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It’s that time of year again.

If you’re one of the roughly 150 million Americans who gets insurance through work, you’re probably going through “open enrollment,” that annual ritual of picking a health insurance plan.

And if you buy an insurance plan via the Affordable Care Act’s marketplaces or pick a private Medicare Advantage plan, you’re facing something similar, too.

A reporter reads a summary of the performance and usage over the first two days of open enrollment of the Massachusetts Health Connector website.
A reporter reads a summary of the performance and usage over the first two days of open enrollment of the Massachusetts Health Connector website.REUTERS

Last year, I went through all this for the first time. After taking a new job at Business Insider, I faced the task of sorting out which of the company’s four health insurance options would be best for me (my previous job had just one plan).

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I should be well equipped to do that. I’ve been writing about health care for years, and my wife’s a doctor.

And yet, I found it difficult to pick the right plan. Looking back, I can tell you now that I made the wrong choice.

But here’s the thing: It was the right choice at the time, and as I look ahead to 2020, I’m making the same wrong choice yet again.

Stick with me.

If you ask around for advice on buying health insurance, you’ll probably be told something like this:

If you’re healthy and don’t think you’ll need to go to the doctor much or take many prescriptions, pick a plan with low premiums that doesn’t cost much up front. If you end up needing medical care, though, you’ll probably pay more out-of-pocket costs, like copays and deductibles.

If you think you’ll need to see a doctor frequently, or take some more costly pills, you might want a more expensive insurance plan with more robust coverage.

The reality, for me, and likely for many of you, is far more complicated.

Last year, I asked for health insurance help from David Anderson, a researcher at Duke University who used to work at an insurance company. He even wrote a blog I found helpful on how he picks his own health insurance.

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It boiled down to this: Financially, the best option for me was likely to be my company’s high deductible plan. Even though I’d face more costs if I got sick or injured, Insider Inc. offers the plan to its workers for free, and the upper limit on how much medical spending I could end up on the hook for was just over $3,000.

By picking that plan, I’d probably save about $1,000 a year.

I should say I’m lucky that Insider has a relatively generous high deductible plan. Some plans can leave you with thousands of dollars more in medical bills before coverage kicks in.

Instead, I opted to spend $1,000 more for a better plan, which Insider calls our “Low PPO” plan.

Here’s why. The biggest drawback to the high-deductible plan is that it offers a more limited selection of doctors, and won’t provide any coverage at all if you get care from doctors outside that network, except in an emergency.

It’s really hard to figure out which doctors are being left out of the high-deductible plan. You can look up individual clinicians and facilities on an insurance company website, but it’s impossible to get a more comprehensive view of what you’re giving up. I was worried that the coverage might come up short just when I needed it most.

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Other journalists have written a lot about the shocking five-figure and even six-figure bills that many people have gotten stuck with from out-of-network doctors. And while the only way to prevent those surprise bills from happening entirely is to change state and federal laws, I figured that choosing a health plan with a bigger doctor network and some coverage for visits even outside of that would offer better protection.

So far this year, I haven’t needed that extra protection, which means I “wasted” $1,000 on the better plan.

But health needs are difficult to predict.

When I wrote about picking an insurance plan a year ago, I said: “I’m thankfully pretty healthy, so I don’t really go to the doctor or take prescriptions much at all.”

In retrospect, I may have been tempting fate. A few weeks later, I found myself in a doctor’s office with stomach pain and trouble eating a full meal. While I got better with some generic medicine and diet changes, those stomach problems easily could have been symptoms of something far more serious.

I know I’m writing this article from a place of privilege — a lot of people aren’t in a position to even consider spending $1,000 for some extra protection or health care peace of mind.

But I hope that when open enrollment comes around in another year, I’ll have “wasted” that thousand dollars yet again. I know there’s a small chance it’ll have been well worthwhile.

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Zachary Tracer is the health care editor for Business Insider.