2026 Open Enrollment Shake-Up: Avoid These Costly Mistakes

If you’ve been juggling flight delays, quota pressures, and the nonstop hustle that defines the medical sales world, you probably haven’t had a whole lot of time to obsess over premiums or deductibles. But come 2026, ignoring what’s happening with open enrollment could cost you thousands. Many companies are projecting a 7–9% spike in employer-sponsored plan costs, and for anyone using the ACA Marketplace, premiums could be going up by a staggering median of 18%. That’s real money coming out of your take-home pay and siphoning dollars away from the goal we all share—making work optional sooner rather than later.

I’m David Dedman, ChFC®, AWMA®, founder of Pulse Wealth. I’ve spent years consulting and building financial game plans for high earners like medical sales professionals. One thing I’ve learned (often the hard way) is that a single open enrollment mistake can easily derail months or even years of strategic saving and planning. So let’s take a good look at what’s different in 2026, where the big cost culprits are lurking, and how you can protect your income and your family time from getting dragged into a financial quagmire.

The News Hook: Record-Breaking Cost Hikes

Sticker shock is unfortunately not new in the world of healthcare benefits. Employers and insurers have been bracing for higher costs for years, but 2026 is shaping up to be particularly dramatic. There are a few key drivers fueling this:

Expiration of Enhanced Premium Tax Credits (eAPTC): If you or anyone you know has been enjoying more generous subsidies since the pandemic era, those expanded benefits are set to expire at the end of 2025. That means out-of-pocket premiums could surge by more than 75% for people who had previously qualified for significant relief. With fewer subsidies to go around, insurers expect some healthier individuals will leave the risk pool, forcing premiums even higher.

Higher Out-of-Pocket (OOP) Limits: In 2026, the maximum OOP for an individual plan hits $10,600. When you’re used to traveling frequently and maybe scheduling care only when absolutely necessary, it’s easy to overlook how quickly your family can burn through that kind of limit if something unexpected happens.

Skyrocketing Prescription Costs: Prescription drug prices haven’t exactly been modest over the last decade, but new specialty meds and rising inflation make 2026 especially pricey. Even employers with large, streamlined benefit plans anticipate that these drug costs will push overall premiums higher, and those costs tend to land right in your paycheck deductions.

General Inflation: While inflation in some areas may stabilize, healthcare inflation tends to outpace general consumer inflation. Factor in provider fee increases, more expensive drugs, and a growing utilization of healthcare services overall, and it’s easy to see how that 7–9% employer plan spike—and 18% marketplace premium jump—can take shape.

The High-Earner’s Dilemma: Don’t Default on Your Decisions

Most of the medical sales folks I work with are used to a certain level of comfort, and that often translates into opting for a Familiar PPO (Preferred Provider Organization) plan. You get wide provider networks and typically don't have to worry about meeting a big deductible before coverage kicks in to a meaningful degree. It’s easy, it’s predictable, and you’ve stuck with it for years. But 2026 might be the year that approach starts feeling so expensive you wonder if it’s worth it.

PPO premiums are generally higher. That may not have bothered you when your goal was simply “get good coverage, keep traveling, focus on the job.” But now that you’re clearing $200k or even $300k and aiming to build real wealth, here’s a harsh truth: you might be throwing away a few thousand extra in premiums—money that could’ve gone into tax-advantaged vehicles like HSAs, 401(k)s, or a supplemental financial strategy to protect your entire income.

A lot of people skip evaluating their plan type each year, figuring it doesn’t matter much. Ironically, for high earners, it matters more, because you have more to lose and more money that can be re-used for other goals. Pay an extra $3,000-$5,000 in premiums? That might sound like a fair trade for comfort, until you consider how huge that money can grow over time if funneled into strategic investments. This year, the typical PPO could be a silent drain on your finances—one that’s about to get bigger if you just default into renewal.

Strategic Move: Re-Evaluating the HDHP and Maximizing the HSA

You might be thinking, “HDHPs (High Deductible Health Plans) are for younger, squeaky-healthy people with no major medical needs.” Honestly, that’s a myth. An HDHP, when paired with a Health Savings Account (HSA), can be incredibly powerful. You get a triple-tax advantage:

1) Contributions are tax-deductible.

2) Money grows tax-free if invested properly.

