Resources for Freelancers & 1099 Workers

The primary guide for sole proprietors filing Schedule C. Covers what income to report, which expenses are deductible, home office, mileage, and more.

How to calculate and pay quarterly estimated taxes (Form 1040-ES). Covers the safe harbor rules, underpayment penalty, and annualized income installment method.

SEP-IRA, SIMPLE IRA, and qualified plan contribution limits and rules. Includes the SE compensation formula for calculating max contributions.

Standard mileage rates, actual expense method, business meal deduction rules (50%), and travel expense documentation requirements.

Home office deduction rules: regular and exclusive use test, simplified method ($5/sq ft, max 300 sq ft), and actual expense method via Form 8829.

MACRS depreciation, Section 179 immediate expensing, bonus depreciation, and listed property rules for computers and vehicles.

For self-employed individuals in agriculture. Cash vs accrual accounting, farm income, and depreciation of farm property.

IRS hub page for self-employed. Links to forms, publications, and resources for sole proprietors and independent contractors.

The core form for sole proprietors. Reports business income and deductions. Net profit flows to Form 1040 and is subject to SE tax.

Calculates the 15.3% SE tax (Social Security + Medicare) on Schedule C net profit. Half of SE tax is deductible on Form 1040.

Quarterly estimated tax payment vouchers and worksheets. Use the current-year IRS deadline guidance below before relying on any specific installment date.

Collect from clients before they pay you, and from any contractor you pay $600+. Required to issue 1099-NECs.

File to elect S-Corp status. Must be filed within 75 days of incorporation or by March 15 of the tax year you want the election to take effect.

Calculate the 15.3% SE tax + deductible half, at any net SE income level.

Estimate Q1–Q4 payment amounts. Includes federal + state and safe harbor comparison.

Full after-tax comparison: employee vs contractor at the same gross income.

Compare SEP-IRA vs Solo 401(k) contribution limits and 30-year projected balances.

Simplified method ($5/sq ft) vs actual expense method — see which saves more.

Standard mileage rate vs actual vehicle expense — compare both methods for your miles.

Your real hourly rate after unbillable hours, overhead, taxes, and benefits costs.

Is a project actually profitable? Model scope, hours, overhead, and taxes.

Calculate exactly how much to charge when invoices go past due.

Is your rate market-competitive? Compare against benchmarks for your industry and experience.

Calculate the safe harbor payment that avoids underpayment penalties entirely.

How much extra hourly rate do you need to replace employee benefits as a contractor?

Official IRS system for making estimated tax payments online. Free. Enroll with your SSN/EIN and bank account. Payments post same day.

Free federal tax filing for AGI under $79,000. Partner software includes H&R Block, TaxAct, and others. Self-employed forms supported.

Make one-time tax payments directly from your bank account — no enrollment needed. Good for annual balance due payments.

Verify the SSA has your self-employment income on record. Self-employed people sometimes have SE tax miscalculated, which affects future Social Security benefits.

View your tax account: balance due, payment history, estimated tax payments, transcripts, and notices. Verify your estimated payments were received.

View your estimated Social Security benefit at various retirement ages based on your actual earnings record. Essential for retirement planning.

Estimate Social Security retirement benefits based on your earnings record. No account needed for basic estimates.

Fast Social Security benefit estimate using your birth year and estimated earnings. Good for quick planning scenarios.

Check what SSA benefits you may be eligible for, including Medicare at 65.

California state income tax. Note: CA has no sales tax exemption on services and applies its own quarterly payment requirements.

Texas has no state income tax but requires franchise tax for LLCs and S-Corps earning $2.47M+ annually.

New York State Department of Taxation and Finance. NYC imposes an additional city income tax (3.08–3.876%).

Florida has no state income tax. Corporate income tax applies to C-Corps.

Illinois flat income tax rate: 4.95%. Self-employment income taxed at the same rate.

No state income tax. However, Washington has a Business & Occupation (B&O) tax on gross receipts.

IRS-maintained list of every state's tax agency website. Find your state's payment portal, estimated tax instructions, and forms.

The IRS hub for sole proprietors: quarterly payments, deductions, retirement plans, and SE tax calculations. Start here if you have a specific IRS question.

SBA guide to registering your business, choosing a structure (sole prop, LLC, S-Corp), and accessing small business resources.

Free courses on business plan writing, marketing basics, government contracting, and financial management. Relevant for freelancers scaling into a business.

SSA publication explaining how self-employment income is credited to your Social Security earnings record and how it affects future benefit calculations.

Department of Labor guidance on independent contractor vs employee classification under the FLSA. Relevant if you hire contractors or are concerned about your own classification.

CFPB financial tools including budget worksheets and guides for consumers with variable income. Useful for new freelancers building financial discipline.

Why most small businesses fail and how to build systems that don't depend on you showing up every day. Required reading for anyone transitioning from employee to self-employed.

Profiles of real solo businesses generating $1M+ in revenue with no employees. Practical models across industries.

A cash management system for self-employed: allocate revenue to separate accounts for taxes, profit, owner pay, and expenses immediately when money comes in.

Written by a CPA and attorney: tax strategy, entity selection, retirement accounts, and asset protection for business owners.

Systematic approach to getting more clients as a solo consultant or freelancer. Foundational for building a pipeline.

CPA Rich Dad advisor explains how to use tax law as it was designed — to incentivize entrepreneurship and investment. More advanced, but accessible.