✍️ Some of you may know that I’ve been writing this award-winning blog for 10 years now. Not monetized — just a labor of love that started out as a way to store articles for myself in an easy-to-search format. But during the pandemic its popularity exploded… not just for small business owners, but for the bookkeepers and accountants that keep them going. (If you didn’t already know my biggest passion is supporting small businesses & the communities that they help thrive and keep vital and colorful, then you must be new here.)
🔢 And I realized — when I help a small business, I help ONE of the key players in keeping local economies healthy. When I help a bookkeeper, I help a multiple of small business owners. When I help many bookkeepers… you can see where this is going…
🐣 Last year I decided that I wanted to focus my efforts on helping bookkeepers and tax pros learn to collaborate, and that the best way to start would be to offer a judgement-free space for bookkeepers to ask ANY QUESTIONS THEY WANT that for whatever reason they can’t ask their clients’ tax preparers (or, if in a firm, they don’t feel comfortable asking the tax department). And thus was born…
🏫 ASK A CPA! A member community designed to provide education, support, and resources for bookkeepers to better serve their clients — by preparing tax-ready books, improving relationships and building knowledge and systems that ultimately help small business owners and their communities.
❤️ We’re starting small, intentionally, and as such we’ll be capping our founding member group at only 50 people — there are only 9 spots left as of August 10th! Get in here and help us create the community you want to see in our industry. (Or feel free to just sign up for our updates if you want to have FOMO like all the time, that’s cool, too.)
For years, we have stressed the importance to our clients of making quarterly estimated tax payments. And unlike many tax preparers, we also do bookkeeping, accounting, and consulting for our small business owners — so we’ve also encouraged them to have us do a quarter-by-quarter calculation of how much to pay.
There were many reasons for this: · Making sure the client had their books up-to-date and reconciled for the quarter, so they can be used for real-time managerial decisions; · Matching the cash flow of a given quarter (or the actual sales and vendor invoices, for accrual-basis clients) to the related tax liability; · Preventing the common situation of getting to tax-time and having a huge refund or balance due.
However, times have changed. We still want folks to make quarterly payments (see my related IRS & Illinois posts for how to do it online), but for the first quarter, at least, we’re asking everyone to use “safe-harbor” calculations.
Why Use 1Q Safe-Harbor Calculations Instead of Annualizing?
For one, the immense number of changes to our tax code since the Tax Cuts & Jobs Act (TCJA) took effect in 2018 has made tax planning substantially more complex than it used to be. The amount of time it takes to do a “back of the envelope” or “paper napkin” calculation has tripled. (And in case you’re curious — we use tax software and Excel, not used envelopes and paper napkins in our firm. That’s how you know you’re working with a real professional.) Both the effort involved and the cost to the client have increased accordingly.
Relatedly, first-quarter estimated tax payments are due on the same day as personal 1040 and C-Corp 1120 taxes are due. And since our tax-time work is a deeper dive than it used to be, and the estimated tax calculations are more complex as well, there simply isn’t enough time to do a full-on calculation for each and every client that requests it — at least, not if we also want to be well-rested and in good health, so we can do our very best on the remaining annual tax returns.
There’s good news, too, however — the state of Illinois — and many other states, used legislation to create a loophole for getting around a pesky TCJA limitation on the State And Local Tax (SALT) deduction. I won’t explain it all here, but the result is that all of our S-Corp and Partnership (aka “Pass-Through Entity”, or PTE) clients are paying their personal state taxes through the company. This is a very easy and predictable calculation, as Illinois charges a flat tax (not socially progressive, but it certainly is simple) and requires the annual liability to be divided by four and paid evenly across the quarterly deadlines.
(Side note: the deadlines are not actually quarterly. Due to the timing of the federal government’s fiscal year-end and individuals’ calendar year-end, they are skewed such that they’re not even the same number of months per quarter. You would think that of all the government departments that could count properly, it’d be the IRS, but apparently not. The due dates are 4/15, 6/15, 9/15 and 1/15 — though many are better off making the final state tax payment by 12/31.)
As a result, quarterly calculations for the state simply aren’t necessary for the first quarter (possibly even the first three quarters, depending). Given that the states seem to live for assessing penalties and interest for underpayment of estimated taxes (they are wildly aggressive about it), this is the best approach to take.
