AI Call Center Hell

By M. Snarky

Rotary telephone, whiskey bottle and glass, ledger, and newspaper on desk
AI generated image.

Being that I am a man of a certain age, I now qualify for Medicare. This does not excite me in the least. I already have great private health insurance, so I don’t need, nor do I want Medicare because, to be perfectly frank, in all of the decades of my adult life, every single one of my experiences with government run programs have been resolutely negative. This is because there is a systemic problem when the government has a monopoly on services, the problem being that the employee attitude is both of impunity and indifference. Don’t get me started on collective bargaining.

Anyhow, the government forces you to pay for and enroll in Medicare anyway. If you don’t enroll,  you’ll be penalized and fined and maybe eventually thrown into a dungeon and beaten by a unionized government worker until you comply or end up in traction. This is the point at which they’ll tell you how great your post-beating medical treatment was, because without it, you’d somehow be worse off.

Like the tooth fairy, leprechauns, chupacabra, dragons, and all other fictitious characters, “free” Medicare simply does not exist. In fact, exactly zero government programs are free, at least not in the technical sense. Not only are they not free, they’re also ridiculously expensive and notoriously inefficient when compared to open markets.

Here’s my argument: If Person A is paying for Person B’s “free” government program, the entire free designation falls flat on its face. At best, it is a Ponzi scheme at the grandest scale possible. At worst, you’ll get someone’s lung transplant while someone else gets your hip replacement.

I don’t believe that “Land of the free” was ever intended to be bastardized into the land of the free stuff. But here we are.

Oddly, the Social Security Administration (SSA) handles Medicare enrollment, premium collection, and eligibility determination for Medicare. I’m not sold on this being a good idea, but I’m equally sure some bureaucrat can throw together a word salad to explain why it is a good idea even if it doesn’t’ make any sense to anyone outside of the beltway.

Now, you might think that enrolling in Medicare would be relatively easy with modern technology, vis-à-vis, the Internet, ID.me, and Real ID, but as is usual with government services, it is anything but easy.

In summary, the lengthy process goes like this:

Step 1: Determine Your Eligibility.

Step 2: Choose Your Enrollment Method.

Step 3: Complete the Application.

Step 4: Await Confirmation and Medicare Card delivery by the USPS.

Step 5: Choose Your Coverage Structure (After Enrollment).

Key Deadlines to Remember

Initial Enrollment Period: 7 months total—starts 3 months before your 65th birthday, includes the month of, and ends 3 months after.

Penalty: Delaying Part B without qualifying employer coverage may result in a late enrollment penalty.

General Enrollment Period: If you miss your window, you can sign up between Jan 1 – Mar 31 each year, with coverage starting July 1, though penalties may apply.

With all of these penalties, you’d think that this was a sporting event.

The foregoing doesn’t include setting up your ID.me account that is required before setting up your SSA account, which is just another huge time suck.

After spending approximately 8-hours just to set up my Medicare account, I finally received my Medicare card a couple of weeks afterward. I needed to make a change to my Medicare Part B coverage because I could not opt out during enrollment, so I called 1-800-MEDICARE to request the change, which went like this:

Ring-ring: “We’re currently experiencing longer than normal hold times. If your call is not urgent, you may wish to call back at a later time. You also can find answers quickly to most questions at http://www.medicare.gov. In a few words, briefly tell me the reason for your call today.” The synthesized, friendly sounding male voice was remarkedly calming, and reassuring.

“Enrollment change.”

“Got it, enrollment change.”

“Did you know that you can find answers to most questions at http://www.medicare.gov?”

My eyes rolled.

“Please say or enter your Medicare card number.”

“D1SR-3SP-3KTS.”

“Did you say, “Dee-one-ess-are-three-ess-tee-three-kay-tee-ess?”

“No.”

“Let’s try that again. Please say or enter your Medicare card number.”

“D1SR-3SP-3KTS.”

“Did you say, “Bee-one-ess-are-three-ess-tee-three-kay-tee-ess?”

“NO!”

“Okay, let’s try that again. Please say or enter your Medicare card number…”

Now the calming reassuring voice sounded paternalistic and patronizing. This is when I saw red and temporarily lost consciousness. I woke up to the rapid BEEP-BEEP-BEEP-BEEP fast busy signal on my phone. They hung up on me.

I called again a day later, and had a similar experience, but this time I just yelled “AGENT!” into my phone anytime the AI programmed call center agent prompted me. After about a half dozen of these, I finally got this response:

“Agent, got it. Would you like me to connect you with an agent?”

