There is no source of truth to help single individuals avoid gaps in healthcare coverage.

Even if a New York State (NYS) resident follows Health Department guidelines on the health plan marketplace, they can still have:

1. Unforeseen difficulty signing up for a plan

2. Gaps in healthcare coverage due to poorly designed software and flaws in the enrollment and appeals process

I believe that the protocols followed by health departments - specifically NYS - and insurance companies are irreconcilable when someone wants to avoid a gap in healthcare coverage.

Each entity either:

1. Assumes plausible deniability when software or work instructions contribute to a gap in healthcare coverage; or

2. They have not adequately trained their representatives to guide applicants to avoid issues altogether.

Single New Yorkers - who do not read this article - and do not have a predictable salary will likely have a gap in healthcare coverage no matter what they do.

They also have to sign up for Medicaid even if they have plenty of cash to cover insurance premiums for plans with companies like Oscar Health.

My first-hand observations after using the NYS marketplace to get healthcare coverage are the following:

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates used to invoice for medical procedures

3. Insurance companies need to be held accountable when necessary

First, this article is not subjective. Even though everything here is based on first-hand experience - and I do express my frustrations about the process of getting healthcare coverage - I am not writing an "opinion piece" in the traditional sense of the phrase. I am not demanding a remedy for the harm that this series of events caused. That ship has sailed. I figured it out. I'm covered. And technically, no one owes me anything.

Second, I have organized these observations clearly and concisely based on several factors. You don't have to read this entire article. If your situation follows the same fact pattern as mine, these results will be repeatable. I doubt anything has changed since I applied for coverage. I also helped a family member get coverage by using these insights.

Third, I have enough distance from the events that took place to voice my frustrations and support them with my notes from over a dozen conversations that I had with representatives from:

1. The NYS Health Department

2. Publicly traded Health Insurance Companies (Oscar Health and Empire).

P.S. I will share the fact pattern - within certain limitations.

I hate when articles turn into dictionaries. Give me the terms, and don't define them, so I can just look them up, or put all of the definitions in one place so I can refer to them if I need to, and then get on with the rest of the article.

I'm going to do the latter.

If you don't want a refresher on all of these terms, you can skip to the section of this article titled "🏥 Why Am I Speaking Up About Healthcare?" It's important to note that I will need to use some of this jargon to explain my experience. Some of these phrases are not common (ex. work instructions used by NYS Health Department reps).

• Healthcare coverage: The ability to go to a doctor's office or hospital and have your medical expenses either fully or partially subsidized or "covered.."

• Open Enrollment periods: An open enrollment period is the time period when individuals and employees may enroll in health insurance or make changes to their coverage.

• Qualifying Events: A qualifying event is an event that triggers a special enrollment period for an individual or family to purchase health insurance outside of the regular annual Affordable Care Act (ACA) open enrollment period.

• Special Enrollment Periods: Special enrollment periods mean that once you have the qualifying event that is listed earlier, you can use the individual marketplace to sign up for coverage within 60 days.

• NYS Health Department: no official definition on their website that I could find.

• New York State of Health (NYSOH): the official health plan marketplace that connects New Yorkers to affordable health coverage (source).

• 15 Day Rule: The 15-day rule is a policy for the NYS of health. It dictates the deadline you need to enroll by in order to get health coverage in the subsequent month. A NYS Health Department representative told me that it is not codified in the NYS law or NYCR. It only exists in the work instructions of each representative.

• Work Instruction: guidelines followed by each NYS Health Department representative when speaking with an applicant.

• Transaction ID: A unique identifier used by both the Health Department and insurance company. Strangely enough, this identifier disappeared for both parties after the estate change that NYS Health Department performed for my account.

In the Greylock podcast episode "Talking Politics," Chris Yeh and Reid Hoffman had a discussion. The podcast begins with Reid making the following statement:

"In an increasingly politicized world, it's harder and harder for CEOs to keep business and politics separate. There are some who believe that it's more important to keep it separate because politicization has grown so much worse. However, I actually believe that this means the opposite. That it's critical for business leaders to speak up…and lead on key things in politics more than ever before. Nevertheless, it's an action that should be approached carefully."

Reid mentioned that he decided to speak up about politics when he realized he was not making partisan comments but speaking on democracy as a whole.

Currently, in my career, as a self-employed individual and founder, I realize it is necessary to comment on the Healthcare system. I am deciding to speak up because I do not feel like my comments are disparaging to the United States, New York, or even to the representatives that I worked with in order to get healthcare coverage. No, my comments are about healthcare as a whole.

In a global pandemic, keeping healthcare and business separate is more difficult. It is critical for business leaders to speak up and lead on key topics in Healthcare. I don't claim to be a business leader, but I would like to open up the conversation to address issues in Healthcare.

