YFP 309: Top 10 Tax Blunders Pharmacists Make

Sean Richards, CPA, EA, outlines the ten most common mistakes he saw pharmacists make throughout the most recent tax season. This episode is sponsored by First Horizon.

About Today’s Guest

Sean Richards, CPA, EA, received his undergraduate degree in Corporate Finance and Accounting, as well as his Master of Accountancy, from Bentley University in Waltham, MA. Sean has been a Certified Public Accountant (CPA) since 2015 and received his Enrolled Agent certification earlier this year. Prior to joining the YFP team, Sean was the Senior Treasury Manager at PRA Group, a global debt buyer based in Norfolk, VA. He began his career at American Tower Corporation where, over 10 years, he held several positions in audit, treasury, and accounting. As the Director of YFP Tax, Sean focuses on broadening the company’s existing tax planning and preparation operations, as well as developing and launching new accounting offerings, including bookkeeping, payroll, and fractional CFO services.

Episode Summary

The tax filing deadline is behind us so time to sit back and relax, right?! As YFP Director of Tax, Sean Richards, CPA, EA, tells us today, it’s important we are keeping tax front of mind year-round to avoid common blunders that show up during tax filing season. During this episode, Sean outlines ten of the most common mistakes he saw pharmacists make throughout the tax season including his thoughts on how year-round planning can help mitigate these mistakes.

Key Points From the Episode

• Sean gives us his tax-season rundown.
• The award for the most difficult state for tax returns! 
• Sean takes us through ten of the most common tax mistakes made by pharmacists. 
• The cause of the ‘unwelcome surprises’ and how to avoid them.
• Not taking advantage of tax laws: energy credits.
• Underestimating the power of the HSA; a grossly underutilized tool of the financial plan.
• A good reminder about over-contribution.
• Having someone in your court to help you avoid taking nonqualified IRA distributions.
• Not saving for taxes when earning additional income.
• Also for our side hustlers: not expecting the FICA tax on self-employment income.
• Some of the mishaps and mistakes that have to do with employer-dependent care.
• Not factoring in PSLF when choosing a filing status.
• Reporting implications: overlooking considerations with cryptocurrency.
• A bonus mishap: education around extensions.
• How year-round strategy planning can help pharmacists optimize their tax situation.

Episode Highlights

“I know, taxes aren’t something that people love to think about and want to be excited about but it’s one of those things where if you sweep it under the rug, it’s not going anywhere, it’s only going to grow under there.” — Sean Richards [0:6:55]

“If you’re making money that’s outside of a W2, whether it’s investment income, capital gains, whether it’s a side hustle, really anything where you’re not seeing that federal income tax withheld line, you better be putting taxes aside or being ready to pay that at the end of the year.” — Sean Richards [0:21:45]

“Crypto is treated like an investment as far as the IRS is concerned. It’s like a stock.” — Sean Richards [0:31:39]

Links Mentioned in Today’s Episode

• Subscribe to the YFP Newsletter
• YFP Comprehensive Tax Planning Service
• Sean Richards on LinkedIn
• RITA
• Inflation Reduction Act (IRS)
• Most Common Tax Mistakes (Made by Pharmacists) Download
• First Horizon Pharmacist Home Loan Requirements
• YFP Disclaimer

Episode Transcript

[INTRODUCTION]

[0:00:00.4] TU: Hey everybody, Tim Ulbrick here, and thank you for listening to The YFP Podcast, where each week, we strive to inspire and encourage you on your path towards achieving financial freedom.

On today’s episode, I welcome the director of tax, Sean Richards, back onto the show. Now that he has had a chance to take a breath from the last few months, working toward the tax filing deadline, I pick Sean’s brain about some of the most common blunders that he saw pharmacists make throughout the season and how year-round planning can help individuals not only avoid these mistakes but also optimize their tax situation.

If you’re looking to learn more about how YFP’s comprehensive tax planning service can help you and your tax situation, go to yfptax.com. Again, that’s yfptax.com Okay, let’s hear it from today’s sponsor, and then we’ll jump into the show.

[SPONSOR MESSAGE]

[0:00:48.3] TU: Does saving 20% for a downpayment on a home feel like an uphill battle? It’s no secret that pharmacists have a lot of competing financial priorities, including high student loan debt, meaning that saving 20% for a downpayment on a home may take years. We’ve been on a hunt for a solution for pharmacists that are ready to purchase a home loan with a lower downpayment and are happy to have found that option with First Horizon.

First Horizon offers a professional home loan option, AKA, a doctor or pharmacist home loan that requires a 3% downpayment for a single-family home or townhome for first-time home buyers, has no PMI, and offers a 30-year fixed-rate mortgage on home loans up to USD 726,200. The pharmacist home loan is available in all states except Alaska and Hawaii and can be used to purchase condos as well. However, rates may be higher and a condo review has to be completed. 

To check out the requirements for First Horizon’s pharmacist home loan, and to start the pre-approval process, visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[INTERVIEW]

[0:02:00.2] TU: Sean, welcome back to the show.

[0:02:01.8] SR: Thanks for having me. Yeah, it feels like it’s been a while but I think that’s just because tax season tends to you know, slow time down for some of us over here.

[0:02:09.7] TU: You look much more rested than I saw you just a few weeks ago. So here we are on the other side of the tax filing deadline. We’re going to talk all in this episode about some of what you saw this season with the hopes that pharmacists can prevent some of those mishaps as they work throughout the year on their taxes but looks like you’ve been – haven’t had a chance to maybe recharge and refresh on sleep. So how are you feeling post-tax of mine?

[0:02:34.3] SR: Yeah, I’m feeling great. I’ve been catching up on some of the things that have been put on side burners so to speak but definitely getting a little bit of sleep, catching up with the family and stuff. It feels good. I’m well rested, there are still some things to tie up from last year but ready to move forward and look ahead to next year and like you said, try to hopefully get some of these ideas in people’s minds so they can plan now and not have any of this kind of hiccups or roadblocks come up next year.

