The law school at my university offers a “legal aid clinic,” where students can get free legal advice. This story does not take place there. It takes place in the philosophy department with a philosophy professor.

Professor: *Answering phone* “Hello, this is [Professor].”

Long pause.

Professor: “Oh, you must want the legal aid clinic. Let me find you their number.”

Longer pause.

Professor: “So, you want to know if there’s an ethical argument here before you consider a legal one?”

Very long pause.

Professor: “No. It’s not ethical to sue your mother because she gave your dog an unoriginal name.”

He hangs up and turns to a colleague.

Professor: “How do I make this an unlisted number?”

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I work in Medicare insurance, getting people coverage through part C and part D. My job has many, many rules, and serious consequences for breaking them. One caller’s situation stands out.

She called in the middle of February, distraught, because another agent had called her and signed up for a new plan. 

This — in the first minute of the call — was my first red flag. It is illegal for a Medicare insurance agent in Wisconsin to cold call anyone, as well as to enroll them in a new insurance plan on an outbound call; agents can only ever enroll people who called them.

After sign-up, she’d run into trouble getting her prescriptions refilled, so she’d wanted to talk to her agent again. She’d spent more than a week trying to get in touch with him and had eventually found my number, thinking that my office was Medicare itself.

My office’s name does have Medicare in the title, but we always immediately clarify that we do not work for the government.

My workplace has an unusual approach to callers: no matter what they called about, spend at least ten minutes helping and continue to help for as long as they need. We are a sales office, but we’re paid hourly and our commission is negligible in order to support this behavior.

I start asking questions and track down the plan she’s been signed into. My first bit of good news is that it’s a plan that I’m contracted with; I can pull up the full contract and can figure out the answers to every one of her questions, but with every question she asks, my internal alarm bells chime a little louder.

Insurance agents are supposed to be responsible to their customers. Whoever this other agent was, he left her not knowing most of what she needed to know; he’d effectively bullied her into changing and then left her high and dry.

The medicine issue was actually coincidental; I told her what she needed to tell her pharmacist to clear things up but asked her to stay on the line and answer a few more questions, and I checked to make sure her family doctor was in the network of her new plan.

He was not, and the other agent had not even told her that changing plans would have restricted her from seeing him. This could have cost her thousands of dollars!

That medication issue that sent her to me saved her from an untold amount of hassle. The plan change could only go into effect at the beginning of the next month; the new plan wasn’t in place yet, and we could overwrite or cancel it just by submitting the paperwork.

I did one last piece of digging. Election periods are the times of year that a person is allowed the opportunity to change their coverage. If this other agent had submitted a change, what had he used? He hadn’t mentioned this to my caller at all. A quick rundown of options left only one answer. The other agent had used an election period called OEP to change her coverage.

OEP is effectively an emergency exit at the start of the year for when someone finds out that their plan is not suitable to their needs. Agents are prohibited from advertising or even mentioning OEP on calls; the customer must request a change or express distress before OEP can be brought up. Using OEP without the customer knowing or even understanding what was being done? Egregious.

So, I go through the paperwork with her and get her signed back into the plan that she had originally, and I give her the appropriate phone numbers to check up with her plan to ensure that she won’t have any trouble. But before we disconnect, I have one final errand for her.

I give her the phone number of the Commissioner of Insurance of the State of Wisconsin: the regulating body responsible for cracking down on bad insurance agents.

Let’s run it down, shall we?

Cold-calling a Medicare insurance customer, uninvited? $25,000 fine. Per person, if he’s called others.

Enrolling her on an outbound call, willfully signing her up into an unsuitable plan, and abusing OEP? Forfeiture of license, along with twice the value of any money they hoped to gain by doing this, plus a $5,000 fine and up to three years in prison. 

That’s three counts of it, mind you, so up to six times the money he tried to make, a $15,000 fine, and nine years in prison, and probably being banned from insurance work in the United States for life.

If he’s done it to one innocent old woman, he’s probably done it to others. I will never know the fallout from the case, but knowing the tools at the Commissioner’s fingertips, I’m reasonably confident I got a swindler his comeuppance.

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I’m pregnant with my second child and I begin to feel a few contractions. I call my doctor and she wants me to get an exam before the upcoming delivery, so I take a rideshare to the hospital. I know, from my first birth, that I’m still hours away before the baby comes out, and the contractions are still manageable without much more than a grunt, but car rides are very uncomfortable under those conditions.

We get stuck in traffic a few blocks from the hospital, and I suggest the driver turns on a different street that, from what I can remember from the last time I went to that hospital, will get us there. But I’m wrong and the driver makes a U-turn to get us back to the right path. It’s a little residential street, and several streets just like this one are two-way streets in this area. But this is not one.

