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What Seniors Wish They Knew Before Enrolling in Medicare at 65

For many seniors, enrolling in Medicare at 65 is a milestone — but also a moment full of surprises. 📅
Too often, retirees only learn after the fact about costs they didn’t expect, benefits they misunderstood, or coverage gaps they didn’t see coming.

Think of Medicare like moving into a new home 🏡 — it’s a huge upgrade, but you still need to know what’s included and what you’ll have to bring yourself. The plan you choose during your Initial Enrollment Period isn’t just for today — it can shape your healthcare, budget, and peace of mind for years to come.

That’s why this guide brings together real stories, local insights, and practical tips so you can make confident decisions before you sign up — not regrets afterward.

You don’t have to learn Medicare the hard way. Let’s walk through what others wish they knew so you can make confident, informed decisions from day one.
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Medicare Isn’t Completely Free — Understanding the Costs

Enrolling in Medicare at 65 can feel like holding a “hot potato” 🥔 — friends, neighbors, and even strangers are quick to offer advice, but few will be the one to tell you what it really costs. The truth? While Medicare is an amazing benefit, it isn’t entirely free. It comes with monthly premiums, deductibles, and copays that can surprise even the most prepared seniors.

Whether you live in a busy city or a quiet ZIP code, budgeting for Medicare is just as important as choosing your plan. Let’s break down what you’ll actually pay — and where the biggest “gotchas” hide.


✅ H3: Breaking Down Your Monthly Medicare Expenses

Evelyn’s Story
“I thought Medicare and Social Security were tied together. Since I wasn’t taking Social Security yet, I assumed Medicare would just start on its own. It didn’t. I almost missed my enrollment window completely. Luckily, my neighbor helped me sign up in time, and I avoided a penalty. I wish I’d known that you have to actively enroll if you’re not already on Social Security.”

When you turn 65, your Medicare costs will likely be different from what you paid with employer coverage. In 2024, most people pay $174.70 per month for Part B — and that’s before adding drug coverage or a supplemental plan.

Here’s what a typical monthly Medicare budget might look like:

CoverageTypical Monthly Cost
Part B Premium$174.70+
Part D Prescription Drug Plan$30–$50
Medigap Supplement$100–$300
Medicare Advantage Plan$0–$200

In states like California or New York, many seniors find their total monthly Medicare costs reach $400+ when all coverage is factored in.

💡 Expert Tip: Part A (hospital coverage) is premium-free if you’ve worked 40 quarters, but Part B always has a monthly cost.


💡 H3: Hidden Costs That Surprise New Medicare Beneficiaries

It’s easy to forget about coinsurance — the 20% you’re responsible for under Part B. For example, a $50,000 surgery could leave you with a $10,000 bill if you only have Original Medicare.

📍 Local Cost Lesson:
“Whether you’re in 85032 Phoenix or 11236 Brooklyn, Medicare supplement benefits are identical — but monthly premiums can swing by $15–$25 depending on your ZIP.”

These location-based differences make it worth checking local rates before you choose your plan.


🚫 H3: What Medicare Doesn’t Cover (And Never Will)

Original Medicare does not cover routine dental, vision, or hearing care. That means:

  • 🦷 Dental work: crowns ($1,200+), dentures ($5,000+)
  • 👁️ Glasses: $400–$800 for new lenses
  • 👂 Hearing aids: $2,000–$7,000 per pair

Without extra coverage, these costs come out-of-pocket. A retired teacher in Ohio may spend $3,000 on dental work, while a couple in Florida could pay $5,000 for hearing aids — none of it covered by Medicare.

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Senior reading plan booklet while advisor points to options on tablet

The Importance of Enrolling During Your Initial Window

🚨 URGENT: Your Initial Enrollment Period (IEP) is a 7-month window — it starts 3 months before your 65th birthday month, includes your birthday month, and ends 3 months after.

Miss it, and you could face lifetime penalties on your premiums. No exceptions. No do-overs. Think of it like a fire drill 🔔 — you have to move at the right time, or the consequences follow you for years.

