Let’s cut through the confusion: if you retire at 65, chances are you’ll end up shelling out over $172,500 (and that’s per person) just to cover your medical costs during retirement. Yep, that's a conservative estimate—one that, frankly, makes some folks want to run for the hills.
But before you worry, let’s flip the script. While the price tag might seem wild, you’ve got options. At The Pimpleton Agency, we help busy families and business owners like you take charge of their future, one dollar (and decision) at a time. Let’s break down exactly where all that money goes—and how you can tackle the healthcare monster BEFORE it even starts growling.
When you add it ALL up—plus annual inflation, which seems to love healthcare—hitting $172,500 or more isn’t just possible; it’s likely.
“But I have Medicare! I’m covered, right?”
Not so fast—Medicare is awesome, but it’s not a magic wand. You’ll still need a plan for everything else.
If you’re still working and have a high-deductible health plan, an HSA is your secret weapon. Think of it like a Roth IRA for your health:
Why HSAs rock:
How much should you save?
For 2025, HSA contribution limits likely exceed $8,000 for families (check IRS updates!), and if you’re over 55, you get catch-up bonuses.
Real talk:
Consistent HSA contributions over 15–20 years can cover a huge slice of your retirement medical bills—especially when used strategically.
Ready to enroll in Medicare? Pause. The choices you make NOW can add up to thousands saved (or lost) over time.
Hot tip:
A 30-minute annual review of your plans can easily save you $500–$1,000 per year. That’s a vacation, or better yet—a year’s worth of prescription copays.
“Don’t just sign up and hope for the best—get a plan that flexes with your needs.”
Need help? Schedule an appointment with a Medicare pro at The Pimpleton Agency.
Here’s the stat no one likes to discuss: 70% of people over 65 will need long-term care at some point. And costs for assisted living or in-home health aides can exceed $80,000 per year. Ouch.
Do you need long-term care insurance? Maybe. If not, consider:
Don’t sweep it under the rug. Your future self will thank you (and so will your family).
Think of this as the “bare minimum” budget every retiree needs. Here’s how to make it work for you:
Example:
If you’re planning on a $50K/year retirement, budget at least $5–$7K just for medical bills—on top of your regular living expenses.
Medical bills can pack a punch, but smart tax tactics help soften the blow:
Questions? Let our team at The Pimpleton Agency help you review your options.
A little prevention = a lot of savings (and way more fun in retirement).
Reality check:
A gym membership or nutritionist now? Cheaper than even a single night in the hospital.
Situations change, and so do Medicare plans, drug prices, and your own health. Make it a habit:
Don’t go it alone! Your local Area Agency on Aging or licensed Medicare advisors (like us!) can help you:
Community matters—lean in and ask for help when you need it.
Here’s the truth: Healthcare expenses in retirement will never be “one-and-done.” Planning early, reviewing often, and staying proactive puts you back in the driver’s seat—because this ride doesn’t have to be scary.
Ready to build a plan (and keep more of your money in your own pocket)?
👉 Book your personal strategy session with The Pimpleton Agency today.
Your Turn:
What’s your biggest fear about retirement healthcare costs—and what’s ONE thing you’re doing now to prepare? Drop your story or question in the comments below. You might just inspire someone else!
If this helped you see retirement healthcare in a new light, share it with a friend or family member. Let’s fend off those $172,500 surprises together!
You've worked your tail off to build your business. You've survived the sleepless nights, the cash flow crunches, and that terrifying moment when you first signed a lease. But here's the thing that keeps me up at night as someone who helps business owners protect their wealth: most of you are making critical insurance mistakes that could wipe out everything you've built.
And it gets worse. Many business owners don't realize that their choice between an LLC and corporation isn't just about taxes, it completely changes their insurance needs too.
Let me share what I've learned from working with hundreds of business owners who thought they had it all figured out... until they didn't.
I get it. Insurance feels like throwing money into a black hole. So you shop around, find the cheapest policy, and pat yourself on the back for saving a few hundred bucks a month.
Here's what happened to Mike, who owns a small manufacturing company in Ohio. He saved $200 a month by choosing basic property coverage with rock-bottom limits. When a fire destroyed his warehouse last year, his insurance covered maybe 40% of the actual replacement costs. The "savings"? They cost him his entire business.
