📚 BOOKKEEPING GUIDES

Learn it once. Use it forever.

Free, plain-English guides to every bookkeeping topic that matters when you’re running a business by yourself.

Learning tracks

Seven guides. Start anywhere.

🌱
Start here

Bookkeeping 101 for the self-employed

Five short chapters: what bookkeeping actually is, why it matters, and the minimum you need to do to stay out of trouble.

5 CHAPTERS· 22 MIN READ
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Structure

Sole prop vs. LLC vs. S-corp

A clear breakdown of each structure's tax, liability, and paperwork tradeoffs, with the specific revenue thresholds where each starts to matter.

4 CHAPTERS· 18 MIN READ
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Taxes

The Schedule C handbook

Line-by-line walkthrough of the IRS form every sole prop and single-member LLC files, including which categories matter most and which ones get audited.

7 CHAPTERS· 34 MIN READ
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Deductions

Every deduction you're missing

The 18 deductions self-employed people forget: home office, mileage, phone, health insurance, retirement, and more, with real dollar examples.

6 CHAPTERS· 26 MIN READ
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Rhythm

The quarterly tax playbook

Four dates, four checks to the IRS. How to estimate, what the safe-harbor rule is, and how to avoid the surprise April bill forever.

4 CHAPTERS· 15 MIN READ
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Year-end

The painless year-end checklist

1099s, mileage logs, receipt cleanup, reconciliation, and the exact files your CPA actually wants. Finish the year in an afternoon.

8 CHAPTERS· 28 MIN READ
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Catch up

How to catch up on bookkeeping

Months behind on your books? A step-by-step plan to get caught up, what it costs to pay someone to do it, and how to stay current afterward.

9 CHAPTERS· 8 MIN READ
Quick answers

Six questions we hear every week

What counts as a business expense?
The IRS standard: ordinary and necessary for your trade. If a reasonable person in your industry would incur the cost to earn income, it qualifies.
Do I need a separate business bank account?
Legally, only LLCs and corps must. Practically, yes. Commingling personal and business spending is the #1 reason self-employed books are a mess.
How does Clarity record income and expenses?
Cash basis only. Income is recorded when money hits your account and expenses when money leaves. Maps cleanly to your bank statements and matches IRS Schedule C.
How long do I keep receipts?
Seven years. The IRS can audit the last three years routinely, six if they suspect under-reporting, and indefinitely for fraud. Seven keeps you covered.
Can I deduct meals?
Fifty percent, if the meal has a clear business purpose (client, employee, or travel). Save the receipt and jot the reason on it.
Home office: is it worth it?
Often yes. If you use a room exclusively and regularly for business, you can deduct a portion of rent, utilities, and internet. The simplified method ($5/sqft, up to 300 sqft) is usually enough.
A note on accuracy. These guides reflect our best understanding of U.S. federal tax rules as of 2026. They are educational and not tax advice. For specific situations, talk to a CPA. Clarity Books AI never files taxes on your behalf; we prepare the numbers, your CPA or your DIY software files them.

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