Decoding Your 2025 Health Insurance Options
Self-employed? Own a small company with a team? Let’s decode your 2025 health insurance options.
In this workshop I cover:
- What all those acronyms mean
- The four most likely options for individuals and small companies
- What it covers, how it works, what you pay
- How to choose your best option
- How to find and choose a policy
- How to run open enrollment
- How to get it done before the December 15 deadline
Frequently Asked Questions
Why are you charging for a webinar?
Every day, I talk to self-employed people who are confused and intimidated by health insurance. They’ve spent hours on free events, only to get either 1) very high-level information that didn’t help them, or 2) a biased sales pitch requiring them to decipher which information is actually relevant to them and which is just spin.
On my blog, I provide a free guide to self-employed and small-business health insurance. If you find the answer there, great! But many of you want more support, especially if you’re in your first year or two of self-employment and choosing your own benefits. So I decided to offer an educational event, 100% focused on self-employed and small-business health insurance answers. I’m charging a nominal amount to cover the cost of my research and my team’s time.
When is it?
The on-demand workshop is 60 minutes of detailed information and actionable advice on individual and small-business health insurance.
What will you cover?
Key health-insurance terms, requirements for individuals and small businesses, eligibility for plans, resources specific to your state and situation, and a comparison of plan options with real costs.
I will use the same information and decision process that my clients across the US have used to choose their own benefits. We work with brokers, SHOP plans, PEOs, health-reimbursement accounts, and individual exchange plans. We’re going to talk about how to do this as a person versus as a company, and the options you will most likely be choosing from.
What do I get?
My goal is to give you back some time and sleep during this already stressful time. In addition to the workshop, you will receive the PDF presentation. If you request referrals, we’ll introduce you to our trusted partners at no additional cost. We also have a complimentary follow-up events on December 12 where you can bring more questions.
What’s the sales pitch?
There isn’t one — that’s why I’m charging a nominal fee. I work with small-business owners and I know how hard it is for most of us to get relevant, specific advice and answers. I have those to share, so I’m doing it. My goal is solely to give you confidence and save you time in navigating our US healthcare system.
Do I have to join your list?
Yes; we need to opt you into my list to communicate with you about this workshop. When you register, you’ll get a welcome email with a link to the workshop. That email has an unsubscribe link. If you’d prefer not to continue on the list beyond this one event, please feel welcome to unsubscribe.
Meet Jill James
I work with self-funded CEO / founders with purpose. Mostly women, but not exclusively. By experience, I’m a business strategist and Chief Operating Officer. I’m really good at helping founders go from early concept to $5–$10 million without giving up equity. I’ve done most of the non-engineering jobs in SaaS and services companies. On the finance side, I have been a personal financial planner, worked in investment banking, and I have an MBA in entrepreneurship and strategy from Chicago Booth.
I’m not a coach, but clients often call me a “business therapist.” (It’s a compliment, I’m not a mental health professional.) Building a company will expose your limiting beliefs about yourself, relationships, and money — often in the context of learning new business skills. We do the work while we do the work. And we’ve done it almost exclusively remotely since 2015 because entrepreneurial moms don’t have time for boondoggles.