[0:02:59.5] TU: So give us the rundown. I know there’s still work to be done with some of the individual and business extensions and some of the more complicated returns but how many returns did you and the team do thus far?

[0:03:09.2] SR: We did over 200 federal returns and a similar number on the state side. So I mean, if you think some folks have multiple states, some people are in states that don’t have taxes so you know, you kind of, they work themselves out there but yeah, over 200 federal returns. We did a fair number of extensions, there are some business returns mixed in there, so it’s kind of all over the place but that’s the rough number between the few of us here.

So definitely, it feels like quite an accomplishment here but yup, I mean, definitely have some of those more complex returns that we want to give a little bit more TLC to, those are still hanging out there. So now that we’re past the big push, we can really focus and try to maximize savings for those folks. So excited.

[0:03:48.1] TU: Which state, Sean? Which state wins the award for the most difficult state when it comes to returns?

[0:03:53.3] SR: Boy, I don’t know if I’m going to be getting a misery love company or if I’m going to be jading people because I feel like a lot of our listeners kind of land in this territory where our headquarters are but I had to say, Ohio, probably gets the cake, Pennsylvania right up there, close second but yeah, those two are probably the worst I’d have to say. 

So again, hopefully, people aren’t sitting there saying, “I love those states” and if that’s the case, you know, all the power to you but not for me.

[0:04:20.8] TU: Yeah and one of the opportunities, challenges, depending on how you want to look with it, you know, we’ve got tax clients, financial planning clients all across the country, which is a unique opportunity and challenge when you think about all of the nuances that happen, especially in the tax side, right? On a state basis or even here in Ohio, we have the RITA, Regional Income Tax Authority, did I get that right Sean?

[0:04:43.1] SR: Yup, you got it right.

[0:04:43.9] TU: Which provides another wrinkle. So it’s fun to hear you and the team complain about Ohio and PA and you know, some of the other states perhaps are a little bit easier. So let’s jump into the most common mistakes Sean, that you and the tax team so far is just making and we’ve compiled these on our website, yfptax.com. If you want to download these and read a little bit more information on each one, please do that.

So we’re going to go through this one by one and again, the hope of this is that we really want to shift the perspective around taxes that the only time we think about taxes are April, when we’re filing, right? This really needs to be proactive year-round planning. We’ll talk more about that at the end of the show and that’s why we thought, “Hey, here we are in the month of May, tax season is over but this is not a, ‘Put it up on the shelf, worry about it ‘till next year.’”

This is the prime opportunity to really be learning from the season that just was and looking at the opportunities ahead of how can we best optimize the situation before we get back into the filing next year. Again, If you want to download a copy of the guide where we talk about some of these mistakes, you can go to yfptax.com and do that. So number one on our list Sean, perhaps the most common, I would presume, you can tell me if otherwise is folks that got a surprise bill or a surprise refund when they got to filing. 

So my question here is, tell us more but what is the usual cause of these unwelcomed surprises?

[0:06:14.7] SR: Yeah, I would say that’s the most common and it’s probably purely because if you take a lot of these other things that we’ll talk about, they all sort of work their way into that at the end of the day. You know, if you’re making a mistake, somewhere along the way, you’re probably going to end up with either a large bill or a large refund, so it kind of encapsulates everything.

Yeah, and just to kind of go back to your point before, this really is the best time to be looking at these things. I mean, any time of the year is good but when you’re coming off tax season, you might be disappointed or looking at things saying, “Oh, that didn’t go the way I hoped it would, I had a bill or I had the refund.” You don’t want to just kind of say, “Oh, finally, I’m done with it, we’re passed the 18th, I’m filed” and sort of shake your hands off and say because what’s going to happen is you’ll be in the same spot next year. 

I mean, I know, taxes aren’t something that people love to think about and want to be excited about but it’s one of those things where if you sweep it under the rug, it’s not going anywhere, it’s only going to grow under there. So yeah, the surprise bills and refunds, I mean, that can really be a litany of different things that can cause it. The biggest thing I would say probably by far is really just simply not withholding correctly at your job.

And this one frustrates a lot of folks and I don’t blame people because you know, people will say, “Hey, I’ve been at the same company for a while now” or “You know, my situation’s not that complex, how can they not be withholding properly?” and I have to say as a tax accountant, I don’t love the new W4 that the IRS rolled out a few years ago. If anyone working for the IRS is listening to this and they want to give me their opinion on it, feel free, my line is open because you know, I’m a tax accountant.

[0:07:43.0] TU: I don’t think we have many pharmacists that are IRS agents.

[0:07:44.7] SR: Oh hey, you never know, there’s a little bit of overlap here. You don’t have to be a pharmacist to listen to the pod but no, I mean, with that one, I just, I really wish there was a way as an accountant to be able to say “Hey, withhold 18% from this client, please. Just withhold 20% from this client” but it’s not that simple. I know what they’re trying to do, they want to make it more user-friendly where folks kind of can’t mess that stuff up, or if they don’t know how to come up with that number, it’s supposed to kind of guide you through it. 

So I think the biggest thing there is that the W4 is sort of designed to try to pick up everything else that’s going on in your financial life aside from just that one job that you’re working and typically, what will happen is folks will get married and they won’t update their filing status or they’ll get married or maybe not even get married but say, they already were married, their spouse gets another job. 

They have a side gig and these are all things that you know if your company – your system doesn’t really know that that’s happening, right? So if you’re making money off to the side, doing another job, you work multiple jobs, your spouse works multiple jobs, you know all those things factor into what your tax bill is going to be at the end of the day and if your company doesn’t know what’s going on then it can’t withhold properly and I say, your company, the payroll company was kind of doing all that stuff behind the scenes.

So that one is tough because there’s not a perfect answer. Really, the best way to do it is to take a look in the middle of the year and say, “Okay, where am I at, where was I at last year?” You know obviously if you had any kind of issues last year, you can submit a new W4 and how to change that but doing a projection midyear, take a look at what you’ve already withheld, what you withheld last year, and try to tweak that now, that’s definitely the best time to do it.