The real cost: Underinsuring your property is like buying a parachute with holes in it. Sure, it's cheaper, but you're going to have a bad time when you need it most.
Higher deductibles mean lower premiums, right? Smart business move? Not always.
I've seen too many business owners choose $10,000 or $25,000 deductibles to save on monthly premiums, then face a crisis when they can't afford the deductible during a claim. Your business is already stressed from whatever caused the claim, now you're scrambling to find cash for the deductible too.
Rule of thumb: Only choose a deductible you can comfortably write a check for tomorrow without checking your bank balance twice.
You wouldn't hire an employee and then hide half the job description from them. So why do business owners constantly hide information from their insurance providers?
Revenue jumped 300% this year? Your agent needs to know. Added a new service line? That's crucial information. Started working with hazardous materials? Definitely relevant.
When you withhold information, you're not saving money, you're creating coverage gaps that could sink your business when you need protection most.
Now, let's talk about something that makes most business owners' eyes glaze over: the tax differences between LLCs and corporations. But stick with me, because this directly impacts how much insurance you need and how you should structure it.
With an LLC, you're looking at pass-through taxation. That means business profits flow straight to your personal tax return. Sounds simple, right?
Here's the catch: you're paying self-employment taxes of 15.3% on your entire share of business profits. That's 12.4% for Social Security and 2.9% for Medicare. For a profitable business, this adds up fast.
Let's say your LLC makes $200,000 profit. You're paying $30,600 in self-employment taxes alone, plus your regular income taxes on top of that.
C-Corporations face what everyone calls "double taxation." The corporation pays 21% corporate tax on profits, then you pay personal income tax when those profits are distributed as dividends.
But here's what most people miss: if you're working in the business, you can take a salary (subject to payroll taxes) and receive additional distributions that aren't subject to self-employment tax.
For profitable businesses, this can actually result in lower overall taxes than an LLC structure.
Here's where it gets interesting: both LLCs and corporations can elect S-Corp tax status. This lets you potentially reduce self-employment tax exposure while keeping pass-through taxation benefits.
It's like getting the best of both worlds, but with more paperwork and compliance requirements.
Your choice between LLC and corporation doesn't just affect taxes, it completely changes your liability protection and insurance requirements.
LLCs offer something called "charging order protection" in most states. This makes it extremely difficult for personal creditors to seize your business ownership interests. Your personal assets get protection from business creditors, and you're protected from other members' actions.
What this means for insurance: You might need different liability limits because your personal exposure is different.
Corporations offer the classic "corporate veil" protection, but only if you maintain proper corporate formalities. Miss those required meetings, mix personal and business expenses, or skip the paperwork? You could lose that protection entirely.
What this means for insurance: You need to consider both corporate liability coverage and potential personal exposure if the corporate veil gets pierced.
Let me tell you about Sarah, who runs a successful marketing agency. She started as an LLC, chose minimal insurance to save money, and thought she was smart by keeping everything "lean and mean."
When a client sued her for $500,000 over a campaign that allegedly damaged their reputation, she discovered three problems:
The lawsuit took two years to resolve. Legal fees alone cost $150,000. The settlement? Another $200,000. Her "money-saving" insurance strategy cost her more than comprehensive coverage would have cost for 20 years.
But here's the kicker: after working with our team, Sarah switched to S-Corp election for tax benefits and implemented a comprehensive insurance strategy that actually costs less per year than what she spent on legal fees in just one month of that lawsuit.
Look, I've been in this business long enough to know that most business owners will read this, nod along, and then... do nothing. Please don't be that person.
The combination of proper business structure and adequate insurance isn't just protection: it's a competitive advantage. While your competitors are playing defense with inadequate coverage and suboptimal tax strategies, you'll have the peace of mind to focus on growing your business.
Here's what you need to do right now:
The cost of getting this wrong isn't just money: it's your business, your family's security, and everything you've worked to build.
Don't wait until you're facing a crisis to realize you've been making these mistakes. The best time to fix your insurance and business structure was five years ago. The second-best time is right now.