“YES!” Please, for the love of god, yes, yes, yes!

“Please hold.”

Queue up the cheesiest on-hold piano music you can imagine. Think of a Liberace wannabe playing a rendition of Hotel California in a smoky off-strip Las Vegas casino. Ten minutes later, I heard a human voice:

“Thank you for calling Medicare, my name is Felicia, how can I help you?”

“Hi Felicia, I need to make a change to my Medicare Part B coverage.”

“Okay, may I please first get your social security or Medicare Card number?”

“D1SR-3SP-3KTS.”

“Date of birth?”

“July 4, 1961.”

“Address?”

“1060 W. Addison St., Chicago, IL 60613.”

“First and last name?”

“M. Snarky.”

“Thank you for your patience, Mr. Snarky. If you need to make a change to your Medicare coverage, you’ll have to call the Social Security Administration. Would you like me to give you that number?”

I replied with a dejected, “Yes, please,” as I was thinking of something like 1-800-EAT-SHIT.

“That number is 1-800-772-1213.”

“Thank you.”

“Is there anything else I can do for you, Mr. Snarky?”

Since it was impossible for Felicia to give me a long pour of whiskey on the rocks over the phone, I replied, “No, thank you for your help.”

I gave myself a long pour of whiskey on the rocks as I researched how to hack an automated phone system.

It took me a few days to mentally prepare myself to call the SSA at 1-800-772-1213.

“Thank you for calling the Social Security Administration. For training and quality assurance, your call will be monitored or recorded. How can I help you today?” This was in an eerily similar synthesized, friendly sounding male voice as Medicare was.

“AGENT!”

“Did you know that you can find answers to most questions at http://www.ssa.gov?”

Or not.

“In a few words, briefly tell me the reason for your call today.”

“AGENT!”

“Did you know that you can find answers to most questions at http://www.ssa.gov?”

My god, the sadistic people that designed this system need to be thrown into a dungeon and beaten to a pulp.

“In a few words, briefly tell me the reason for your call today.”

“AGENT!”

“Agent, got it. Would you like me to connect you with an agent?”

“YESSSS!” A tear rolled down my cheek.

“Please hold.”

Another cheesy on-hold music experience; a seriously bad Musak rendition of Herb Alpert’s, Tijuana Brass tune.

“Thank you for calling the Social Security Administration, my name is Rudy, how can I help you?”

“Hello Rudy, I need to make a change to my Medicare Part B. Can you help me with this?”

“Yes, but first, may I please get your social security or Medicare Card number?”

“D1SR-3SP-3KTS.”

“Date of birth?”

“July 4, 1961.”

“Address?”

“1060 W. Addison St., Chicago, IL 60613.”

“First and last name?”

“M. Snarky.”

“Thank you for your patience, Mr. Snarky. Since you are a new enrollee to Medicare, if you need to make a change to your Medicare coverage, you have to call Medicare directly. Would you like me to give you that number?”

Again, I saw red, and the last thing I remembered was an empty whiskey bottle shattering on the floor.

For round three, I decided to train up. I scoured the interwebs for as much data as I could get to prepare myself for victory. This ended up being a hellish black hole of misleading, often contrary information that I barely escaped from with my sanity intact.

Indeed, it turns out that the SSA is in charge of managing Medicare accounts, and I must’ve had the bad luck of either getting an SSA agent on his first day in the call center, or Rudy was just gaslighting me for fun to score points with his call center colleagues.

I lined up six shots of whiskey, one for every time the AI agent asked me to repeat myself. I wasn’t sure six would be enough, but it was a start.

I called call the SSA again at 1-800-772-1213.

This time, I changed my tactic; instead of yelling AGENT! whenever prompted, I politely said, “Medicare coverage change.”

…“In a few words, briefly tell me the reason for your call today.”

“Medicare coverage change.”

“Did you say, ‘Medicare coverage change.’”

“Yes!” One shot down.

“Did you know that you can find answers to most questions at http://www.ssa.gov?”

Most is definitely the keyword here. I had to bite my lip. This qualified as a repeat prompt, so I took another shot.

“Please hold, I’ll connect you to an agent.”

HUZZAH! I think I hacked the system!

