey, Mrs. Financial Advisor, why don’t I have all my documents already? It’s okay. If we can proactively remind people when these things happen, which is why you and I are talking about this in November and not January, when we proactively let people know what to expect, we just, create better outcomes. And then the other thing that I always like to remind people of anytime we talk about estimated payments, and you mentioned making sure that we’re on track because January 15th is our last chance to get on track with the safe harbor provision. So we want to make sure we’re aware of that. I’m a huge advocate for ending our estimated payments in a dollar amount that corresponds with the quarter. So when we make our January 15th payment, it should end with a four. If I’m making $10,000 estimated payments,the January 15th one should be 10,004 because every year, it’s the exception, not the norm, but it happens every year. A payment gets missed by a client, it gets misapplied by the IRS. We end up with this, what happened here? And when we end our payments with that dollar amount, we immediately know which payment we’re talking about. I had this happen just a month ago with a client where they weren’t entirely sure what had happened. We pulled up their records and we’re like,the payment that ended with 10,003 never got made. It’s Q3 was the problem. We were able to go back and more quickly identify here’s where the issue is. And then one of the reasons I love working with financial advisors is we get to keep leveling this stuff up. And so one of the changes we’ve made in this recommendation now is that if you make an extension payment, which we’ll talk about April 15th here in a minute, when you make an extension payment, go ahead and make that amount end with a five so that again, we still have this really clear record of what’s going on and why. yeah, I mean, just even just to kick off the year, we’ve got a couple of key dates there in January.

Brooke Cecil (08:05)
Yeah, absolutely. And I would say, you know, it’s a new year. So maybe we’ve done some things historically in the past that, you know, like you were saying, your numerical numbers, like this is a great place to start, right? It’s a fresh start as we kind of look into 2026. So what are those things that we could potentially do a little differently? I would say, you know, from a financial advisement perspective, these, lot of times, you know, we…think that we should own all of these things. And this would be a great thing that, you know, an assistant or someone else within your team could easily take on to make sure your clients are up to speed and are handling things. It’s not something that you necessarily have to own. The power of delegation.

Steven Jarvis, CPA (08:45)
Yeah, absolutely. Yeah, you don’t need three letters after your name to remind somebody of a deadline or to communicate what tax forms they should be expecting. It doesn’t require a PhD or CPA or CFP. So great reminders there. And so then as we get into February, the fund doesn’t stop. And this year with the changes with the 03BA, I would go ahead and bet that it’s possible that when the IRS opens the tax filing season might actually even slip into February this year. So we want to, that’s why even as you mentioned it, you said that’s about the time the season opens. And so we want to be paying attention to that just to, again, to make clients aware so they’re not surprised. But then really as we get into the middle of February is when the rest of the 1099s things like 1099Bs from financial institutions are gonna be coming out. So this is again where we can help our clients have clear expectations by letting them know here’s when you should expect these documents and really it’s early to mid February before you’re going to have everything you need to get to your tax preparer to make sure this gets prepared. That’s whether your clients do their own taxes or work with a third-party professional. Somebody has to prepare their taxes and if we’re trying to submit a tax return before the middle of February, there’s a good chance we’re missing some.

Brooke Cecil (09:49)
Absolutely, and nobody wants to file an amendment later on once they find that it’s just a pain. like I said earlier, power of the pause, let’s just hold off. But if we’re doing all of those things beforehand, as soon as we get all of that information, it will be really easy to transition over to whether it’s yourself that’s completing the information or a third-party professional. And that kind of leads us to March 15th, which is really that first deadline. So that’s for partnerships and S-corps to file unless they request an extension. So that’s definitely one that we see a lot of our clients marching towards. Now, know, K-1s kind of get in there, and so it starts getting a little dicey because those seem to be a little delayed as well as people are closing out the books. But I think that there’s something that, you know, we can proactively do for client expectations. Like I said, we don’t need to rush it. And so as long as we’ve got those payments in place, I think those estimated payments is okay for us to file that extension to make sure that we have all the documentation, especially those K-1s.