Ready to protect what you've built? Schedule a consultation with our team and let's make sure you're not making these costly mistakes. We'll review your current situation and show you exactly how to optimize both your business structure and insurance strategy.
Your future self will thank you for taking action today instead of hoping nothing bad ever happens to your business.
Even the smartest professionals make mistakes. Professional Liability Insurance, also known as Errors & Omissions (E&O), protects service-based businesses against lawsuits for negligence, bad advice, or failure to deliver promised results.
Tony Robbins critiques 401(k) plans, widely used retirement savings vehicles holding over $3.5 trillion in assets and generating substantial profits for financial institutions, for often falling short of ensuring financially secure retirements. He underscores the issue of the “tyranny of compounding fees,” a term introduced by Vanguard founder John Bogle, as a major drawback that gradually erodes savings. Robbins points out that many 401(k) participants remain unaware of these fees; an AARP study found that 80% of individuals are oblivious to their plan’s costs, with 70% mistakenly believing they pay no fees at all, despite significant fee variations even among comparable investments.
A sign stands outside a branch of Wells Fargo bank Wednesday, April 17, 2024, in Littleton, Colo. (AP Photo/David Zalubowski, File)
This savings account still promises 10% — plus 9 more of the highest APYs of January 2025Here’s what you need to know about the best savings account rates right nowSavings account rates are on the decline at the start of 2025, but banks and credit unions with the highest available rates of return this month continue to promise 5% annual percentage yield or more. Whether or not those returns remain, however, is another story, pros say. (See some of the best savings rates you can get now from our partner Bankrate.)
Wall Street is really worried about bonds. It might be time to buy some.
Real estate investments can be an excellent way to earn returns, generate cash flow, hedge against inflation, and diversify an investment portfolio. However, buying physical properties can be costly, difficult, and risky. Instead, you can buy shares of diversified real estate investment trusts, or REITs, which are public companies that own large portfolios of real estate and pay dividends to investors. There are many different types of REITs, providing access to residential, commercial, and specialty real estate. Here are 10 of the best REITs to buy in 2025, according to Morningstar analysts:
After nearly 8 months of consolidation and volatility, bitcoin’s price has broken above $100,000 and has pushed higher into uncharted territory. Where might it go next? Could the incoming administration and shifts in Congress have any impact? And will Ethereum’s price catch up to Bitcoin’s?
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Even the smartest professionals make mistakes. Professional Liability Insurance, also known as Errors & Omissions (E&O), protects service-based businesses against lawsuits for negligence, bad advice, or failure to deliver promised results.
Tony Robbins critiques 401(k) plans, widely used retirement savings vehicles holding over $3.5 trillion in assets and generating substantial profits for financial institutions, for often falling short of ensuring financially secure retirements. He underscores the issue of the “tyranny of compounding fees,” a term introduced by Vanguard founder John Bogle, as a major drawback that gradually erodes savings. Robbins points out that many 401(k) participants remain unaware of these fees; an AARP study found that 80% of individuals are oblivious to their plan’s costs, with 70% mistakenly believing they pay no fees at all, despite significant fee variations even among comparable investments.
A sign stands outside a branch of Wells Fargo bank Wednesday, April 17, 2024, in Littleton, Colo. (AP Photo/David Zalubowski, File)
This savings account still promises 10% — plus 9 more of the highest APYs of January 2025Here’s what you need to know about the best savings account rates right nowSavings account rates are on the decline at the start of 2025, but banks and credit unions with the highest available rates of return this month continue to promise 5% annual percentage yield or more. Whether or not those returns remain, however, is another story, pros say. (See some of the best savings rates you can get now from our partner Bankrate.)
Wall Street is really worried about bonds. It might be time to buy some.
Real estate investments can be an excellent way to earn returns, generate cash flow, hedge against inflation, and diversify an investment portfolio. However, buying physical properties can be costly, difficult, and risky. Instead, you can buy shares of diversified real estate investment trusts, or REITs, which are public companies that own large portfolios of real estate and pay dividends to investors. There are many different types of REITs, providing access to residential, commercial, and specialty real estate. Here are 10 of the best REITs to buy in 2025, according to Morningstar analysts:
After nearly 8 months of consolidation and volatility, bitcoin’s price has broken above $100,000 and has pushed higher into uncharted territory. Where might it go next? Could the incoming administration and shifts in Congress have any impact? And will Ethereum’s price catch up to Bitcoin’s?
