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Accounting for Sole Proprietors: Tax & Bookkeeping Tips

Started by ruggedheron13 · · 👁 50 views · 2.2K replies

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Participants ruggedheron13rowdyhawk25shadowwalker79Robin Cook4Brenda Chase3stormybadger8placidlynx92Taylor Rogers2Henry Edwards33Lisa Hernandez5driftingfox24Robert Young4cosmictinker24Joshua Barrett31James Morgan21David Green642Kyle Rogers8Chris Murphy8Nicole Lee6fadedcrane92Thomas Brown50Keith Martinez5Nancy JonesCharles Stewart69 …
Brandon Rogers41 Brandon Rogers41 Newcomer
5 messages
joined Apr 2017
#1721 ·
driftingmoose39 said:Hello,
I have a question regarding the annual income tax filing for self-employed freelancers. Does the total tax liability for 2016 get reduced by prepayments made specifically by December 31, 2016, or does it include all prepayments applicable to the 2016 tax year (including those paid in January or February of 2017)? My accountant insists that my obligation should be offset by all prepayments pertaining to 2016, but according to the IRS guidelines, it seems they only accounted for what was actually paid by December 31, 2016. As it stands, I'm looking at a significant balance due along with a mountain of interest penalties. Who is correct here? Is there a specific place where this rule is documented...
Thanks in advance for any help you can provide.

You should always just call the IRS and ask them exactly how much was credited on a specific date, because honestly, nobody truly knows how they run their math behind the scenes. It never seems to match what’s written in the manual. Usually, the instructions say everything paid by February 2nd counts if you don't have an outstanding balance, so following that is your safest bet—just make sure to stay on top of the FARC regulations regularly.
Henry Edwards33 Henry Edwards33 Regular
678 messages
joined Aug 2015
#1722 ·
Christmas. Another year, another frantic scramble to pretend that buying overpriced plastic junk and pretending we’re all merry is a substitute for actual connection. It’s become this massive, exhausting performance where everyone's stressed about gift lists and shipping delays, acting like the fate of the world depends on whether a specific gadget arrives by the 24th. Honestly, it feels less like a holiday and more like a seasonal endurance test designed to drain your bank account and your patience. kaže:
Look, let’s be real—market value is mostly just a number used by the IRS to start an argument. It doesn't actually help anyone. Even if you sell something for less than what's on the books, that gap between the sale price and the book value still has to be recorded as receipts. You can't just go around depreciating more than what the law allows just to dump the difference into expenses. You play by the rules, or they come after you.

Think of it this way: the proceeds represent your total sale price, while the expense is just the remaining unamortized amount left on the books at the moment you close the deal.

Look, an asset is an asset, regardless of how much you had to bleed to get it. If a business owner is forced—for whatever reason—to sell something for less than what they originally paid, that’s just a loss. You can't try to book that original purchase price as income later on to make up the difference. If you try to play it that way, you’re essentially getting hit twice for the same mistake. It doesn't work like that.

The 2016 annual report just dropped, and if you’re looking for a reason to feel optimistic about the state of American business, you might want to look elsewhere. It’s essentially a roadmap of how much we’ve lost ground over the last year. Looking at the numbers, it feels like we’re trying to run a marathon through knee-deep mud. We talk a lot about "innovation" and "agility," but the reality on the ground looks more like a slow grind against mounting costs and shrinking margins. It’s the classic squeeze: everyone wants more, but there’s less to go around. One thing that sticks out is the sheer weight of bureaucracy and regulatory overhead. It’s getting harder for even the most established companies to maintain momentum when they're constantly being tripped up by new red tape. It’s like trying to drive a high-performance car while someone keeps pulling the emergency brake every few miles. You might still move forward, but it’s exhausting, expensive, and frankly, a bit ridiculous. We also see a massive gap between the big players who can absorb these shocks and the smaller businesses that are basically fighting for air. For a lot of the mid-sized firms, this year wasn't about growth; it was about survival. At the end of the day, the report paints a picture of an economy that’s working harder just to stay in the same place. We aren't seeing that sweeping upward trajectory we were promised. Instead, it’s a cycle of managing decline and trying to patch holes in a sinking ship. It’s not exactly inspiring reading, but then again, I wasn't expecting a fairy tale.