Steven Jarvis, CPA (10:49)
Yeah, it’s a really interesting topic with extensions because for business owners, this becomes just routine, that they just know that most likely they’re going to go on extension because they’re waiting for documents. The tax payments are always still due at the initial filing deadline. So on March 15th for pass through entities, obviously, there’s not a payment due because that gets passed on to the individual returns. But we’ve got to make sure that we’re remembering that extensions of the filing requirements are not an extension of the payment deadline. And then for taxpayers who have never been through an extension before, my experience is that everyone initially will assume that an extension is a terrible thing, that they’ve somehow committed a crime by going on extensions. You’ll get clients who are just like almost aggressively opposed to the idea of being on extension. And so this one’s easy for me and for financial advisors listening who are business owners themselves, just tie this back to your own situation. When I can tell a client, hey, listen, I go on extension every year and here’s why, and here’s why. I don’t get in trouble with the IRS and all these things. It helps them feel better about it. And you might think, hey, that’s silly. They shouldn’t freak out about it. Well, maybe it’s silly, maybe it’s not. But I’m solving for great client experiences. Like, I’m not trying to sort through the psychology of taxes.
And Brooke, as we talk through some of these deadlines, the other thing I want to remind our listeners of is that this time of year, when we get into the beginning of calendar year, which is the tax filing season, we also want to remember that it’s really important that we’re super intentional with our communications with the CPAs, enrolled agents in our lives that we work with. That, really, your thought process this time of year should be, I’m only going to reach out to tax professionals if it’s critical for the upcoming filing deadline. I’m a huge advocate for people building really high-quality relationships with centers of influence, including tax professionals, but February and March is not the time to reach out and say, Hey, could I pay for an hour of your time to talk about the most recent tax law change? No, no, no. You should only be reaching out if it’s relevant to one of your shared clients for this upcoming filing deadline. Let’s be respectful of the fact that these deadlines are coming up and that we want these professionals to be doing high quality work for our clients. Absolutely, we want to keep building relationships, but that time of year really should be focused on how do I help my clients have the best tax experience coming up to these deadlines as possible. Well then, Brooke, of course, as we get through March, then we get into April, which is the tax filing deadline that everybody knows about. Good old April 15th. April 15th is the tax filing deadline where we can file for an extension, but tax payments are still due. Which is why, personally, I’m a big fan of getting as many tax returns done by the April 15th deadline as possible because we don’t get an extension of the payments. We probably have to do a lot of the work anyways to figure out what that payment should be. My goal every year is that my team is staffed in a way that it’s never because of capacity limitations on our side that we’re extending someone’s return. And we do a really good job of following through on that. Now, we still extend returns because of K1s, because of late documents, whatever the case might be, but that’s always the approach I’m gonna take, which…We do see this kind of trend in the accounting space to just, I’ll meet firm owners who just extend everyone, because they want more time to deal with it, but in my experience, the longer we let last year stay open, the less likely it is we’re gonna move on to focusing on this year or planning for the future. So I’m a big fan of, let’s get this done and let’s.

Commercial (13:57)
retirementtaxservices.com/OBBBA

Brooke Cecil (14:28)
I love that, I love that. And I think that, you know, the longer we, then we tend to forget, right? You know, I always joke with clients that we work with, even from an expense management perspective. Like I can’t remember what I bought at Target two weeks ago. So thinking through what happened in January, 2024, maybe there’s a question regarding a transaction. I don’t recall what that is. So let’s just go ahead and let’s handle it as quickly as we can.

