Streamline Your Paperwork: A Contractor's Guide
- Jennifer Boaz
- Mar 26
- 4 min read
Welcome to the world of independent contracting! You are now your own boss, you set your own hours, and you’re in control of your own destiny. With this new world of contracting comes a new world of recordkeeping! After several years of navigating the 1099 landscape, I've learned a thing or two about managing important paperwork.
Keep It Organized!
1099 work involves a multitude of documents: contracts, receipts, tax forms, client communications, and more. While the majority of business documentation has transitioned to the digital realm, it is vital to manage both. Letting your files pile up, whether physical or digital, is a recipe for disaster.
Get organized from day one. Don't wait until tax season to scramble through receipts or a chaotic digital folder. You can start by setting up a dedicated filing system. This can be physical, digital, or a combination of both.
Physical Files: For your paper records, invest in a filing cabinet or storage boxes. Label them clearly: "Contracts," "Invoices," "Receipts," "Tax Documents," etc.
Digital Files: I operate largely in digital formats, but I still focus on keeping the records labeled and well-organized. Create folders on your computer or in the Cloud (more on that later) with the same organized structure, using subfolders to keep things even more organized. For example, within "Contracts," create folders by the year or client name. Whatever organizational convention you use, be consistent and timely in managing your records.
Contracts
Do not start work without a signed contract. This document outlines the scope of work, payment terms, deadlines, and other crucial details. A signed contract protects you. Keep a copy of every contract, both physical and digital. Make sure to keep backups.
Invoices
Develop a consistent invoicing system. Use a digital template that includes your name, contact information, client details, a clear description of services, and payment terms. Number your invoices sequentially for easy tracking. Sending invoices digitally is the standard and allows for much quicker payment.
Receipts
Every business expense is a potential tax deduction. Keep meticulous records of all receipts. Use a dedicated folder or box for physical receipts and immediately scan or photograph them for digital storage. This is simple, can be done from your phone, and leads to efficient and precise record-keeping.
Tax Documents
Keep all 1099-MISC (or 1099-NEC) forms, estimated tax payment records, and other tax-related documents in a separate, easily accessible location. Digital storage is ideal, as you can easily search for specific documents.
Communications
Save important emails and messages. This can be invaluable if disputes arise. Create folders within your email to organize communications by project or client name.
Tools of the Trade
Thankfully, we live in a digital age, and there are tons of free or affordable tools to help manage your paperwork.
The Cloud
Cloud storage, such as Dropbox, is essential. These platforms allow you to store and access your documents from anywhere. They also offer collaboration features, which can be useful if you work with a team.
Everlance
Automatically tracks your mileage and allows you to log business expenses. The free version includes basic mileage tracking and expense recording, while paid plans unlock more features, such as unlimited trips, PDF reports, and card synch for expense tracking.
Wave
Helps track income and expenses, generate invoices, and even run basic reports—all without a subscription fee. For those who want more, the subscription plans include auto-importing transactions, payment reminders, and additional users.
Expensify
Free individual plans let you scan receipts, track mileage, and upload travel details. Expensify also integrates with various accounting tools and other apps.
Adobe Scan/Google Drive Scan/Notes
Turn your smartphone into a portable scanner. These apps allow you to scan physical documents and save them as PDFs.
Dedicated Email Folders
Use email filters and folders to automatically sort incoming client emails.
You can easily find reviews and feedback on apps by searching online. Many websites and forums offer user reviews, so you can get a sense of how these tools work in real-world situations before deciding if they’re right for you.
Top Tips for Managing Paperwork
Schedule Regular Paperwork Time
Don't let paperwork pile up, whether physical or digital. Set aside a specific time each week to organize your documents.
Automate Where Possible
Use online tools to automate invoicing, expense tracking, and other tasks.
Back Up Your Data
Regularly back up your digital files to avoid data loss. Use redundant backup systems.
Consult a Professional
If you need help, get it. If you are unsure about any aspect of paperwork management or taxes, consult with an accountant or tax advisor.
Make It a Habit
Managing paperwork might seem tedious, but it's an essential part of being a successful independent contractor. By staying organized, embracing digital tools, and maintaining consistent habits, you can minimize stress and focus on what you do best. Remember, a well-organized paper trail, both physical and digital, is your key to a smooth and profitable 1099 career.
Until Next Time,
President, Investigative Service Division
EMT Holdings, LLC
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