I realize that speaking about a topic as delicate as healthcare in America - especially when I am not a healthcare professional - is a reason for approaching this topic with caution. But in the past few months, I have noticed the extent of the issues in America's Healthcare System and I would like to outline these issues.

To reiterate, my first-hand observations are:

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates

3. Insurance companies need to be held accountable

Now, what does all of that mean?

I'll succinctly explain my experience with as little jargon as possible. Note that this analysis will focus on the enrollment process in NYS, of which I am a resident. I'll tell this story in chronological order because it's easy to follow that way.

On November 9th I enrolled in a medical and dental plan, only to find out in mid-December that I wasn't eligible for either.

As a byproduct of the 15-day rule, I experienced a two-month gap in healthcare coverage even though I was proactive in avoiding that gap. When I applied for a plan, I picked Oscar and Empire because I knew those companies and they had the lowest monthly premium. I projected I could still make the premium payments, despite my business' cash burn rate.  The additional good news is that I would also have a grace period of 30 days to make the first premium payment.

My plan was scheduled to begin on December 1st - see the 15-day rule in the Health Insurance 101 section above - so I wouldn't have to make the payment until December 31st.

So then the question is, why did I have an issue getting insurance?

The enrollment period.

Up until that time, I had believed signing up in November 2021 would lead to coverage for the rest of 2021 and 2022.

What this meant was I was signing up for a 2021 open enrollment period, but I was getting rejected because Oscar perceived I was in a special enrollment period for 2021 due to a qualifying event. Oscar got confused and kicked my application to the curb. It took over 10 calls to get Oscar and NYS to clarify why they rejected the application. Oscar and NYS said the application was canceled due to nonpayment but this is flat out wrong. I had a 30 day grace period to make the first premium payment. In fact, it was an Oscar representative that told me about this grace period.

By the time I figured everything out, it was too late to get coverage for December 2021.

Now let me be clear, I am focusing on how I tried to avoid not having coverage in November-December 2021, and why neither party (NYS or Oscar) understood what was going on.

When I was trying to avoid having a gap in healthcare coverage, I input my 2021 income. Makes sense. I was enrolling for 2021 coverage.

That income was over the threshold for Medicaid - which I learned about on December 13th. But, due to the plan tier that I selected when I first submitted my application the marketplace software had no idea how to handle my situation. But it wasn't just the software. It was the employees at Oscar and the New York State of Health (NYSOH) marketplace.

Why? I'm glad you asked. This is very important.

NYS and Oscar canceled my application due to their perception of my ineligibility for the special enrollment period. I was applying because of my perception of an open enrollment period. Both NYS and Oscar were doing the equivalent of the spiderman meme for the better part of a month, plausibly denying their ignorance of the fact that:

1. I was eligible for the 2021 open enrollment period

2. My income for 2021 was high enough that I should have been eligible to keep the Oscar medical plan starting in December.

3. Nonpayment was not a factor because I had a 30 day grace period

It's possible that someone familiar with the healthcare system could disagree with the above comments for a few reasons.

First, they could say I'm wrong and I missed the open enrollment period for 2021. My only option was the special enrollment period of 60 days that begins after involuntary loss of coverage, or a different qualifying event.

Second, they could say the healthcare plan tier I selected was not open for special enrollment.

Neither of these arguments is valid.

I didn't miss open enrollment. But what do I mean I didn't miss open enrollment? I mean that my conclusion about being able to apply for healthcare coverage whenever I wanted was right, even though my logic was wrong.

I wrongly assumed that even if we weren't dealing with a global pandemic, I could enroll in health insurance whenever I wanted, so I applied on an ordinary day in November. My conclusion was correct because Cuomo made an announcement that literally made this true for 2021. I haven't researched open enrollment periods for years like 2018, but I don't think I could have written this four years ago.

The following quote is from a Frequently Asked Questions (FAQ) document titled "NYSOH COVID-19 related Q & A's" issued by the official New York State Health Plan marketplace:

"Governor Cuomo announced on March 23, an extension of the Open Enrollment Period to December 31, 2021. Extending the Open Enrollment Period to December 31, 2021 helps to align New York with the federal Public Health Emergency which HHS signaled they will extend through the end of 2021."

Here's a link to the press release about the announcement. But you don't have to click it. The link is broken and has been for multiple months: press release

In my opinion, there is a fundamental issue with the software of the NYS Marketplace. It was never updated to address Governor Cuomo's announcement. Granted, individuals looking to sign up for a plan should have some basic level of knowledge to sign up for coverage, but there should be:

1. Guardrails: Guardrails that enable top-down announcements - like the one from Cuomo - to make their way into the software or at least the work instructions of NYS Health reps.

2. Culture: A culture that prioritizes the implementation of those guardrails in the software.

“Software can help with this if you can create a culture around it.” - Alexis Ohanian

How many people in NYS had a gap in healthcare coverage because of this oversight?