3) As long as you use it for qualified medical expenses, withdrawals remain tax-free.

This combination can be a real game-changer for someone who’s trying to retire early or simply wants to keep more of what they earn. The caveat, of course, is that you’ll have a higher deductible—often in the range of a few thousand dollars. But if you’re historically healthy or you have enough savings to manage a higher deductible in the worst-case scenario, the premium savings can be substantial.

Let’s put some approximate numbers on it to make things clearer. Consider the table below, which compares a hypothetical HDHP vs. PPO structure for 2026:

When you factor in that you might save a few hundred dollars per month on premiums alone—and simultaneously gain a tax-advantaged investment vehicle—it can make a lot of sense to try the HDHP route. In 2026, the family HSA contribution limit is expected to be around $8,300. If you’re in, say, a 24% marginal tax bracket, that’s nearly $2,000 in tax savings simply by contributing to the HSA. And remember, many employers sweeten the deal by contributing their own chunk of money into your HSA each year, especially if they’re steering employees toward an HDHP option.

Sure, some folks worry about coverage quality. But keep in mind, preventive care is typically covered 100%, even on an HDHP. Yes, you’ll pay more out of pocket if you have to see the doctor frequently or have a major procedure. But many in medical sales are comfortable setting aside an emergency fund—so consider how that strategy might save you money overall, and potentially turbocharge your longer-term goals.

Strategic Move: Protecting Your Biggest Asset—Your Income

It doesn’t matter if you’re 35 or 45, your greatest wealth-building machine right now is your ability to earn a healthy six-figure income. Yet most people take their group disability coverage at face value without ever reading the fine print. Employer plans typically replace only about 40–60% of your base salary—and that’s before we talk taxes. If commissions make up a solid chunk of your total comp, you could be in for a rude awakening if you can’t work for an extended period.

High earners in medical sales also have monthly living costs that match their income tier. Mortgages, family obligations, travel—these don’t just pause if an illness or injury suddenly knocks you out of the workforce for six months or a year. Let’s look at a quick comparison:

That small additional premium for a supplemental policy could mean the difference between comfortably meeting your financial commitments if you’re out of work versus scrambling to figure out your next move. A big part of building a “work optional” lifestyle is making sure that if you ever get sidelined, your finances don’t unravel. Disability insurance is your first line of defense.

Strategic Move: Aligning Benefits with Your “Work-Optional” Goal

Many high earners get so focused on short-term success that they forget to intentionally design their benefits around the long run. It’s not just about which health plan you pick. It’s about using every tool at your disposal—401(k)s, HSAs, even non-qualified deferred compensation (NQDC) if your employer offers it—to maximize savings and reduce your tax bill over time. The magic is in layering these strategies together:

1) 401(k) Contributions: If your company offers a match, that’s an immediate return on part of your income, but don’t stop at just the match. If your objective is to step away from the daily grind by, say, your mid-50s, you’ll appreciate every extra dollar you sheltered from taxes and allowed to compound. For 2026, the employee deferral limit is projected to be around $23,000 (plus a catch-up if you’re 50+).

2) HSAs: Yes, we keep harping on HSAs, but that’s because they’re one of the only accounts that give you triple-tax benefits. You can invest those funds in a diversified portfolio while you’re healthy, giving them the potential to grow for decades. You might never need to spend it all on medical expenses right now, but someday, you’ll be grateful for that nest egg to cover future healthcare costs—tax-free.

3) Non-Qualified Deferred Compensation (NQDC): Some medical device or pharmaceutical companies offer NQDC programs for top earners. You can defer a chunk of your compensation to future years—ideally, years when you anticipate being in a lower tax bracket (like early retirement). This helps you reduce your taxable income today, potentially saving you thousands annually. If you need help coordinating this with your broader tax picture, consider our comprehensive tax-planning services.

4) Dependent Care FSAs: If you have young children or dependents requiring paid care so you can keep working, this account can be a nice little tax break. You can put away up to $5,000 pre-tax to cover qualified childcare expenses. That’s not pocket change when you consider the cost of after-school or daycare, especially if you’re traveling a lot for work.

