How to Be Boring: a Rookie P.I.’s Guide to Surveillance

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Be boring.

Want to be an effective surveillance operative?

Be unremarkable, uninteresting, and uninterested.

If you ask an outsider to describe a PI, they’ll invariably use the word “cool.” They’ve seen the movies—the gunsmoke, the shadows, the bottles of bourbon—and they think that the best PIs are the coolest. From Magnum P.I. to Jessica Jones, private eyes in media embody coolness—i.e. flash, good looks, and style. You can’t not notice them.

I promise never to tell any of those outsiders the truth: that we PIs are actually doing our best work when we’re as far from cool as possible. When we aren’t flashy. When we aren’t noticed at all.

In fact, on surveillance, the best thing we can be is boring.

To work cases as a PI without drawing attention to myself, I’ve had to learn to be unremarkable, uninteresting, and uninterested.

Unremarkable

As a short white guy from the Midwest with a degree in politics, it came as a huge surprise to me that I took to boringness like a fish to water.

I learned on one of my very first assignments that going undetected is best done when you are as unremarkable as possible. Needing to covertly take pictures in a restaurant, I hid my phone behind the menu. I took fake selfies while actually aiming at something over my shoulder.

At one point, I tried stealth—sliding the phone into my lap to sneak a few shots. But my attempts to be covert only made me look like the one frat boy in yoga class: awkward, sweaty, and definitely there for the wrong reasons. The friend I’d brought with me as cover told me to stop with the sneaking right now.

My attempts to be covert made me look like the one frat boy in yoga class: awkward, sweaty, and definitely there for the wrong reasons.

I learned that day that the best way to take pictures with my cell phone in the restaurant was to take pictures with my cell phone in the restaurant. Taking cell phone photos is possibly the single most unremarkable activity in the age of Instagram. It was blatant, but boring, and no one gave me a second look.

Uninteresting

Sometimes it’s enough to be unremarkable. But on one of my first process service assignments, I learned that it’s also important to be uninteresting. The intended recipient was someone my firm had been attempting to serve for a while, but his coworkers and family were always happy to tell us that he was out of the country or on vacation.

As I drove to the business address on the paperwork, I imagined how a better PI than myself might talk their way past the employees to find the person in question. As the voice on my GPS announced that I was two miles from my destination, a voice dripping with disembodied accusation (“Sooo, what’s the plan?”), a memory flashed into my mind: Before becoming a private detective, I’d spent a summer as a flower delivery guy.

If there’s any one person who gets ignored in an office setting, it’s the delivery guy whom you don’t have to tip.

I pulled into a supermarket and bought a $2.99 potted flower. With the flower in one hand and papers in the other, I walked into the business and asked one of the workers where I could find the man I was looking for. Not only did the girl (who turned out to be his daughter) tell me where he was, she drew me a map of the route that lead me straight to him.

*Author’s note: You then get to go home to your wife or girlfriend with flowers. Surprise—you’re interesting again!

Uninterested

Being unremarkable and uninteresting have definitely helped me along the way, but being uninterested turned out to be the most helpful of all.

In a word, the best way to be boring is to be … bored.

A mentor of mine who worked in the intelligence community once shared with me this rule: No one ever suspects the person who looks socially unaware. So if your surveillance target is getting wary and seems likely to start noticing you, pick your nose. Fix your hair in the mirror. Sing along to something on the radio. (Quietly. You’ll probably get more attention for belting out “Call Me, Maybe.”)

I saw the value of boredom in action on my first surveillance case. My partner and I had stopped the car in view of a subject, and we were taking turns getting out to watch what he was doing. I went first, waiting just around the edge the block, so I could see the target out of the corner of my eye.

As I waited, the pedestrian crossing light changed and I moved with the group of people so as not to stand out. I pretended to be texting and kept an eye on the subject from a distance as I walked back and forth along the street, trying not to be in any one place too long. When I got back to the car (having gotten my entire week’s worth of exercise), my partner took his turn.

I was confident in how well I’d avoided detection, but also interested in seeing how a more experienced PI could accomplish that sort of secrecy. I watched my partner walk toward where the subject’s vehicle was parked and stand on the sidewalk by the wall. He lit a cigarette, and then he just stood there. He continued to stand there until he finished the cigarette, and then walked back to where I waited.

Suddenly, all the smoking PIs in the old movies made sense. A non-smoker outside has to have something to do or somewhere to be, but someone smoking outside can just be bored and having a cigarette.

Suddenly, all the smoking PIs in the old movies made sense. A non-smoker outside has to have something to do or somewhere to be, but someone smoking outside can just be bored and having a cigarette. Because he looked totally uninterested in the world around him, my partner went entirely unnoticed by the subject.

So there’s my public service announcement for any kids out there reading: No matter what the PIs did in the old movies, smoking’s not cool. In fact, it’s boring. That’s why it works so well for us surveillance operatives.

The truth is, to go undetected, we have to look unremarkable, uninteresting, and uninterested. Looking cool is out of the question. Don’t worry, though—the secret’s safe with me. Because I’ve learned something else: Looking bored while keeping up surveillance on a moving target, looking alone at a restaurant while orchestrating movements with a team set up in different places, driving a car that’s not flashy so that you can tail someone secretly—turns out, it’s cooler than fedoras after all.

 

Jeff Davis photoAbout the Author:

Jeff Davis is an investigator with Phyleo, LLC, a PI agency in Alexandria, VA.  He is an Iowa native but enjoys being a Virginia transplant.  In his spare time, he is also a motorcyclist, writer, and avid traveler.