Contents

Acknowledgments

Introduction

Part 1 Self-Employment Basics

1. Being Self-Employed and On Your Own

What Does Self-Employment Mean?

Legal Consequences of Self-Employment

Practical Issues in Self-Employment

Tax Terminology

Being 1099ed

What's Ahead

2. Getting Set Up for Tax Reporting and Business Operations

Preliminaries

Keeping Books and Records for Tax Reporting

Business Reasons for Recordkeeping

Tax ID Number

Tax Year

Accounting Method

Decide Your Business Name

What's Your IP?

Obtain Licenses, Permits, and Permission

What's Ahead

3. Using Schedule C

Tax Filing on Schedule C

When, Where, and How to File

What's Ahead

Part 2 Reporting Income and Expenses

4. Reporting Your Income

Payment Types Don't Matter

Alternative Payments

Where to Report Payments

What to Do about 1099s

What to Do When You Don't Get Paid

Losses

What's Ahead

5. Writing Off T&E Expenses

Vehicle Expenses

Local Transportation

Business Meals and Entertainment

Business Travel

Business Gifts

Strategies for Saving on T&E Costs

What's Ahead

6. Deducting Office-Related Costs

Rental Expenses

Home Office Use

Materials and Supplies

Furniture and Fixtures

Computer-Related Costs

Insurance

Utilities

Miscellaneous Office-Related Costs

What's Ahead

7. Claiming Deductions A to Z

Advertising Costs

Bad Debts

Banking Fees

Casualty and Theft Losses

Charitable Contributions

Dues

Education Expenses

Impairment-Related Expenses

Interest

Legal and Professional Fees

Licenses and Regulatory Fees

Materials and Supplies

Moving Expenses

Payments for Outsourced Workers

Penalties, Fines, and Damages

Repayment of Income

Startup Costs

Subscriptions

Supplies

Taxes

Utilities

Checklist of Nondeductible Expenses

What's Ahead

8. Protecting Yourself with Medical Coverage and Retirement Savings

Medical Insurance

Health Savings Accounts

Tax Deduction for Health Coverage

Retirement Savings

SEPs

Solo 401(k)s

Pension Plans

IRAs

Roth IRAs

Strategies for Retirement Savings

What's Ahead

9. Taking Tax Credits

Business-Related Tax Credit

Personal Credits Arising from Business

What's Ahead

Part 3 Strategies for Your Business

10. Paying Your Taxes

Self-Employment Tax

Additional Medicare Tax on Earned Income

Additional Medicare Tax on Net Investment Income

Estimated Taxes

When You Pay Estimated Taxes

Sales Taxes

What's Ahead

11. Strategizing Year-Round for Tax Savings

Tax-Savvy Business Decisions

Year-End Planning

Post-Year Tax Elections

Lease Instead of Buy?

Don't Overlook Carryovers

Audit-Proof Your Return

What's Ahead

12. Strategies as Your Business Grows

Moving to Larger Quarters

Hiring Employees

Changing Legal Status

Selling the Business

Final Thoughts

Index

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