Going out on your own — freelancing, consulting, running a side business, or building a full company — means taking on the money decisions an employer used to handle for you. Choosing a business structure, getting an EIN, separating your business and personal finances, keeping books, paying estimated taxes, and building business credit. These guides walk through the practical setup decisions in plain English, so you can spend less time guessing and more time running the business.
Start Here: Taxes for the Self-Employed
The biggest surprise for most new self-employed people is taxes. No employer is withholding for you, you owe self-employment tax on top of income tax, and the IRS expects payments four times a year. These three guides cover the essentials before your first tax season arrives.
Self-Employment Tax Explained
The 15.3% Social Security and Medicare tax the self-employed pay on their own — how it’s calculated, the deduction for half of it, and why it catches first-year freelancers off guard.
Quarterly Estimated Taxes
When and how to pay the IRS four times a year, the safe-harbor rule that avoids penalties, and how to estimate what you owe when your income is uneven.
W-2 vs 1099
Employee or independent contractor? The difference decides who pays which taxes, what benefits you get, and what records you have to keep — the starting point for anyone going self-employed.
Setting Up Your Business
The structural decisions you make early shape your taxes, your liability, and how hard your business is to run. These guides cover the foundational setup — what entity to form, the tax ID you’ll need, and how to keep your business money separate from your personal money from day one.
Sole Proprietor vs LLC vs S-Corp
The most common business structures compared — how each affects your taxes, personal liability, paperwork, and cost. How to know when it’s worth forming an LLC, and when an S-corp election starts to pay off.
How to Get an EIN
What an Employer Identification Number is, when you actually need one (and when your SSN is fine), and how to get one free from the IRS in minutes — without paying a third-party service.
Business Banking Basics
Why a separate business bank account matters for taxes, liability, and bookkeeping — what documents you need to open one, and how to choose a business checking account with low fees.
Running the Money Side
Once the business is set up, the day-to-day money work begins — tracking income and expenses, building credit in the business’s name, and planning before you start. These guides cover the habits and tools that keep a small business financially healthy and ready to grow.
Bookkeeping Basics
How to track income and expenses without an accounting degree — cash vs accrual, what records the IRS expects, which expenses are deductible, and the simple systems (spreadsheet or software) that keep you organized.
How to Build Business Credit
How business credit differs from personal credit, why it matters for loans and supplier terms, and the step-by-step path to building a business credit profile from scratch.
How to Write a Business Plan
A simple, practical business plan you’ll actually use — the sections that matter, how to think through your market and numbers, and why even a one-page plan beats no plan at all.
Money Management for the Self-Employed
Beyond the setup, running a business for yourself means paying yourself the right way, claiming the deductions you’re owed, saving for retirement without an employer plan, protecting the business with insurance, pricing your work, and getting paid on time. These guides cover the day-to-day money decisions of working for yourself.
How to Pay Yourself
Owner’s draw vs salary — how to actually take money out of your business, why the method depends on your structure, and how to keep draws clean so they don’t hurt your taxes or liability protection.
The Home Office Deduction
A valuable write-off for the self-employed who use a dedicated space — who qualifies, the exclusive-use rule, and the simplified vs regular calculation methods for claiming it.
Retirement Accounts
No employer 401(k)? The SEP-IRA and Solo 401(k) let the self-employed save more than a regular IRA — how each works, how they differ, and how to choose.
Small Business Insurance
The core policies that protect a small business — general liability, professional liability, commercial property, workers’ comp — and the money-saving Business Owner’s Policy.
How to Price Your Work
Pricing is where many businesses quietly lose money. How to price by covering real costs, checking the market, and charging for value — plus the common pricing mistakes to avoid.
How to Invoice & Get Paid
Getting paid on time is a skill — what a good invoice includes, payment terms that get you paid faster, and how to handle clients who don’t pay.
Funding, Taxes & Growing Your Business
As your business grows, the money decisions get bigger: keeping business and personal finances apart, claiming every deduction you’re owed, handling sales tax, financing growth, bringing on help the right way, and keeping cash flowing through the lean months. These guides cover funding, taxes, and growth for the self-employed.