[0:09:19.1] TU: Yeah, and we’re going to come back to that topic Sean, of a mid-year projection, why it’s so important on the tax side as we get into the summer months. So stay tuned for more. Again, we’re going to be talking tax all throughout the year as we think it’s certainly an important part of the financial plan. So that’s number one, would be a surprise bill of refund at filing. 

Number two Sean, not taking advantage of tax laws. This makes me think of some of the recent changes that you’ve talked about before on the show surrounding the inflation reduction act, and the electric vehicle credits. I know this seemed to cause a fair amount of confusion and concern this year during tax season, and maybe some surprises as well. So what are you referring to here as it relates to not taking advantage of the tax laws?

[0:10:00.8] SR: Yeah, and with that in particular, I mean, we keep kind of harping on the energy credits but that’s where the tax law tends to be going now. I mean, all these things that are coming out, there are changes sort of across the board but the biggest piece and where the biggest dollar savings are tend to be these renewable energy credits, improvements to your home that are energy efficient, things like that.

And yeah, at the end of last year, the inflation reduction act went in and there was a lot of confusion as to which credits change when those credits change. So some of the electric vehicle stuff happened at the day that the law actually went into effect, whereas some of the other energy credits like home improvements like I mentioned, windows and things like that, didn’t really increase until this year, 2023 going forward. 

So there were folks who spent money last year and were expecting a larger credit for their taxes in 2022 and didn’t see that. So it’s really just, you know, it’s difficult to stay on top of the tax law, especially if you’re not a tax accountant or aren’t familiar with those types of things and especially if you want to stay out of politics too but it’s really challenging because it’s one of those things where if you’re not spending the money in the right timeframe, it’s not something you can go back and change after the fact. 

You know, if you put windows on your house now that’s a 2023 event. When we’re doing your taxes in 2024, we can’t say “Hey, I wish you had not done your windows because they’re already done.” So it’s something where it’s really important to make sure that if you’re spending money, thinking that you’re going to get a credit or you’re hoping you’re going to get a credit, really understanding when those things go into effect, what the dollar value is, and what the limits are. 

That’s another thing that some of these things, they’re increasing their limits but they do still exist. So you know, if you spend, USD 50,000 on an improvement, you’re not necessarily going to get a USD 50,000 credit.

[0:11:42.6] TU: Yeah, and we’ve got some info on this, yfptax.com, we’re going to be updating this throughout the year as well so make sure to check out the information there and Sean, this is just another testament to why the year-round planning is so important, right?

If we’re looking at this in the tax year, so here we are, now in 2023, obviously, next spring, spring 2024, we’ll be filing for 2023. At that point, right? Decisions have been made in terms of what happened during that year.

So are there adjustments that we can be making mid-year or are there tax laws and situations like this that we can make sure we’re up to speed or at least have the right understanding before we make some of these bigger purchases that may or may not have the impact that we’re hoping they’re going to have.

So that’s number two, not taking advantage of the tax laws. Number three, Sean. I have to say this one pained me a little bit because we’ve talked so much about this on the show.

[0:12:34.4] SR: So much.

[0:12:35.1] TU: Which is, underestimating the power of the HSA, the health savings account. You know, we’ve continued to emphasize how this – only has tax advantages but we still see this as an utter underutilized tool in terms of the financial plan. So tell us more about what you’re seeing here.

[0:12:51.8] SR: Yeah, I think with the HSA, it’s one of those things where people think, “Oh, I need to have a lot of medical expenses to take advantage of it. If I’m putting money there and I don’t use it, I’m not going to get the full advantage of it” but really, you need to not have that mindset and really think of it as a secondary retirement vehicle basically where if you do have expenses that you need to take advantage of it, it exists for you. 

But if you think of it almost as a second IRA or something like that, then it kind of shifts that mindset of, “Oh, I need to have these health expenses” but yeah, HSAs, I know, ad nauseum we talk about it but they have the triple tax benefit. You get the deduction for your contributions, you get tax-free growth and you get to take it out tax-free. So you rarely see that triple tax benefit. This is one of those ones where there is a little bit more flexibility. 

I just mentioned some of those credits and having to get the dollar spent during the year. You have a little bit of flexibility with the HSA where you usually have up until the filing deadline to actually make contributions or on the flip side and we saw a lot of this is people who work multiple jobs or got married in kind of weren’t talking to their spouse and over-contributed. So you want to make sure if you did that, you pull that money out so you avoid any penalties there.

And again, you have a little bit of flexibility after year-end to make those changes but to any extent you can avoid that, obviously, it makes sense but yeah, the limits are going up next year. I think 77.50 for a family plan, you have to be on a high deductible plan but if you are and you’re not taking advantage, you’re really just losing out on that benefit honestly.

[0:14:15.5] TU: Sean, I’m glad you mentioned the over-contribution mishap that might happen here and I think it’s a good reminder. Tim Baker was my ear, you know, anytime we talk about backdoor or Roth IRAs, he’s always beaten the drama of you know, really there’s a lot of nuances to consider and we see on the planning side, our planning team works with a lot of folks that you know, are trying to unwind some of the mistakes related to the backdoor Roth IRA contributions.

And I think it’s a good reminder that as there’s more and more information out there, right? We talk about HSAs, it’s readily available, something you can learn about that yeah, we still have to cross out Ts and dot our Is and I think having someone in your corner, right? Financial planners, tax professionals, perhaps both that can help make sure we’re executing this properly, really, really important. 

Number four on the list, Sean, taking nonqualified IRA distributions. We are talking before the show, perhaps maybe even a little bit broader than IRAs, tell us more about this one.

[0:15:09.0] SR: Yeah, IRAs are really just kind of retirement plans in general. I know we just mentioned HSA as they’re a sort of a secondary retirement vehicle but just not taking advantage or properly utilizing IRAs. So we’ll start with the IRA piece, there are a couple of different things there. You can get a deduction for traditional IRA contributions.

