Business finances
Insurance, banking, and bookkeeping
Insurance to consider
- General liability: covers third-party injury and property damage.
- Professional liability: matters for consultants, designers, IT workers, and bookkeepers.
- Business owner’s policy: bundles general liability and commercial property.
- Auto coverage: personal auto policies may exclude business use.
- Home-based coverage: homeowners policies typically limit or exclude business property and liability. Ask about a home-based business endorsement.
- Workers’ compensation: required with one employee. A solo owner may buy coverage for themselves but is not required to.
- Disability insurance: replaces income if you cannot work.
One broker’s customer estimates, not Illinois-specific: general liability averages about $45 a month in that broker’s customer data, with annual premiums roughly $265 to $3,030.
Health insurance
Get Covered Illinois is the state’s marketplace and the only place to get premium tax credits. Open enrollment for 2026 coverage starts November 1. Self-employed people may be able to deduct premiums.
Opening a business bank account
General practice; requirements vary by bank:
- Sole proprietors typically need photo ID, an SSN or EIN, and the county assumed-name certificate if using a DBA.
- LLCs typically need filed Articles, an EIN, an operating agreement, and ID.
See assumed-name filings and LLC formation documents.
Keep the money separate
Mixing personal and business funds, or commingling, is a classic reason courts pierce the veil and hold an LLC owner personally liable. It also makes tax records harder to defend. Pay yourself by transfer.
Monthly bookkeeping
Track income, expenses, mileage, and receipts monthly. Common software includes QuickBooks Online, Xero, Wave, and FreshBooks; spreadsheets can work for very simple businesses. These are examples, not endorsements.
The IRS generally recommends keeping records at least 3 years, longer in some cases.
When to bring in professional help
| Professional | When to consider help | Estimated cost |
|---|---|---|
| CPA or enrolled agent | S-corp decision, sales tax, or an IRS notice. | $300–$800 for a Schedule C return; $1,000–$3,000+ for an S-corp return. |
| Bookkeeper | Rule of thumb: over about 50 transactions a month. | $200–$600 a month. |
| Independent insurance agent | Before the first client contracts. | Ask the agent for a quote. |
| Payroll provider | S-corp salary or first employee. | $40–$150 a month. |
| Attorney | Operating agreement, series LLC, contracts, or classification questions. | Flat fees of $500–$2,000 are common estimates for LLC packages. |
Read about S-corp tax status, series LLCs, and hiring and contractors.
Not sure which structure fits? Try the Structure Finder, or request help. Call (331) 261-4788
General information, not legal or tax advice.