Five ways to end up in a Pursuit Magazine “How Not to Do This” story.
Five ways to ruin our industry, destroy our credibility, and perpetuate the stereotype.
When I opened my small investigations firm several years ago, I made all the rookie mistakes: Failing to collect a retainer before starting a job. Agreeing to work for clients who are clearly insane. And of course, thoroughly botching surveillance assignments.
Anyone who does surveillance has failed at surveillance at some point. I have been burned, thrown under the bus, and nearly arrested for surveillance mistakes. So I want to be clear: I understand that surveillance work is difficult, and the potential for being identified as a PI is always there. Been there, done that.
But earlier this summer, when I found myself under surveillance, I realized that there are categories of surveillance fail that I was not previously aware of.
Over a period of several weeks, we spotted a number of “operatives” parked near our office multiple times. We spotted them trailing us in the grocery store, and later the same day, sitting near us at a bar. We’ve identified each of the investigators personally, with pictures. They are all either former or current law enforcement, and they have all been burned, shamefully so.
In a word, the buffoons who followed our team are particularly inept at the job. Here’s what they did wrong, and what you (and we all) should avoid doing:
1. Look like a PI stereotype.

If you wear 5.11 tactical pants while on surveillance in a grocery store, you should look for other work. And the matching 5.11 tactical boots? Seriously?
Now I will say that the ever-so-subtle “dry-fit” sports shirt you somehow stretched over that generous gut almost fooled me. But then you went and blew it with the whole special-operator-sunglasses-black-5.11 baseball-cap look. “What? Don’t notice me, I’m just examining this kumquat…intensely.”
When you’re following two people and they split up, maybe check your six before scampering down aisle 8 (jams, jellies, nut-butters, and dressings), all Jonathan Ames-like, crouching down comically to peek around the corner chasing A…while B is waltzing up from behind to ask you which is the best brand of almond butter. This actually happened.
2. Wear the same outfit in several places.
If you do surveillance work and you don’t carry a change of clothes, you should look for other work. Dude: Pack several outfits. And the 5.11 I-wish-I-coulda-been-a-special-operator-but-the-whole-morbid-obesity-thing-got-in-the-way look shouldn’t be one of them.

When you get burned at Whole Foods, it’s probably best to move on and let another investigator pick up the eyeball. But if you have to work it yourself (which sometimes happens), maybe, just maybe, consider at least a costume change. Because the GI Joe look that failed in the health-food market isn’t working any better at the tapas bar in the hipster part of town.
3. Get really close to your subject. I mean really close.
If you feel the compunction to get so close to your subject that he can smell you, you might want to look for another line of work. And if one of your subjects has asked you, earlier that day, which variety of almond butter you prefer, it might be best not to plop down next to him on a barstool a few hours later.
The fact that the shoot-me-first-I’m-an-ex-cop-5.11-tactical-pants you insist on wearing are a bland shade of khaki doesn’t make you any less conspicuous.
4. Park directly in front of the subject’s house.
If you insist on parking your nondescript-limo-dark-custom-SUV with its array of antennae directly in front of your mark’s house, you need to quit this business.
Did I wake up inside a sitcom? Who actually thinks this is a stealth maneuver?
5. Keep coming back for more.
If you’re somehow convinced that 5.11 tactical gear acts as an invisibility cloak, leave this profession. Please, just quit.
After you’ve been burned, bring in another guy. After you’ve been spotted five times in one week, bring in another gal. After your subject walks up to you in Whole Foods and asks you which organic almond butter you like best, it’s time to go home. We can see you.
It has been said that common sense is so rare it’s almost like a superpower. If you do surveillance work, use a little bit of common sense. Prepare. Learn where and when the subject hangs out. Study how people dress in those places. Figure out how to fit in.
Every clique has a uniform. Hipsters wear selvage denim jeans. Mid-level professionals own a closetful of pleated khaki pants. Commercial real-estate agents in LA don Zegna suits. Music producers love ironic t-shirts.
The same goes for your vehicle. For a cul-de-sac suburb, borrow a minivan. Or slap a magnetic “Green Thumb Landscapers” sign on your truck’s door panel and throw some mulch in the truck bed. Look like you belong, and you will become invisible.
As a professional surveillance operative, you need to be able to discern the proper street wear (and vehicle) and find a way to blend. If you can’t, bring in someone who can, because your client isn’t paying you to be featured in Pursuit Magazine.

