Insights
Insights
Fourteen explainers, grouped by the situation that sends you looking for one: income with no withholding on it, the S-corp decision, a letter from the IRS.

This is a library, not a blog. Something goes up here when a question has come up enough times in consultations that writing it down properly once beats explaining it badly again. Fourteen pieces so far, sorted below by the problem that brings people to them rather than by the date I wrote them.
When a rule changes or a figure moves, I edit the article instead of publishing a fresh one on top of it. Current-year numbers mostly live in the tax center rather than inside the explainers, so a piece doesn't rot around a dollar amount. The 2025 standard deduction is $15,750 for a single filer and $31,500 for married filing jointly, per the IRS, and it moves every year. Most of what ranks online was written once and never touched again.
Income with no tax taken out of it
Moonlighting and Locums Income: The Mistake I See Most is the piece I send most often to physicians. A hospital W-2 plus 1099 shifts, a locums assignment, or an expert witness engagement makes you a sole proprietor on Schedule C and Schedule SE, whether or not you ever filed anything to become one. The mistake is rarely a missed deduction. It is that the 1099 stream got treated as extra pay for eleven months, so the tax on it, the timing of that tax, and the retirement account it could have funded were all decided by default.
1099 or W-2: Why the Classification Actually Matters is the engineering version of the same territory. Classification turns on control, not on what the contract says, and the same person can be a legitimate contractor on one project and an employee on the next. It covers what actually changes when the income arrives on a 1099, and how to price a rate that accounts for it instead of discovering the gap in April.
Quarterly Estimated Taxes, in Plain English is the mechanics of paying it on time: who genuinely owes estimates, why the four quarters are not equal lengths, how the safe harbor protects you even in a year you owe a lot in April, and why the penalty is really just interest.
The Home Office Deduction: What Actually Qualifies turns on two words in the IRS rule: exclusive and regular. The dining table you also eat at fails both. It compares the simplified method ($5 per square foot, 300 square feet maximum, $1,500 cap) against the regular method and the depreciation you recapture when you sell the house. It also says plainly that a W-2 employee generally gets nothing here, because the TCJA suspended unreimbursed employee business expenses.
How the business gets taxed
S-Corp vs. LLC: How to Actually Decide starts by refusing the question as asked. An LLC is a legal entity. An S-corp is a tax election, made on Form 2553, and an LLC can make it. Once that is straight, the real question is arithmetic: does the self-employment tax you save on distributions exceed the cost of running real payroll, filing quarterly 941s, issuing yourself a W-2, and filing a separate 1120-S every March.
Should Your Practice Be an S-Corp? runs that math for a practice that is already a PC or PLLC, where the election changes nothing about the entity and everything about how profit is taxed on its way to you. The answer hinges on the Social Security wage base. That is why the election is real money for a practice owner with meaningful net profit and mostly noise for an employed physician with a little 1099 income on the side.
What "Reasonable Salary" Actually Means is the follow-up nobody wants. There is no safe harbor percentage, no 60/40 rule, and no dollar floor. What exists instead is a published set of factors, a line of Tax Court decisions applying them, and roughly an hour a year of writing your reasoning down, which settles most of the argument before anyone else is involved.
When the IRS writes to you
What to Do When You Get an IRS Notice covers the first 48 hours. Find the notice number in the upper right corner before you read anything else, because it tells you what kind of letter this is. A CP2000 is not an audit and not a bill. Then the response date, what it actually controls, and when it is worth signing a Form 2848 so I can talk to the IRS on your behalf instead of you doing it.
What Actually Triggers an Audit separates the fear from the mechanism. In fiscal year 2025 the IRS closed 497,621 examinations of every kind while the automated matching program closed 987,460 cases, per the IRS Data Book. Document matching runs at roughly twice the volume of auditing. It is a different problem and it takes a different fix.
Which Tax Records to Keep, and For How Long is the one to read before you throw anything out. Three years is the default. Four exceptions extend it, and the basis records tied to an asset you still own follow a different rule entirely, one that outlives every retention window on the list.
Two things people get wrong about their own return
Your Tax Bracket Is Not Your Tax Rate exists because this misunderstanding drives real decisions, like turning down overtime or a raise. Brackets are marginal, so a raise never cuts your take-home. A single filer with $120,000 of wages in 2025 sits in the 24% bracket and pays about 14.9% of that income in federal tax, and both of those numbers are correct.
A Big Refund Is Not a Win says the part your neighbor does not want to hear at the cookout. A refund means you overpaid and the government held your money all year without interest. The piece covers how withholding works now that W-4 allowances are gone, when a large refund is genuinely fine, and how to adjust yours without walking into an underpayment penalty going the other direction.
Whether you need me at all
When You Need a CPA, and When You Honestly Don't argues against hiring me in a good share of the situations it describes. One W-2 and the standard deduction is a software return, and I will tell you that on the call. The line where filing becomes judgment rather than data entry sits further out than most firms admit, and the article says where I think it actually is. There is more on that at who this practice fits.
How to Switch Accountants Without It Being Awkward handles the part people dread for no reason. There is no exit interview, no release form, no notice requirement, and no need for your old preparer's cooperation. It is a document handoff. The article covers what to bring, what you do not need, how a mid-year switch works, and when amending a prior return is worth the trouble.
How something ends up here
The filter is narrow on purpose. Nothing here was written to chase a search ranking.
- A question that keeps coming up in first conversations
- A rule where the exception matters more than the rule
- A deadline with teeth, like March 15, 2027 for partnership and S-corp returns
- A place where the common advice online is confidently wrong
- Something I would explain the same way sitting across a desk from you
All of this is general, written for a reader whose facts I do not know. That is a real limit. One more state, one K-1, one year of unfiled returns, and the answer can flip. Read these to understand the mechanics, not to make the call on your own return. For the version that accounts for your actual situation, the first conversation is the place to start.
