Clearwater Medicare Planning helps people in Wisconsin and Michigan understand how Medicare works, compare plans from the carriers we represent, and decide at their own pace.
Medicare made clear.
Who we work with
- People turning 65 in the next year or so
- People still working past 65 who aren't sure what to do about Part B
- Anyone leaving an employer, retiree, or COBRA health plan
- People already enrolled who want to know whether their coverage still fits
- Couples on two different Medicare timelines
Most Medicare marketing is built to create urgency. Ours isn't.
By the time most people turn 65, they've received a stack of Medicare mail and more phone calls than they'd like. We work differently. We explain the tradeoffs, tell you plainly what we do and don't offer, and give you time to decide.
Independent
We're not captive to any one insurance company. We compare plans from the carriers we represent and show you how they differ.
Education first
Before we talk about any plan, we make sure you understand how Medicare Parts A, B, C, and D fit together.
Here after you enroll
We check in each fall during the Medicare Annual Enrollment Period, October 15 to December 7, and whenever your situation changes.
Medicare costs don't happen in a vacuum. Premiums, income-related surcharges, and out-of-pocket limits all land in your household budget, and we look at your options with that in mind.
What we help with
- Choosing between Medicare Advantage and Original Medicare with Medicare Supplement Insurance — the central tradeoff, explained both ways
- Prescription Drug Plans (Part D) and how your medications affect your choices
- Enrollment timing, and how to avoid late-enrollment penalties
- Moving from employer, retiree, or COBRA coverage to Medicare
- An annual review during the Medicare Annual Enrollment Period
- A second look if you're already enrolled
How it works
A first conversation
About 30 minutes, by phone or video. We'll ask about your doctors, your prescriptions, how you travel, and what matters most to you. There's no obligation.We do the comparison
We review plans from the carriers we represent that are available in your county.You decide
We walk through the tradeoffs and answer your questions. Nothing gets signed until you're ready.We stay in touch
Annual reviews, plan changes, and questions as they come up.
What does it cost to work with us?
You don't pay Clearwater a fee. Like other licensed insurance agents, we're paid by the insurance companies we represent when you enroll in a plan.
If we don't represent a plan that fits you, we'll tell you so. You can always get information on all of your options at Medicare.gov or 1-800-MEDICARE.
Who you'll be working with
Sean Stockman · Founder · Licensed Insurance Agent
I'm Sean Stockman, founder of Clearwater Medicare Planning and a licensed insurance agent in Wisconsin, Michigan, and additional states. Most of the people I work with come by referral and arrive a little tired of the mail. My job is to explain how Medicare actually works — what your doctors and prescriptions change, and how plans from the carriers I represent differ — and then let you decide.
Based in Waukesha County. Meetings by phone, by video, or by appointment.
Common questions
Can I keep my doctors?
It depends on the path you choose. With Original Medicare and a Medicare Supplement Insurance policy, you can generally see any provider in the country who accepts Medicare. Most Medicare Advantage plans use provider networks, and the rules differ between HMO and PPO plans. Checking your doctors against a plan's network is one of the first things we do.
Do I need a Medicare Supplement, or is Medicare Advantage enough?
They're two different approaches. A Medicare Supplement policy usually means a higher monthly premium and more predictable costs when you use care. A Medicare Advantage plan often has a lower premium, with copays and an annual out-of-pocket limit, inside a network. Neither is right for everyone. We'll lay out both sides for your situation.
Why is my Part B premium higher than my neighbor's?
Medicare adjusts Part B and Part D premiums for higher incomes. It's called the Income-Related Monthly Adjustment Amount, or IRMAA, and it's generally based on the tax return you filed two years earlier. We can explain how it works and what it means for your premiums.
I'm still working at 65. What should I do?
It depends on your coverage. If you have health coverage through your own or your spouse's current employer, you may be able to delay Part B without a penalty — and the rules depend partly on the size of the employer. This is one of the most expensive questions to get wrong, so it's worth a conversation before you turn 65.
What happens if my health changes and I want to switch later?
This is the most under-explained part of Medicare. You have a six-month Medicare Supplement open enrollment period that starts when you're 65 or older and enrolled in Part B. During that window, you can buy any Medicare Supplement policy sold in your state without medical questions. Outside it, insurers in most situations can review your health history. State rules vary, and we'll explain the ones that apply to you.
Will I end up on a call list?
No. We don't buy leads, we don't sell your information, and we don't call people who haven't asked us to.
Start with a conversation
Pick a time that works for you, or give us a call. Booking opens our scheduling page in a new window.
Schedule a Medicare conversation- Enrollment line
- (414) 888-6532 · TTY 711
For talking through plans and enrolling. Calls on this line are recorded. - By calling this number, you will reach a licensed insurance agent.
- sean@clearwatermedicareplanning.com
- S30W24896 W Sunset Dr, Ste 102-123
Waukesha, WI 53189
We do not offer every plan available in your area. Currently we represent 3-4 organizations which offer 16-42 products in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
Clearwater Medicare Planning, LLC is an insurance agency and is not connected with or endorsed by the U.S. government, the federal Medicare program, or any government agency.
Plans are insured or covered by a Medicare Advantage organization with a Medicare contract and/or a Medicare-approved Part D sponsor. Enrollment in the plan depends on the plan's contract renewal with Medicare.
Clearwater Medicare Planning and Hugo Wealth Partners are separate businesses. Medicare insurance services are offered through Clearwater Medicare Planning. Investment advisory services are offered through Hugo Wealth Partners.
Clearwater Medicare Planning, LLC · S30W24896 W Sunset Dr, Ste 102-123, Waukesha, WI 53189 · (414) 888-6532 · TTY 711 · sean@clearwatermedicareplanning.com
© 2026 Clearwater Medicare Planning, LLC