For Early Retirees Under 65

The bridge between your last paycheck and Medicare — without burning your nest egg.

I map private PPO and ACA coverage around the income drawdown plan behind your bridge years, so coverage works with your retirement plan, not against it.

Family reviewing insurance options together

Trusted Protection

A coverage blueprint you can count on.

Independent Broker

Licensed in 43 states + DC, working for you.

Personalized Service

Plans matched to your health, income, and timing.

Built on Integrity

Clear guidance and reliable support every step.

One-on-One Consultation

I get to know you first, then match the coverage.

I start with your doctors, prescriptions, health needs, budget, income, and timing. Then I compare private PPO and ACA marketplace options and help match you with the coverage that best fits your specific situation.

Your Real Options

Three paths across the bridge years.

Most early retirees default to COBRA because it's the path their HR packet hands them. That's almost never the cheapest option for the full bridge — and the real choice depends on how you plan to draw income.

1

Private PPO

Best when your MAGI is too high for ACA help. If you're drawing significant taxable income — Roth conversions, brokerage withdrawals, sizable dividends, rental income — private PPO is usually cheaper than full-price ACA, with much wider networks. If you're healthy, this is often the right anchor for higher-income years of the bridge.

2

ACA Marketplace

Often dramatic savings with a managed drawdown. Most early retirees control MAGI more than they realize. The order you tap accounts — Roth vs. traditional vs. taxable — directly affects what subsidy you qualify for. Plus guaranteed coverage with no underwriting, which matters at 55+ when pre-existing conditions are common.

3

COBRA bridge

Limited but occasionally useful. Usually capped at 18 months and rarely the cheapest option, but COBRA can hold a specific network or carry you through a short gap. I'll quote it honestly against your real alternatives so you see whether it's worth keeping or skipping.

What Most Early Retirees Don't Know

Three things to understand before you pick a strategy.

1. ACA subsidies use MAGI — and MAGI is largely controllable in early retirement. Modified Adjusted Gross Income includes traditional retirement withdrawals, capital gains, dividends, interest, and Social Security — but not Roth withdrawals or qualified HSA distributions. Most early retirees have flexibility on which buckets to tap and when. A managed drawdown can keep MAGI low enough for substantial ACA help in the years you need it most — sometimes $10–20K/year in premium savings for couples.

2. Pre-existing conditions are normal by 55+, and they matter for plan type. Almost any non-ACA plan can ask about your health history and decline, exclude, or rate up based on what they find. ACA marketplace plans are guaranteed-issue with no underwriting — same plan, same price regardless of your health. If you have an active condition, ongoing prescriptions, or anything that might trigger underwriting flags, ACA is usually the safer foundation even if it's a little more expensive than a private alternative.

3. Spouse timing creates household-level math. If you're 62 and your spouse is 58, you have very different windows to plan for. The right strategy thinks through when each of you ages into Medicare, what coverage looks like in the gap, and how to keep premiums manageable across the full household. Treating each person independently almost always costs more than running the math at the household level.

How It Works

Three steps. Usually under thirty minutes.

01

Tell me your retirement picture

Ages, state, expected drawdown, any health considerations. The more honest the picture, the better the math.

02

I model your bridge years

Private PPO, ACA with realistic MAGI projection, and COBRA — quoted against each other across the full timeline.

03

You pick the strategy that wins

We enroll in the right plan now, and I'm here to revisit it each year as your situation changes — and again at 65 for Medicare.

Real Clients

What a bridge-planning call looks like.

"

I retired at 58 thinking I'd just stay on COBRA for eighteen months and figure out the rest later. Christian spent an hour going through Roth conversion timing, when to start drawing from my brokerage account, and how all of it interacted with ACA subsidies. We ended up with an ACA plan and a withdrawal sequence that saved us about $14,000 a year in premiums. He coordinated with my CPA. I've already referred two friends.

David and Karen H.Early retirees · Clients since 2024
Common Questions

What early retirees ask before they pick a plan.

How does ACA work if I have no W-2 income anymore?

ACA looks at MAGI — Modified Adjusted Gross Income — which includes traditional IRA/401(k) withdrawals, taxable interest, dividends, capital gains, and Social Security, but not Roth withdrawals or qualified HSA distributions. Many early retirees have substantial assets but very controllable MAGI, which can unlock significant subsidies. Honest income projection is the most important input — I help you get that number right.

Can I just stay on COBRA until Medicare?

Usually no. Federal COBRA runs 18 months for most qualifying events, so unless you retire after age 63.5, COBRA can't carry you all the way to 65. Even within those 18 months, it's rarely the cheapest option for early retirees — private PPO or ACA almost always beats it on premium. We'll run all three so you see the real numbers.

What happens to my coverage when I turn 65?

You enroll in Medicare. There's a specific 7-month Initial Enrollment Period around your 65th birthday — 3 months before, the month of, and 3 months after — and getting the timing right matters. Late Part B and Part D enrollment can mean lifelong premium penalties. I handle the Medicare transition for my bridge-years clients, so the handoff is seamless rather than a scramble.

Should I do Roth conversions during early retirement?

That's a financial-planning question with insurance implications — every dollar you convert is MAGI, and every dollar of MAGI affects your ACA subsidy. Generally, large Roth conversions and ACA subsidies are in tension. The right answer depends on your current vs. expected future tax bracket, how much subsidy is on the table, and your overall drawdown sequence. I work with your CPA or financial advisor to coordinate — I'm not your tax planner, but the insurance math has to fit into theirs.

Plan the bridge before you cross it.

The right strategy is worth $10–30K to most early retirees over the bridge years. A fifteen-minute call gets you to the right plan — and I'm still your broker when you age into Medicare.

Plan your bridge years

Tell me where you are in the bridge — I'll model your real options and call you back.

Plan your bridge years

Tell me where you are in the bridge — I'll model your real options and call you back.

Or book a free consultation directly.

By submitting, you agree that Christian Medford may contact you by phone or email about your quote request and insurance options. Text messages are sent only if you check the SMS consent box above. You can submit this form without agreeing to texts. Reply STOP to opt out of texts or HELP for help.

Got it — talk soon.

I'll be in touch shortly. Need to talk right now? Call (941) 241-0210.

Call (941) 241-0210