Health Insurance on Your Own Terms
If you don’t get insurance through an employer, figuring out your options can feel overwhelming. Connecticut Insurance Group works with self-employed individuals, freelancers, retirees not yet on Medicare, and anyone in between to find coverage that fits, without the confusion.
Individual health insurance is not one-size-fits-all. The right plan depends on how often you use healthcare, what doctors and prescriptions matter to you, and where your income lands relative to federal subsidy thresholds. Connecticut Insurance Group walks through all of it before making any recommendation.

Coverage for the Self-Employed
When you work for yourself, health insurance doesn’t come with the job.
That means you’re navigating costs, coverage, and enrollment on your own without an HR department to help. Connecticut Insurance Group specializes in helping self-employed individuals, sole proprietors, and freelancers find plans that work for their situation and budget.
One thing most people don’t realize: self-employed individuals may be eligible for premium tax credits through the ACA marketplace that significantly reduce monthly costs. Income, filing status, and household size all factor in. Running those numbers before choosing a plan is always the first step.
What to Think About as a Self-Employed Individual
- Your income can fluctuate, which affects subsidy eligibility from year to year
- You can deduct health insurance premiums as a business expense in many situations
- Network matters, make sure your preferred doctors are covered before you enroll
- Prescription coverage varies widely between plans, so your medications need to be checked against each plan’s formulary
Connecticut Insurance Group helps self-employed clients compare plans, check networks and drug coverage, and understand what they’re actually signing up for before enrollment.
ACA Marketplace Plans
The Affordable Care Act marketplace offers health insurance plans at four coverage levels: bronze, silver, gold, and platinum. The tier you choose affects how costs are shared between you and the plan throughout the year.
How the Metal Tiers Work
Lower-tier plans like bronze carry lower monthly premiums but higher out-of-pocket costs when you use care. Higher-tier plans like gold have higher premiums but lower costs at the point of service. Silver plans sit in the middle and are the only tier where cost-sharing reductions can apply for eligible enrollees.
The right tier isn’t automatically the cheapest. Someone who rarely needs medical care may do well with a bronze plan. Someone managing a chronic condition or expecting significant healthcare use may save money overall with a gold plan, even with the higher premium. Connecticut Insurance Group looks at the full picture before making a recommendation.
Subsidy Eligibility
Premium tax credits are available to people who purchase coverage through the marketplace and whose income falls within a certain range relative to the federal poverty level. These credits reduce your monthly premium directly. Eligibility is recalculated each year based on your projected income, so it’s worth reviewing annually, even if you’ve had a marketplace plan for years.
Connecticut Insurance Group helps clients estimate subsidy eligibility, understand how income changes could affect their credit, and avoid common mistakes that result in having to pay credits back at tax time.
What If You Missed Open Enrollment?
Missing the ACA open enrollment period doesn’t automatically leave you without options.
Depending on your circumstances, you may qualify for a Special Enrollment Period that lets you enroll outside the standard window.
Qualifying Life Events That Trigger a Special Enrollment Period
- Losing job-based health coverage
- Getting married or divorced
- Having or adopting a child
- Moving to a new coverage area
- Losing eligibility for Medicaid or CHIP
If you don’t have a qualifying event, there are also alternative coverage options outside the ACA marketplace that aren’t restricted by open enrollment. These aren’t comprehensive major medical insurance, but they can provide a bridge while you wait for the next enrollment window. Connecticut Insurance Group helps clients evaluate whether these alternatives are appropriate for their situation before recommending them.
Coverage Between Retirement and Medicare
If you retire before 65, there’s often a gap between your employer coverage ending and Medicare beginning.
That gap can last anywhere from a few months to several years, and finding the right coverage for it is one of the most common situations Connecticut Insurance Group helps with.
Options for this window include ACA marketplace plans, which may come with significant subsidies if your income is lower in early retirement, as well as COBRA continuation coverage from your former employer. Connecticut Insurance Group helps pre-retirees compare costs, understand subsidy eligibility, and time their Medicare enrollment correctly to avoid penalties.
This is also one of the strongest client pipelines for the practice. Someone who comes to Connecticut Insurance Group at 62 for a marketplace plan is already on a path to Medicare at 65, and staying with the same advisor through that transition makes the process significantly smoother.

Common Questions
Click on a question to find out more.
Subsidy eligibility depends on your estimated annual income for the coverage year and your household size. If your income falls within the eligible range relative to the federal poverty level, you qualify for premium tax credits. A quick conversation with Connecticut Insurance Group can help you figure out where you stand before you start comparing plans.
If your income changes significantly after you enroll, it can affect your subsidy amount. Reporting changes through the marketplace promptly helps avoid a surprise at tax time. Connecticut Insurance Group checks in with individual health clients annually to help catch these situations before they become problems.
The perception that marketplace plans are poor quality is a generalization that doesn’t hold up in every situation. A bronze plan works well for someone who is generally healthy and rarely needs care. A gold plan may actually save money overall for someone who uses healthcare regularly. The real question is whether a plan fits your specific situation, which is exactly what Connecticut Insurance Group evaluates before making any recommendation.
Dental and vision coverage can typically be added as separate plans alongside a medical plan. They’re not usually bundled into individual health insurance the way they sometimes are in group plans. Connecticut Insurance Group helps clients evaluate whether adding these makes financial sense based on their expected use and budget.
Not Sure Where to Start?
Individual health insurance has a lot of moving parts. The best way to find the right plan is to walk through your specific situation with someone who knows the options. Connecticut Insurance Group offers no-cost consultations with no pressure, just clarity.