But it’s not just the states that issue penalties and interest for underpayment of taxes — the IRS does, as well. Much less aggressively, however, and they do still have the notion (that the new Illinois PTE tax law does not) of “annualizing” your quarterly taxes. This means that you presume the amount you made year-to-date is representative of the whole year, and paying quarterly tax based on that projection. It works great for small business owners who have lower income in the first three-quarters of the year and then make most of their profit in the final quarter.
Just to be clear: we still do this for our clients… but we wait until the second or third quarter, and in some unusual cases, we wait until November and then do a thorough analysis of the year thus far. It’s just that there’s little point in running these calculations for the first quarter anymore — it’s almost never representative of the rest of the year, and it places them into a precarious situation where they may end up underpaying by too much and then owing penalties and interest. Or, at the very least, having to pay us at tax-time to fill out the complicated annualization schedule on the tax return. If you want to be more accurate with your calculation, because you expect your income to be substantially higher or lower than last year, then ask to book a May tax-planning session to get squared-up for the 2Q payment, due June 15.
Last, but not least — we’ve decided to have all our clients commit to a monthly bookkeeping and accounting contract with us. Doing annual clean-ups during tax season simply is no longer sustainable (to be honest I’m not sure it ever was, which is one of many reasons so many CPAs are burned out), and isn’t cost-effective. It’s also not fair to our other clients — who are on a monthly schedule — to have to wait in line while we work on those who swing through just once-a-year. And most importantly, we truly believe that all small business owners should be looking at their financial statements regularly to help them make impactful decisions throughout the year — ones that can sometimes be the difference between turning a profit or enduring a loss. And since everyone will be on a monthly schedule, the motivation no longer exists to do quarterly reviews for estimated tax purposes, purely as a way to get clients motivated to catch up on their books.
Where To Find Your Safe-Harbor Amounts and How To Pay Them
If you’re a client of ours, or of pretty much any tax professional out there, calculating safe-harbor quarterly estimates can and should be a part of preparing your annual tax return.
After reviewing and signing your return, your CPA (or EA, JD or non-credentialed preparer) will e-file it, and once it’s accepted by the IRS and state agencies, they will either send over vouchers (which I wouldn’t bother using, because we want to pay taxes online almost every time that’s an option), or a list of required payments — whether that’s in a letter or a little chart form where you can check ’em off. However you get them — put them in your calendar now. Do not rely on your tax preparer to remind you. This is not their job. You are a grown person running your own business, surrounded by technology that is designed for precisely this kind of thing.
And if you’re in a panic and can’t find the amounts, the general rule is that you want to pay 1/4th-ish of your total tax liability for the prior year (a bit higher for some states, such as Illinois). Again, if we do your taxes, you should have already received these totals for 2024, or will be receiving them as soon as your return is finalized.
Frequently Asked Questions
1) What if I have an extension? Two options here: a) provide your tax preparer all the docs you already have and ask them to do their best to give you an estimate; they can even add that to the amount you’ll need to pay with an extension — which means if your extension payment estimate is short, the 1Q estimate will make up the difference, and either way, you’ll just apply the balance to the current tax year; or, b) go ahead and keep paying the same amount you paid for last year’s quarterly taxes; some payment is better than none.
2) What if I don’t have a tax preparer? All the DIY tax programs out there can do this, too — they’re not very helpful for the tax planning that we do with our clients for 2Q & 3Q, and certainly not for 4Q — but they do a perfectly fine job with safe-harbor estimates. Alternatively, check out my colleague Hannah Smolinski‘s great YouTube primer on how to calculate estimated taxes.
And since you asked, here’s a fabulous photo of Hannah and me at QuickBooks ConnectFest.
3) What if I can’t afford to pay my quarterly estimates? Pro tip: Did you know you can break your quarterly payment into smaller chunks? Let’s say you owe $2400 per quarter and you’re worried that you won’t have enough set aside by the time the due date arrives, because it’s so hard not to raid your own savings account when opportunities call. Just go online and pay $800 per month instead. Or $200 per week. It gets tricky with the weird quarterly tax due dates, but you are a smart cookie and can figure out the math. The point is that you don’t have to save it all up and then make the payment. If you have cash on hand, you can go in there now and do it while it’s on your mind, even if it’s a partial payment. Something is better than nothing.
4) What if I forgot to pay for a quarter? Go in there and make a payment now. The penalties are per day, so the sooner you make up the difference the better.
