Jake Lawson here. After 15+ years helping entrepreneurs choose the right business structure, I need to be straight with you about sole proprietorships: they’re often the wrong choice. Yes, they’re simple to start—in fact, you’re probably already operating one if you’re making money from business activities. But simple doesn’t mean smart. In Illinois, the risks usually outweigh the benefits. Let me explain why, and if you still decide to go this route, I’ll show you exactly how to do it right.
Thinking about starting a sole proprietorship in Illinois? Before you make that decision, let me give you the unvarnished truth about what you’re actually signing up for.
What Is a Sole Proprietorship, Really?
A sole proprietorship isn’t a formal business entity—it’s what happens by default when you start making money from business activities. The moment you begin selling products, providing services, or taking any business actions with the intent to profit, Illinois considers you a sole proprietor.
Here’s the thing: You don’t file paperwork to “create” a sole proprietorship. You already are one if you’re doing business activities alone.
Example: Sarah starts tutoring students and charges $50 per session. She hasn’t filed any business documents, but legally, she’s operating a sole proprietorship the moment she accepts her first payment.
The Brutal Truth About Sole Proprietorships
Let me cut straight to the chase: sole proprietorships are usually a bad idea for anyone serious about building a business. Here’s why:
The Personal Liability Nightmare
The biggest problem: Zero liability protection. When your business gets sued (not if, when), your personal assets—house, car, savings, retirement accounts—are all fair game.
Real scenario: A client slips and falls at your Illinois business location. They sue for $100,000. With a sole proprietorship, they can come after your home, your personal bank accounts, everything you own. With an LLC, they can only pursue business assets.
The Credibility Problem
Sole proprietorships signal “amateur hour” to potential clients, vendors, and partners. When someone sees “Sarah’s Tutoring” versus “Academic Excellence LLC,” which sounds more professional and established?
The Conversion Headache
Starting as a sole proprietorship and later converting to an LLC is a paperwork nightmare involving:
- New business formation with the state
- EIN changes with the IRS
- Bank account transfers
- License and permit reapplications
- Contract renegotiations
- Website and marketing updates
Bottom line: If you can afford the $150 Illinois LLC filing fee, skip the sole proprietorship headache and start with proper protection.
When Sole Proprietorships Might Make Sense
I’m not completely against sole proprietorships. They can work in very specific situations:
Ultra-Low-Risk Businesses
- Content creation with no physical products
- Digital consulting with proper insurance
- Writing or design services are conducted entirely online
Cash Flow Emergencies
- You need to start earning immediately and literally cannot afford $150 for an LLC
- You plan to convert to an LLC within 6 months once cash flow improves
Testing Business Ideas
- You’re validating a concept and want to see if it works before investing in formal structure
- You’re doing small-scale activities to test market demand
Important: Even in these cases, I strongly recommend getting business insurance and moving to an LLC as soon as financially feasible.
How to Start a Sole Proprietorship in Illinois (If You Insist)
If you’ve decided to proceed despite the risks, here’s how to do it properly:
Step 1: Business Planning Reality Check
Before you dive in, seriously consider these questions:
- Business model: How exactly will you make money?
- Risk assessment: What could go wrong, and how much could you lose?
- Growth plans: Will you hire employees or partners later?
- Competition: How do professional competitors structure their businesses?
Pro tip: If your competitors are mostly LLCs or corporations, that’s a strong signal you should be too.
Step 2: Naming Your Business (DBA Considerations)
By default, your business name is your legal name. Want to use something else? You’ll need a DBA (Doing Business As) registration.
Illinois DBA Requirements:
- File with the county clerk where you operate
- Required for any name other than your first and last name
- Costs vary by county ($25-50 typically)
- Must be renewed periodically (usually every 5 years)
Example: James Smith wants to operate as “Chicago Web Solutions.” He must file a DBA with Cook County because he’s not using his legal name.
