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
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