Note, that NYSOH enrollment surged in 2021. To see a press release that explains how much enrollment surged, click here. What are they defining as enrollment? Technically I enrolled for coverage through the marketplace, but NYSOH canceled it.

Why do I keep talking about the NYS marketplace? I can hear people saying:

"Why didn't you just go to Oscar's website and apply for the coverage if the marketplace process is so bad…"

You can't.

I confirmed with Oscar and NYS that all roads - for individuals not covered by employers - lead to the NYS marketplace website…soo, yup.

Further, because I faced no friction in signing up for a plan with Oscar, I assumed everything was all good and I could at least get coverage starting in December.  Here comes the peanut gallery again:

"Why did you think everything was all good? Clearly, it wasn't."

The answer is, Oscar mailed me an insurance card LOL.

So far, I've addressed why as a single individual you cannot avoid the NYS marketplace and its issues.

Up until now, I've been describing how my medical coverage was canceled. I haven't described its effect on my vision and dental coverage.

NYS' system needs you to select two plans. Picture it like the marketplace wants a PB&J sandwich. Your healthcare coverage is the PB&J sandwich - I don't like jelly - but you get the idea.

If you pick Peanut Butter (vision and dental) but no Jelly (medical)… NO SOUP FOR YOU!

Or rather, no healthcare coverage for you. The NYS system has a guardrail that keeps you from enrolling in vision and dental if you don't have medical.

So when my Oscar plan was rejected, I automatically got removed from vision and dental coverage. Hence I had a two-month gap in healthcare coverage for no reason.

Now, I want you to close your eyes - not literally because you're reading this article - but pretend I had $100,000 in the bank and wanted to get the most expensive plan the marketplace had.  New York says it don’t matter.

I could not get an Oscar plan. I could not get an Empire vision and dental plan. I was only eligible for Medicaid. Yes, you heard me right. It doesn't matter if you're a millionaire in New York and can afford the premium payments to the insurance company. If you don’t have a guaranteed salary you have to go on Medicaid.

But I can kind of understand that. What would the insurance market be like if people were given the freedom to pause their insurance because they can't afford the insurance premiums that month?

The only logical answer I can think of is that maybe insurance companies don't make as much money, and therefore can't spread risk across a large enough number of plan holders. But is there an authoritative source that prevents them from rejecting applications for that reason? Shockingly I would find out that the most likely answer to that question is no.

What I can't understand is why I didn't find this out on November 9th when a NYS representative walked me through my application. I also didn't find out at my November 30th court appeal to backdate my coverage so I could get a checkup.

I didn't find this out on November 30th because NYS canceled my appeal an hour prior to my scheduled time because there "was no one available for my hearing."

Are you kidding?

THEY PICKED THE DATE FOR THE APPEAL.

I would have been okay with learning this information on either of those dates - November 9th or November 30th . To make matters worse, the appeal will only backdate your coverage to cover medical costs that were already incurred.

To put it differently: you are not incentivized to be proactive. If I had just said, fuck it, I'm going to get a check-up anyway, and pray NYS will help me, hilariously that would be a better scenario. But why should I have to take that risk?

Let me ask you something. Would you take that risk? I didn't think so.

I bit my tongue for an entire month. I planned to take the L until my new scheduled court appeal on December 29th.

But on a random day in December, I couldn't take it anymore. I could no longer get coverage for 2021 and so I picked up the phone to voice my frustrations again. By sheer dumb luck, I spoke with a knowledgeable rep named Tammy who told me that for 2022 I was only eligible for Medicaid. I did not want to mention her name in this article, but I wouldn’t have coverage this year if she did not explain this to me. Thank you, Tammy.

I'd like to go on a slight tangent from telling this story in chronological order for a bit. I need to provide some more context about the road that led me to realize how big of an issue this is.

I've had health insurance for most of my life. When I wasn't covered by an employer I had the benefit of being covered under my parents' insurance. So my entry point into discovering that I was only eligible for Medicaid was through the NYS marketplace and their reps who follow department work instructions.

I can hear the responses to that: "If you did your research you would have found out you were only eligible for Medicaid. You don't need someone else to tell you."

To that, I would say that is a lazy response to the case I am making for a better healthcare system. Remember, the entire premise of my argument is how to avoid gaps in health coverage.

If you think I should have done my research, I would ask you this question: What makes someone think that they need to sign up for Medicaid as opposed to a different plan? And do you even know what Medicaid is?

In fact, I purposely left it out of the definitions in the above section "Health Insurance 101" to drive the point home.

If you've ever been out of work, do you think: hmmm, I think I want to sign up for Medicaid tomorrow? NO!

Remember, I called NYS and they walked me through the application. Not once did they ask about qualifying events, or explain special enrollment based on plan types .

