Plain answers to the questions owners ask.
Original, sourced guides written for owner-led businesses, plus the wider article archive. Everything here is general information rather than advice for your situation.
Guides by who you are
- 23 guides
Individual tax returns
Plain guides to 2025 and 2026 federal and Massachusetts individual returns: the new federal deductions, what Form 1 still taxes, deadlines and checklists.
Open the guide → - 31 guides
Sole props & S corps
Plain-English guides for Massachusetts sole proprietors, single-member LLCs and S corporations: self-employment tax, S elections, owner pay and state costs.
Open the guide → - 23 guides
Booster clubs & PTOs
Plain-English guides for Massachusetts booster club and PTO treasurers: IRS 990 filings, Form PC, raffle permits, sales tax and treasurer handovers.
Open the guide → - 31 guides
IRS Fresh Start
The IRS Fresh Start program is not one application. See the 2026 rules for payment plans, liens, offers and penalty relief, with every figure sourced to IRS.gov.
Open the guide →
Choosing help
Bookkeeper, accountant or tax preparer — who does what, and which you need.
Bookkeeper, accountant, tax preparer: who does what
The practical differences between a bookkeeper, an accountant and a tax preparer, and how to work out which one an owner-led business actually needs.
Read →When should a self-employed owner hire an accountant?
The signals that indicate an owner-led business needs accounting help, the situations where it genuinely does not, and what to ask before committing.
Read →What to bring to a first meeting with an accountant
What is actually useful in a first conversation with an accountant, what you should not prepare, what to ask, and what a good first meeting looks like.
Read →
Self-employed accounting
Records to keep, when to hire someone, separating business and personal.
What records should a self-employed owner keep?
The categories of records a self-employed owner needs, why reconstruction after the fact rarely works, and where to find the official guidance.
Read →Keeping business and personal money separate
Why mixing business and personal spending costs more than it saves, how to separate them without disruption, and what to do about a history that is already mixed.
Read →
Tax planning
Preparation versus planning, records, and the questions worth asking early.
Tax preparation vs tax planning
The difference between reporting a finished year and examining one still in progress, why most owners only ever buy the first, and when planning is actually possible.
Read →What to gather for business tax preparation
The records a business return is built from, why the list differs by entity type, and how to send documents safely. A working checklist, not a substitute for advice.
Read →Quarterly estimated taxes for self-employed owners
What federal estimated tax is, who generally has to pay it, the four 2026 payment dates from the IRS, and why current books change the figure more than any formula.
Read →
Bookkeeping & cleanup
What monthly bookkeeping includes, month-end close, catching up.
A month-end close checklist for small businesses
What closing a month actually involves, why categorized is not the same as closed, and a practical checklist an owner or bookkeeper can work through.
Read →Catch-up bookkeeping: a readiness checklist
What to gather before catching up months or years of books, how far back you actually need to go, and why you should not tidy anything first.
Read →
Advisory & growth
Reading the numbers, reviewing regularly, deciding what to do next.
Latest from the archive.
All 2,180 articles →- August 10, 2026
Video Tips: What Is Claim of Right?
Read → - August 7, 2026
Treasury Signals Increased Scrutiny of Sophisticated Tax Investment Strategies: What High-Net-Worth Investors Should Know
Read → - August 7, 2026
Unlocking the HSA; A Rare Triple Tax Break for Medical and Retirement Planning
Read → - August 6, 2026
2026 Sales Tax Holidays: Where Shoppers Can Save This Back-to-School Season
Read → - August 5, 2026
The IRS Is Updating Its Voluntary Disclosure Program for Cryptocurrency: What Crypto Investors Need to Know
Read → - August 4, 2026
Succession Planning for Business Owners; Protecting Your Company, Your Family and the Tax Outcome
Read →
Your business is not.
Everything here is general information for owner-led businesses. What applies to you depends on your structure, your records and your circumstances.
Get an answer for your business, not a general one.
These pages cover what applies broadly. What applies to you depends on how the business is set up — which is a conversation rather than an article.
Please don't send Social Security numbers or tax documents through this form.