When it comes to tax deductions, you don't get to claim depreciation the second you buy something. You have to wait. Under current rules, you can only start recognizing that depreciation expense starting on the first day of the month following the one in which the asset was actually put into service. It’s just one more bit of bureaucratic timing you have to account for.
When you sell, donate, or otherwise get rid of fixed assets, you can write off the depreciation expense as a tax deduction through the end of the month that asset was actually being used. It’s pretty straightforward—once it stops working for you, the clock on that specific deduction stops too.
When you finally offload, gift, or scrap a piece of long-term equipment, that leftover bit of unamortized cost doesn't just vanish into thin air. You get to write off the remaining book value as a tax expense during the same period the asset actually leaves your hands—whether you sold it, gave it away, or it simply broke down and hit the landfill.


That’s exactly why regulators run into such a headache when trying to pin down fair market value. If an asset is particularly high-stakes, my standard advice is to bring in an appraiser. The cost of getting a formal valuation is usually peanuts compared to the alternative, and it effectively kills any suspicion that someone is trying to offload property at a discount just to dodge taxes or cut corners.

It’s been a long time since I’ve had to deal with selling something for less than what it cost me to get it—thankfully. But I still vividly remember those chaotic stretches where we were basically paying people to take our inventory because the overhead was eating us alive.
The bottom line was pretty straightforward: the small business owner ran that equipment until it was completely shot, then sold it off for scrap. At the end of the day, that salvage value counted as revenue.

Brandon Rogers41 said:You should always just call the IRS and ask them exactly how much was credited on a specific date, because honestly, nobody truly knows how they run their math behind the scenes. It never seems to match what’s written in the manual. Usually, the instructions say everything paid by February 2nd counts if you don't have an outstanding balance, so following that is your safest bet—just make sure to stay on top of the FARC regulations regularly.

Anything paid by December 31, 2016, goes directly toward covering the obligations for that same year.
It’s handled differently here, at least. Any payments made since the start of the year get applied toward your installments without any drama. If you end up overpaying your prepayments, you can just file a request to have that balance transferred over to cover what you owe under the CDC filing.
I’m with you there—if things get messy and we end up with two different versions of the truth, I’d be calling the IRS myself.
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Thomas Diaz8 Thomas Diaz8 Member
28 messages
joined May 2015
#1723 ·
A small business owner has leased a personal vehicle that is officially registered in his wife's name. I find myself wondering about the logistical implications here: is he required to maintain a meticulous mileage log? Furthermore, can the vehicle be used for personal errands, such as trips taken by his spouse? Specifically, regarding tax compliance, would he need to record a fringe benefit for personal use via payroll, or is simply applying a 30% reduction to the tax-deductible expenses sufficient?
Brandon Rogers41 Brandon Rogers41 Newcomer
5 messages
joined Apr 2017
#1724 ·
Thomas Diaz8 said:A small business owner has leased a personal vehicle that is officially registered in his wife's name. I find myself wondering about the logistical implications here: is he required to maintain a meticulous mileage log? Furthermore, can the vehicle be used for personal errands, such as trips taken by his spouse? Specifically, regarding tax compliance, would he need to record a fringe benefit for personal use via payroll, or is simply applying a 30% reduction to the tax-deductible expenses sufficient?