I bet if I asked them, they probably weren't aware of Governor Cuomo's announcement earlier that year…

I mentioned I spoke with a woman named Tammy on December 13th. She explained the nuances to me. She was clearly experienced enough to fill in the gaps in my knowledge.

She said people with a projected income under 12k are on Medicaid no matter what. My 2021 income had no effect on what coverage I was eligible for in 2022.

When I heard her say this on the phone my heart dropped into my stomach.

Is every single founder in the United States on Medicaid? Now I get why Sara Blakely was selling Spanx while working in door-to-door fax machine sales. But she was in Georgia, I'm in New York, and income alone doesn’t qualify you for Medicaid in Georgia.

All in all, I'd sum up the journey of getting covered in the following way:

Issues in the individual marketplace's appeal process and a lack of guardrails for self-employed individuals signing up for coverage led me to have a gap in healthcare coverage for the final two months of 2021. I also caught COVID-19 in December. This could have been a huge issue if I had medical complications from the virus.

I was relentless and got healthcare coverage for 2022, I have also been able to keep some of my doctors. But I didn't keep my therapist for example. Not everyone takes Medicaid.

To further comment on mental health professionals and acceptance of insurance, I'm willing to go out on a limb and say that no virtual-based mental health professional companies (including BetterHelp, Talkspace, etc.) take Medicaid. Isn't this an important component of healthcare?

For background, I left an employer in July 2021 and after procrastinating for several reasons I decided to use the marketplace. But it didn't matter that I procrastinated, I am positive I would have faced the same issue whenever I applied.

That's the problem with Healthcare in the United States.

So with all that being said how do these events relate to the three observations I listed at the beginning of this?

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates

3. Insurance companies need to be held accountable

We need to reevaluate the rules that dictate enrollment because there is no real reason to have them for single individuals in NYS. The 15-day rule is unwritten and is only used by insurance companies to avoid doing what I believe they are ethically required to do: allow people to buy insurance.

We need laws for billing dates because patients are neither:

1. Listened to when service dates should be changed due to unforeseen circumstances, or

2. Incentivized to make payments (services billed during a gap in healthcare coverage go to collections but don't get reported to credit agencies)

Billing dates by doctors and care providers are dictated by insurance company HIPPS codes. So if you go to the doctor for a procedure, they will use the codes provided by your insurance company to determine if they will subsidize the procedure.

For example, I had to get something called a Holter monitor toward the end of January 2021. Because of a snowstorm in New York, I could not return the Holter monitor until February 2021 (my coverage stopped on Feb 1st). My insurance company billed the entire procedure in February, and will not adjust it. So I am forced to pay out of pocket. If I was aware of the date they were going to bill me for the Holter monitor, I would have declined it.

Something to consider is: How do we design the enrollment process to help new individual marketplace applicants avoid high bills simply due to billing dates - assuming the doctor accepts that method of insurance?

The work instructions of NYS Health Department representatives and protocols of Insurance company representatives like Oscar and Empire are irreconcilable. In some cases, protocols create gaps in healthcare coverage even when NYS residents follow marketplace guidelines in good faith.

A NYS Health Department representative told me she knows of people that paid premiums for 6 months only to find out the following: the insurance company canceled their coverage, and their healthcare services were billed in a gap period… they were forced to pay out of pocket). How many people are being affected by this?

These issues cannot be resolved by the NYS Health Department alone. Representatives who speak to health insurance applicants on the department's behalf are operating within a limited scope of authority and so is the entire Health Department.

By law, insurance companies are not required to backdate coverage. This means that it doesn't matter if the Board of Health passed a resolution about racism being a Public Health Crisis they cannot solve this issue regarding gaps in Healthcare coverage.

I believe resolving this issue means following formal processes for complaints and rule changes  - similar to how Daniel Lubetzky filed a citizen petition when the FDA forced Kind to stop calling four of their products "healthy" because they contained plant-based fats.

We must follow the proper channels for legislative action. We must be respectful yet stand firm on the principles I have outlined. We must demand accountability on the part of Insurance companies.

We must advocate for transparent reporting by the NYS Health Department to quantify how much these protocols contribute to gaps in healthcare coverage, high out-of-pocket medical bills, and coverage cancellations for residents of NYS. I cannot speak to the process in other states, but I imagine that this is an issue across the U.S.

Something to think about: How many people are playing catch up with medical bills simply because of plausible deniability by health insurance companies? The world may never know…

But we will only never know if we choose not to act once we have this information.  I plan to submit a formal proposal to NYS for a rule change. If you would like to contribute as an informal supporter (by reviewing or discussing the document), or if you would like to be a formal supporter and sign the proposal, please send me an email at Lance.counteducation@gmail.com

There is no source of truth to help single individuals avoid gaps in healthcare coverage.

