Most creators and freelancers don’t realize how messy their finances are—until tax time hits. Suddenly, you’re digging through old receipts, hunting for invoices, and scrambling to remember what counts as a deduction.
Whether you’re a YouTuber, influencer, podcaster, or freelance graphic designer, your income doesn’t come on a predictable schedule. Some months are great, others are slow—and that makes managing your money even harder.
This is where a good accounting checklist becomes your best friend.
If you’re a solo creative in Chicago, this step-by-step guide will help you stay on top of your business finances all year round. From setting up the right structure to tracking income, expenses, and taxes, we’ve got you covered.
At Aced Accounting, we work with freelancers and content creators every day to make sure their books are in order and their taxes are accurate. Use this checklist to keep your finances clean and your stress low. Bookmark it or download the free PDF version at the end—and save yourself a lot of headaches later.
Why Creators & Freelancers Need a Financial Checklist
Freelancers and creators face unique money challenges. Your income comes from different places—brand deals, affiliate links, YouTube ads, clients—and it’s rarely consistent. On top of that, you don’t get taxes withheld, so you’re fully responsible for setting that money aside.
The IRS treats you as self-employed, which means you must pay both income tax and self-employment tax. If you don’t stay organized, you could miss important deductions or fall behind on payments.
A clear accounting checklist helps you stay on top of things, avoid penalties, and make smart money decisions. At Aced Accounting, we specialize in accounting for freelancers in Chicago and can help you build a system that works.
Step-by-Step Accounting Checklist
✅ A. Set Up Your Business Structure
Before anything else, decide how you want to operate your business. Most freelancers start as sole proprietors, but as you grow, switching to an LLC can offer legal protection and help with taxes.
In Illinois, you’ll need to register your business with the state and choose a name. This process is fairly simple and can be done online.
You’ll also need an EIN (Employer Identification Number) from the IRS. Even if you don’t have employees, it’s often required to open a business bank account and file taxes.
Not sure which structure is right for you? Aced Accounting can help you understand the differences between a sole proprietorship and LLC, and what makes sense based on your income level and goals.
✅ B. Open a Dedicated Business Bank Account
Mixing personal and business finances is one of the biggest mistakes new freelancers make.
Open a separate business bank account so you can clearly track income and expenses. This makes bookkeeping easier and gives you a cleaner record in case of an audit.
Chicago has great options like Chase, BMO Harris, and local credit unions that offer low-fee business accounts. Keep this account strictly for business transactions—no groceries or Netflix here.
Aced Accounting can help you choose the right setup and connect your bank feeds to your bookkeeping tools.
✅ C. Track All Sources of Income
As a creator, your income might come from multiple platforms:
- YouTube AdSense
- Affiliate links
- Sponsorship deals
- Freelance gigs
- Merchandise or course sales
Use a system that helps you track it all in one place. Tools like QuickBooks Self-Employed, Wave, or even custom Notion templates are great options.
Make sure to record every dollar that comes in and tag it by type. This helps when you file taxes and understand which income streams are growing.
We at Aced Accounting help many clients streamline this step, especially those dealing with 1099 income tracking or inconsistent monthly payments.
✅ D. Save and Categorize All Expenses
The key to maximizing your tax deductions is good recordkeeping.
Track every expense related to your business, including:
- Camera gear and editing software
- Office supplies and subscriptions
- Travel for work
- Internet, phone bills, and utilities (if you work from home)
Use tools like Expensify, Google Sheets, or QuickBooks to categorize everything. Always save receipts—either physical copies or digital backups using scanning apps.
Keeping your expenses organized means you’ll never miss a deduction. For example, “tax deductions for influencers” might include makeup or wardrobe used for shoots, which many overlook.
Pro tip: Set aside 30 minutes each week to update your expense records. Trust us, it’s much easier than trying to remember everything in April.
At Aced Accounting, we help creatives build smart, simple systems for tracking—and maximizing—every business expense.
✅ E. Understand & Plan for Taxes
Unlike traditional jobs, taxes aren’t automatically taken out of your income. As a self-employed professional, you’re responsible for paying quarterly estimated taxes—to both the IRS and the Illinois Department of Revenue.
Here’s what you need to know:
- You’ll likely file Form 1099-NEC if you’re paid for services.
- Platforms like YouTube or Patreon may issue a 1099-K if your income crosses certain thresholds.
- Don’t forget about self-employment tax—this covers Social Security and Medicare.
Missing payments or filing late can lead to penalties. Use tools like IRS Direct Pay or Illinois MyTax to stay current.
We recommend putting aside 25–30% of each payment you receive. That way, you won’t feel the pinch when it’s time to pay.
Aced Accounting offers freelancer tax checklists in Chicago, so you can stay compliant without stress.
✅ F. Know Your Deductions
One of the biggest benefits of being self-employed is claiming business tax deductions—but only if you know what to look for.
Popular deductions for creators include:
- Home office space
- Internet and phone bills
- Cameras, microphones, and lighting
- Editing software like Final Cut or Adobe Suite
- Business mileage (for shoots or client meetings)
- Marketing or ad spend on Instagram, Facebook, etc.
Even small purchases can add up. The more you track, the more you save.
Searches for “tax deductions for YouTubers and influencers” spike every tax season—don’t wait until the last minute. Keep a running list all year long.
At Aced Accounting, we review all your expenses to make sure you’re not leaving money on the table. We’ve helped countless Chicago creators get thousands back simply by identifying overlooked deductions.
✅ G. Use the Right Software
The right software can make your life so much easier.
Top tools for creators:
- QuickBooks Self-Employed: Great for tracking income, mileage, and tax estimates.
- FreshBooks: Easy invoicing and time tracking.
- Xero: Clean interface, perfect for scaling.
Each has its pros and cons, depending on how complex your business is. Some offer mobile apps, while others work better on desktop.
Not sure what to choose? Aced Accounting helps you set up the best accounting software for freelancers—and can even manage it for you.
When to Hire a Bookkeeper or Accountant
DIY accounting can work in the beginning. But as your brand grows, your finances get more complicated.
If you’re spending more time on spreadsheets than content, missing tax deadlines, or unsure about what you owe—it’s time to bring in help.
Working with a professional frees up your time and gives you peace of mind. A local expert also understands Chicago tax laws and can offer personal support.
At Aced Accounting, we offer bookkeeping services in Chicago for content creators, freelancers, and solo entrepreneurs. We’re here to take the stress off your shoulders so you can focus on doing what you love.
Bonus: Year-End Financial Wrap-Up Tips
Before the year ends, do a financial cleanup:
- Reconcile your bank accounts
- Generate income and expense reports
- Review your yearly goals and adjust budgets
- Organize documents for tax season
Doing this in December means a smoother tax filing process—and fewer surprises in April. It also gives you a clear picture of what worked (and what didn’t) financially.
Aced Accounting offers year-end services to help you close your books and prep for tax season with confidence.
If you’re a content creator, freelancer, or solo entrepreneur in Chicago, staying on top of your finances is one of the smartest things you can do. A solid accounting routine not only saves you money on taxes—it helps your business grow.
At Aced Accounting, we specialize in helping creators simplify their bookkeeping, track their income, and stay compliant with tax laws. Whether you’re making your first $1,000 or scaling past six figures, we’re here to support your journey.
Let us handle the accounting—so you can stay focused on creating.
Visit acedaccounting.com to schedule a free consultation today.