We come out, going the wrong way, to find out the cause of the traffic jam was a police block. The cop is very excited to bust my poor driver for going the wrong way.

Cop: “You are going the wrong way; what were you thinking?”

Driver: “Sorry, I—”

I know all this is my fault, and I feel awful, so I open my window to intervene.

Me: “Sorry, officer! It was my fault!”

I feel a contraction coming and I let out a roaring scream like in the movies. I catch my breath and continue.

Me: “You see, I’m having a baby and we need to get to the hospital—”

I point to the hospital, just a block away

Me: “—and I thought this street got us there.”

The officer gets very alarmed and tells us to follow him.

I’m very happy he let the driver go without a ticket, especially since cops here are notorious for asking for bribes. But my driver is almost freaking out.

Driver: “WAIT! YOU’RE IN LABOR?”

I let out a very relieved laugh and explained to him that, well, technically, I was, but the baby was still hours away. 

The cop got in his car and escorted us the short distance, sirens blazing. It was all very cinematographic and completely unnecessary since there was no traffic past the police block.

We got there in minutes and all was well with us. I even went back home and then back to the hospital — no wrong roads this time — before having my baby later that day.

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I am driving to work one morning and get stuck in traffic near the interstate exit lane. The lady behind me tries to switch lanes but hits my rear bumper. I get out and inspect the damage. There’s enough to justify exchanging insurance information. The lady who hit me gets out.

Lady: “Don’t call the cops!”

Me: “I need a police report for my insurance.”

In retrospect, I smelled alcohol, but the accident plus the rush-hour traffic have me more focused on exchanging information without getting killed than putting two and two together.

Lady: “Don’t call the cops! I’ll pay for the damage!”

Me: “Lady, I don’t know you from Adam. I can’t take your word for it.”

Lady: “I swear on my kid’s lives, I’ll pay for the damage! Please don’t call the cops!”

The police roll up without me having to call them because, you know, it’s rush hour and a huge line of traffic is conspicuous.

Policeman #1: “Please return to your cars.”

I get in my car and watch the following unfold via my rearview mirror: [Policeman #1] talks to [Lady]. He makes a call on his walkie-talkie. Another police car rolls up. So far, I don’t think anything strange is going on. 

Then, an unmarked police car rolls up. Then, a second unmarked car rolls up and a policewoman gets out. All the while, a lot of talking is going on with [Lady]. The policewoman handcuffs [Lady]. [Policeman #1] walks up to my car. After checking my license and registration:

Policeman #1: “You’re good to go. You can pick up the police report tomorrow after 9:00 at the downtown office.”

Me: “Oh, uh… Will that have her insurance information in it?”

Policeman #1: “She doesn’t have insurance.”

Me: “You’re kidding.”

Policeman #1: “No. She doesn’t have insurance. She just got off her shift at [Bar]. She’s driving on an expired license. In her mother’s car. Which has an expired plate and registration. That, plus she’s DUI, means she’s going to jail.”

Me: “So… I guess my insurance will have to cover this one.”

Policeman #1: “Yep.”

I end up going to her court date. I am still mad that someone could be that irresponsible. I am told to meet with the prosecutor and let him know I am there and why. I walk into an eight-by-ten office packed floor to ceiling with paperwork. There are at least four other guys in that office all working furiously.

A very haggard-looking attorney looks up at me and says, with a sigh:

Attorney: “Can I help you?”

I explain why I’m there, and he gets a puzzled look on his face, which I like to interpret as “Huh, an actual concerned citizen,” but could also be “What a dufus; I’m busy.”

Attorney: “You can go. We don’t need your testimony. She’s got some other stuff going on. She’s going to jail for a while.”

I’m roadtripping with my mom and step-dad from my home in Florida to their home in Vermont, along with my best friend. We’re on the last leg of the journey and I’m driving while everyone else is asleep, as it’s around six or seven.

The roads are familiar to me but I’m not used to driving over hills, so when I crest a hill at speed, I’m unable to slow down enough before crossing into the construction zone on the other side.

Of course, I’m immediately pulled over, though I try to be as smooth about it as possible to not wake everyone else.

Officer: “License, registration, and insurance?”

I hand them over.

Officer: “Do you know why I pulled you over?”

Me: “Speeding in a construction zone. Sorry, sir, I’m not used to driving over hills.”

At this, the officer does a double-take at my Florida license, then walks behind the car and takes a good hard look at the Florida plate, and then walks back up to the window and hands back my documents.

Officer: “Is your destination close?”

Me: “Yes, sir. Next town over.”

Officer: “Carry on. Drive safe.”

Me: “Thank you, sir.”

I drove off just as my passengers were stirring from the talking and lack of car movement. I told them to go back to sleep and then later regaled them with my short tale of how being a silly Flatlander got me out of a nasty speeding ticket.