Even if a New York State (NYS) resident follows Health Department guidelines on the health plan marketplace, they can still have:

1. Unforeseen difficulty signing up for a plan

2. Gaps in healthcare coverage due to poorly designed software and flaws in the enrollment and appeals process

I believe that the protocols followed by health departments - specifically NYS - and insurance companies are irreconcilable when someone wants to avoid a gap in healthcare coverage.

Each entity either:

1. Assumes plausible deniability when software or work instructions contribute to a gap in healthcare coverage; or

2. They have not adequately trained their representatives to guide applicants to avoid issues altogether.

Single New Yorkers - who do not read this article - and do not have a predictable salary will likely have a gap in healthcare coverage no matter what they do.

They also have to sign up for Medicaid even if they have plenty of cash to cover insurance premiums for plans with companies like Oscar Health.

My first-hand observations after using the NYS marketplace to get healthcare coverage are the following:

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates used to invoice for medical procedures

3. Insurance companies need to be held accountable when necessary

First, this article is not subjective. Even though everything here is based on first-hand experience - and I do express my frustrations about the process of getting healthcare coverage - I am not writing an "opinion piece" in the traditional sense of the phrase. I am not demanding a remedy for the harm that this series of events caused. That ship has sailed. I figured it out. I'm covered. And technically, no one owes me anything.

Second, I have organized these observations clearly and concisely based on several factors. You don't have to read this entire article. If your situation follows the same fact pattern as mine, these results will be repeatable. I doubt anything has changed since I applied for coverage. I also helped a family member get coverage by using these insights.

Third, I have enough distance from the events that took place to voice my frustrations and support them with my notes from over a dozen conversations that I had with representatives from:

1. The NYS Health Department

2. Publicly traded Health Insurance Companies (Oscar Health and Empire).

P.S. I will share the fact pattern - within certain limitations.

I hate when articles turn into dictionaries. Give me the terms, and don't define them, so I can just look them up, or put all of the definitions in one place so I can refer to them if I need to, and then get on with the rest of the article.

I'm going to do the latter.

If you don't want a refresher on all of these terms, you can skip to the section of this article titled "🏥 Why Am I Speaking Up About Healthcare?" It's important to note that I will need to use some of this jargon to explain my experience. Some of these phrases are not common (ex. work instructions used by NYS Health Department reps).

• Healthcare coverage: The ability to go to a doctor's office or hospital and have your medical expenses either fully or partially subsidized or "covered.."

• Open Enrollment periods: An open enrollment period is the time period when individuals and employees may enroll in health insurance or make changes to their coverage.

• Qualifying Events: A qualifying event is an event that triggers a special enrollment period for an individual or family to purchase health insurance outside of the regular annual Affordable Care Act (ACA) open enrollment period.

• Special Enrollment Periods: Special enrollment periods mean that once you have the qualifying event that is listed earlier, you can use the individual marketplace to sign up for coverage within 60 days.

• NYS Health Department: no official definition on their website that I could find.

• New York State of Health (NYSOH): the official health plan marketplace that connects New Yorkers to affordable health coverage (source).

• 15 Day Rule: The 15-day rule is a policy for the NYS of health. It dictates the deadline you need to enroll by in order to get health coverage in the subsequent month. A NYS Health Department representative told me that it is not codified in the NYS law or NYCR. It only exists in the work instructions of each representative.

• Work Instruction: guidelines followed by each NYS Health Department representative when speaking with an applicant.

• Transaction ID: A unique identifier used by both the Health Department and insurance company. Strangely enough, this identifier disappeared for both parties after the estate change that NYS Health Department performed for my account.

In the Greylock podcast episode "Talking Politics," Chris Yeh and Reid Hoffman had a discussion. The podcast begins with Reid making the following statement:

"In an increasingly politicized world, it's harder and harder for CEOs to keep business and politics separate. There are some who believe that it's more important to keep it separate because politicization has grown so much worse. However, I actually believe that this means the opposite. That it's critical for business leaders to speak up…and lead on key things in politics more than ever before. Nevertheless, it's an action that should be approached carefully."

Reid mentioned that he decided to speak up about politics when he realized he was not making partisan comments but speaking on democracy as a whole.

Currently, in my career, as a self-employed individual and founder, I realize it is necessary to comment on the Healthcare system. I am deciding to speak up because I do not feel like my comments are disparaging to the United States, New York, or even to the representatives that I worked with in order to get healthcare coverage. No, my comments are about healthcare as a whole.

In a global pandemic, keeping healthcare and business separate is more difficult. It is critical for business leaders to speak up and lead on key topics in Healthcare. I don't claim to be a business leader, but I would like to open up the conversation to address issues in Healthcare.