Steven Jarvis, CPA (14:51)
Yeah, a couple of other things we need talk about before we get past the April 15th deadline is that there are several tax planning opportunities that really, that get tied into the end of the calendar year and the April 15th deadline. So there’s some things we have to do before the calendar turns over. So we’re recording this in 2025. So we use 2025 as the example. If I want credit for charitable giving for 2025, that has to happen in 2025. If I want credit for doing a Roth conversion for 2025, it has to happen in 2025. But as I get into the beginning of 2026, there are still some other things I can do and attribute them to 2025, making contributions to qualified accounts, things like IRAs, HSAs, employer contributions to certain retirement plans. We’ve got to be really careful with the documentation to make sure they get attributed to the correct year. But there are a lot of those contributions that can happen after the end of the calendar year, but before we file our tax return. We have to make an extra distinction here because like our IRA contributions, have to happen by April 15th, whether we extend or not. But if we extend our return to October 15th, we can also extend when we make our solo 401(k) contributions, for example. And so as we have clients that have access to these different types of accounts, we got to make sure that we’re paying attention to which year these things are applicable to and that we’re getting those reported and filed correctly. And then of course the other one, Brooke, that I know that you’re very familiar with because whether we’re working on last year’s tax return or not, the IRS, the states don’t exactly have that much patience for next year’s payments. So as we get to April 15th, 2026, not only do we need to file our return and pay any remaining taxes due, we also need to go ahead and make our Q1 estimated payment if we need to make estimated payments for 2026.

Brooke Cecil (16:31)
Yes, absolutely. We waste no time. We waste no time. And it needs to end in one, as you shared.

Steven Jarvis, CPA (16:35)
Yeah. Exactly. And this is where, especially if you are a business owner yourself or you work with business owners, I feel like I can’t stress enough the importance of having a quality bookkeeper on your team, because it can be easy to focus on, well, it’s the tax filing season. Let’s focus on getting last year’s taxes filed. That doesn’t mean we could ignore bookkeeping for three months. And I’ve known plenty of financial advisors who, when they start their firm, they’re like, I can do bookkeeping myself. I can have my kid do it. I can have my spouse do it. We can just figure this out. And kind of like DIYing your taxes. That can work for a little while. At some point, like you’ve got you’ve got to like enter the adult leagues and have someone who specializes in bookkeeping do this stuff for you. Because like anything else that you could DIY, like someone who does this all the time is always going to be better than you at that skill that that’s the only skill they practice. So whether you have a full-time bookkeeper on your team, whether you use a great resource like Belay, like at some point you’re going to graduate to this level where you need someone else on the team who really has that skill set. So, people listening, like what are some of those things you look for to help people identify, like hey, maybe it’s time for better help on bookkeeping.

Brooke Cecil (17:36)
Yeah, think, you know, especially as we talk through taxes, you know, there’s a lot that we’re managing, right? Not only are we thinking about our businesses, but we’re thinking about our clients and making sure that they have all the information that they need to move forward. And so it can be, we’ve got our hands over here in this pot and this pot, can often, you know, we are the ones that we think about last. And so if that is, you know, your books aren’t up to date in order to provide those estimated payments or whatever it might be, that to me is a quick sign that you do in fact need bookkeeping. If you have no concept of what your revenue was last month or what your gross margins are, that might be a sign that you do need your bookkeeping completed.

Steven Jarvis, CPA (18:21)
Yeah, well, we mentioned at the top of the episode, but you can text RTS to 55123 and get just a handy list of all of these dates. But what I’d encourage you to do, because some, if not all, of these dates are applicable to every single person listening to this podcast. So download that list and go through it and go ahead and put the initials next to each date of the person on your team responsible for making sure those things are complied with. And if your initials as the financial advisor are next to even half those dates, a quarter of those dates, it’s time to find someone else to help you out with this.These are important dates, but it’s not the highest and best use of your time. especially if you’re early on or like you’re hitting this transition point, like I’m not trying to shame you that that’s been the case to this point. Like we’ve all been there. It’s time to figure out how you delegate this to someone else on your team, because really, the dates we’ve been talking about so far are more focused on the individual side and how it attacks taxpayer whether that’s you as a business owner or your clients but as the taxpayer side like when should I be looking for things but there I there’s a few other things in there like getting W-2s filed and reported the 1099s that you might have to issue as a business owner those are all due in January and somebody needs to be paying attention to those and then again we can’t just put bookkeeping and reporting on pause as we’re getting the tax filing deadlines wrapped up for income tax reporting, we still have all the payroll reporting. We have the 941 that comes due at the end of April. Like, so there’s all these moving pieces that, again, as you go through that list of important dates, somebody’s initials need to go next to each one of them and they really shouldn’t be you.

