Open Enrollment 101: Facts, Tips & Tricks Every Entrepreneur and Family Should Know
Katherine Moskal • 7 October 2025
As a 32-year-old business owner and someone who works closely with ambitious entrepreneurs and family-focused professionals, I know firsthand how overwhelming health insurance can feel, especially during Open Enrollment. Whether you're running your own business, raising a family, or both (superhero status, honestly), the pressure to make the right healthcare choice for the next year is real.
So let’s cut through the noise. This guide breaks down Open Enrollment 101 with the essential facts, smart tips, and insider tricks to help you make confident choices that actually work for your lifestyle and financial goals.
What Is Open Enrollment?
Open Enrollment is the once-a-year window where you can enroll in, renew, or change your health insurance plan for the upcoming year, no special life event needed.
• 2025 Open Enrollment Dates (Colorado): November 1, 2025 – January 15, 2026
• The specific dates can vary by state, so you should always check your state’s health insurance exchange for its particular schedule and deadlines
If you miss this window, you’ll typically need a qualifying life event (like marriage, birth, or job loss) to make changes later. So yes, the clock matters.
Why It’s Especially Crucial for Entrepreneurs & Self-Employed Professionals
If you're self-employed, you don’t have an HR department doing this for you. You're the CEO, CFO, and now... benefits manager.
Choosing the wrong plan can mean:
• Overpaying thousands annually
• Being stuck with networks that don’t cover your preferred providers
• Surprise bills that wreck your financial goals
But the right plan? It frees you up to focus on scaling your business and caring for your family, knowing you’re covered.
Health Insurance Jargon—Decoded
Here are 3 terms that trip up even the savviest people:
• Premium: What you pay monthly just to have the plan.
• Deductible: What you pay out-of-pocket before insurance kicks in.
• Out-of-Pocket Max: The most you’ll pay in a year, period. After this, insurance covers 100%.
Pro Tip: Don’t just chase the lowest premium. For growing families or busy entrepreneurs, it often pays to invest a little more upfront to avoid huge surprise bills later.
Open Enrollment Checklist
Before you start shopping for plans:
1. Review this year’s medical usage
Did you meet your deductible? Any surprise costs? Anticipate next year’s needs (kids' braces, a new baby, surgery, etc.).
2. Check your doctor’s network
Just because you love your provider doesn’t mean they’re covered in every plan.
3. Compare prescription coverage
If anyone in your household takes regular medications, this could be a huge cost difference.
4. Estimate your total yearly costs
Add premium + deductible + expected out-of-pocket expenses. That’s the number that really matters.
Insider Tips from a Pro (That’s Me)
After helping thousands of families and business owners across the US, here are some game-changing tips:
• Bundle strategically: If you’re married and both self-employed, it’s not always best to be on the same plan. Crunch the numbers, you might save by splitting.
• HSA-eligible plans can be a goldmine for tax savings, especially if you're in a higher income bracket or run a successful LLC. Keep in mind they are not a good fit for everyone so be open to non HSA-eligible plans.
• Don’t trust the first plan you see online. Algorithms push what they’re paid to show. A licensed broker (like me) can compare ALL the options and tailor them to your needs, for free.
• Apply early. Broker’s schedules fill up quick, especially those with competitive options. Get your appointment on the books ASAP.
Ready to Make This Easy?
Let’s be honest: you didn’t start your business to learn the ins and outs of coinsurance and tiered networks.
That’s where I come in.
Whether you're:
• A solo entrepreneur scaling your dream,
• A dual-income family juggling daycare and deadlines,
• Or somewhere in between...
I make sure your health coverage actually covers you, while maximizing tax benefits, managing risk, and keeping your preferred doctors.
Book a free strategy session today and we’ll craft a plan that fits your life, not the other way around.
Final Thought
Health insurance shouldn’t be confusing. And it definitely shouldn’t be one-size-fits-all. The right strategy doesn’t just protect your health. It protects your time, your income, and your family’s peace of mind.
Let’s build something healthier together.