I realize that speaking about a topic as delicate as healthcare in America - especially when I am not a healthcare professional - is a reason for approaching this topic with caution. But in the past few months, I have noticed the extent of the issues in America's Healthcare System and I would like to outline these issues.

To reiterate, my first-hand observations are:

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates

3. Insurance companies need to be held accountable

Now, what does all of that mean?

I'll succinctly explain my experience with as little jargon as possible. Note that this analysis will focus on the enrollment process in NYS, of which I am a resident. I'll tell this story in chronological order because it's easy to follow that way.

On November 9th I enrolled in a medical and dental plan, only to find out in mid-December that I wasn't eligible for either.

As a byproduct of the 15-day rule, I experienced a two-month gap in healthcare coverage even though I was proactive in avoiding that gap. When I applied for a plan, I picked Oscar and Empire because I knew those companies and they had the lowest monthly premium. I projected I could still make the premium payments, despite my business' cash burn rate.  The additional good news is that I would also have a grace period of 30 days to make the first premium payment.

My plan was scheduled to begin on December 1st - see the 15-day rule in the Health Insurance 101 section above - so I wouldn't have to make the payment until December 31st.

So then the question is, why did I have an issue getting insurance?

The enrollment period.

Up until that time, I had believed signing up in November 2021 would lead to coverage for the rest of 2021 and 2022.

What this meant was I was signing up for a 2021 open enrollment period, but I was getting rejected because Oscar perceived I was in a special enrollment period for 2021 due to a qualifying event. Oscar got confused and kicked my application to the curb. It took over 10 calls to get Oscar and NYS to clarify why they rejected the application. Oscar and NYS said the application was canceled due to nonpayment but this is flat out wrong. I had a 30 day grace period to make the first premium payment. In fact, it was an Oscar representative that told me about this grace period.

By the time I figured everything out, it was too late to get coverage for December 2021.

Now let me be clear, I am focusing on how I tried to avoid not having coverage in November-December 2021, and why neither party (NYS or Oscar) understood what was going on.

When I was trying to avoid having a gap in healthcare coverage, I input my 2021 income. Makes sense. I was enrolling for 2021 coverage.

That income was over the threshold for Medicaid - which I learned about on December 13th. But, due to the plan tier that I selected when I first submitted my application the marketplace software had no idea how to handle my situation. But it wasn't just the software. It was the employees at Oscar and the New York State of Health (NYSOH) marketplace.

Why? I'm glad you asked. This is very important.

NYS and Oscar canceled my application due to their perception of my ineligibility for the special enrollment period. I was applying because of my perception of an open enrollment period. Both NYS and Oscar were doing the equivalent of the spiderman meme for the better part of a month, plausibly denying their ignorance of the fact that:

1. I was eligible for the 2021 open enrollment period

2. My income for 2021 was high enough that I should have been eligible to keep the Oscar medical plan starting in December.

3. Nonpayment was not a factor because I had a 30 day grace period

It's possible that someone familiar with the healthcare system could disagree with the above comments for a few reasons.

First, they could say I'm wrong and I missed the open enrollment period for 2021. My only option was the special enrollment period of 60 days that begins after involuntary loss of coverage, or a different qualifying event.

Second, they could say the healthcare plan tier I selected was not open for special enrollment.

Neither of these arguments is valid.

I didn't miss open enrollment. But what do I mean I didn't miss open enrollment? I mean that my conclusion about being able to apply for healthcare coverage whenever I wanted was right, even though my logic was wrong.

I wrongly assumed that even if we weren't dealing with a global pandemic, I could enroll in health insurance whenever I wanted, so I applied on an ordinary day in November. My conclusion was correct because Cuomo made an announcement that literally made this true for 2021. I haven't researched open enrollment periods for years like 2018, but I don't think I could have written this four years ago.

The following quote is from a Frequently Asked Questions (FAQ) document titled "NYSOH COVID-19 related Q & A's" issued by the official New York State Health Plan marketplace:

"Governor Cuomo announced on March 23, an extension of the Open Enrollment Period to December 31, 2021. Extending the Open Enrollment Period to December 31, 2021 helps to align New York with the federal Public Health Emergency which HHS signaled they will extend through the end of 2021."

Here's a link to the press release about the announcement. But you don't have to click it. The link is broken and has been for multiple months: press release

In my opinion, there is a fundamental issue with the software of the NYS Marketplace. It was never updated to address Governor Cuomo's announcement. Granted, individuals looking to sign up for a plan should have some basic level of knowledge to sign up for coverage, but there should be:

1. Guardrails: Guardrails that enable top-down announcements - like the one from Cuomo - to make their way into the software or at least the work instructions of NYS Health reps.

2. Culture: A culture that prioritizes the implementation of those guardrails in the software.

“Software can help with this if you can create a culture around it.” - Alexis Ohanian

How many people in NYS had a gap in healthcare coverage because of this oversight?