He definitely needs to track the mileage, though everyone seems to think leasing a vehicle is a simple workaround.
If he wants to lease the car from his wife, he’ll need a formal lease agreement, head down to the IRS to pay the rental tax (for the wife), and only then can he claim 70% of the car expenses; for the remaining 30%, he'll be paying taxes on the reported income since it bumps up the taxable base. It works similarly for the lease amount itself, which is also only 70% deductible.
Honestly, if he's already stuck keeping a log, wouldn't it be smarter to just record everything and calculate the reimbursement $0.67 per mile whenever he has the cash flow?
As for his wife driving it, sure, why not? He's just leasing it from her, but the mileage log remains mandatory.
Nathan Peterson10 Nathan Peterson10 Newcomer
7 messages
joined Aug 2015
#1725 ·
I'm not quite sure which sub here is best for this question. I know a sole proprietor—no employees, just himself—who just received notice from the Department of Labor on July 1st stating he's eligible to retire. However, it turns out he hasn't fully cleared all his outstanding payroll taxes and social security contributions yet.
Is it actually possible for him to transition into retirement now and then settle those back payments later? Specifically, how does his official retirement status get finalized in a situation like this?
Thanks.
Chloe Jones6 Chloe Jones6 Newcomer
1 message
joined May 2017
#1726 ·
Greetings to everyone on this forum. I am reaching out because I would appreciate some insight from anyone who has navigated a similar situation before.
Two small business owners are operating out of the same commercial unit, which has been split into two separate spaces, yet they share a single electricity meter. Currently, Exelon issues the entire bill to just one of these businesses. One owner is registered for sales tax, while the other is not—at least for the time being. To settle their shared utility costs, the first owner intends to re-invoice a portion of the Exelon bill to the second owner. My question is this: would such an invoice be considered a valid, legitimate document for the second owner to use when recording electricity expenses as a business deduction?
Keith Martinez5 Keith Martinez5 Active Member
167 messages
joined Mar 2014
#1727 ·
Hey everyone, where has everybody gone??? I just received a payout from State Farm for some property damage we sustained at the workshop—so now I’m trying to figure out the cleanest way to record this in my books. Since the insurance policy was set up without sales tax, I don't claim any sales tax when I pay my premiums. Would it be okay to book this incoming payment under business receipts—specifically for a sole proprietorship—also excluding sales tax? Thanks in advance for the help!
Olivia Cruz86 Olivia Cruz86 Active Member
114 messages
joined Nov 2014
#1728 ·
Does anyone here actually know how to properly close out an enforcement proceeding through Goldman Sachs?
So, here’s the deal—my lawyer finally went after a client who refused to pay their bill. We filed for enforcement, and we’re including all those legal costs the attorney is entitled to under the standard fee schedule. Since we're on a VAT setup, I already booked the notary fees and claimed the input tax.
Now that we’re forcing the collection through the system, I’m trying to figure out the best way to wrap up the books... I've been reading a bunch of different takes online, and honestly, I have no clue which way is the "correct" way to handle this mess.
The principal amount is easy enough to clear, and obviously, the interest will be coming in too.
As for that notary expense, I was thinking about just tossing it into receipts (without splitting out the VAT),
but then there’s the whole situation with the filing fees, the finality documents, and the costs for sending everything over to Goldman Sachs—you know, the stuff the lawyer is legally allowed to charge back. Do I actually send a formal invoice to the debtor for those specific costs?
If there’s anyone out there working in bookkeeping for a law firm who can bail me out here, please help!!!
Susan Martinez29 Susan Martinez29 Newcomer
4 messages
joined May 2017
#1729 ·
I've got a few questions about setting up a sole proprietorship just to make sure I haven't missed anything important:

1. So, if I launch the business and immediately apply for sales tax registration, that should be fine, right? I’m looking at some pretty significant upfront costs for the workspace—buying furniture, setting up restrooms, all that—so I want to be able to claim those tax credits back.

2. If I opt into the sales tax system voluntarily, am I stuck in that system for three years? What happens if things don't go as planned and I need to shut down the business—can I just walk away, or am I locked in? Also, since sales tax is filed quarterly, can I handle the paperwork myself or am I going to be forced to hire an accountant? And if I have a quarter where I pull in zero revenue, what does the filing process look like then?

3. If I'm running this as my primary self-employment gig, my monthly contributions will be around $633, but if I'm already employed somewhere else, the rates are lower and they just settle everything at the end of the year, right?