Every month you delay past your IEP adds 10% to your Part B premium — forever. A senior who waits just 2 years to enroll pays 24% more every month for the rest of their life.


📅 H3: Your Medicare Timeline Checklist

The clock starts ticking ⏰ exactly three months before your 65th birthday. Smart seniors:

  • 🗓️ Circle the date on a wall calendar
  • 📱 Set reminders on your phone
  • 📂 Start comparing plans early — don’t wait until the last week
What to DoWhen to Do It
Begin research & gather documents3 months before 65
Compare at least 5 plans2 months before 65
Confirm doctor & pharmacy networks1 month before 65
Enroll in MedicareBefore your birthday month ends

📊 Regret Matrix — Avoid These Mistakes

What Seniors Wished They’d KnownHow to Avoid This Regret
“I thought enrollment was automatic”Actively enroll 3 months before turning 65
“I didn’t know about the penalty”Never miss your 7-month Initial Enrollment Period
“I picked a plan without checking my doctors”Verify provider networks before enrolling
“I ignored Part D thinking I didn’t need it”Get drug coverage even if you take no medications
“I switched from Medigap to Advantage”Understand you can’t always switch back

⏰ H3: Special Circumstances That Change Your Deadline

Expert Insight:
If you’re still working at 65 and have creditable employer coverage, you can delay Medicare without penalties — but you must keep documentation from your employer.

A man in Michigan delayed Part B for 2 years without coverage and now pays $84 extra every month — over $10,000 wasted over a decade.


🎯 H3: Making the Most of Your Enrollment Window

Your 3-month lead time is your chance to:

  • Compare multiple plan types
  • Check if your doctors are in-network
  • Calculate annual costs (premiums + deductibles + out-of-pocket)

Mid-Article CTA:
💬 Many seniors overpay simply because they didn’t compare plans. We’ll help you find the right fit at the right price.

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Why Supplemental Coverage Matters More Than You Think

Original Medicare is like the picture on a puzzle box — it shows the whole scene, but when you open it, you realize several pieces are missing. Without supplemental coverage, those missing pieces can leave you with big medical bills that eat into your retirement savings.

Many seniors don’t realize there’s no cap on what you could spend under Original Medicare alone. A short hospital stay, unexpected surgery, or ongoing treatment for a chronic condition can add up to tens of thousands of dollars.


📖 H3: Harold’s Story — A Hard Lesson Learned

Harold, a retired handyman who still mows lawns for extra income, thought Medicare would be “like a free health plan.” After a quick hospital stay, he received a $1,200 bill. That’s when he learned Medicare doesn’t cover everything.

With the right guidance, Harold added a supplemental plan to protect himself from surprise bills. He now says, “I wish someone had explained this to me on day one.”


🛡️ H3: Medigap vs. Medicare Advantage — The Critical Choice

  • Medigap: Lets you see any doctor in the U.S. who accepts Medicare — great for travelers.
  • Medicare Advantage: Often has lower premiums and extra benefits like dental or vision, but limits you to a provider network.

Expert Tip: Original Medicare doesn’t cover dental, vision, hearing, or long-term care. That means:

  • Root canal: $1,200+
  • New glasses: $400+
  • Hearing aids: $4,000+
  • Nursing home care: $8,000/month

💰 H3: Calculating Your True Risk Without Supplements

Under Original Medicare alone, there’s no maximum to what you might pay. One serious diagnosis can cause medical debt that takes years to recover from. Supplemental coverage acts like a shield 🛡️, protecting your savings and giving you peace of mind.


✅ H3: How to Choose the Right Supplemental Plan

When picking your coverage, think about:

  • Your health: Do you have ongoing conditions or expensive prescriptions?
  • Your budget: Can you handle higher monthly premiums to avoid big bills later?
  • Your lifestyle: Do you travel often or stay local?

Frequent travelers often prefer Medigap for nationwide flexibility, while homebodies sometimes choose Medicare Advantage for lower monthly costs and included extras.

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How Medicare Advantage Differs from Original Medicare

Choosing between Original Medicare and Medicare Advantage is like comparing two very different report cards — each has strengths and weaknesses, and the “best” one depends on what matters most to you.

