Health Insurance for 1099 Workers in Hampton Roads: What You Need to Know

If you’re self-employed in Hampton Roads — whether you’re a contractor in Norfolk, a freelance graphic designer in Virginia Beach, or a rideshare driver in Chesapeake — one of the hardest parts of working for yourself is health insurance.

Most 1099 workers think their only option is the Marketplace. But here’s the problem: Marketplace plans for 2025 are getting more expensive without offering better benefits. For someone with an unpredictable income, that’s not exactly helpful.

The good news? You have other options.

Why Marketplace Plans Don’t Always Work for 1099s

The Marketplace might look convenient, but it has some major downsides for independent workers:

• Premiums are rising in 2025. You could pay more each month with no added value.

• One-size-fits-all plans. They aren’t tailored to the unique needs of freelancers or gig workers.

• Unpredictable costs. Even if you find a “cheap” plan, deductibles and out-of-pocket expenses can wipe you out.

• Time wasted. Navigating Marketplace jargon takes hours you don’t have.

For someone juggling projects, clients, and invoices, it’s overwhelming.

Private Market Plans: A Better Fit for Independent Workers

As a health insurance broker in Chesapeake, I specialize in helping 1099 workers across Hampton Roads find private market plans that make sense. These plans can often:

• Lower your monthly costs compared to Marketplace options

• Fit your lifestyle by covering what you actually need (and skipping what you don’t)

• Give you flexibility if your income changes

• Protect you from major medical expenses without draining your budget

Instead of trying to force your situation into a Marketplace plan, private coverage allows us to find something built around you.

A Virginia Beach Freelancer’s Story

One of my clients, a freelance social media consultant in Virginia Beach, spent weeks trying to pick a Marketplace plan. Every option felt too expensive for what she was getting.

We sat down, reviewed her needs, and found a private plan that:

• Lowered her monthly costs

• Covered her preferred doctors

• Gave her peace of mind in case of emergencies

She left saying, “I finally understand my coverage — and it actually fits my budget.”

How I Help Find Health Insurance for 1099 Workers in Hampton Roads

Here’s how the process works when you meet with me:

1. We start with your real needs. Do you travel a lot? Do you need certain prescriptions? Are you just worried about big emergencies?

2. I shop over 100 companies. You’ll see options you won’t find on the Marketplace.

3. We compare side by side. You’ll know exactly what’s covered, what it costs, and how it fits your life.

4. You get ongoing support. If your situation changes, I’ll help you adjust your plan.

And the best part? It doesn’t cost you a dime extra to work with me.

The Bottom Line

If you’re a 1099 worker in Hampton Roads, don’t get stuck thinking the Marketplace is your only option. Private market health insurance often gives freelancers, contractors, and gig workers more affordable, flexible coverage — without the stress.

I’m Jason Ruhlman, a Chesapeake-based health plan advisor, and I’m here to make health insurance simple for you.