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Health
#Disability Insurance
#Self-Employed
#Colorado
#Small Business

The Insurance Most Self-Employed People Skip

Uncle Sheldon

By Uncle Sheldon

Uncle Sheldon Writing Team

Published Sep 21, 2026 3 min read
The Insurance Most Self-Employed People Skip

What would happen to your income if you couldn’t work for six months?

For someone with a steady job, there’s often at least some answer to that question, a little sick leave, maybe a benefit through work. For the self-employed, the honest answer is usually nothing. The invoices stop when the work stops.

At Uncle Sheldon we work as a concierge agency, which means we look at everything a person has insured and ask what’s missing. For freelancers, consultants and small business owners, the answer is nearly always the same. Disability insurance is the policy we bring up most often, and it’s the one they’re most likely to have never bought. Many assume it’s only for people with dangerous jobs. It isn’t. Most of the time, what keeps people off work for a long stretch is an illness or an injury from ordinary life, not an accident on a job site.

Here’s how we think about it. Your ability to earn is usually your largest asset, bigger than your house or your retirement account, because it’s what pays for both. Disability insurance replaces part of your income if an illness or injury keeps you from working. It doesn’t make anyone rich. It keeps the lights on and the mortgage paid while you recover.

We find disability insurance, along with accident coverage, to be one of the most valuable policies a person can own, and it’s often more affordable than people expect when it’s set up thoughtfully. The details matter a great deal, though. How long you wait before benefits begin, how long they last, and how the policy defines being unable to work all change both the cost and the protection.

If you’re self-employed in Colorado, it’s worth reading about disability insurance in Colorado as a starting point. The right setup depends a lot on the kind of work you do and how steady your income is. A designer with irregular months needs something different from a physician with a full calendar. For consultants and advisors, it often sits right alongside professional liability as the two policies that protect the business you’ve built from the two very different ways it can be interrupted.

It’s a hard question to sit with. It’s a much easier one to answer once there’s a plan behind it.

About the Author

Uncle Sheldon

Uncle Sheldon

We're the small writing team behind Uncle Sheldon Insurance. We write about insurance, but also about the local communities where we offer it. Our goal is to help readers better understand the world of insurance and their local communities.

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