DBA Limitations:
- Doesn’t provide liability protection
- Doesn’t create a separate legal entity
- Can be used by other businesses (no exclusive rights)
Step 3: Get an EIN (Employer Identification Number)
Why you need an EIN:
- Protects your Social Security number
- Required if you plan to hire employees
- Makes banking and contracts more professional
- Separates business and personal finances for tax purposes
How to get one:
- Apply directly with the IRS online (free)
- Takes about 15 minutes
- Receive your EIN immediately
- Don’t pay third-party services for this—it’s free from the IRS
Step 4: Business Licensing and Permits
Illinois doesn’t require a general business license, but you may need:
Industry-Specific Licenses:
- Professional services (accounting, legal, medical)
- Food service and restaurants
- Retail sales (sales tax permit)
- Construction and contracting
- Transportation services
Local Requirements:
- City business licenses
- County permits
- Zoning compliance
- Health department permits
Research Resources:
- Illinois.gov business portal
- Your city/county websites
- Industry association requirements
Step 5: Business Banking
Open a separate business bank account immediately. This is crucial for:
- Tax organization and reporting
- Professional appearance
- Legal protection (shows business separation)
- Financial record keeping
What you’ll need:
- Photo ID
- EIN confirmation letter
- DBA filing (if applicable)
- Initial deposit (varies by bank)
Bank selection tips:
- Compare business account fees
- Look for no-minimum-balance options
- Consider online banks for lower fees
- Ask about business credit card options
Step 6: Record Keeping and Taxes
Essential records to maintain:
- All business income and expense receipts
- Bank statements and canceled checks
- Tax returns for at least 3 years
- Equipment and asset purchase records
- Client contracts and invoices
Tax obligations:
- Report business income/loss on Schedule C
- File with your personal Form 1040
- Pay quarterly estimated taxes if profitable
- Consider hiring an accountant for optimization
Illinois-Specific Considerations
State Tax Registration
Most Illinois businesses must register with the Illinois Department of Revenue for:
- Sales tax (if selling products)
- Use tax obligations
- Withholding tax (if hiring employees)
Local Requirements
Illinois has 102 counties and hundreds of municipalities, each with potentially different requirements:
- Business registration
- Local licenses
- Zoning compliance
- Signage permits
Insurance Considerations
Illinois doesn’t require business insurance for sole proprietorships, but you absolutely should consider:
- General liability insurance
- Professional liability (errors & omissions)
- Product liability (if selling products)
- Business interruption insurance
The LLC Alternative: Why It’s Usually Better
Here’s why I recommend Illinois LLCs over sole proprietorships:
Cost Comparison
Sole Proprietorship:
- Formation: $0
- DBA (if needed): $25-50
- Annual requirements: Minimal
- Hidden cost: Unlimited personal liability
- Formation: $150 state fee
- Annual report: $75
- Registered agent: $0 (if self) or $100-150/year
- Benefit: Personal asset protection
The Math
You’re risking everything to save $150. That’s not smart business.
Tax Similarities
Single-member LLCs are taxed exactly like sole proprietorships by default. You get the same tax treatment with better protection.
Common Sole Proprietorship Mistakes
After 15+ years in this business, I’ve seen these errors repeatedly:
Mixing Personal and Business Finances
Using personal accounts for business transactions destroys any semblance of business legitimacy and complicates taxes.
Ignoring Insurance Needs
Thinking “I’m just a small business” doesn’t protect you from lawsuits. One incident can wipe you out.
Not Planning for Growth
Starting as a sole proprietorship and converting later is expensive and complicated. Plan ahead.
Forgetting Quarterly Tax Payments
The IRS expects quarterly estimated tax payments. Missing these results in penalties and interest.
Making the Smart Choice
Here’s my decision framework:
Choose LLC if:
- You can afford the $150 filing fee
- You interact with customers or clients
- You have any physical business location
- You plan to grow beyond a solo operation
- You have personal assets to protect
Consider sole proprietorship only if:
- You’re testing a very low-risk business concept
- You literally cannot afford LLC formation
- You plan to convert to LLC within 6 months
- Your business has virtually no liability exposure
The Bottom Line
Sole proprietorships are legal entities for people who don’t want legal entities. They’re what happens when you don’t make a conscious choice about business structure.
In Illinois, with relatively affordable LLC formation costs and straightforward requirements, there’s rarely a good reason to accept unlimited personal liability when protection costs just $150.
Yes, sole proprietorships are simple to start—you’re probably already operating one. But simple and smart aren’t the same thing. Your business deserves proper protection, and so do you.
If you’re determined to start as a sole proprietorship, follow the steps above carefully. But do yourself a favor: as soon as you can afford it, convert to an LLC. Your future self will thank you.
My recommendation: Skip the sole proprietorship entirely and start with an Illinois LLC. The minimal additional cost provides invaluable protection and credibility that will benefit your business from day one.
Questions about business structure choices or need help deciding what’s right for your specific situation? That’s exactly why I built llciyo.com—to provide honest guidance based on real experience, not theoretical advice.
Ready to make the smart choice? Check out our comprehensive guide to forming an Illinois LLC, including step-by-step instructions and cost breakdowns. No sales pitches, just the facts you need to protect your business and personal assets.