Brooke Cecil (19:44)
Absolutely. Well, and I will say, know, from a bookkeeping perspective with those W-2s, the 1099s, 941s, those are all things that your team, you know, whether that is an on-site bookkeeper or a virtual solution like we have here at Belay, they can provide all of that to where that’s not even something that has to be on your radar as a business owner.

Steven Jarvis, CPA (20:04)
And it’s way better if it’s not on your radar. Like I love the fact that on a quarterly basis, my bookkeeper is just telling me about these things getting filed. Or maybe there’s one or two questions I have to answer, I mean, Brooke, don’t tell anyone. It’s not like there are thousands of people listening to this, like mechanically, I don’t know how a lot of that stuff works. Like I make sure I have a bookkeeper on my team to keep this stuff moving because that’s not the highest or best use of my time either. There are people who are experts in these things. Of course, mean, April 15th is a big, huge deadline. And if you extend your return, like that gets pushed out to October 15th for the individual returns, September 15th for the partnership and S-Corp returns. And just to keep things fun, it’s actually September 30th for the trust extended returns. Like we can’t have anything be consistent, but there’s a couple of important dates kind of in between those times just to make sure we keep on track with our estimated payments, because even though they’re quarterly estimated payments, they don’t happen evenly throughout the quarters, because Q1 is April 15th, Q2 is June 15th, Q3 is September 15th, and then of course Q4 is in the next year on January 15th. And yes, we’re saying January 15th, or the 15th of each of these months, if there’s a federal holiday, these things, or it’s on a weekend, they’ll move just a little bit, but let’s be ahead of these things. And then again, it might seem simple and silly. But making sure those payments end with a number that corresponds with a quarter can really save you in, although it’s not super common, you work with enough clients, it’s gonna happen on a pretty regular basis. Something gets misapplied or just missed entirely.As we get past the, you know, kind of the big tax filing deadline, like what are other things to just keep in mind throughout the year, whether it comes to bookkeeping or tax compliance?

Brooke Cecil (21:34)
Yeah, think a couple of things. One of the things that we always recommend for our clients, as it pertains to 1099s, is we ask that our bookkeepers specifically that they do a quarterly audit just to make sure that We have all W9s on file so we can easily process those at year end. So just keeping tabs on that. And that again should be something that you could easily delegate to your team to manage, not something that you need to manage. Ideally we always recommend that we have a W9 before we process payment, but sometimes it doesn’t work that way, and so we need to do that. So that would be an audit recommendation that we have. But also that you’re just sitting down on a quarterly basis with your bookkeeper to review the financials to make sure, know, in light of maybe some tax strategy or whatever you’ve got going on within your business that you’re making sure that things are categorized appropriately, that things are up-to-date and accurate so you can go into tax season with ease. And I would say that’s both for you as well as your clients.