Start here
- 1What to Do When You Get an IRS NoticeMost IRS mail is a computer reporting that its records and your return disagree, and the code in the upper right corner tells you which kind of disagreement you have.
- 2Your Tax Bracket Is Not Your Tax RateA single filer with $120,000 of wages in 2025 sits in the 24% bracket and pays 14.9% of that income in federal tax, and both of those numbers are correct.
- 3When You Need a CPA, and When You Honestly Don'tHalf of this page points away from hiring me: the line is about whether your return contains decisions, not about what you earn.
By topic
Try it yourself
Every article
- IRS HelpYou Owe the IRS: Payment Plans, Penalties and Interest
Interest runs until the balance is paid, the late-payment penalty is 0.5% a month, and an installment agreement cuts that penalty to 0.25% if you filed on time. Here is what each option costs.
- Real EstateRental Depreciation: How the 27.5-Year Schedule Works
Depreciate the building, not the land, over 27.5 years from the month it is ready for rent. Skip the deduction and your basis still goes down.
- Self-EmployedEstimated Taxes Without Guessing: Which Safe Harbor Fits You
Skip the forecasting. Pay 90% of this year's tax or 100% of last year's (110% if last year's AGI topped $150,000) and the underpayment penalty cannot apply.
- Small BusinessThe QBI Deduction: What It Is, Who Gets It, and How It Is Limited
If you own a sole proprietorship, partnership or S corporation, you may be able to deduct up to 20% of your business profit. Above certain income levels, the rules get stricter.
- Stock CompensationExercise ISOs Without an AMT Surprise
Exercising ISOs creates no regular tax, but the spread counts as AMT income. Here is where the 2026 AMT starts, with a worked example.
- Stock CompensationRSU Withholding Is Often Too Low. Here Is the Gap and the Fix
Vested shares are wages. Many employers withhold a flat 22% on them, and if your bracket is higher, you pay the difference when you file.
- Tax PlanningThe 2026 Year-End Tax Checklist: What Has to Happen by December 31
Some tax moves expire on December 31. Others wait until the filing deadline. Here is how to sort them, with the 2026 limits and a worked example.
- IRS HelpYou Filed an Extension. Here Is What Still Has to Happen
An extension moves the filing deadline to October 15. It never moved the payment deadline, and interest has run on any balance since April 15.
- The CarolinasLive in South Carolina, Work in Charlotte: How the Two Returns Fit Together
The state line runs through the Charlotte metro, and so does your tax bill. Here is how the two returns relate, and why neither state’s withholding settles the question on its own.
- Real EstateRental Property Depreciation Recapture: What You Owe Back When You Sell
Depreciation is a deduction you take for years and a tax you meet once, at the sale. Knowing the size of that bill beforehand changes what you do first.
- Self-EmployedSelf-Employment Tax, Explained for Your First Freelance Year
It is the part of a freelancer’s bill that nobody mentions until April, and it is not the same thing as income tax.
- Tax PlanningWhen You Need a CPA, and When You Honestly Don't
Half of this page points away from hiring me: the line is about whether your return contains decisions, not about what you earn.
- Small BusinessS-Corp vs. LLC: How to Actually Decide
The election trades self-employment tax on your profit for payroll filings, a second return, and a salary number you have to defend.
- Small BusinessWhat "Reasonable Salary" Actually Means
No safe harbor percentage, no 60/40 rule, no dollar floor: what exists is a published set of factors, a line of Tax Court cases, and a memo you write before the year starts.
- Physicians & DentistsShould Your Practice Be an S-Corp?
The election is real money for a practice owner and mostly noise for a moonlighter, and the difference comes down to the Social Security wage base.
- Physicians & DentistsMoonlighting and locums income: the mistake I see most
What a moonlighting dollar actually keeps, how to get the tax paid without a penalty, and why the solo 401(k) is smaller than the calculators promise.
- Self-EmployedQuarterly Estimated Taxes, in Plain English
Four payments, unequal windows, and one rule that keeps the penalty off your return even in a year when you write a large check in April.
- IRS HelpWhat to Do When You Get an IRS Notice
Most IRS mail is a computer reporting that its records and your return disagree, and the code in the upper right corner tells you which kind of disagreement you have.
- IRS HelpWhat Actually Triggers an Audit
Most IRS mail is a computer comparing your return against documents it already had, which is a different problem than an audit and takes a different fix.
- Self-EmployedThe Home Office Deduction: What Actually Qualifies
Most of these claims fail on the word exclusive, long before anyone gets to the arithmetic.
- Small Business1099 or W-2: Why the Classification Actually Matters
Engineering work sits close enough to the line that the same person can be a legitimate contractor on one project and an employee on the next.
- Tax PlanningYour Tax Bracket Is Not Your Tax Rate
A single filer with $120,000 of wages in 2025 sits in the 24% bracket and pays 14.9% of that income in federal tax, and both of those numbers are correct.
- Tax PlanningA Big Refund Is Not a Win
What the refund number actually measures, how withholding works now that allowances are gone, and how to change yours without walking into an underpayment penalty.
- IRS HelpWhich Tax Records to Keep, and For How Long
Three years is the default, four exceptions stretch it, and the records tied to an asset you still own follow a rule of their own.
- Tax PlanningHow to Switch Accountants Without It Being Awkward
Your old preparer's cooperation is helpful, not required, and nothing about the calendar says this has to wait until January.
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