Below is a quick Medicare Insurance Report Card to help you see the differences at a glance:

Medicare Insurance Report Card

Coverage AspectOriginal MedicareMedicare AdvantageGrade
Doctor ChoiceAny doctor accepting MedicareNetwork onlyB- vs C+
Out-of-Pocket MaxUnlimitedCapped (avg $7,550)F vs A
Extra BenefitsNoneOften includes dental/visionD vs B+
Prior AuthorizationRarely neededOften requiredA vs C
Travel CoverageNationwideLimited/Emergency onlyA+ vs D

Understanding these differences before your Initial Enrollment Period can save you from costly mistakes and years of frustration with the wrong plan type.


🏥 H3: Network Restrictions That Can Surprise You

Harold’s Quote:
“I just picked the cheapest drug plan without checking my medications. I thought they were all the same, but my prescriptions weren’t covered under that plan’s formulary. I ended up paying full price for months. If I’d known to check my drug list during enrollment, I could have saved hundreds.”

Medicare Advantage plans limit you to their network of doctors and hospitals. If your longtime doctor isn’t in-network, you may have to switch — even if you’ve seen them for decades.


🎁 H3: Extra Benefits vs. Trade-Offs

Advantage plans often offer $0 premiums and extras like:

  • Dental allowances
  • Vision coverage
  • Gym memberships

But these perks can come with trade-offs:

  • Prior authorization for treatments
  • Network restrictions
  • Possible delays in care approval

Ask yourself: Is saving $150 a month worth the extra hoops?


📍 H3: Why Your ZIP Code Determines Everything

Your ZIP code affects:

  • Which plans you can choose
  • How much they cost
  • Which doctors are included in their networks

A senior in rural Montana may have only a few plan options, while someone in Chicago might have dozens. That’s why local guidance can make all the difference in finding the right fit.

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Senior man comparing plan summaries with pharmacist at counter

Prescription Drug Coverage Isn’t Automatic

Think of your prescription coverage like the gas pedal in a car 🚗 — the right plan keeps you moving smoothly, but the wrong one can send your costs speeding out of control.

Part D (prescription coverage) isn’t included automatically with Original Medicare, and if you pick the wrong plan — or skip it entirely — you could end up paying full retail prices for medications that might cost pennies with the right coverage.


📖 H3: Suzanne’s Story — A Costly Assumption

Suzanne, known to her grandkids as the “Facebook Grandma,” saw an ad for a Medicare Advantage plan on TV and signed up without checking the details. She didn’t realize her doctor was out-of-network, and her prescriptions cost far more at her usual pharmacy. After switching to a plan that matched her needs, she said, “I should’ve checked everything before I signed up.”


💊 H3: Understanding Drug Formularies and Tiers

Every Part D plan has its own formulary — a list of covered medications, grouped into tiers:

  • Tier 1: Generic drugs (lowest cost)
  • Tier 2: Preferred brand-name drugs
  • Tier 3-5: Higher-cost brand-name or specialty drugs

Your $300 brand-name medication might be Tier 2 ($45 copay) on one plan but Tier 4 ($150 copay) on another.

💡 Expert Insight: The same prescription can cost $15 at one pharmacy and $60 at another, depending on your plan’s preferred network.


🏪 H3: Preferred Pharmacies Save Serious Money

Many Part D plans have “preferred” pharmacy networks that offer lower copays. For example:

  • Using Walgreens instead of a corner pharmacy might save $20–$50 per prescription.
  • Some plans offer 90-day mail-order supplies at a discount — a big help for maintenance medications.

📍 ZIP Code Price Difference Example:
In 30331 Atlanta, Plan N might cost $104/month. In 97206 Portland, the same plan could be $118. Always compare local pricing.


⚠️ H3: The Donut Hole and Catastrophic Coverage

While the donut hole is mostly closed, you still pay 25% of drug costs after meeting your deductible until you reach catastrophic coverage. For expensive medications, this can mean thousands in out-of-pocket costs.

Mid-Article CTA:
💬 Medicare doesn’t cover everything — knowing the gaps now can save you from costly surprises later.