Note, that NYSOH enrollment surged in 2021. To see a press release that explains how much enrollment surged, click here. What are they defining as enrollment? Technically I enrolled for coverage through the marketplace, but NYSOH canceled it.

Why do I keep talking about the NYS marketplace? I can hear people saying:

"Why didn't you just go to Oscar's website and apply for the coverage if the marketplace process is so bad…"

You can't.

I confirmed with Oscar and NYS that all roads - for individuals not covered by employers - lead to the NYS marketplace website…soo, yup.

Further, because I faced no friction in signing up for a plan with Oscar, I assumed everything was all good and I could at least get coverage starting in December.  Here comes the peanut gallery again:

"Why did you think everything was all good? Clearly, it wasn't."

The answer is, Oscar mailed me an insurance card LOL.

So far, I've addressed why as a single individual you cannot avoid the NYS marketplace and its issues.

Up until now, I've been describing how my medical coverage was canceled. I haven't described its effect on my vision and dental coverage.

NYS' system needs you to select two plans. Picture it like the marketplace wants a PB&J sandwich. Your healthcare coverage is the PB&J sandwich - I don't like jelly - but you get the idea.

If you pick Peanut Butter (vision and dental) but no Jelly (medical)… NO SOUP FOR YOU!

Or rather, no healthcare coverage for you. The NYS system has a guardrail that keeps you from enrolling in vision and dental if you don't have medical.

So when my Oscar plan was rejected, I automatically got removed from vision and dental coverage. Hence I had a two-month gap in healthcare coverage for no reason.

Now, I want you to close your eyes - not literally because you're reading this article - but pretend I had $100,000 in the bank and wanted to get the most expensive plan the marketplace had.  New York says it don’t matter.

I could not get an Oscar plan. I could not get an Empire vision and dental plan. I was only eligible for Medicaid. Yes, you heard me right. It doesn't matter if you're a millionaire in New York and can afford the premium payments to the insurance company. If you don’t have a guaranteed salary you have to go on Medicaid.

But I can kind of understand that. What would the insurance market be like if people were given the freedom to pause their insurance because they can't afford the insurance premiums that month?

The only logical answer I can think of is that maybe insurance companies don't make as much money, and therefore can't spread risk across a large enough number of plan holders. But is there an authoritative source that prevents them from rejecting applications for that reason? Shockingly I would find out that the most likely answer to that question is no.

What I can't understand is why I didn't find this out on November 9th when a NYS representative walked me through my application. I also didn't find out at my November 30th court appeal to backdate my coverage so I could get a checkup.

I didn't find this out on November 30th because NYS canceled my appeal an hour prior to my scheduled time because there "was no one available for my hearing."

Are you kidding?

THEY PICKED THE DATE FOR THE APPEAL.

I would have been okay with learning this information on either of those dates - November 9th or November 30th . To make matters worse, the appeal will only backdate your coverage to cover medical costs that were already incurred.

To put it differently: you are not incentivized to be proactive. If I had just said, fuck it, I'm going to get a check-up anyway, and pray NYS will help me, hilariously that would be a better scenario. But why should I have to take that risk?

Let me ask you something. Would you take that risk? I didn't think so.

I bit my tongue for an entire month. I planned to take the L until my new scheduled court appeal on December 29th.

But on a random day in December, I couldn't take it anymore. I could no longer get coverage for 2021 and so I picked up the phone to voice my frustrations again. By sheer dumb luck, I spoke with a knowledgeable rep named Tammy who told me that for 2022 I was only eligible for Medicaid. I did not want to mention her name in this article, but I wouldn’t have coverage this year if she did not explain this to me. Thank you, Tammy.

I'd like to go on a slight tangent from telling this story in chronological order for a bit. I need to provide some more context about the road that led me to realize how big of an issue this is.

I've had health insurance for most of my life. When I wasn't covered by an employer I had the benefit of being covered under my parents' insurance. So my entry point into discovering that I was only eligible for Medicaid was through the NYS marketplace and their reps who follow department work instructions.

I can hear the responses to that: "If you did your research you would have found out you were only eligible for Medicaid. You don't need someone else to tell you."

To that, I would say that is a lazy response to the case I am making for a better healthcare system. Remember, the entire premise of my argument is how to avoid gaps in health coverage.

If you think I should have done my research, I would ask you this question: What makes someone think that they need to sign up for Medicaid as opposed to a different plan? And do you even know what Medicaid is?

In fact, I purposely left it out of the definitions in the above section "Health Insurance 101" to drive the point home.

If you've ever been out of work, do you think: hmmm, I think I want to sign up for Medicaid tomorrow? NO!

Remember, I called NYS and they walked me through the application. Not once did they ask about qualifying events, or explain special enrollment based on plan types .