5) What if I have additional questions about the process? Throw whatever you can at the quarterly estimates and contact a CPA to help you… after Tax Day. Please be respectful of the plight of tax preparers right now. It will not serve you long-term to try to wedge yourself onto someone’s calendar last-minute: almost all the good ones had a deadline for submitting tax materials weeks ago; we’re all exhausted and likely to make mistakes this time of year if we’re taking on too much and not taking care of ourselves; and you want to start off on a good foot when building a relationship with a trusted advisor. The amount of penalties and interest that will be due if you underpay slightly is not that significant if you’re going to be making up the difference in a month, so just pay what you can and get on-track later.
Now, get yourself online and go make those first-quarter safe-harbor quarterly tax payments, already!
If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.
If you’re a regular reader, you already know that I’m a huge fan of the National Association of Tax Professionals (NATP), for a bunch of reasons:
Fabulous and affordable education with top-notch instructors
Straightforward “how-to” resources
Practical monthly newsletter with case-studies
On-demand “pay as you go” research service
And a very fun group of folks at the annual conference! (That last one’s a teaser for the final photo in this post.)
I’m especially indebted to NATP because when I first started doing taxes, I wasn’t a CPA yet — and spoiler alert: they don’t really teach you that much about tax preparation when studying for your CPA exams; in fact, three-quarters of the test aren’t related to taxes at all. In those early days, NATP education was the best-quality, most affordable that I could find without being a member of AICPA. (And I tried *all* the groups out, to be clear.)
Anyway, point here is that not only do you not have to be a CPA or EA to take and benefit from their classes — in fact, you don’t even have to be a tax preparer. I am a passionate proponent of teaching bookkeepers what they need to know about taxes to be better at their jobs, coordinate and communicate effectively with their clients’ tax preparers, and level-up by providing value-added advisory services to their clients.
To that end, here’s an upcoming NATP webinar that I suspect will be pretty dang useful for anyone doing client accounting work — bookkeeping, tax, advisory, CAS, and so on. You don’t even have to be a member to attend.
I get a lot of questions and see a great deal of misinformation out there about entity choice… here’s an opportunity to learn more about how to help your clients decide which entity structure is the best choice for them.
(Note: this is *not* a referral link — I’m just really excited about this education getting out there into the world. The presenter, Larry Pon, is a great guy and super-knowledgeable about all the ins-and-outs of this topic.)
From NATP:
Proficient knowledge in selecting the optimal entity structure is vital as it directly shapes a business’s tax outcomes. Strategic choices can enhance deductions, reduce liabilities and ensure regulatory compliance, contributing significantly to a business’s financial well-being and long-term success.
We know you want the best for your clients, so we want to arm you with the knowledge to do so.
As clients start new businesses, one of the major decisions to make is what entity type is best for them? Limited liability companies are by far the most commonly selected type, but did you know, the IRS doesn’t recognize LLCs as an official entity? LLCs can default to a disregarded entity or a partnership depending on the number of members they have, or they can select S or C corporation status.
(Many thanks to the AICPA Town Hall for allowing members to leverage their resources, such as the slides included in this article. The opinions shared here are the author’s and not those of AICPA or CPA.com.)
Tax preparers everywhere spent the past two months gearing up for yesterday’s “opening day” of tax season, January 29th. It was an exciting time for us, as it was finally going to be a return to normal. What does that even mean anymore, you might ask? Well, most of the pandemic financial relief programs have wrapped up (save a straggler ERC claim here or there); amendments resulting from that era have almost all been filed; the odd rebates and credits that no one remembered the amounts for were a thing of the past; there were no last-minute tax extenders; and the season end-date actually lands on April 15th for the first time in ages. It felt like we finally had a handle on things and were back to the “normal” amount of seasonal overwork — rather than a Herculean lift, as was the case for the past four years.
Enter Congress. Despite the fact that The American Institute of Certified Public Accountants (AICPA), National Association of Tax Professionals (NATP) and small business advocacy groups have been lobbying for over a year to get an extension of certain popular tax benefits that expired in 2023, our leaders somehow managed to wait until after year-end to introduce legislation to that effect — Tax Relief for American Families and Workers Act — in a spectacular show of bipartisan ignorance. Never mind that the IRS e-file has been offline since November 18th, because it takes over two months to reprogram the systems for new tax laws, updates, and edits to tax forms.
Some of the anticipated changes if the legislation passes as-written include popular business expensing programs that are designed to be leveraged throughout the year. Making them retroactive does nothing to spur the economy, as the decisions to buy equipment, invest in R&D, or take out loans were already made, last year.