Folks typically phase out of that pretty quickly and then the next kind of phase-out level will be your Roth contributions and kind of what you were just alluding to is that folks also kind of pretty quickly phase out of that as well and that’s one of those things where you don’t want to end up at the end of the year saying, “Ah, you made too much money but you already contributed this to your Roth.” 

So now you’re going to go back and pull it out and then try to do the backdoor that Tim was talking about. So yeah, to any extent, again, you can have somebody in your corner where you can say, “Hey, this is what I’ve done so far this year, does this make sense? Am I going to over contribute, am I going to be in a good spot? Do I have room to contribute more?” Definitely make sense to do and again, you know the IRA limits are going up next year.

Again, the contribution limit. So taking advantage of that makes a lot of sense and the other piece that you didn’t really mention there but we kind of alluded to is just retirements in general. I mean, 401(k)s at people’s businesses, not taking advantage of those. You know, having extra cash on hand and not maxing out your 401(k) whether it’s a Roth to get the benefits in the future or a traditional to get that tax benefit now. 

I mean, either way, we saw a lot of situations where folks had a lot of cushion there and could have contributed more and that’s one where that at 1231, you can’t go back. So can’t turn back time, got to get those in before the year and again, having someone in your court to say, “Hey, you know, you’ve only contributed up to 30% of your 401(k) and we’re already in October, you might want to do some catch ups” is really important.

[0:16:47.8] TU: Sean, did you get a feel, I’m just curious, from folks that, if I heard you correctly, it looked like they’re wise margin there. They could have made those contributions or as cash on hand but didn’t. You know is that just a, “Hey, we overlooked it” or do you have a sense of you know, some of the volatility in the market, inflation, what’s going on in the broader economy, that there’s some hesitancy in the contributions into the retirement vehicles and people wanting to hold on to more of that cash.

[0:17:11.2] SR: It could be a lot of different things. I mean, it could also just be an education thing. I mean, I know, even when I first started out at a corporate job coming out of the school, you get all these different paperwork and everything and they say, “Here’s your 401(k), here’s this, here’s that” and you’re just saying, “Okay, I want to get the company match. Great, I’ll put this amount down and everything” and you don’t really realize that you have a limit that you can hit yourself and kind of capitalize on. 

So I think it’s really just a matter of maybe not looking at cash flow, like you were saying, potentially not taking a look at that in the middle of the year. I don’t think there’s a whole lot of hesitancy with the market or anything like that. I think it’s more just a matter of, you kind of set it and forget it and you know, you come to the end of the year and somebody says to you, “Hey, did you know that you could have knocked USD 5,000 off of your taxable income if you’d contributed more to your 401(k)?” and a lot of people just say, “I didn’t know that” so.

[0:17:59.3] TU: Yeah, yup. Seeing the numbers, right? I think in help and hindsight and you know, once you see the impact on the tax situation like, “All right, got it, point made, I’ll make that a correction for next year.” Number five, Sean, I think is one we have not yet talked enough about on this show, which is not employing a bunching strategy for charitable giving.

So here without talking obviously about donations and really looking at how to potentially alternate as you look at the standard deduction and then bunching these and those off year. So tell us more about this one.

[0:18:30.5] SR: Yup. So this one is more of a unique scenario. It’s one that we always take a look at but not everybody’s going to fall into this bucket but if you do, it’s something that if you’re able to take advantage of, it can be very, very powerful. So the idea of bunching is really trying to pull itemized deductions as much as you can into one year and then in the next year, not having as many and taking the standard deduction because it just getting higher and higher nowadays. 

I mean, just the number of folks that we see taking the standard deduction, even though they have things like mortgage interest and taxes that they’re paying for still taking advantage of the standard deduction because it’s so much higher. 

So yeah, if you’re looking at it and you say, “Hey, you know, I was USD 500 away from the standard reduction” or “I itemized USD 500 more than the standard deduction this year” and you had quite a bit of charitable contributions, if you’re able, again, sort of pull those in and say, “Hey, if I’m going to do a thousand dollars over the next two years, I’m going to do a thousand dollars this year and maybe not anything next year” and you can do it on 1231 so you kind of the same feel for giving to them that the charity.

But, if you’re able to do that and take advantage of it, it can be really powerful, and that way you’re not losing out. That was one thing we got a lot of is, “Hey, I have a house and I paid this mortgage interest but I am taking the standard deduction. So am I losing that benefit?” and it’s not the best way to look at it but you’re not really getting the full benefit if you’re doing it that way.

[0:19:50.1] TU: Yeah, as you mentioned, this really applies, not to say that everyone, depending on the amounts of folks are giving but especially for those individuals that are giving additional dollars to various organizations, churches, nonprofits, communities, et cetera, there could be some real benefits to the bunching strategy and I’m you know, one who is victim to this in terms of just behavior, right? 

Where you might have contributions on an automatic monthly payment or you’re planning for it throughout the year and you just don’t take the time to take a step back and say, “Okay, from a strategy standpoint, I’m going to do the standard deduction this year and then we’re going to do the bunching strategy next year.” So again, just some proactive planning to make this happen.

[0:20:31.6] SR: And it doesn’t always work for everybody because I mean, I talk to people who said, “Hey, that doesn’t match my giving strategy” and that’s perfectly fine.

[0:20:37.8] TU: Sure, yup.

[0:20:38.3] SR: It’s really just if you wanted to help out your financial strategy, there are options out there. I’m not saying you should change the way you give to your charities. It just exists, right?

[0:20:48.6] TU: Number six and number seven are specifically for folks out there that are earning some additional income, side hustling, business income. So number six, Sean, not saving for taxes when earning additional income.

It sounds obvious but we see more and more pharmacists that are dabbling in various side hustles, consulting businesses, so I think this is becoming a more prevalent mistake, probably one that maybe you make once and then you don’t make again but talk to us about what you’re saying here.