Separate Business & Personal Finances
The habit everything rests on — why mixing the two muddies your taxes, hides your real profit, and risks your liability protection, and how to set up clean separation even as a sole proprietor.
Small Business Tax Deductions
Every dollar you legitimately deduct is a dollar you don’t pay tax on. The ordinary-and-necessary rule, the most common write-offs, the tricky ones, and why tracking is everything.
Sales Tax for Small Businesses
If you sell products you may have to collect sales tax and remit it to the state. How nexus decides whether you must collect, the rules for online sellers, and how to handle it correctly.
Business Loans & SBA Financing
Most businesses need outside money at some point. SBA loans, term loans, lines of credit, equipment financing and microloans — what lenders look for, and how to borrow smart.
First Employee vs 1099 Contractor
Bringing someone on isn’t a free choice — the law decides based on control. The real difference, what each costs and requires, and why misclassification is so expensive.
Cash Flow Management
A profitable business can still run out of money. Why profit isn’t cash, how to speed up money in and smooth money out, and how to build a buffer so timing gaps don’t become crises.
More Self-Employed & Side-Business Guides
Self-employment and side businesses touch taxes, banking, and insurance across the site. These guides go deeper on the topics that matter most when you work for yourself.
What Is a Schedule C?
The form sole proprietors and single-member LLCs use to report business income and expenses — line by line, with the deductions most often missed.
What Is a 1099?
How independent-contractor income gets reported, the 1099-NEC and 1099-K forms, and what to do with the ones that arrive in your mailbox each January.
Self-Employed Insurance
Health, liability, and disability coverage when you don’t have an employer plan — where to shop, what’s deductible, and how to protect your income.
Gig Economy Taxes
Driving, delivering, or freelancing through an app? How gig income is taxed, the mileage and expense deductions you can take, and the quarterly-payment trap.
Side Hustle Taxes
When a side gig becomes a taxable business, what you can deduct, and how to keep a small side income from creating a big tax surprise.
Freelancing & Consulting
Turning skills into self-employed income — setting rates, finding clients, and the money setup that keeps a one-person consulting business running smoothly.
Latest Small Business Articles
- Cash Flow Management for the Self-Employed
A profitable business can still run out of money — cash flow is about timing, not profit. Why profit isn’t cash, how to speed up money in and smooth money out, and how to build a buffer so timing gaps don’t become crises. - Hiring Your First Employee vs a 1099 Contractor
Bringing someone on as an employee or an independent contractor isn’t a free choice — the law decides based on control. The real difference, what each costs and requires, and why misclassification is so expensive. - Small Business Loans and SBA Financing
Most small businesses need outside money at some point. The main financing options — term loans, SBA loans, lines of credit, equipment financing, microloans — what lenders look for, and how to borrow smart. - Sales Tax for Small Businesses
If you sell products, you may have to collect sales tax and remit it to the state. What sales tax is, how nexus decides whether you must collect, economic-nexus rules for online sellers, and how to handle it correctly. - Small Business Tax Deductions: What You Can Write Off
Every dollar you legitimately deduct is a dollar you don’t pay tax on. The ordinary-and-necessary rule, the most common deductions for the self-employed, the tricky ones, and why tracking is everything. - How to Separate Business and Personal Finances
Mixing business and personal money muddies your taxes, hides whether you’re profitable, and can put your personal assets at risk. Why separation matters, how to actually do it, and the slip-ups to avoid.
View all Small Business articles →
Related Sections
Taxes — Self-employment tax, quarterly estimates, deductions, Schedule C, and everything else on the tax side of working for yourself.
Jobs & Career — W-2 vs 1099, gig and side-hustle taxes, benefits, and the money side of work.
Extra Income — Freelancing, consulting, hobby income, and part-time work in retirement.
Banking — Choosing accounts, avoiding fees, online banking, and how to handle business and personal banking.
Credit & Debt — Credit scores, building credit, loans, and managing debt for individuals and businesses.
Insurance — Health, liability, and disability coverage, including options for the self-employed.
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