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Doctor and Hospital Choice Can Change With Your Plan

Your Medicare choice isn’t just about cost — it also determines which doctors you can see and where you can get care. Think of it like a compass:

  • North (Freedom) → Original Medicare + Medigap = See any doctor nationwide
  • South (Savings) → Medicare Advantage = Lower costs, network restrictions
  • East (Extras) → Advantage plans often include dental, vision, hearing
  • West (Warnings) → Switching between plan types can get harder over time

🔍 H3: Checking Provider Networks Before Enrolling

Never assume your doctor accepts every Medicare plan.

  • Original Medicare is accepted by most providers nationwide.
  • Medicare Advantage plans each have their own network — and they change.

Always call your doctor’s office directly to confirm participation. Don’t rely solely on online directories, which can be outdated.


🏥 H3: Hospital Networks and Emergency Care Rules

James’ Experience
Friend: “Don’t you have VA coverage?”
Me: “Yes, but it didn’t cover the hospital I had to use.”
“I learned that Medicare and VA benefits work together, but VA alone can leave big gaps. I wish I’d enrolled in Medicare at 65 — it would have saved me a huge bill.”

While emergency care is covered at any hospital, follow-up visits and scheduled procedures with Medicare Advantage must be at in-network facilities. If your preferred hospital is out-of-network, you could face higher bills or be forced to use unfamiliar facilities.


Best Plan If… Matrix

If You…Best OptionWhyMonthly Cost Range
Travel frequentlyOriginal + MedigapNationwide coverage$250–$450
Rarely leave townMedicare AdvantageLower costs, extra benefits$0–$150
Have complex health issuesOriginal + MedigapNo prior authorization$300–$500
Are healthy & budget-consciousMedicare AdvantagePreventive focus$0–$100
Value doctor choiceOriginal + MedigapAny Medicare provider$250–$400

🔄 H3: When Doctors Leave Your Network

Expert Insight: Even if your doctor is in-network today, they can leave at any time — sometimes mid-year. Original Medicare avoids this problem because it’s accepted nationwide, while Advantage members must re-check networks annually to avoid care disruptions.

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Dental, Vision, and Hearing Care Aren’t Included

Medicare is like a light switch that only powers certain rooms in your house 🔆 — it leaves whole areas of care in the dark. Dental, vision, and hearing services are often the ones seniors need most, yet Original Medicare doesn’t cover them at all. Without extra coverage, these costs can be a major hit to your retirement budget.


📖 H3: Margaret’s Story — Hearing Loss and Hard Choices

Margaret from Wisconsin assumed her hearing aids would be covered after decades of employer insurance. The $5,000 bill for a pair of devices forced her to delay retirement by six months. “Nobody told me Medicare doesn’t cover what I actually need most,” she says, adjusting her new devices that she finally afforded through a personal loan.


🦷 H3: The Real Cost of Dental Care Without Coverage

Without dental insurance, many seniors skip important care, leading to pain, infection, and even more costly treatments later. Common out-of-pocket prices include:

  • Single crown: $1,200–$2,000
  • Root canal: $1,500+
  • Dentures: $5,000+

Some Medicare Advantage plans offer dental benefits, but most have low annual limits of $1,000–$1,500.


👁️ H3: Vision Care Beyond Basic Exams

Medicare covers eye exams for certain conditions like glaucoma but doesn’t pay for routine vision exams or eyeglasses. Common costs include:

  • Progressive lenses: $400–$800
  • Cataract surgery copays: can still be hundreds of dollars

Standalone vision insurance or Advantage plans with vision benefits can help, but always check coverage limits.


👂 H3: Hearing Aids and Audiology Services

Hearing aids cost $2,000–$7,000 per pair, and Original Medicare offers zero coverage. Some Advantage plans provide allowances, but amounts vary greatly — often not enough to cover the full cost. Untreated hearing loss can lead to balance issues, social withdrawal, and cognitive decline, making this a gap you can’t afford to ignore.

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Senior couple on phone with advisor while viewing laptop quotes

Why Reviewing Plans Every Year Saves Money

Here’s the truth — Medicare plans change every year, and if you don’t review yours, you could be paying hundreds (or even thousands) more for less coverage.