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Let's face it – building a retirement that actually lasts is harder than ever. With inflation hovering around 3%, market volatility keeping everyone on edge, and Americans living longer than ever before, the old "save a bunch and hope for the best" approach just doesn't cut it anymore.
Here's the reality check: the average 65-year-old today has a decent shot at living another 20-30 years. That's amazing! But it also means your money needs to work harder and smarter than previous generations.
So what's the solution? Creating your own personal "retirement paycheck" – a reliable income stream that shows up month after month, regardless of what the market decides to do. And two powerful tools for building this paycheck are often overlooked: life insurance and annuities.
Remember when people worked at the same company for 40 years and got a nice pension? Yeah, those days are mostly gone. Today's retirement landscape looks totally different:
The biggest problem? Uncertainty. When you're working, an occasional market dip is no big deal. But when you're withdrawing from those accounts to live on, market drops can permanently damage your retirement security.
When most people think about life insurance, they think about the death benefit – money that goes to your loved ones after you're gone. But certain types of permanent life insurance can be powerful retirement planning tools while you're very much alive.
Unlike term insurance that expires, permanent policies like whole life and fixed indexed universal life build cash value over time. This cash value has some unique advantages:
At The Pimpleton Agency, we've helped countless clients use these strategies to create tax-efficient retirement income. For example, our fixed indexed universal life policies offer growth potential tied to market indexes without the downside risk.
Want to learn more about how life insurance can supplement retirement income? Check out our guide on how life insurance policies help with retirement planning.
If you're looking for guaranteed income that lasts as long as you do, annuities deserve a serious look. Think of an annuity as creating your own personal pension – you contribute money, and in return, you get regular income payments.
In 2025, several types of annuities can help construct your retirement paycheck:
Fixed Annuities: These offer guaranteed rates of return – currently between 5.25% and 6.80% for multi-year guaranteed annuities. The certainty is comforting in uncertain times.
Fixed Indexed Annuities: These provide growth potential linked to market indexes while protecting your principal from market losses. Our fixed indexed annuities offer competitive rates with principal protection.
Immediate Annuities: Ready for income now? Immediate annuities convert a lump sum into a guaranteed income stream starting right away. Current payout rates for 65-year-olds range from 6.5% to 7.5%.
Deferred Income Annuities: These are designed to start payments later – perhaps at 75 or 80 – providing higher payouts when you need them most and effectively insuring against longevity risk.
The magic happens when you combine these tools with traditional retirement accounts. Here's a real-world approach we recommend to clients in 2025:
Bucket 1: Guaranteed Income Foundation Combine Social Security, any pension you might have, and annuity income to cover your essential expenses. This ensures your basic needs are always met, regardless of market conditions.
Bucket 2: Flexible Income Use traditional investments (IRAs, 401(k)s, brokerage accounts) to fund discretionary spending. In good market years, you can withdraw a bit more for travel or gifts. In down years, you can cut back without affecting your essential lifestyle.
Bucket 3: Tax-Efficient Legacy Growth Permanent life insurance serves double duty – providing tax-advantaged access to cash value during retirement while maintaining a death benefit for heirs.
Let me show you how this works with a simplified example:
The Johnsons, both 65, have accumulated $1 million for retirement and want $60,000 annual income (plus Social Security).
Traditional Approach:
Optimized Approach:
The difference? An extra $12,250 per year in retirement income, with a greater portion guaranteed for life.
Ready to create your own reliable retirement income stream? Here's how to begin:
Take stock of your current situation Calculate your essential expenses vs. discretionary spending. Understand your existing resources including Social Security benefits, savings, and investments.
Identify your income gap Determine the difference between your guaranteed income sources and your essential expenses. This gap is what you'll want to fill with additional guaranteed income tools.
Explore your life insurance options If you have 5+ years until retirement, permanent life insurance with cash value accumulation can provide tax-advantaged income. Schedule a consultation to see which type might be right for you.
