Open Enrollment 101: What You Need to Know Before November 1st

It’s that time again, open enrollment season. Starting November 1, millions of Americans will have the chance to review, renew, or change their health insurance coverage. Whether you’re a full-time employee, a freelancer, or an entrepreneur running your own business, understanding your options can save you money, stress, and headaches all year long.

Here’s your complete guide to navigating open enrollment like a pro.

What Is Open Enrollment?

Open enrollment is the one time each year when you can sign up for, switch, or update your health insurance plan without a qualifying life event (like marriage, birth, or losing other coverage).

For most people, it runs from November 1 through January 15, but check your employer’s specific dates, since job-based plans often have shorter enrollment windows.

For W-2 Employees (Traditional Workers)

If you receive benefits through your employer, your HR or benefits department will send you a packet or email outlining your options. Here’s what to pay attention to:

1. Review what’s changed

Check premium costs (the monthly amount you pay).
Look for updates to deductibles (what you pay before insurance kicks in).
Review co-pays and coverage limits, especially for prescriptions and specialist visits.

Tip: Don’t assume last year’s plan is still the best deal. Even small changes in provider networks or drug coverage can cost you big later.

2. Compare plan types

PPO (Preferred Provider Organization): More flexibility in choosing doctors; higher premiums.
HMO (Health Maintenance Organization): Lower cost, but requires referrals and in-network providers.
HDHP (High Deductible Health Plan): Pairs well with a Health Savings Account (HSA) if you’re healthy and want to save tax-free for medical expenses.

3. Don’t forget supplemental benefits

Vision, dental, disability, and life insurance are often optional add-ons, but they can make a big difference for overall protection.

For 1099 Workers & Freelancers

If you work independently, you won’t have an employer offering insurance, but you do have options:

1. Marketplace plans

Go to HealthCare.gov or your state marketplace to compare plans side by side.

Premium tax credits may lower your monthly cost if your income falls within certain limits.
All marketplace plans cover essential benefits like preventive care, prescriptions, maternity, and mental health.

2. Consider a Health Savings Account (HSA)

If you choose a high-deductible plan, you can open an HSA.

Contributions are tax-deductible.
The money rolls over year to year.
You can use it for anything from prescriptions to dental visits.

3. Look into professional associations

Groups like the Freelancers Union or National Association for the Self-Employed (NASE) offer group health plans or access to discounted coverage.

For Entrepreneurs and Small Business Owners

If you have employees, or even just yourself, there are smart ways to cover your team while keeping costs manageable.

1. Small Business Health Options Program (SHOP)

Through HealthCare.gov, small businesses (with 1–50 employees) can buy group health insurance.

You may qualify for a Small Business Health Care Tax Credit to offset costs.
You control how much to contribute toward employee premiums.

2. Individual Coverage HRA (ICHRA)

This newer option allows employers to reimburse workers for individual health plans instead of providing a group policy. It’s flexible and often more cost-efficient for startups or growing teams.

3. Private health plans

Some entrepreneurs prefer private insurers or brokers for more customized coverage or larger provider networks. Just compare carefully, private plans can vary widely in cost and quality.

Don’t Miss These Key Deadlines

November 1, 2025: Open enrollment begins.
December 15, 2025: Last day for coverage starting January 1, 2026.
January 15, 2026: Open enrollment officially ends.

After this date, you’ll need a qualifying life event to make changes.

How to Choose the Right Plan

When comparing options, ask yourself:

How often do I see the doctor?
Frequent visits may justify higher premiums but lower co-pays.
Do I take regular prescriptions?
Make sure your meds are covered affordably.
What’s my budget?
Balance your monthly premium with your deductible and out-of-pocket max.
Are my doctors in-network?
Out-of-network visits can lead to surprise bills.

BDO Tip: Preventive care, like annual checkups, blood pressure screenings, and vaccines, is always free under most ACA-compliant plans. Take advantage of it.

Final Thoughts

Health insurance isn’t just about covering emergencies; it’s about protecting your peace of mind, your finances, and your family’s future. Whether you’re clocking in, freelancing, or building your empire, open enrollment is your opportunity to take control of your health coverage.

Don’t wait until the deadline. Review your options, ask questions, and make sure your plan fits the way you actually live and work.

By BlackDoctor | Published October 22, 2025