60-Second Rant:
Every October 15th, the Annual Enrollment Period (AEP) starts. That’s when insurance companies reshuffle the deck — premiums jump, doctors leave networks, drug coverage changes, and benefits vanish. Your $0 premium Advantage plan? It might be $35 next year. That $20 generic medication? Suddenly $75. Your trusted doctor? Gone from the network.

Yet 70% of seniors never check their plan during AEP. They auto-renew, pay more, and get less. One hour of research in October can save you hundreds (sometimes thousands) for the entire year. Don’t let the insurance companies profit from your complacency.


📅 H3: Annual Enrollment Period Basics

Robert’s Story – Retired Firefighter
“I ignored the Annual Enrollment Period thinking nothing would change. My premium jumped $45 monthly and my cardiologist dropped out. Now I’m stuck until next October.”

The AEP runs from October 15 to December 7 every year. It’s your chance to:

  • Switch between Medicare Advantage and Original Medicare
  • Change drug plans
  • Adjust coverage to match your health and budget needs

Expert Tip: Special Enrollment Periods (SEPs) exist for life changes like moving, losing employer coverage, or qualifying for Extra Help — but you must know the rules to use them.


🔍 H3: What Changes to Watch For

Every year, review:

  • Doctor and hospital networks
  • Drug formularies and preferred pharmacies
  • Premium changes
  • Benefit changes (dental, vision, hearing, etc.)

💰 H3: Real Examples of Annual Savings

  • A Midwest couple saved $2,400/year by switching from separate Medigap plans to a combined Advantage plan when their health stabilized.
  • A California woman cut her prescription costs by $1,800/year just by changing her Part D plan.

Mid-Article CTA:
💬 Your choices at 65 can be hard to change. Let’s make sure you start with a plan you’ll want to keep.

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How to Avoid Lifetime Late Enrollment Penalties

Enrolling late in Medicare is like climbing into the top bunk bed — the longer you wait, the harder (and more expensive) it gets.

The penalties aren’t one-time fees. They follow you forever, raising your premiums for the rest of your life. Here’s what you need to know:


🚨 H3: Part B Penalties That Never Go Away

Delay Part B for two years without creditable employer coverage, and your premium jumps 20% permanently.

Example:

  • Standard Part B premium: $174.70/month
  • With penalty: +$34.94/month
  • Over 20 years, that’s $8,385 in extra costs — and it only grows as premiums rise.

💊 H3: Part D Penalties Add Up Fast

The Part D penalty is 1% per month without creditable prescription coverage. It may seem small, but it stacks quickly:

  • 14 months late = 14% higher premium forever
  • With an average $40/month premium, that’s +$67/year wasted — every single year

3 Seniors, 3 ZIPs, 3 Different Plans

Senior StoryZIP CodeMonthly PremiumOut-of-Pocket MaxBest Choice
Active traveler, healthy10013 (NYC)$285UnlimitedMedigap Plan G
Homebody with diabetes75201 (Dallas)$35$6,700Medicare Advantage HMO
Part-time worker, good health98101 (Seattle)$0$7,550Medicare Advantage PPO

✅ H3: Creditable Coverage Exceptions

You can delay Medicare without penalties if you have creditable coverage, such as:

  • Employer coverage from active work
  • VA benefits
  • TRICARE

But you must enroll in Medicare within 8 months of losing that coverage — and keep proof. Medicare will require documentation to waive penalties.

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The One Step That Makes Medicare Enrollment Stress-Free

Enrolling in Medicare doesn’t have to be overwhelming. Think of it like a traffic light:

  • 🔴 STOP — Don’t enroll in the first plan you see advertised
  • 🟡 CAUTION — Watch out for high-pressure sales tactics and “limited time” offers
  • 🟢 GO — Work with a licensed Medicare advisor who can show you all your options, not just one company’s plans

This one step alone can save you from years of overpaying or being stuck in the wrong coverage.