4. Besides the membership fees for the U.S. Chamber of Commerce, what other expenses am I looking at? If I run the business out of my own house or a family member's place, do I still have to deal with rent or similar overhead? I've noticed with larger corporations that they always seem to "rent" space from themselves and move money around even if they own the building, so I'm wondering if there's any requirement like that for me. 🙄

Thanks in advance 🙂
Edward Stewart Edward Stewart Member
44 messages
joined Feb 2013
#1730 ·
Quincy:
I find myself reflecting on the recent discussions surrounding our fiscal landscape, much like how one might contemplate the slow, steady drift of a summer cloud over the Midwest. It seems we are constantly circling back to the same fundamental questions of stability and growth. I was reading some thoughts from Susan Martinez29 earlier—she always has such a keen way of dissecting these complexities—and it struck me how much our current trajectory mirrors those periods of intense transition we saw in the markets a few years back. There is a certain gravity to these shifts, isn't there? One cannot simply breeze past them without considering the long-term implications for the average household. I suppose my tendency to dwell on these matters is a bit of a habit, but I truly believe that if we don't pause to consider the structural integrity of our financial institutions, we risk losing sight of the very foundation we're building upon. It’s a bit like trying to renovate an old Victorian home in Chicago; you can't just slap on a new coat of paint and hope the plumbing holds up. You have to look deep into the bones of the thing. kaže:
I have a few questions regarding the process of setting up my own small business, just so I can ensure I haven't missed any critical steps in my planning:

So, my plan is to register my small business and immediately apply for VAT registration right out of the gate. It seems like the most logical move, really, because the physical space where I’ll be operating requires quite a bit of upfront capital—you know, all those initial investments like outfitting the place with furniture, installing the necessary plumbing and restrooms, and getting everything up to code. By being in the system from day one, I should be able to claim those tax credits back on my initial startup costs.
It all truly depends on the nature of those clients; if we are talking about corporate entities or legal persons, then there is certainly a much more compelling reason to step through that door...
You didn't specify your industry, which is actually a pretty crucial detail here; so many variables depend on what you actually do for a living. Honestly, you’ll find that the most helpful insights will probably come from other members of this forum who work in that same field, or perhaps something closely related to it.

Quincy:
Broxigar As Chloe Jones6 mentioned:
If I decide to voluntarily opt into the sales tax system, I understand there is a commitment to remain in that system for a three-year period, but what happens if life takes an unexpected turn? If circumstances change such that I need to wind down my small business entirely, am I permitted to close shop before that three-year mark hits, or am I effectively locked in? Furthermore, since sales tax is calculated and filed on a quarterly basis, is it feasible for me to manage those filings personally, or does the complexity necessitate hiring a professional accountant? Lastly, I find myself wondering about the mechanics of a quiet quarter—if my revenue drops to zero during a specific period, what exactly is required in terms of reporting and payments?
I am quite perplexed by this entire situation regarding the closing process, especially since the Tax ID remains absolutely unchanged; perhaps there has been some recent clarification posted on the IRS website that I simply haven't had the opportunity to review yet.
Whether you decide on monthly or quarterly filings really just comes down to how much turnover you're pulling in; honestly, when you're first getting off the ground, sticking to a quarterly schedule usually makes the most sense. If you happen to be running a business that is relatively straightforward from an accounting standpoint—say, a service-based venture without the headaches of physical inventory or heavy manufacturing—then handling your sales tax calculations and submitting everything through the IRS isn't exactly rocket science. It’s quite manageable once you get the hang of it.
If you find yourself in a stretch where you haven't issued any outgoing invoices—meaning you haven't collected any sales tax—you essentially end up sitting on a credit. In practical terms, this means you’re in a position to request a refund from the IRS, though most people find it much more convenient to simply carry that balance forward as a credit to offset future payments. After all, you are almost certainly going to have some incoming invoices with sales tax to deduct; if nothing else, you'll at least have your monthly cell phone bill or internet service to account for.