When you piece these elements together thoughtfully, each open enrollment season turns into an annual checkpoint for your bigger financial picture. It’s not just an “HR formality,” it’s a chance to reevaluate: Are you maxing the right accounts? Should you redirect some of that money you’ve been sinking into a high-premium plan into an HSA or a supplemental disability policy? Every year, you can adapt your strategy based on new benefits or changes in your workplace. This is exactly how you inch closer to a flexible lifestyle—step by step, enrollment by enrollment.

Projected 2026 Employer Plan Costs

Before you settle on a plan, make sure you grasp the basic landscape of where premiums are trending. Below is a simplified snapshot to illustrate potential cost increases. These numbers can vary widely by region, employer, and plan design, but they help highlight the overall trend that you should confirm in your own benefits packet.

The reality is no plan is immune to price hikes. By seeing how each type of plan might shift, you can plan your budget accordingly. If you’re getting hammered by extra travel and sales quotas at work, the last thing you need is a nasty surprise in January when you see the “updated” deduction on your paycheck. Better to know now and make a proactive adjustment.

Disability Insurance Bite-Size Comparison

We talked earlier about the importance of protecting your income. Below is a quick reference chart that highlights how different disability coverage scenarios might look if you’re a high-earning professional in medical sales. This is especially pertinent if you rely on a big chunk of your total compensation from commissions or bonuses.

Think of it this way: If you have a $15,000 monthly need (mortgage, family costs, etc.) and your employer’s coverage only nets you $5,000 after taxes, that’s a $10,000 hole each month until you’re back on your feet. Supplemental coverage is about ensuring that your savings and wealth-building strategy don’t get shredded by an unforeseen medical event. This is especially relevant if you’re trying to retire or partially retire in your 50s—one big setback could push that timeline back years.

Final Thoughts and Next Steps

Your 2026 open enrollment decisions might seem like routine tasks—until you realize how much money is at stake. For high-income professionals, these choices can accelerate (or hinder) your path toward making work optional. The big changes this year—expiring subsidies, higher deductibles and out-of-pocket costs, and more stringent verifications—mean it’s time to get proactive. If you don’t reevaluate each piece of your benefits puzzle, you could be leaving thousands on the table or exposing your family to unnecessary risk.

Whether it’s switching to an HDHP and leveraging that HSA, beefing up disability coverage to keep your income safe, or finding new ways to shift compensation into tax-advantaged accounts, every move should align with your end game. That’s how you create the freedom to decide exactly when you want to take your foot off the gas in that high-pressure sales environment. If you’re not sure which plan or combination of strategies is best for you, I’m here to help.

If you’d like personalized guidance that cuts through the noise, schedule a free intro call. We’ll map out what’s best for your family and your work-optional goals—or, if you prefer, start with our no-cost financial assessment to get a high-level overview first.

FAQ

How do I determine if a High Deductible Health Plan actually saves me money?

Start by comparing the monthly premium difference between the HDHP and the PPO, then add in how much you’d potentially contribute to your Health Savings Account. If the amounts you save on premiums and taxes outweigh what you might pay in deductibles, the HDHP can be a win. Also consider whether your employer provides an HSA contribution—this can tip the balance in favor of the HDHP.

Can I switch from a PPO mid-year if costs become too high?

Generally no, unless you experience a qualifying life event such as a marriage, birth, or job change. Otherwise, you typically have to wait for the next open enrollment period, so it’s crucial to run the numbers early and make an informed decision now.

What documents or information do I need to confirm my eligibility for subsidized plans?

Official income verification documents (like recent pay stubs, W-2 forms, or prior-year tax returns) are usually required, especially since 2026 will bring stricter income verification rules and no automatic re-enrollment for subsidized plans. Have these ready before open enrollment kicks off.

Why might employer disability coverage fall short for higher earners?

Most group plans only cover a portion of your base salary (40–60%), and any payout can be taxed if your employer pays the premium. Since many medical sales roles include commissions and bonuses, you could be left with significantly less income replacement than you need. That’s where supplemental or individual coverage fills the gap.

Is an HSA really that beneficial for higher earners?

In many cases, yes. You can contribute tax-deductible money, invest it for years, and then make withdrawals tax-free for qualified medical expenses. Because you’re in a higher tax bracket, your tax savings on contributions can be considerable. Over time, an HSA can function like a powerful, extra retirement account—especially if you pay current medical costs out of pocket and let your HSA investments grow untouched.