🤝 H3: Working With Licensed Medicare Advisors

Independent advisors:

  • Compare every plan in your ZIP code
  • Know which networks stay stable year after year
  • Spot hidden costs in plans before you sign

They can match your health needs, medications, and doctor preferences to the plan that actually works for you.


📋 H3: Documents to Gather Before Enrolling

Barbara’s Story – Retired Nurse
“My advisor had me list all my medications and doctors before we met. In 20 minutes, she found a plan saving me $1,100 a year compared to what I’d picked myself.”

Gather:

  • A complete medication list with dosages
  • Names and addresses of all your doctors
  • Your Medicare card or eligibility details

This prep allows your advisor to run accurate, side-by-side comparisons.


🎯 H3: Making Your Final Decision

When you’re ready to choose:

  • Look at total annual cost, not just the monthly premium
  • Consider your likely healthcare needs in the next few years
  • Weigh convenience, customer service, and plan stability alongside price

💡 Expert Insight: Changing later isn’t always easy. Medigap has health underwriting after your initial window, and Medicare Advantage changes are limited to certain periods each year.

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Your choices at 65 can be hard to change. Let’s make sure you start with a plan you’ll want to keep.
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❓ Frequently Asked Questions

Yes. Medicare doesn’t start automatically if you’re not getting Social Security. You must enroll yourself during your 7-month window around your 65th birthday.

Most people pay a Part B premium, plus a drug plan and maybe a supplement. Costs vary by ZIP code and plan type, so compare local options before you choose.

You can delay if you have creditable employer coverage from active work. Get proof from your employer and enroll within 8 months after that coverage ends to avoid penalties.

Original Medicare doesn’t cover routine dental, glasses, or hearing aids. You’ll need a separate plan or a Medicare Advantage plan that includes these benefits.

You’ll pay lifetime penalties on Part B and possibly Part D. Those extra charges never go away, and they increase as premiums rise.

If you want more freedom, consider Original Medicare with a Medigap plan. Advantage plans can be good too, but you must check that your doctor and hospital are in-network.

Each plan covers drugs differently and has preferred pharmacies. Your medicine could be cheaper at one pharmacy than another, so always check the plan’s pharmacy list.

It’s a stage in drug coverage where you pay 25% of costs for a while. If you take expensive meds, you could spend more until you reach catastrophic coverage.

Yes. Premiums, drug lists, and networks can all change on January 1. Review your plan between October 15 and December 7 so you don’t overpay next year.

Yes. A licensed, independent advisor can review all local plans for you. They’ll check your doctors, drugs, and budget to find the best fit.

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“I Wish I Knew This Sooner”

Senior: “I thought I was getting the best Medicare plan… until I learned I’d been paying for things I didn’t use.”

Agent: “Most people don’t realize that until it’s too late. Let’s match your plan to your actual needs — before you enroll.”

Senior: “I wish I knew this sooner.”

Agent: “That’s why we talk before you sign anything.”

✅ At Palmetto Mutual, we help seniors avoid the “if only I had known” moment. You don’t have to learn Medicare the hard way. We’ll walk you through what others wish they knew so you can make confident, informed decisions from the very start.

Whether you’re months away from 65 or scrambling at the last minute, personalized guidance makes all the difference. Our licensed Medicare advisors:

• Know your local market
• Understand which plans offer stable benefits
• Show you exactly how different choices affect your budget and coverage

📞 Don’t become another “I wish I’d known” story. Get your questions answered by someone who puts your needs first — not a call center quota.

🎯 Speak with a licensed Medicare advisor in your area today
📍 Get help based on your ZIP code — no call centers, just real answers tailored to you
✅ Start with confidence, not confusion

Get Help Now →

📚 Suggested Reading

About the Author

Dvir Mosche is an award-winning independent insurance agent and the founder of Palmetto Mutual, a trusted insurance brokerage specializing in Medicare, final expense, and senior benefits in North and South Carolina and across the country. Since entering the industry in 2017, he has been recognized multiple times as a top agent for his dedication to educating and assisting seniors in finding the proper coverage. His mission is to simplify the process, provide honest and personalized guidance, and ensure that every client gets coverage they can depend on for life.

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