Quincy:
I find myself reflecting on our recent discussions, much like how one might ponder the complexities of a long-winded legal brief or a particularly dense piece of literature. It seems we are constantly circling back to these fundamental questions of stability and economic foresight. I was just thinking about what Susan Martinez29 mentioned earlier—it’s quite a thought, isn't it? To look at the way institutions operate and realize how much we rely on that underlying structure. It reminds me of those slow, methodical afternoons spent contemplating larger systemic shifts rather than just reacting to the immediate noise. We must be careful to remain deliberate in our assessments. kaže:
If I am working as a self-employed contractor, my monthly contributions usually hover around... $633If I'm working somewhere else entirely, does that mean my rates are lower, and then everything just gets settled through some kind of year-end reconciliation?
It’s actually been brought up quite a few times within this particular thread if you take a moment to look back through the history... so, in a general sense, yes, it has.

Quincy:
Broxigar As Chloe Jones6 points out:
What other expenses should I be looking at beyond the standard dues for the U.S. Chamber of Commerce? And if my business is operating out of a space I already own, or perhaps even a property belonging to a family member, am I still on the hook for rent or any similar fees? I’ve noticed that with some established companies, there seems to be a requirement to "rent" the space and pay a monthly amount, regardless of whether they actually own the building or not. 🙄
You're looking at roughly $50 to $33 every month just to keep your checking account and online banking active. Then you have to factor in your annual corporate taxes—which usually hover around $300, though local municipal taxes can vary depending on which city you settle in—plus about $390 for Goldman Sachs services regarding your digital credentials, specifically that e-certificate and the USB security key required for your interaction with the IRS, whether you handle that yourself or hand it off to an accountant. As for physical office space, that really depends on what kind of business you're running; some industries don't even need a brick-and-mortar setup.
Susan Martinez29 Susan Martinez29 Newcomer
4 messages
joined May 2017
#1731 ·
Thanks for clearing that up... since I'm looking at providing intellectual services—let's just call it that—rather than dealing with retail or manufacturing, being able to handle all the sales tax filings online would be a huge relief. It saves me from having to deal with an accountant on top of everything else 👍

If anyone has the inside scoop on how the shutdown process actually works, I’d appreciate the heads-up. If I opt into the sales tax system voluntarily, I'm locked in for three years, and I'm wondering if that commitment changes anything regarding closing things down.

Alright, the bit about the checking account makes sense... but what about the corporate tax? Wasn't that scrapped at the start of the year? And those $130 for Goldman Sachs, is that some kind of annual fee?
Edward Stewart Edward Stewart Member
44 messages
joined Feb 2013
#1732 ·
Well, if that happens, bookkeeping should become an absolute breeze, shouldn't it?
Between handling sales tax and navigating the various supplemental filings on the IRS portal—like those monthly contribution reports due by the 15th, not to mention the year-end reconciliation forms—it’s quite a bit to manage.

As for the business tax, I truly hope you're right about it being scrapped; in my experience, nothing ever actually gets abolished... it's always just a case of "out with the old, in with the slightly different new."
They made similar promises regarding a reduction in the Chamber of Commerce fee, yet here we are seeing another increase this year. It seems they've conveniently tied their tribute directly to the increased standard deduction—essentially hiking their cut just because the non-taxable income threshold went up.

Regarding the IRS, it comes out to USD 487.50 annually, including sales tax.
Unfortunately, we all end up footing the same bill regardless of how massive or tiny our business turnover actually is.
Carol Price4 Carol Price4 Regular
380 messages
joined Nov 2019
#1733 ·
Susan Martinez29 said:Thanks for clearing that up... since I'm looking at providing intellectual services—let's just call it that—rather than dealing with retail or manufacturing, being able to handle all the sales tax filings online would be a huge relief. It saves me from having to deal with an accountant on top of everything else 👍

If anyone has the inside scoop on how the shutdown process actually works, I’d appreciate the heads-up. If I opt into the sales tax system voluntarily, I'm locked in for three years, and I'm wondering if that commitment changes anything regarding closing things down.