I was connected to a nice person named “Theo,” who was able to direct me to an online form buried deep within the bowels of http://www.ssa.gov (specifically, form CMS-1763-508C) which allows a person to modify their Medicare coverage…but you either have to mail it in or drop it off at a local SSA office. No electronic submission option. This is mind numbingly dumb. Anyway, that was all there was to it. This was all I needed from the beginning—a short form to fill out. Why was this process so damn hard…and so unbelievably frustrating?

This entire process took about 12-hours of my personal time—a half of a day of my life burned for AI call center hell, and bureaucratic paper shuffling bullshit.

I’m filing this complaint letter:

Dear Uncle Sam,

My time is not free. Not only is my time not free, but my time is also extremely limited, and my time has immense value. In fact, this is true for everyone else’s time that is consumed for Medicare, Social Security, or IRS paperwork.

How dare you require us to give our time for free and threaten us with punitive fines or incarceration if we don’t comply. Wasn’t slavery abolished way back in 1865 with the 13th Amendment? How exactly is it that what you are imposing upon us—forcing people to provide free labor without compensation—not a form of enslavement in and of itself?

Tell me, where do we send the invoices for our time? At the very least you should send each of us a bottle of good old American whiskey for our trouble. I’ll take a bottle of Indiana Rye.

Yours truly,

A. Disgruntled Citizen

Might be dungeon worthy, but someone has got to take a stand, right?

Instagram: @m.snarky

Blog: https://msnarky.com

©2026. All rights reserved.

Zombie Shifts

Story 41 of 52

By M. Snarky

For the last three months I have been working the overnight shift on a retail store network equipment refresh project for a global shoe brand. Due to contractual obligations, I am not at liberty to disclose the company name, but what I can say is that they’re kind of a big deal and I’m grateful for being part of this project.

However, working the night shift is hard for us humans. It throws our circadian rhythm so far out of whack that what once was perhaps a pleasant samba groove in 4/4 time becomes an offbeat primal sound more like that of a chimpanzee on meth beating on a metal trash can with a crowbar.

Getting out of the familiar 8 AM to 6 PM daytime rat race schedule and into the 6 PM to 4 AM nocturnal racoon schedule – the wee hours of which, incidentally, are the same as those of the tweakers, serial killers, zombies, vampires, and aging rock stars – is certainly not for everyone. I don’t love it, but it is necessary and mercifully temporary.

Your instincts are that when it gets dark outside, you are supposed to be winding down, not up. By 2:00 AM, you find yourself in an epic mental battle between your mind desperately wanting to sleep and your mind needing to stay wide awake and mentally sharp. You oscillate between these wildly opposite mental states. It’s not easy. It’s an eternal battle between Greek gods Hypnos and Argus Panoptes.

But you find ways to stay awake, like reading a book, listening to upbeat music, or playing a newly discovered online version of Whist, a popular 19th century card game that Dostoevsky mentions in The Brothers Karamazov that I had to Google when I read it. Whist was a predecessor of modern Contract Bridge, which is my dad and stepmom’s favorite card game. Sometimes I find myself doing all of these at once.

I feel oddly guilty about pouring a dram of whiskey at 4:00-AM and getting up at the crack of noon. It feels strange going to sleep for 8-hours and waking up on the same day. And even though I do typically sleep for 8-hours, I still feel tired. But why though? I mean, it’s just a time shift, right? I should feel totally normal, right? Well, not exactly…

In 1972, geologist Michel Siffre, one of the early pioneers of experiments on human circadian rhythms, spent six months in Midnight Cave in southern Texas. Siffre suffered both acute and lasting effects, only partially recovering from the isolation physically, mentally, and emotionally. His internal clock shifted to 48-hours, and he completely lost track of hours, days, weeks, and months. He stayed awake for 36-hours straight and slept for 12-hours at a stretch. His Day 63 inside Midnight Cave was really Day 77 above ground.

Siffre later described the experience as: “A slow slide into madness.” He talked to insects for company. He found comfort in his own voice, but silence always returned, crushing and relentless. After 180 days, Siffre’s team removed him from the cave. To him, only 151 days had passed. 29 days were unaccounted for in his daily diary. Time literally slowed down, stretched out, and slipped away from him.

So, from Siffre’s experiments we can conclude that our circadian rhythm is nothing to trifle with or you just might risk losing your mind a little bit. Duly noted. It’s still May, right?

I have one more week to go. I hope I make it. But if you see me talking to insects, you’ll understand why.

Instagram: @m.snarky

Blog: https://msnarky.com

©2025. All rights reserved.