My first job out of law school was as a state prosecutor in Broward County, Florida. I took my job very seriously. I routinely got up before 5 a.m. and got home at 8 p.m. I earned every cent of that starting salary of $25,000. It was 1997. It was the government.

After three years I started to think about applying to the FBI. I felt like I could do more than just trial work. I wanted to be an agent. An investigator. I wanted to have a bigger impact. 9–11 hadn’t happened yet.

So I started the process.

“I think the first duty of society is justice.”

— Alexander Hamilton

The First Part Was Easy

Applications. Letters of recommendation. I think. I can’t even remember how much information I had to give, but it felt like a lot. I was already working a government job where I had been fully vetted so this process was an easy one. It was basically a wait to see if I qualified to even start the testing process.

Why the FBI and Why It Was a Pipe Dream

I made friends with someone who worked for The Bureau. He made it sound so cool. I think I was enamored with doing more and being more and not so much the actual job. I was kind of a wimp.

The first time I held a gun was in court. When I went to put it into evidence in a robbery case. The first time I saw cocaine was in court. When I went to put it into evidence.

Random fact: Back when I started as a prosecutor we sent drugs back into the jury room if they requested it. It was sealed and all, but if the jurors were feeling frisky (and interested in getting arrested) they could have taken a couple bumps while deciding my case.

Random fact #2: Back when I started as a prosecutor we sent both the gun and the ammunition back into the jury room if they requested it. Until a bailiff told the Judge that they could load the gun that way.

Although I talked a big game in court, I wasn’t amped at the thought of facing down a cartel member or terrorist. I didn’t want to shoot a gun. I didn’t want to get shot. I didn’t want to get stationed in Alaska.

This wasn’t well thought out.

When the Testing Began

I passed the background testing. Next up was the first round of actual testing. The exam kind. No physical activity required.

They sent me something to prepare, but I was cocky. I didn’t look at it. I’m sure that’s what the FBI is looking for in an agent.

I arrived for the written exam, nervous. Looking back, I think I was scared to do well. Because I was scared to do the job. But at the time I just chalked it up to test jitters.

I got sidetracked right away when I saw someone from law school. She was arguably the prettiest girl in our class. We were pretty good friends. But I couldn’t tell if it was her. I hadn’t seen her in three years.

And then I was like, she wants to be an FBI agent? I wasn’t being sexist. I was being an asshole. Her grades were way better than mine. She took law school more seriously than I had. I had no idea if she had ever held a gun. I was just being competitive.

I never found out if it was actually her. She’s probably doing some bad-ass Jason Bourne sh*t right now, while I am typing this. I am ok with that. But I am also impressed.

The One Question That Derailed My Potential Career in the FBI

One of the things they tell you up front is that you better not lie. If you do, they will find out. And you are out. Pretty simple I thought. I never lie. Just wait though to hear where this goes sideways and why.

The first section was pretty easy. Standard life questions if I remember correctly. But one thing you have to understand about me is, I am extremely analytical and have a hard time answering multiple choice questions without reflection.

I would argue the validity of the question instead of answer the question. I would argue that there should be one right answer and not one that is just better than another. I would analyze whether the answer was technically correct even though I knew it was the “right” answer. I would focus on a spelling error over and over.

Then came the one question that derailed my potential career in the FBI:

Do you litter?

These were the only answers available:

Yes.
Sometimes.
Never.

For someone with my personality, this one question ended a career I didn’t want anyway. So I should be thankful. But I still don’t know how to answer.

Some Things Are Worth Analysis and Some Aren’t

Yes would mean I litter all the time. I crossed this off out right away.

Never would mean I had never littered in my entire life. I couldn’t remember times of outright littering, but I was sure I had. I didn’t want to lie. I didn’t want to be knocked out for lying. About litter. Maybe one time I missed a bin and didn’t pick it up. Yeah, never wasn’t an option.

This is what I was doing in a very tightly timed test. No one was finishing all the questions unless they were laser focused. I was contemplating my entire litter history in great detail. Again, exactly what they were looking for in an agent I’m sure.

That left sometimes. For some people, they could just check this box and move on. But not me. Nope. Sometimes indicated to me a pattern of occasional litterbug activities. And this was not me. Worst case scenario I littered three times in my life. Two of them by mistake. And one because I was an assclown toddler playing games.

And here was my conundrum. One worthy of a mid-test silent meltdown inside my head.

“There aren’t many things that are universally cool, and it’s cool not to litter. I’d never do it.”

— Matthew McConaughey

F*ck! Never was a lie. Sometimes was an enormous exaggeration. Which is less of a lie?

I probably spent three to five minutes on this mind diarrhea.

The Result

I didn’t finish this section on time for obvious reasons.

The math section was next. Math was my best subject. But this was like math combined with head games and logic problems and a small dose of LSD. I think I was on question number seven when the time ran out.

I knew I didn’t pass. Maybe I didn’t want to.

Or maybe if they had “Very Rarely” as a f*cking answer I would be the one doing Jason Bourne sh*t right now.

Either way, I failed. And never looked back.

I found out my wife was pregnant soon after that. Then 9–11 happened.

I was happy that one question derailed my potential career in the FBI.

But I also learned that some questions don’t require Edisonian analysis. Once in a while you just need to check the box and move on.

How One Question Derailed My Career in the FBI