I bet if I asked them, they probably weren't aware of Governor Cuomo's announcement earlier that year…

I mentioned I spoke with a woman named Tammy on December 13th. She explained the nuances to me. She was clearly experienced enough to fill in the gaps in my knowledge.

She said people with a projected income under 12k are on Medicaid no matter what. My 2021 income had no effect on what coverage I was eligible for in 2022.

When I heard her say this on the phone my heart dropped into my stomach.

Is every single founder in the United States on Medicaid? Now I get why Sara Blakely was selling Spanx while working in door-to-door fax machine sales. But she was in Georgia, I'm in New York, and income alone doesn’t qualify you for Medicaid in Georgia.

All in all, I'd sum up the journey of getting covered in the following way:

Issues in the individual marketplace's appeal process and a lack of guardrails for self-employed individuals signing up for coverage led me to have a gap in healthcare coverage for the final two months of 2021. I also caught COVID-19 in December. This could have been a huge issue if I had medical complications from the virus.

I was relentless and got healthcare coverage for 2022, I have also been able to keep some of my doctors. But I didn't keep my therapist for example. Not everyone takes Medicaid.

To further comment on mental health professionals and acceptance of insurance, I'm willing to go out on a limb and say that no virtual-based mental health professional companies (including BetterHelp, Talkspace, etc.) take Medicaid. Isn't this an important component of healthcare?

For background, I left an employer in July 2021 and after procrastinating for several reasons I decided to use the marketplace. But it didn't matter that I procrastinated, I am positive I would have faced the same issue whenever I applied.

That's the problem with Healthcare in the United States.

So with all that being said how do these events relate to the three observations I listed at the beginning of this?

1. We need to reevaluate the rules that dictate enrollment

2. We need laws for billing dates

3. Insurance companies need to be held accountable

We need to reevaluate the rules that dictate enrollment because there is no real reason to have them for single individuals in NYS. The 15-day rule is unwritten and is only used by insurance companies to avoid doing what I believe they are ethically required to do: allow people to buy insurance.

We need laws for billing dates because patients are neither:

1. Listened to when service dates should be changed due to unforeseen circumstances, or

2. Incentivized to make payments (services billed during a gap in healthcare coverage go to collections but don't get reported to credit agencies)

Billing dates by doctors and care providers are dictated by insurance company HIPPS codes. So if you go to the doctor for a procedure, they will use the codes provided by your insurance company to determine if they will subsidize the procedure.

For example, I had to get something called a Holter monitor toward the end of January 2021. Because of a snowstorm in New York, I could not return the Holter monitor until February 2021 (my coverage stopped on Feb 1st). My insurance company billed the entire procedure in February, and will not adjust it. So I am forced to pay out of pocket. If I was aware of the date they were going to bill me for the Holter monitor, I would have declined it.

Something to consider is: How do we design the enrollment process to help new individual marketplace applicants avoid high bills simply due to billing dates - assuming the doctor accepts that method of insurance?

The work instructions of NYS Health Department representatives and protocols of Insurance company representatives like Oscar and Empire are irreconcilable. In some cases, protocols create gaps in healthcare coverage even when NYS residents follow marketplace guidelines in good faith.

A NYS Health Department representative told me she knows of people that paid premiums for 6 months only to find out the following: the insurance company canceled their coverage, and their healthcare services were billed in a gap period… they were forced to pay out of pocket). How many people are being affected by this?

These issues cannot be resolved by the NYS Health Department alone. Representatives who speak to health insurance applicants on the department's behalf are operating within a limited scope of authority and so is the entire Health Department.

By law, insurance companies are not required to backdate coverage. This means that it doesn't matter if the Board of Health passed a resolution about racism being a Public Health Crisis they cannot solve this issue regarding gaps in Healthcare coverage.

I believe resolving this issue means following formal processes for complaints and rule changes  - similar to how Daniel Lubetzky filed a citizen petition when the FDA forced Kind to stop calling four of their products "healthy" because they contained plant-based fats.

We must follow the proper channels for legislative action. We must be respectful yet stand firm on the principles I have outlined. We must demand accountability on the part of Insurance companies.

We must advocate for transparent reporting by the NYS Health Department to quantify how much these protocols contribute to gaps in healthcare coverage, high out-of-pocket medical bills, and coverage cancellations for residents of NYS. I cannot speak to the process in other states, but I imagine that this is an issue across the U.S.

Something to think about: How many people are playing catch up with medical bills simply because of plausible deniability by health insurance companies? The world may never know…

But we will only never know if we choose not to act once we have this information.  I plan to submit a formal proposal to NYS for a rule change. If you would like to contribute as an informal supporter (by reviewing or discussing the document), or if you would like to be a formal supporter and sign the proposal, please send me an email at Lance.counteducation@gmail.com