Consider the right annuities for your situation Depending on your timeline and goals, different annuity products make sense. The key is understanding the power of fixed indexed annuities in today's environment.
Integrate all pieces into a comprehensive plan The most successful retirement strategies coordinate all these tools alongside traditional investments, tax planning, and healthcare considerations.
Before implementing any strategy, understand the tax implications. For instance, did you know that life insurance benefits can sometimes become taxable? Learn more about when life insurance becomes taxable to avoid unexpected tax bills.
Similarly, annuity withdrawals are generally taxed as ordinary income, but only on the earnings portion. Proper structuring can help minimize the tax impact.
Building a retirement paycheck strategy isn't a DIY project. The rules are complex, products change regularly, and mistakes can be costly. At The Pimpleton Agency, we specialize in creating custom retirement income plans that balance:
Ready to create a retirement paycheck that won't run out? Schedule your appointment for a complimentary retirement income analysis. We'll help you understand where you stand today and how life insurance and annuities might fit into your optimal retirement strategy.
Remember, the earlier you start planning, the more options you'll have. But even if you're approaching retirement quickly, there are still powerful strategies to enhance your income security.
Don't leave your retirement income to chance. Build a paycheck you can count on, no matter what happens in the markets or how long you live.
Ever feel like retirement is that mythical land—always there, but somehow still out of reach, especially when juggling family schedules or running a business? Good news: 2025 has shaken up the retirement rules with some major upgrades to 401(k) catch-up contributions—giving you a shot at the kind of financial cushion that’s actually within reach.
Here’s your down-to-earth cheat sheet to making the most of these new limits, written for real life (not textbook land), and packed with strategies that work even when you’re short on time.
Let’s cut to the chase. If you’re 50 or older, 401(k) “catch-up” contributions have been your secret weapon to supercharge your nest egg. But now—with the IRS giving folks aged 60–63 an even juicier bump—there’s real money on the table. For many, this is the difference between an okay retirement…and a wow, is this what freedom feels like? retirement.
So what’s new? Here’s a crash course:
Heads up: Your plan has to offer these boosted catch-up contributions. Not every 401(k) will be ready to roll with the new rules out of the gate, so check with your plan sponsor or HR.
| Age | Maximum Employee Contribution | Catch-Up Contribution | Total Possible Contribution* |
|---|---|---|---|
| <50 | $23,500 | $0 | $23,500 |
| 50–59, 64+ | $23,500 | $7,500 | $31,000 |
| 60–63 | $23,500 | $11,250 | $34,750 |
*Add employer contributions for a possible combined $70,000 annual limit.
Juggling student concerts, team carpools, AND retirement planning? We get it. But here’s why you should pay extra attention:
Every extra dollar is an investment in your family’s future flexibility.
Today’s catch-up is tomorrow’s travel fund—or the backup plan for surprise life events.
If you’re in your early 60s, go big while you can.
The 60-63 catch-up window gives you only four years of this supercharged limit. Don’t blink and miss it!
Running a business? You’ve got the magic combo: entrepreneur + employee. Here’s how you can max out like a pro:
Solo 401(k)?
You act as both employer and employee. Contribute up to the annual employee limit (including catch-ups if eligible), then add employer contributions up to that $70,000 total cap.
Pro Tip: Use profit-sharing.
If you had a strong year, a profit-sharing contribution can push you to the very max—AND build in a business deduction.
Don’t let that “catch-up” window close while you’re buried in admin; delegate payroll tasks or work with a retirement specialist to automate moves.
Not every plan has instant access to these increased limits. Call HR or your 401(k) administrator. Ask: “Is our plan set up for the 2025 special catch-up provisions?”
Don’t wait until December—start maxing out from January so your contributions are spread over smaller per-paycheck bites.
How to do it:
If your plan requires declaration of catch-up, submit a formal letter or email to the 401(k) administrator. Don’t assume it’s automatic.
Check pay stubs and plan statements quarterly. Mistakes can happen; act quickly if something doesn’t look right.
