“Fail Often so you can succeed sooner.”

—Tom Kelly.

Mistakes and failures in surveillance, surveillance detection and special protective operations are things I write about quite frequently. I’ve examined them from every which way, explained how they look, discussed many case studies and talked about how to avoid them. One aspect I haven’t touched on enough though, is the bright side of mistakes and failures.

Most thinking people understand that making mistakes is an inevitable part of life, and that learning from them can be very useful. But from my experience in surveillance detection and special protective operations, it’s not just that the learning process contains a few inevitable mistakes, the process is practically based on your making mistakes. There are important lessons that cannot really be learned any other way. This is why a good SD course should cause you to make important mistakes and to experience failure (even if it’s just a perceived failure). It’s not that trainees should never experience success during training, of course they should—they have to. But when people only experience success, they stop looking for ways to improve—they stop learning—which can be a problem.

Don’t get me wrong, accepting a mistake or a failure isn’t easy for most people (myself included). I should also tell you that almost every single mistake I point out to others is one that I myself have also made. But having made so many mistakes, and having failed as many times as I have, I can tell you that these are vital ingredient for success.

In fact, why don’t I put my money where my mouth is, and actually let you in on one of my juicier failures?

My introduction to the field of surveillance detection was in the summer of 2008, when I was sent to Israel to receive SD training. By that time, I had already acquired a few years of field experience in terrorist activity prevention and high-end protective operations. I had worked for or alongside many political organizations, Fortune 500 corporations, the Israeli government, wealthy Silicon Valley executives, Jewish organizations, multiple foreign governments, and every single law enforcement and federal agency in the San Francisco Bay Area. In short, I expected my skills and experience to help me succeed in the SD course, and therefore entered it with quite a bit of confidence.

As it turned out, nothing could have knocked that false sense of confidence out of me faster than the SD course I took. The course was almost exclusively conducted in the field and ranged (quite wildly) from the Tel-Aviv beachfront to the ancient, bustling markets of Jerusalem’s Old City. Incorporated into the field exercises were trainers and hostile surveillance role-players who had real-world government sector experience. There was nothing theoretical about it, and my trainers were introducing me to a very hidden, yet very real dimension I had not been aware of.

I would have loved to boast about how I used my skills and experience to detect these individuals, but the little that I did manage (right at the end) was pretty much due to their purposely allowing me to detect them so I could experience at least a modicum of success. To say that this was a humbling experience would be a gross understatement.

It turned out that in addition to my inability to detect the hostile surveillance activities they were role-playing during the exercises, these experienced professionals had also been covertly following and keeping tabs on me much of the time. I was even shown photos of this. When I met some of them after my final exercise, they gave me a rundown on my mistakes and failures, and the list was quite long.

This zoomed-in photo of me was taken by my SD instructor during a field exercise in the Old City of Jerusalem in 2008. My cover was of an American tourist, taking in the sites. As much as I’m trying to act cool and blend in, I’m quite clearly a ball of stress, holding my camera too tightly and clutching my backpack like a suicide-bomber. Despite the fact that I’m looking right at where my instructor was, I neither noticed him there nor realized I was being photographed.

I’m sharing this personal story with you not just because it’s a funny example of an overconfident guy being cut down to size, but because it beautifully illustrates how mistakes and failures can be the catalyst for real learning and development. This was by far the most humbling experience I’ve had in my professional career, but had it not taken place, I would never have gotten to where I am today, you would have never heard of me and this very article (along with everything else I’ve written) would never exist.

People love the classic ‘karma’ stories about the overconfident guy getting ‘schooled’—falling on his face and having it pointed out to him. But if you look at it more closely, it’s that overconfident guy who ironically gets the most out of it. Take my case for example; not only did I learn an important lesson about checking my ego (always a good thing), but I very quickly learned a ton of facts I never knew.

Ego checking, fact learning and time-saving, what could be better? It’s a win-win-win, as far as I can see. Why do so many people think that getting ‘schooled’ is a bad thing?

Being good at something doesn’t necessarily mean you don’t make mistakes. It means you learn from your mistakes, improve and go on to make even better mistakes. Many security professionals, attempting to project strength and confidence, tend to miss this point, and pretend they’ve never made any mistakes.

I often encounter security professionals who tell me that the Israeli Defense Forces (IDF) is one of the best militaries on the planet (if not the best). I usually point out that this isn’t because it’s filled with flawless Super-Men, the IDF is just a very experienced military, one that makes a point of learning from its experiences. I can tell you from my time in the IDF that we used to make tons of mistakes: bad mistakes, messy mistakes and in some cases, deadly mistakes. But we always made sure to learn from them.

I’ll leave you with this final thought. Just because you’ve failed in the past and learned from your mistakes, doesn’t mean you should never fail or make mistakes in the future. That would be like saying you should stop learning or altogether stop doing anything important. I obviously still fall on my face from time to time, and I occasionally even get ‘schooled’ (if I’m lucky).

Failure is just a type of currency you pay for learning important lessons. Spend it wisely, but generously.

“I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

—Michael Jordan.

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