Avoiding Business Nightmares: Business Health Checklist

For New and Established Businesses

Use this checklist to review where your business stands and what needs attention. If you can’t check a box yet, that’s okay. Treat it as your next action step.

Formation & Compliance

☐ I chose the right business entity type for my goals and liability needs.
☐ I verified that my business name is available and properly registered.
☐ I’ve filed my formation documents with the Secretary of State.
☐ I’ve registered for state and local tax and business licenses.
☐ I file annual renewals and report ownership or address changes.
☐ I understand what a DBA (Trade or Assumed Name) is and how it applies to my business.
☐ I maintain separate business and personal bank accounts.

Contracts & Legal Protection

☐ I use a written Client Service Agreement for every client or project.
☐ My contracts clearly define scope, payment terms, IP ownership, and dispute resolution.
☐ I use Independent Contractor Agreements for freelancers or consultants.
☐ I use NDAs when sharing sensitive information with vendors or collaborators.
☐ I review and update all contracts annually.
☐ I store signed agreements digitally and securely.
☐ My contracts act as both protection and a guide for clients to understand my process.

Risk & Insurance Management

☐ I maintain General Liability and Professional Liability insurance.
☐ I’ve evaluated Property, Cyber, and Business Interruption coverage.
☐ My contracts are updated and signed before work begins.
☐ My contracts include liability limitation and indemnification clauses.
☐ My contracts include a dispute resolution clause requiring steps before litigation.
☐ I include disclaimers on my website, proposals, or invoices when appropriate.
☐ My personal and business assets are completely separated.

Intellectual Property & Brand Protection

☐ I understand the difference between trademarks and copyrights.
☐ My business name, program names, and brand assets are protected.
☐ I’ve purchased my domain and secured matching social media handles.
☐ My contracts specify who owns the work created for or by my business.
☐ I have rights or licenses for all visuals, media, and creative assets I use.
☐ I use NDAs for sensitive internal or vendor conversations.

Employment & Workforce Compliance

☐ I’ve classified all workers correctly as employees or contractors.
☐ I use the right forms: W-4 and I-9 for employees, W-9 for contractors.
☐ I maintain up-to-date employee handbooks and wage policies.
☐ I carry workers’ compensation insurance.
☐ I comply with current state and local leave, break, and pay laws.
☐ I review workplace safety practices annually.
☐ I stay informed of changes to Oregon and Washington labor laws each year.

Financial Health & Accounting

☐ I have a bookkeeper or accountant who understands my business.
☐ I track valid business expenses and categorize them correctly.
☐ My business uses cloud accounting software such as QuickBooks, Wave, or Xero.
☐ I keep personal and business funds completely separate.
☐ I back up financial and contract data securely.
☐ I retain business records for at least seven years.
☐ I review cash flow monthly or quarterly and know my burn rate.
☐ I anticipate and calendar upcoming financial changes such as rent increases or new hires.

Technology & Data Security

☐ I know whether my business handles sensitive or regulated data.
☐ I use multi-factor authentication and secure passwords for all key accounts.
☐ I encrypt sensitive documents and client data using secure software.
☐ I back up my systems both in the cloud and locally.
☐ I have a clear data privacy statement on my website.
☐ I have considered or obtained cyber liability insurance.
☐ I have consulted a technology or cybersecurity expert about best practices.

Ongoing Health & Annual Review

☐ I conduct an annual legal and compliance check-in.
☐ I review contracts, insurance, and taxes every year.
☐ I update my Operating Agreement or Bylaws if ownership changes.
☐ I audit my website, branding, and listings for accuracy.
☐ I meet regularly with my CPA or bookkeeper.
☐ I schedule recurring internal reviews to track progress toward my goals.