Starting a Business? The Insurance Deadlines Freelancers Miss

Direct answer: New freelancers and business owners commonly miss three insurance deadlines: a roughly 60-day health insurance special enrollment window after leaving employer coverage, business liability insurance that clients or landlords require before work begins, and disability income insurance that's easy to postpone indefinitely without an employer plan defaulting it for you.

Health insurance

Leaving a job to go self-employed is itself a qualifying life event, generally giving you about 60 days to enroll in a marketplace plan without waiting for open enrollment.

Business liability insurance

Unlike health insurance, general liability or professional liability coverage has no federal enrollment deadline — but many landlords and clients require proof of coverage before signing a lease or contract, effectively creating a deadline of "before you can start working."

Disability income insurance

Without an employer plan automatically enrolling you, disability coverage is the easiest protection to postpone indefinitely. Financial planners commonly suggest reviewing options within the first quarter of self-employment, before an illness or injury makes new coverage harder to obtain.