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Health insurance when you work for yourself

Two things stopped being handled for you the day you went out on your own: health coverage, and what happens to your income if you cannot work. Most self-employed people have sorted the first one out. Almost nobody has addressed the second. We look at both — free, and with no obligation.

Reviewed by Luay Sadqi, Licensed Agent · NPN 21370662 · Updated September 2026

You built your own job. Did you build your own safety net?

When you work for yourself, two things that used to be handled for you are now yours: health coverage, and what happens to your income if you cannot work. Most self-employed people we meet have sorted out the first one, more or less, and have done nothing at all about the second.

Freelancers, consultants, contractors, and business owners without employees normally use the individual Marketplace. Savings there are based on your estimated household income for the year — not last year's W-2 — which is why owners whose income moved often qualify for help they assumed was not available to them.

Health coverage when there is no employer plan

The gap almost nobody covers: disability income. The Social Security Administration estimates that a 20-year-old worker has about a one-in-four chance of becoming disabled before full retirement age. When you are the business, a bad six months is not a sick day — it is the whole operation. Yet coverage is much less common among the self-employed than among employees at large firms.

What income protection actually looks like

Think of it as paycheck protection rather than catastrophe insurance. A properly structured disability income policy replaces a portion of your earnings if you cannot work in your occupation. For practice owners and contractors there is also business overhead expense coverage, which keeps the lights on — rent, staff, loan payments — while you recover.

Underwriting here depends on your occupation and health, so it is generally easier and cheaper to arrange while you are healthy and working than to arrange later.

What else tends to come up

  1. Term life if anyone depends on your income, or if you have a mortgage or a business loan with a personal guarantee.
  2. Key-person or buy-sell funding if you have a partner or a business worth protecting.
  3. Retirement and long-term care planning once the immediate coverage is settled.
  4. Employee benefits the moment you hire your first W-2 employee — see benefits for 2 to 25 employees.

We do not open all of these at once. We start with the coverage you need now and only raise the rest when there is a documented reason to.

Owner benefits gap review

Health coverage now, income protection if you cannot work, and a benefits path as you hire. Free, no obligation.

Book an owner benefits review

What we charge

Nothing. Independent agents are compensated by the insurance carrier when a policy is placed. Your rate is set by the carrier and filed with the state — it does not go up because you used an agent, and it does not go down because you skipped one. What you get is a person who is accountable to you at claim time, at renewal, and when something changes.

And because we represent many carriers rather than one, we are not steering you toward a single company's shelf. If what you already have is the right thing to keep, we will tell you that.

Common questions

Self-employed coverage FAQ

How do self-employed people get health insurance?
Freelancers, consultants, contractors, and business owners without employees normally use the individual Marketplace. Savings are based on estimated household income for the year. Off-exchange individual plans and a spouse's employer plan are also worth comparing, and if you recently left a job you may have a limited Special Enrollment Period.
Are Marketplace savings based on last year's income?
No — they are based on your estimated household income for the coverage year. This matters a great deal for self-employed people whose income varies. Owners whose income dropped often qualify for help they assumed was unavailable to them. The Marketplace makes the final determination.
Do I need disability insurance if I am self-employed?
It is the most commonly skipped coverage among owners and often the most consequential. The Social Security Administration estimates a 20-year-old worker has roughly a one-in-four chance of becoming disabled before full retirement age, and disability coverage is far less available to the self-employed than to employees at large firms. Whether you need it depends on your savings, obligations, and who depends on your income.
Can I write off health insurance premiums?
Self-employed people may be able to deduct health insurance premiums, but the rules depend on your business structure, income, and whether you or your spouse had access to another employer plan. We are not tax advisors — confirm your situation with your CPA.
What happens when I hire my first employee?
Your options change. You may be able to offer a group plan, a QSEHRA, or an ICHRA depending on your size and goals. It is worth a 20-minute conversation before you commit to anything, because the right answer depends on your team's ages, locations, and what you can contribute monthly.

One honest call can make all the difference.

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