Key Takeaways

• Never “auto-renew” your health plan; your needs, plan costs, and doctor networks change every year.
• Your true cost is not the monthly premium. 
• Review your entire family’s anticipated health needs for the coming year.
• Before committing, verify that your preferred doctors, specialists, and prescription drugs are still covered.
• Connect your health plan choices to your long-term financial goals.

Choosing health insurance coverage can feel overwhelming, especially with rising costs and constant policy updates. Being thoughtful about your choices now helps prevent surprise costs and coverage gaps later.

Let’s simplify the process so you can choose coverage that feels right, not rushed.

Enroll Today, Not Tomorrow

Procrastination is one of the biggest mistakes you can make. The longer you wait, the harder it becomes to find time, compare plans, and get support from brokers or healthcare exchanges.

Even if you’re unsure about potential subsidies or tax credits, it’s still smarter to enroll now. If anything big changes, your plan can be updated automatically later.

Your Step-by-Step Open Enrollment Checklist

Step 1: Gather Your Information

You can’t shop smart if you don’t have your facts straight. Gather these documents:

• Your Current Plan Details: Know your premium, deductible, out-of-pocket maximum, and plan type (HMO, PPO, etc.).
• Providers: Write down the names and locations of your family’s doctors, specialists, and preferred hospitals.
• Prescriptions: List every medication your family takes (including dosage).
• Income Information: Have recent pay stubs or your latest tax return. 
• Dependent Information: You will need Social Security numbers and birthdates for everyone getting coverage.

Step 2: Establish Your Health Profile

This is the step people skip, and it’s where financial planning for health insurance truly begins. 

• Do you expect any major medical events (e.g., a planned surgery, the birth of a child)?
• Does anyone need ongoing care (e.g., physical therapy, mental health services)?
• Are there new prescriptions to account for?
• Will a child need specialized dental or eye care?

A family that only visits the doctor for checkups has vastly different needs than a family managing a chronic condition. 

Step 3: Where to Get Coverage

You typically have three places to enroll:

1. Your Employer’s Plan: If you’re a W-2 employee, this is typically your primary option. Your HR department will provide the “when” and “how.”
2. The Health Insurance Marketplace: This is the government-run site (HealthCare.gov or your state’s specific exchange). This is where individuals, the self-employed, and small business owners can shop for plans and access tax credits (subsidies) based on income.
3. Insurer Direct: You can always buy a plan directly from a carrier. But you can only get income-based subsidies if you go through the official marketplace.

Step 4: Compare Total Costs

The monthly premium is just the sticker price; it’s not what the plan will actually cost. A low-premium plan often has a high deductible, so you pay for everything until the plan kicks in.

Here’s your “Total Cost Formula”:

• Premium: Your fixed monthly cost.
• Deductible: The amount you must pay out-of-pocket before your health insurance coverage pays its share.
• Out-of-Pocket Maximum: The absolute most you could pay for covered services in a year. 

If you choose a High-Deductible Health Plan (HDHP), add an HSA to the mix. It helps you save pre-tax dollars for care while building a tax-free cushion.

Step 5: Verify Your “Must-Haves”

Once you’ve narrowed it down to two or three plans, it’s time to do your final due diligence. This is the last item on your open enrollment checklist, and it is non-negotiable.

• Check the Provider Network: Call your doctors’ offices directly. Do not rely solely on online directories; they are often outdated.
• Check the Prescription Formulary: Look up your specific medications. Are they covered? What “tier” are they on? A drug that costs you a $20 copay on one plan might cost you 100% on another.

Make Open Enrollment Easy 

Health coverage choices can feel complicated, but you don’t have to navigate them alone. Goldstein Financial helps individuals, families, and small business owners make confident, informed decisions that align their health insurance coverage with long-term financial goals. Our team ensures your protection, savings, and peace of mind all work together.

Contact Goldstein Financial today to create a personalized strategy that keeps your 2026 health coverage (and your finances) on track.