With care,
Katherine Moskal
Founder, Katherine Moskal Health Plans
Licensed Health Insurance Advisor
Based in Colorado | 303-900-5666 | Katherine@MoskalHealthPlans.com

It sounds so nice at first glance: a Christian community helping each other pay medical bills. The ads are full of smiling families and promises of faith, compassion, and “affordable healthcare.” But look closer, and the truth about Medi-Share and similar “healthcare sharing ministries” is far darker. This isn’t health insurance. It’s a financial trap wrapped in religious language, one that can leave you bankrupt when you need help most. Don't get me wrong, I am a Christian Women with a child in a Christian School. But I REFUSE to agree with this type of "health coverage" being offered to people. Here are the things to consider: 1. It’s not insurance and they admit it (in fine print): Medi-Share is legally classified as a “health care sharing ministry,” not an insurance company. That means it doesn’t have to pay anything. There’s no contract, no guarantee, and no regulatory oversight. If you rack up $100,000 in hospital bills, Medi-Share can simply decide your need doesn’t “qualify” and walk away. You’ll be stuck dealing with collection agencies. 2. They can deny coverage for nearly any reason: Medi-Share applies “Biblical guidelines” to determine what medical costs they share. That sounds noble until you realize it means they can deny coverage for anything they consider immoral. That can include: • Birth control or fertility treatments • Mental health counseling • Substance-abuse treatment • Injuries related to drinking or “sexual sin” • Even pregnancy complications outside marriage Your medical care shouldn’t depend on a stranger’s religious judgment, but with Medi-Share, it does. 3. Preexisting conditions? They’ll just say no: Have asthma? Diabetes? Anxiety? A C-section five years ago? Medi-Share can label those as “preexisting conditions” and exclude them indefinitely. You could pay into the program for years and still have every meaningful claim denied. It’s like paying premiums for fake insurance that only covers paper cuts and sprained ankles. 4. No ACA protections, no safety net: Under the Affordable Care Act, real insurance must cover essential benefits and can’t reject you for health issues. Medi-Share exists outside those rules. No required preventive care. No guaranteed coverage. No limits on how much they can refuse to pay. They can, and often do, cap coverage, delay payments for months, or deny bills outright. 5. You’ll probably have to pay up front: Many doctors and hospitals won’t accept Medi-Share at all. They’ll demand cash payment before treatment, because they know how unreliable “sharing” reimbursements are. So you’ll pay thousands up front, then wait months to maybe get reimbursed, assuming your request doesn’t get rejected for violating some obscure “eligibility guideline.” Don't believe it? One of my team members worked in billing for a hospital and she states "it was rare that Medi-Share actually covered people's claims and people were always left in shock with their bills after. They were the biggest pain in the rear to deal with". 6. Zero accountability: Because Medi-Share isn’t insurance, state insurance regulators can’t help you. There’s no appeals process, no consumer protection, no legal obligation to honor claims. If they deny your medical expenses, there is absolutely nothing you can do. The Department of Insurance wont even step in, why? Because its not real insurance. 7. Moral policing and personal intrusion: Joining Medi-Share means signing a “Statement of Faith” and agreeing to live by their version of “Biblical principles.” That means they can cancel your membership and your access to funds for things like drinking, smoking, or sex outside marriage. Your personal life becomes a financial risk factor. Your healthcare depends on your compliance with their religious rules. 8. Financial instability — your money isn’t safe: Medi-Share doesn’t have to maintain reserve funds like a real insurer. If too many members file big claims, the system can run dry overnight. They can delay or ration payments. And since it’s not regulated, they can get away with it. 9. A false sense of security: The cruelest part? Medi-Share markets itself to people desperate for affordable coverage, young families, small business owners, people between jobs. They believe they’re protected. But when a medical crisis hits, they find out too late that Medi-Share is built on loopholes and moral judgments, not guarantees. Some lose their life savings. Some lose their homes. All lose trust. Bottom line: Medi-Share looks cheap and community driven, but in reality, it’s a faith based gamble with your health and finances. You could pay in for years, follow all the rules, and still be left broke when you need care the most. Medi-Share isn’t a true safety net, it’s a faith-based alternative that can look like insurance but doesn’t come with the same legal protections or guarantees. It’s a system where your health, privacy, and financial stability can be left vulnerable, and too often, members find out only after facing a major medical expense. If you want real peace of mind, consider traditional health insurance. It may cost more upfront, but at least you’ll have something reliable and protected by law standing between you and medical bankruptcy.