To be clear: I’m not saying these aren’t potentially good changes for tax law, business, and the economy. Just that doing it at this late date is misguided in far too many ways.
And the part I really don’t understand is this: IRS Commissioner Werfel told reporters last Friday, “If there’s a change that impacts your return, we will make the change, and we will send you the update — whether it’s an additional refund or otherwise — without you having to take additional steps.” This is simply impossible for most of the business expensing features of the law, which are voluntary elections on the part of the taxpayer. Presumably this is a reference to the child tax credit provisions in the legislation — which have gotten the most press, but have little effect on small business owners, and are a small portion of the actual bill.
The House Ways and Means Committee released a statement recently indicating that the IRS “confirmed its intention to make necessary systems updates by around six weeks after the date of enactment”. Six weeks. Most refunds are issued within three. Six weeks takes us past the S-Corp and Partnership filing deadline. Six weeks?
Speaking of that deadline, many states announced e-filing would begin on the same date as the IRS opened federal tax season, but it turns out that our state (and I’m guessing others) did not release their S-Corp or Partnership forms with enough advance notice for our third-party tax software to program them into their system, so we are unable to e-file any Illinois business tax returns until February 7th. And we were freaking out about that delay. I can’t imagine what six weeks will look like.
To say nothing of the fact that the next government shutdown deadline is scheduled for one week before business tax returns are due. This should make for an even more laid-back season.
And to add to all of this, that the bill is being funded by an early end to the Employee Retention Credit program, as of January 31, 2024. We spent all of last week scrambling to get the remaining claims in, and won’t know whether that sprint was worth the anxiety or not until this bill passes (or doesn’t) — I feel terrible for those who find out in February that their claim’s due date is suddenly in the past.
Again, some of the provisions in this bill are great ideas — well thought-through, balanced, as well as good for business, families, and potentially the economy. Bad players in the world of ERC mills will finally have to deal with some consequences, and the 1099 burden for small vendors and freelancers will be eased as the threshold is finally indexed for inflation. Some good stuff.
So let’s pass this as 2024 legislation, just in time for the new year, as it should be… and get out of the way of tax season, already!
If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.
UPDATE 12/31/21: Sigh. The step-by-step instructions I painstakingly wrote out below, with screenshots (for making business replacement income tax estimated and extension payments) are now out-of-date because IDOR revamped their MyTaxIllinois website in September (grrrrr). Please see this blog post instead: How To Make IL Dept Of Rev (IDOR) Business Tax Payments Online: Estimates & Extensions – UPDATED | The Dancing Accountant — the basic concepts are the same, but the layout and workflow is totally different now.
Unlike individual tax payments — extensions, estimated tax, etc. — for business payments you will need to log in to MyTax Illinois, using the same credentials you usually use for paying sales tax or monitoring state payroll taxes.
On the main page, you should see a list of all your accounts with IDOR & IDES, something like this:
Click on the “Business” link. You will see a list of periods.
Click on the period for which you want to make the payment. It is very important to pick the correct period. Keep in mind this is usually the prior year’s ending date, if you’re trying to pay income tax (aka “business replacement tax”) for a return or an extension. You would choose the current year’s ending date if you are trying to make a quarterly estimated tax payment for your business.
Then click “Make a Payment” in the upper-right corner of this portion of the screen, under “I Want To”.
Then click “Bank Account Debit”.
That link will take you to a page where you will select a payment type. It is very important that you select the correct payment type.
They changed the forms a couple of years ago so that there’s no separate extension tax payment form — you just make a payment under the type of income tax form that your business usually files.
For example, a partnership or multi-member LLC would usually select IL-1065 payment — whereas an S-Corp would file an IL-1120-ST. Confirm that you are selecting the correct type that corresponds with your annual business tax return.
It will prompt you to enter your payment information.
And then click Submit. Make sure to save or print the confirmation page that pops up as a pdf — for your files, but also please send it along to your amazing and dedicated tax preparer.
(If you miss that last bit, then please go into your payment history for this account and do a print-screen that includes the status section; it will show the amount, confirmation number, and date/time.)
If this or any other posts on the website were useful to you, and your financial situation permits it, please consider contributing to my tip jar. Ths allows me to continue to provide free accounting resources to small businesses who do not have the funds available to hire a CPA.