[0:21:16.4] SR: Yeah. So I mean, it does sound simple on the surface but again, if you’re not used to it or it’s not something that you’ve kind of done before, it’s not second nature, I guess. So right, if you, you know, you work a W2 job, that federal income tax is being taken out, hopefully correctly, although as I mentioned in the first thing here, sometimes it’s not correct but you know, hopefully, your income tax is being taken out at the end of the year.

You sort of do a true-up and maybe owe a little bit, maybe you get a little bit back but that’s that. If you’re making money that’s outside of a W2, whether it’s investment income, capital gains, whether it’s a side hustle, or really anything where you’re not seeing that federal income tax withheld line, you better be putting taxes aside or being ready to pay that at the end of the year and like you said, typically, that’s one where if you make the mistake, you don’t do it again in the future. 

But you know, I think some people are just really excited about making money and they want to pour the money back into their business, which is perfectly fine. You know, we want to encourage people to build their businesses and invest back in but just make sure you’re setting aside enough at the end of the year to kind of make sure you have at least a little bit of a cushion there and having somebody to do that calculation for you. 

Because you know, just because you’re going to – you think you’re going to net this much at the end of the year, doesn’t mean that that’s what your tax bill will be. I mean, there’s lots of ins and outs there, different things you can do. So having somebody to be able to take a look and say, “Hey, you know, as of right now, you’ve made 50k of non-withheld income so you’re going to want to put 20% of that aside, 25% of that aside, just be ready for it.”

[0:22:45.8] TU: Yeah, and I think there’s here, a couple of pieces you’re highlighting, right? Which are the mechanics of where do I save it, how much should I be saving based on how much I’m earning, and then at what point do I need to be making quarterly estimated payments and I do this, right? 

I reached out to you and say, “Hey Sean, we’re coming up on the Q1 estimated payment.” Like based on what we’re seeing in terms of the financial statements like, what’s the plan, and then we’re saving in a tax account along the way to be ready for those payments. So good thing, right? If you’re paying tax, you’re growing the business. 

[0:23:15.0] SR: Exactly and I will admit the IRS estimated payment process, it doesn’t really even feel that natural. I mean, you are kind of doing the math yourself, going onto the website and just saying, “All right, here it is” and they just take it and then at the end of the year, it does. It comes into your play, it’s one of the lines where you basically say, “Okay, what did you withhold? What did you pay in? What did you owe?” and we do the math on it. 

But it just feels like you’re sort of sending money out into the abyss when you make the payments. So I kind of understand that folks are a little apprehensive and would rather hold off but again, I mean, I’m conservative. I’m a tax accountant but at the end of the day, I’d rather get a little bit more money back than owe a lot of money. 

[0:23:55.0] TU: Yeah and Sean, a separate conversation for a separate day. This is a little bit more to the business strategy but one of the things that I like about withholding at least a quarter of it but at least on your own side even on a monthly basis is it forces you to look at the financials of the business a little bit more closely, right? 

So I think there can be a tendency if I am not paying tax and then I get either caught off by a surprise bill or I just wait until the end of the year and pay it, you know, you may fall into the trap of assuming your business is more profitable than it actually is and so really looking at what is the service, what’s the product you’re offering and what’s the true financials if you’re considering the tax. 

[0:24:31.1] SR: Not to go too far off but another big thing is that a lot of people kind of just assume that cash and profit are the same thing. 

[0:24:36.4] TU: Exactly. 

[0:24:37.1] SR: That’s not always the situation, right? So you could have a big profit at the end of the day but if you are pouring that cash back in, you might not have any cash on hand. So they don’t always go one for one and if you get away from that it can really end up causing some problems for sure. 

[0:24:51.7] TU: Preach it, Sean. We need to come back and do an episode on that, the difference between cash on hand and profit of a business, so that’s a good one. 

[0:24:58.3] SR: Yeah, that one, I’ll make a note because that could be like a double episode but yep, I’ll put that one on the back burner for sure. 

[0:25:04.7] TU: So that’s number six, not saving for taxes when you’re earning additional income. Number seven, also for our side hustlers and those that are running a business, not expecting the FICA tax on self-employment income. Tell us more about the FICA tax here. 

[0:25:17.7] SR: Yep, so that’s kind of similar varied, similar vein as to what we were just talking about really just having to kind of put that money aside but again, something that’s not second nature. It’s not something that you’d really be typically thinking about until you get into this and potentially make a mistake, hopefully not but right. When you have these W2 jobs and the money is being taken out, you’re withholding for yourself and you’re paying social security and Medicare, which we call FICA for yourself. 

Your employer is paying half of that for you whether you realize it or not and when you are self-employed, so you have a partnership or your own kind of business and you are getting that money in, you have to pay that portion of FICA yourself. Now, the benefit is that you get that employer portion that the employer typically would be paying for you on a W2. You do get that as a deduction, so it helps a little bit but yeah. 

I mean, that what was it? 15.7% or whatever for FICA is coming out of your bill at the end of the day. So on top of the regular income tax you have to set aside, you should really be saving for that as well. That’s where you’ve heard me say before, you know, 20, 25%, maybe up to 30% depending on what your bracket is, you start to add that FICA in on top of it and you could be looking at quite a bit to be setting aside. 

[0:26:27.6] TU: Yeah Sean, this was one I would add to this as well. You know, the surprise of the cost of health insurance. This is one as well, you put those together and you go from a W2 job to running your own business is like, “Oh, okay.” So again, right? You’re looking at the financials in a very different way. 

[0:26:44.5] SR: Yep, exactly. Things to keep in mind. 

[0:26:46.8] TU: Number eight, Sean, has to do with some of the mishaps and mistakes with employer-dependent care. Tell us more about this one. 

[0:26:53.3] SR: Yeah. So there is a lot of different things with dependent care benefits that you can add to dependent care FSA. So it’s a little bit different than the HSA but with that, that one really is a little bit more of the, you know, I was saying with the mindset within HSA, “Oh, if I don’t have medical expenses and I don’t use it, you know it’s not going to be worth it for me.” It turns into an investment vehicle if you don’t use it. 