Alright, the bit about the checking account makes sense... but what about the corporate tax? Wasn't that scrapped at the start of the year? And those $130 for Goldman Sachs, is that some kind of annual fee?

You can file online, but you can't actually do the full calculations there—it's just for the filing part.
Since you mentioned not wanting to "deal" with an accountant, I'm assuming you're comfortable handling all your own tax forms, deadlines, and the specific regulations that apply to you—otherwise, you'll run into trouble if the IRS ever comes knocking. 😉

Good luck!
Susan Martinez29 Susan Martinez29 Newcomer
4 messages
joined May 2017
#1734 ·
Carol Price4 said:You can file online, but you can't actually do the full calculations there—it's just for the filing part.
Since you mentioned not wanting to "deal" with an accountant, I'm assuming you're comfortable handling all your own tax forms, deadlines, and the specific regulations that apply to you—otherwise, you'll run into trouble if the IRS ever comes knocking. 😉

Good luck!

To be honest, I'm not entirely sure yet, but I enjoy picking up new skills and I tend to catch on quickly. 😉I'm not dismissing anything outright; I'm just gathering enough info to figure out exactly what the deal is.🙂
Donna Ward33 Donna Ward33 Newcomer
1 message
joined May 2017
#1735 ·
A sole proprietorship issues an invoice at $5667 (not in the VAT system) using a reverse charge mechanism to a buyer that is a corporation registered for VAT. How does this impact both parties, and what are the actual implications? Thanks.
David Mitchell4 David Mitchell4 Active Member
61 messages
joined Apr 2011
#1736 ·
If both parties are based here in the States, you just issue the invoice without sales tax—no transfers, no fuss, no nothing.
rowdybison3 rowdybison3 Member
13 messages
joined Feb 2016
#1737 ·
Hey,

My sole proprietorship has a car listed under fixed assets. I didn't buy it through the business originally; I just added it to the asset list later via a formal entry. I'm wondering if I should just issue a regular invoice with a 10% sales tax, or if I shouldn't include tax at all. The person looking to buy it claims they heard that when you buy a vehicle from a small business, you don't have to pay sales tax. I'm not so sure about that, I guess.
Thomas Diaz8 Thomas Diaz8 Member
28 messages
joined May 2015
#1738 ·
We recently took over a lease on some commercial space, and since the bathroom was in a state of total disrepair, we went ahead and renovated it. I am trying to determine how to handle the accounting for the renovation costs—specifically the ceramic tiles, the fixtures, the adhesive, and all the other materials used. I suppose I am wondering whether these expenses can be recorded as current operating costs, or if they must be capitalized as intangible long-term assets?
Thomas Diaz8 Thomas Diaz8 Member
28 messages
joined May 2015
#1739 ·
We recently took out a lease on some commercial space, and we ended up having to gut and renovate the bathroom because it was in pretty rough shape. I am trying to figure out the proper accounting treatment here. Can the costs for the renovation—things like the ceramic tiles, the fixtures, the adhesive, and all the other materials—be booked as current expenses, or would they have to be classified as intangible long-term assets?
placidlynx92 placidlynx92 Active Member
92 messages
joined Jan 2013
#1740 ·
Thomas Diaz8 said:We recently took out a lease on some commercial space, and we ended up having to gut and renovate the bathroom because it was in pretty rough shape. I am trying to figure out the proper accounting treatment here. Can the costs for the renovation—things like the ceramic tiles, the fixtures, the adhesive, and all the other materials—be booked as current expenses, or would they have to be classified as intangible long-term assets?

The general rule is that anything which significantly bumps up the value of your fixed assets gets capitalized. In your specific situation, though—given you're just fixing up a rental—it looks more like standard maintenance to me. I'd say go ahead and book them as current expenses, but a word of advice: make sure you keep the invoices for both the materials and the actual labor. If an auditor decides to take a closer look, you don't want to be caught without proof that the work was actually performed.

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