The Scary and Confusing World of Health Insurance


The Scary and Confusing World of Health Insurance with Christine MacLaren - 179

This Week's Money Talking Points


1. What health insurance plan is right for you?

Choosing the right health insurance plan can feel like trying to read a foreign language, full of terms like premiums, deductibles, co-insurance, and out-of-pocket maxes. But here’s what I’ve learned: your choice should ultimately come down to two things—your cash flow and your expected medical usage. If you’re pretty healthy, don’t go to the doctor often, and want to keep your paycheck a little bigger, a High Deductible Health Plan (HDHP) might be your best bet. You’ll pay less each month and can pair it with a powerful HSA (which I’ll talk about below). On the flip side, if you know you’re going to be using your insurance a lot—maybe you’ve got a surgery coming up or frequent doctor visits—then a traditional PPO or low-deductible plan might save you more in the long run, even if it costs more each month.

The key takeaway? Don’t just default to last year’s plan. Every year is a new opportunity to re-evaluate your needs and pick a plan that fits this season of life. And if you’re not sure what the best option is, ask your HR team or reach out to someone who can walk you through the math. Trust me, taking 20 minutes now can save you hundreds—if not thousands—of dollars later.

2. How can you use an HSA to minimize taxes?

Let me tell you, the Health Savings Account (HSA) is one of the most underutilized tax-saving tools out there. It’s honestly like a unicorn in the financial world—money goes in tax-free, grows tax-free, and comes out tax-free when used for qualified medical expenses. That’s the triple tax advantage. And there’s even a fourth benefit if you contribute through payroll at work—you avoid payroll taxes too. My wife and I have used ours to build a little investing powerhouse that also acts as a medical emergency fund. We contribute regularly, invest the balance in a total market index fund, and then, when a big medical bill hits, we can pay ourselves back, even years later. It’s like reimbursing your future self with investment gains. How cool is that?

If you’re able to pay out-of-pocket for smaller medical costs now and let your HSA grow untouched, you can turn it into a tax-free retirement tool. We keep enough in cash to cover our deductible and invest the rest. The key is careful documentation—track your expenses and hold onto receipts so you can reimburse yourself down the line. And if you’re not investing your HSA yet or you’re stuck with a high-fee provider, consider rolling it over to something like Fidelity, which has no fees and great investment options.

3. Why is disability insurance important?

This one often gets overlooked, but it might just be the most important insurance you never think about. Think about it: if you were injured tomorrow and couldn’t work for months, would your income dry up? That’s where disability insurance comes in. It replaces part of your paycheck if you can’t work due to injury or illness. I’d even argue it’s more important than life insurance—because if you die, yes, your income stops, but your expenses usually go down too. If you’re disabled, your expenses often increase, and the bills don’t stop coming.

It's likely that you could be in a car accident and out of work for some time. Your short-term disability insurance was the only thing keeping money coming in. I see too many people skip over this coverage because they want to save a few dollars on premiums, but if your employer offers it, consider taking it. Even better—add long-term disability if you can. It’s a small price to pay for protecting your income and your financial future.

This week's Money Buddy

With over 25 years of experience in Human Resources, Christine MacLaren has developed a strong passion for benefits administration. In recent years, she expanded her expertise to include financial coaching, becoming a certified budget coach with MyBudgetCoach and YNAB. Christine is deeply committed to supporting individuals in achieving greater financial well-being.

Enjoy your week and get out there and have a money talk!


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