Dependent care FSAs, flexible spending accounts, if you have cash in that, that is more of an “if you don’t use it, you lose it” kind of thing. So that is something where if you’re pushing cash aside, they are pre-taxed dollars. You want to make sure you are using that for dependent care expenses during the year and the other thing is that if you are getting benefits from your company, you want to make sure that you are also putting that and actually spending that on dependent care. 

When I say that, I mean a nanny or a daycare or even if it’s a family friend but somebody that you’re putting their social security down and saying, “Hey, I paid this person this much money to watch my children” otherwise, that can become a taxable event. So you want to make sure that if you have kids, you’re getting these benefits, that you are utilizing the cash during the year and not kind of ending up with excess in those accounts at the end of the year exactly. 

[0:27:58.9] TU: Number nine Sean, an oldie but a goodie, one that I think has lots of attention given the three-year loan pause and that is, not factoring in PSLF when choosing a filing status. Tell us more about this one. 

[0:28:11.3] SR: Yeah and this one, I mean, you just eluded to it. It’s been very, very challenging, especially with the client base that we work with having that ambiguity on what’s going on with the loan system and trying to give guidance on this front because it’s really tough when you’re saying, “Hey, we’re not exactly sure if they’re going to turn back on and how all that looks and when we’re going to have to recertify all these things.” 

But yeah, what we’re talking about here is that typically when folks get married, if filing joint tends to be the best approach there and we always do a comparison at least on our side to say, “Okay, you know all else equal from an objective tax standpoint, filing jointly will save you X number of dollars versus filing separately” but when you are talking about PSLF and you get into these income-based repayment plans and are looking at AGI, that can really swing very, very rapidly between what your AGI is as merely filing separate individual versus your combined AGI with your spouse when you’re filing joint. 

So this is one where it’s a classic like you just mentioned Tim Baker, the old “it depends” really depends on your individual circumstances here. You’re going to want to look and say, “Hey, what do I have on my side? What does my spouse have on their side? If you separate us, what does that look like? What is my income base repayment plan? What numbers are they looking at?” and really like we just said, “When do I have to recertify these things?”

“When am I going to have these payments?” because it’s a matter of you could save $200 by filing jointly this year but if you are saving $50 a month on your payment by filing separately, that adds up very quickly. So it’s something where there’s a lot of moving pieces but it is something where if you are not looking at those pieces, you can very, very quickly end up spending a lot more money than you think. 

[0:29:49.3] TU: Yeah and it is so important. You know, we’re talking about PSLF here but the intersection of student loans and the tax strategy is one of many examples where the financial plan and the tax plan need to be jiving, and this example specifically brings us back to the origins of FYP Tax, right? I remember Tim Baker talking about, “Hey, we would develop these beautiful student loan repayment strategies and plans.”

Then they’d be, “Hey, go talk to your accountant” and not all accountants are well-versed in student loans, which is fair, right? Based on how nuanced they are and right now, how rapidly this information is changing. So shoutout to you Sean, the YFP Tax team, you know working with a tax prepare, working with an accountant that understands student loans. Again, this is just one example but really, the intersection of the financial plan and the tax plan is so important that those are jiving in the same direction. 

[0:30:39.8] SR: Yeah and like you said, I mean, not all accountants know about it and I know enough to be dangerous with it but you have to have financial planners that know about that too. I mean, that is something where I could be working with you and say, “Hey, I think from a tax standpoint it looks like this” and you could go bring that to your planner, and if they’re not really thinking about these implications, they can really get away from you quickly, you’re right. 

[0:30:58.3] TU: Number 10 on our list of ten common mistakes, mishaps that pharmacists were making during the most recent tax season is overlooking considerations with cryptocurrency. I mean, what would be a tax episode if we didn’t talk about crypto in digital assets, so what do we see here? 

[0:31:12.4] SR: Well, this one probably is a little bit different than we’ve seen in the past with crypto. It wasn’t so much that we are seeing people with these big gains that they were necessarily expecting. In fact, if anything it might have been the opposite given what kind of happened with the market and everything last year but in that and what I would say with that is you know, if you kind of take the gain-loss implications aside, the biggest thing I would say here is just the reporting aspect of it.

So cryptocurrency again and I feel like I harp on this all the time is crypto is treated like an investment as far as the IRS is concerned. It’s like a stock, so if you go and you’re doing all these microtransactions all the time and you’re using your crypto wallet to buy coffee down the street, that is effectively saying, “Okay, I’m going to sell X number of shares at this price on this day” whatever I bought it for back in the day that same security. 

You need to look at what your basis was and do the math, so if you are doing hundreds and thousands of these transactions every year, the reporting implications are significant and that’s not something where you can say and I am not just saying this because I’m an accountant, I’m biased where you can’t just say to your accountant, “Hey, here is my list of a thousand transactions, you know, figure it out for me.” 

You need to make sure that whatever system you’re using can spit that out in a digestible manner whether it is actually getting a form from the IRS or kind of getting a summary and one thing that we have seen is in a lot of these companies and I don’t blame them necessarily but a lot of them will kind of rope you in and say, “Hey, you know it is going to cost you five dollars a month for the basic crypto wallet” and everything like that. 

Then you get to the end of the year and all the tax forms that you need will be kind of an extra charge and you are not thinking about it and folks will say, “Well, I have an accountant, they can kind of do that for me” but I mean, again, and I am not just saying that because I don’t want to do it. It really is a matter of an accountant simply can’t take thousands of transactions and stick them onto a form. 

It is not a practical thing that can happen. So you want to make sure that whatever you’re doing and again, if you want to do all those transactions, hey, power to you but keep in mind it’s like you’re selling shares. You need to make sure you are getting something out of your system that an accountant can then use and file your taxes with because it’s not like spending money. It’s like selling stocks. 