Deciding between pre-tax or Roth contributions? If you expect to be in a higher tax bracket later (or just love the idea of tax-free withdrawals), divert a slice of your contribution to the Roth side.
Note: Roth 401(k) catch-up contributions are still limited by the annual cap.
Here’s how the pros make every dollar count—even in a hectic year:
Retirement isn’t one big leap—it’s a series of small, smart decisions. Start by having a five-minute conversation with your HR or plan admin, or review your 401(k) dashboard this week.
Ready to create a step-by-step strategy just for you or your business? Our team at The Pimpleton Agency is on standby with free, friendly advice that actually makes sense for busy lives. Schedule your appointment here!
Got questions, or a hot tip for maxing retirement savings? Drop your thoughts below! What’s the best (or worst!) financial move you made for your family or business—and what did you learn from it?
For more on optimizing your retirement and avoiding costly pitfalls, check out our post on 7 Crucial Retirement Mistakes.
You walk into your business one morning, coffee in hand, thinking about your next big move. Suddenly, your phone rings: a key partner is gone—temporarily, permanently, or for good. What happens next?
Will the company you’ve poured your heart into become a battlefield between heirs and partners, or will it thrive against all odds? For a surprising number of business owners, the answer is “I have no idea.”
Let’s make sure that’s not you.
You didn’t build your business to see it fade because of a twist of fate. But here’s the ugly truth:
Almost 50% of small businesses don’t have a plan for the unexpected—be it illness, accident, or a partner’s sudden exit. When chaos hits, it’s usually too late to write a calm, clear plan. That’s why savvy business owners (and their families) turn to two secret weapons: buy-sell agreements and key person insurance.
Let’s break this down. A buy-sell agreement isn’t just legal mumbo-jumbo. It’s a life raft that keeps your business afloat when waves get choppy.
In plain English:
A buy-sell is a legal contract made by business co-owners (or with key staff) that spells out exactly what happens if one of you wants out, dies, gets disabled, or simply walks away.
Trigger situations covered:
Quick Pro Tip:
If your partnership or LLC doesn't have a buy-sell, you don't own a business—you own a ticking time bomb.
Think of key person insurance as the superhero cape for your company. It’s simple but powerful:
If the “big brains” (or the rainmaker) of your operation becomes suddenly unavailable, this policy pays a lump sum so everyone else isn’t left scrambling for payroll, accounts, or even to keep the lights on.
Let’s get real. You can use the money from a key person policy to:
How it works:
The business owns and pays for the policy on the key person (like an owner, top salesperson, or tech genius). If calamity strikes, the business pockets the proceeds—no tax headaches.
Key person insurance isn’t just smart—it can be tax-savvy, too. Premiums aren’t deductible, but payout is usually tax-free. Think of it as a crisis management fund, ready to deploy at a second’s notice.
Here’s the golden rule:
A buy-sell agreement without funding is just a wish.
Key person insurance without a plan is an expensive Band-Aid.
When you combine them? Pure business magic.
Result?
Your business doesn’t break stride—clients stay confident, staff keeps showing up, and your company’s value is protected.
Real-Life Scenario:
Sarah and Mark co-own a thriving construction firm. Mark gets sick and can’t work—thanks to their buy-sell agreement, Sarah automatically gains the right to buy Mark’s shares at a fair price. The cash? Comes directly from their key person insurance policy. Sarah keeps building the business while Mark’s family gets the payout he earned—no lawsuits, no awkward negotiations, no distress sales. Win-win.
Still not sure what these tools would look like for your business?
Schedule your free consultation with The Pimpleton Agency and let’s put you in the driver’s seat—even if you’re not always there to steer.
A thriving business isn’t just a source of income. It’s your employees’ paychecks, your family’s nest egg, and your biggest achievement. Buy-sell agreements and key person insurance don’t make you paranoid—they make you a pro.
Want to spare your loved ones (and your team) from chaos? Lock in your business legacy now.
Question for you: What would your business look like if you were out of the picture tomorrow?
Share your story or your biggest “what if” in the comments—we love connecting smart owners and learning from each other.
And if you found this useful, share it with a partner who really needs to read it. (You know the one.)
Ready to make your business bulletproof?
Let’s talk.