Steven Jarvis, CPA (22:34)
Brooke, as you were describing that, it made me think of something that always makes me laugh when it happens. And maybe you can articulate it better, because I’m probably going to do the best job of this. So we have memberships for financial advisors. We throw an event every year for financial advisors. So we collect quite a bit of money from financial advisors. And without fail, every year, beginning of the year, I get a dozen emails from financial advisors wanting us to complete a W-9 so they can send us a 1099. And I try to, as nicely as possible, explain to them, hey, great news. You paid with a credit card, it’s irrelevant. And sometimes they know just enough to be dangerous, so they’ll say, wait, but StVhen, I paid you X amount of money, so I have to send you a 1099. Like, no, no, no, this probably is a good sign you need to hire a bookkeeper, because you clearly don’t understand how this stuff works, and you’re probably wasting a lot of time asking for W9, sending out 1099s that are completely irrelevant. So give us a little bit of context on why these financial advisors don’t need a W9 for me when I’m charging them through a credit card.

Brooke Cecil (23:26)
Yeah, so I mean, the easy thing, first of all, payments over $600 should be something that your bookkeeper should at least be vetting. Let’s say that, we’ll use that term loosely. And so really what that goes to is it is those individuals who are providing contract work, right? That it isn’t just any expense over $600 is going to, we get…Sure, we’re going to expense that charge, but it’s not necessarily something that we need to be providing a 1099. It’s truly a service that this individual is providing for your entity. I will say that IRS does a great job detailing out what.. deems a 1099 and what does not. So it’s truly that service. While, you know, we love the conferences that you put on, SteVen, and they are outstanding, but it does not require a 1099 for that item.

Steven Jarvis, CPA (24:20)
Yeah, Brooke, you’re absolutely right. mean, the information’s all out there. And another great example of not the highest and best use of a business owner, of a financial advisor, this is where we need people on our team to help us with these things so that we can focus on what that, really what that main purpose we should be spending our time on is. So yeah, love that. And again, we’ve gone through a lot of different dates here. And rather than have to write them all down or commit them memory, text RTS to 55123. If you’re serious about taking back some of your time and getting to focus that on higher value activities, go through that exercise, print out that list of dates and put initials next to them, because you’re going to find a couple of things. One, some of you might find that really you can’t assign anybody’s initials to them because nobody’s taking this seriously yet. And that’s a huge opportunity for you to deliver more value to your clients. Or you might be in a situation where it’s, well, I’m the one whose initials go next to all of these. In which case, would strongly recommend that you find somebody on your team or you add somebody to your team. Again, whether that’s through somebody like Belay or you find another way to make sure that gets delegated, that’s what I care about most is that you take action on this stuff and that responsibilities are going to the appropriate level of experience. And hey, if you already can assign somebody else’s name to every single one of those dates, great, take a picture and send it to me. I’ll post that on LinkedIn and brag about you all day if you’re already delegating those things. Like let’s celebrate some wins here. Yeah, Brooke anything else that that comes to mind as we wrap up this conversation on key dates?

Brooke Cecil (25:40)
. I think obviously awareness is important for all of us to make sure that we are marching towards and doing all that we can. So I think the communication that you have with your team as well as just your client base, to ensure that they are staying in front of these, I think it can do a lot for the partnerships that you have and really build that trust with your clients.

Steven Jarvis, CPA (26:00)
Yeah, Burke, the last thing I’ll say for our listeners here is that I’m sure for many people listening to this, like all of these dates we’ve talked about, like you’ve heard of these dates before. Like you’re at least familiar in concept, but they come back around every single year. Even if they sound familiar to you, for most of your clients, they aren’t gonna be familiar, and so it’s worth revisiting this. And more importantly, this is why Belay took the time to put all on a reference guide for everyone, is that we need to be anticipating these things, just like when we get, if you’re not thinking about March 15th until March 15th gets here, like you’ve missed your opportunity to be proactive. So being able to have these in a concise place, being able to delegate them to a team member is going to really elevate the client experience that you are able to create for people. So one last time, RTS to 55123, shoot that text off. You can download that reference guide. And Brooke, as always, really appreciate your time. Thanks so much for being here.

Brooke Cecil (26:46)
Yeah, thanks for having me.

Steven Jarvis, CPA (26:48)
And to everyone listening until next time, good luck out there and remember to tip your server, not the IRS.