[0:33:19.6] TU: Yeah, I am hopeful Sean, this is another one you know, where you can make this mistake once and you maybe approach it differently in the future, right? I think this is an education where your explanation is spot on. If we look at this in the eyes of the IRS, which is that we’re making a transaction in terms of like we were selling stock and especially if we’re using it to purchase things on a daily basis, right? 

A store, a cup of coffee, groceries, whatever like we don’t think about our stocks like that typically and so I think that — not to say people may not transact crypto for purchases just like you would dollars out of a brokerage account but maybe not on the frequency that it’s happening if you are able to think of it in that way and understand the reporting and the tax implications there, so great explanation. 

[0:34:04.6] SR: Exactly. I think like I said, that the basis is really the biggest thing and I, you know, people, if you talk to me you’ll hear me say it all the time and you’re probably sick of it but it is really being able to trace back and say again, like it’s like a stock, right? So if I sell XYZ NFT today, I need to make sure I know what I purchase XYZ NFT for in the future, and when you are doing all these things and you’re day trading so to speak, and saying, “All right, I am going to flip this one here and I’m going to go buy crypto with this one” and kind of moving, each one of those things has to be kind of traced back to the origin. 

If you don’t have that information, you could end up paying more, honestly. You know, if you don’t have the basis information and you are just going to end up sell, reporting it on your sale price and not have the basis in there, you can end up either paying more or again, reporting incorrectly. Both of those are not what we’re hoping for in our side at least. 

[0:34:55.9] TU: So if anyone heard Sean correctly as I heard him, all of your handwritten crypto transactions, your reports, your chicken scratch, you can email those to [email protected]. He will gladly – just kidding. 

[0:35:07.8] SR: Yep, I will go through all of it in all of my free time now. Absolutely, I will break it all down for you, please. 

[0:35:14.0] TU: Awesome. So that’s our ten common mistakes that you saw pharmacists making throughout the tax season. Can I add one more? We’re going to do a bonus round here for a moment and – 

[0:35:22.5] SR: Yeah, go for it. 

[0:35:23.2] TU: I think we need to do some education around extensions, right? I think this is an area where I know firsthand the first time I extended several years ago and I have gotten used to that practice now. It can feel uncomfortable, am I doing something wrong, does that mean I’m delinquent? But as you eluded to at the beginning of the show, there are some extensions that are happening with the more complex returns. 

We want to make sure that we have the time that we need. The misperception I think, I could be wrong, that’s out there is extension means bad or extension means delinquent but that’s not the case, right? So tell us more about the use of extensions and why they may be appropriate. 

[0:36:01.9] SR: Yeah, glad you’re giving me the bonus round. I would have had this as 1-A on my list if I would have thought that you would have actually allowed me to record this podcast if I did that. I thought that I came over the top of that one, we might be deferring this recording out to a future date but no, extensions, yeah. So it is actually kind of twofold. I would say that from who I’ve talked to and this could be clients. 

I mean, even family members that I was talking to during the tax season, checking up on how things are kind of going, I would say with the negative connotation, it’s one of two camps. It’s either, “Hey, the extension means bad and delinquent” or extension means, “Hey, I’m this crazy tax guy who has offshore accounts and you know, I make five million dollars and I need to have my accountant spend the extra time to do all of this stuff.” 

Those are really the two mindsets that I got a lot of. I mean, like I said, I talk to people that I know, I’ve known for a long period of time who I consider to be financially sound individuals and they said, “Oh extensions, those must be for your big ticket clients, right?” and the answer is not really. I mean, extensions simply give us, your accountant, and you more time to get your things together to allow us to dedicate the time to find you tax savings, get your things right, and not rush them. 

I mean, I know Paul, my team who I’m sure you’ve heard talk on this pod before but he’ll always say, I mean, if you have a surgeon who needs to do a thousand surgeries in a year, would you rather him do them all in three months or her do them all in three months or have them do it throughout the course of the year, you know, with X number during each month. So you got me all fired up because you know, extensions are near and dear to me. 

But I mean, really what it comes down to is we’re trying to do a lot of different returns and a lot of people have very complex situations but we want to make sure we get it right. We talked about states and local, moving states, and making sure states don’t talk nice to each other even ones that border each other are not – don’t always agree with how things are picked up and everything, and just getting all that information together, making sure we can parse through it, maximize your tax savings and everything, extensions just give you the time to do it. 

Now, the one thing I will say is it does not extend your due date to pay. That’s the biggest thing. So what you want to do is get an estimate, and make your payment if you think you are going to owe or in April or even beforehand but after that’s done, it really is a one-click kind of thing. It’s an automatic extension, once you do it, it’s six months. You get until October and that’s that. It really is not for delinquents. 

It is not for folks who didn’t get their stuff in on time or like I said, are using offshore accounts to do X, Y, and Z. It’s just simply to give your accountant more time to get it right. 

[0:38:41.5] TU: Well, thanks for allowing me to throw some kindling on the fire, so I appreciate that. 

[0:38:45.3] SR: Thank you, I appreciate that. 

[0:38:45.8] TU: You know, I think it is a good reminder not only in the perception of it but also you know, some folks may hear this and say, “Well, you know there is an opportunity cost that if I am getting a refund” and we don’t file that for three months, four months, five months later, whatever that those dollars could have been used elsewhere. True but my counterpoint to that would have been, one, if we are planning correctly throughout the year, we shouldn’t be expecting a massive refund. 

Second to that would be is that most often, extension doesn’t mean we’re buttoned up against the October deadline. It means that maybe instead of April 18th, it’s May 1st or 15th or even the end of April or into later in May or early June, whatever. So you know, it allows kind of that stretching out of the season to make sure that we’re doing the job that needs to be done, be done well, we are optimizing the situation. 

I think that certainly for folks that have more complicated returns, I think what we’re seeing in the industry in my perception even with an accountant we used to work with before building our own practice internally was, “Hey, you’re a small business owner. Hey, you own a bunch of real estate” hey, whatever like you’re automatically extended. You know, that’s just kind of the process of what they do to make sure that they have the time to do those returns well. 

[0:39:55.5] SR: Right and like you said, the idea of year-round tax planning is you’re working with your accountant throughout the course of the year. You are getting the information, you have rentals, you’re getting them, “Hey, I sold this place in November” and you are giving them the information in November so your accountant can already have that stuff ready to go and it’s not a situation of you’re in March and you say, “Hey, I forgot” or “FYI, sold my house back in January of last year. Here’s the 5,000 documents for it. Can we get this filed next week?” 

The answer is, I mean, we probably can but you know if we are thinking about these things ahead of time, we can spend the time that we think it deserves to get everything right, and if you are doing that planning throughout the course of the year, you can get 90, 95% of a tax return effectively done through the conversations that you’re having with your account throughout the year. So yep, absolutely. 

[0:40:40.4] TU: So Sean, let’s wrap up by talking through how the year-round planning can help pharmacists not only prevent these mistakes but again, better yet optimize your tax situation. That really is the focus of what you and the team are doing through the comprehensive tax planning, what we refer to as CTP. Again, not just that transactional return month of April, got to get it done but really that year-round strategy and planning. 

So you know, what is comprehensive tax planning? What do we offer? Why is it needed and who is it for and perhaps, not for as well? 

[0:41:11.3] SR: Yeah. So comprehensive tax planning is designed to really attack everything on this list, right? So it’s where you’re doing proactive planning and thinking about your tax situation now and not at the end or not in the beginning of next year looking back on this year and again saying, “I wish I could have done this” or “How could I have done this differently?” It’s getting ahead of those things now so you don’t have to worry about that. 

So things like mid-year projections, “Hey, let me grab your paystub, let me talk about some of those side gigs you’re doing, give me an updated PNL” or even if we’re doing your books for you, I’ll pull down the updated PNL and we’ll take a look. “Hey, you know you’ve withheld this much money so far, your side gig is going to make this much money we think so far. Have you put that money aside yet? Did you make an estimated payment?” 

“I think you should make a payment of this much” checking in on those things or being able to have the conversations of you know, “Hey, I just bought a rental property. Tell me about the short-term rental loophole” or “Tell me about what it’s going to take for me to be considered a real estate professional and be able to offset some of my active income with this passive income” or “Hey, I just bought the rental and hearing all about all these tax credits.” 

“How does that work? How do those tax credits affect my personal return and then how does it affect my rental property? Are those going to be different? Can I maximize them?” These are the conversations that we’ve been having with folks over the past few months looking back on last year but proactive tax planning is you’re having these conversations now. You are having them in May, June, and July and getting ahead of these things. 

So when we talk about March and April that big push, it is really a matter of, “Hey, did we do what we say we’re going to do? Excellent, great. Okay, what are your tax bills? Zero. As expected. Awesome, file? Done. Food to go.” Just really having that phone-a-friend CPA to ask questions for, “Hey, you mentioned bunching when we looked at my return last year. You said I was close to the itemizing. How can I actually employ that now?” 

Or “Hey, this is what I’ve contributed in my 401(k) so far this year, do I have room to add more?” things like that. Just getting ahead of it now while there’s room to make changes and not looking back and saying, “Ah, I really wish I did that.” 

[0:43:19.9] TU: Great stuff. So you know it’s again, not only that finally and it’s the mid-year projection, it is having an accountant in your corner to make sure you are executing throughout the year, answering those questions as they come up. So folks can learn more at ypftax.com. You can read more about that service, you can book a free discovery call to see whether or not it’s a good fit for your personal situation. 

And again, whether you came off the season and you’re like, “Hey, I did that myself and I never want to do that again” or you were surprised by a refund or a bill or perhaps you have a situation that’s changing, right? It could be moving, a new job, dependents, acquiring real estate, or building a small business, all are these I think there’s a few examples of things that we want to be thinking about in planning throughout the year. 

So again ypftax.com, you can learn more and book a free discovery call to see whether or not that’s a good fit. Sean, thanks so much for taking the time. I appreciate you coming on the post-tax season and looking forward to having you on throughout the year. 

[0:44:15.6] SR: Yeah, thanks, Tim. Glad to be back and hopefully next time, we’ll be able to talk more about some of these backburner items. So I am looking forward to it. 

[0:44:22.1] TU: Awesome. Thanks, Sean. 

[0:44:23.1] SR: Thanks. See you. 

[END OF INTERVIEW]

[0:44:25.3] TU: Before we wrap up today’s show, I want to again thank this week’s sponsor of the Your Financial Pharmacist Podcast, First Horizon. We’re glad to have found a solution for pharmacists that are unable to save 20% for a down payment on a home. A lot of pharmacists in the YFP community have taken advantage of First Horizon’s pharmacist home loan, which requires a 3% down payment for a single-family home or townhome for first-time home buyers and has no PMI on a 30-year fixed-rate mortgage. 

To learn more about the requirements for First Horizon’s pharmacist home loan and to get started with the preapproval process, you can visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[DISCLAIMER]

[0:45:10.4] TU: As we conclude this week’s podcast, an important reminder that the content on this show is provided to you for informational purposes only and it is not intended to provide and should not be relied on for investment or any other advice. Information on the podcast and corresponding materials should not be construed as a solicitation or offer to buy or sell any investment or related financial products. We urge listeners to consult with a financial advisor with respect to any investment. 

Furthermore, the information contained in our archived newsletters, blog post, and podcast is not updated and may not be accurate at the time you listen to it on the podcast. Opinions and analyses expressed herein are solely those of Your Financial Pharmacist unless otherwise noted and constitute judgments as of the dates published. Such information may contain forward-looking statements, which are not intended to be guarantees of future events. Actual results could differ materially from those anticipated in the forward-looking statements. For more information, please visit yourfinancialpharmacist.com/disclaimer. 

Thank you again for your support of the Your Financial Pharmacist Podcast. Have a great rest of your week.

[END]

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