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5 Tips From A Con Man On How To Handle Being In Over Your Head


We’ve all been there: you talked a big game and now it’s time to walk the walk, but you have no idea what you’re doing. Perhaps you were more than a little generous with your skills on your CV or you spent the whole drive up the mountain bragging about your skiing prowess to your friends even though you haven’t seen snow in 10 years. It’s best to be humble and honest to avoid such situations, but sometimes we slip up, and sometimes life thrusts you into such a situation through no fault of your own; you’re in over your head, now what?

Frank Abagnale, who you may know either due to his autobiography or the movies by the same name – Catch me if you can – is one of the best-known con-men. After dropping out of high school, he travelled the world by posing as a Pan Am pilot, impersonated a doctor at a Georgia hospital, passed the bar test (even though he never went to law school) and became a prosecutor, taught sociology as a college professor, and forged two million dollars in checks. All this, before the age of 20. This is a man who knew how to deal with being out of his depth, so here’s five of his techniques.


1) Relax and be confident
It’s normal to feel awkward and out of place, but you need to stay calm and project confidence in order to avoid drawing attention to yourself. We often feel as though everyone is dissecting every little aspect of us and can see through our ruse, but the truth is we’re much more concerned with ourselves than with others.

“When the guard turned to confront me, I was combing my hair with my fingers, my hat in my left hand. I didn’t break stride. I smiled and said crisply, “Good evening.” He made no effort to stop me, although he returned my greeting. A moment later I was inside Hangar 14…I hesitated in the lobby, suddenly apprehensive. Abruptly I felt like a sixteen-year-old and I was sure that anyone who looked at me would realize I was too young to be a pilot and would summon the nearest cop. I didn’t turn a head. Those who did glance at me displayed no curiosity or interest.”
-Frank Abagnale. Catch Me If You Can

There was a study done on an American university where a researcher would stop and talk with a student. Then in the middle of their chat 2 men would walk between them carrying a large door or mirror (I know, this is cartoon material!), during which time the researcher would duck out and another would take his place. Once the workers and door had passed, the student would be talking with a different person, and the majority didn’t even notice!

So, knowing that people aren’t paying particular attention to you, stay calm as doing so is critical in order to look the part.


2) Look the part
A friend from university who works for a firm that tests the digital security of giant companies and government agencies once explained to me the most common and easiest weakness to exploit; he would dress up as a delivery man (with a package and all) and simply walk right into the building as if he owned the place. He looked the part and no one would ever question him, giving him complete freedom to find an important computer or server he needed to access the data and completely bypass expensive firewalls. If you look and act like you belong, people will assume you do.

“The transaction also verified a suspicion I had long entertained: it’s not how good a check looks, but how good the person behind the check looks that influences tellers and cashiers.”
-Frank Abagnale. Catch Me If You Can

Frank Abagnale found that wearing a uniform went a long way to backing up his story, just like my postman friend. Now, you likely won’t need an actual uniform, but being appropriately dressed will go a long way. At a fancy cocktail party with a wealthy friend? If you’re not dressed correctly, you’ll stick out like a sore thumb killing any chances of blending in the second you show up.


3) Play catchup like mad
If you find yourself in a position where you don’t have the needed skills or knowledge, then you don’t have any spare time, every minute is catchup time. If you told your boss you’re an ace at something you don’t know how to do, you’re going to be having working lunches, late nights and early mornings; you’ve got until the due date to learn how to do it and then actually do it too! If you’re on a skiing holiday with friends and you’ve forgotten how to parallel turn get on YouTube while you sit on the toilet, tell them you’re feeling sick the first morning and that you’ll catch up with them at lunch (though, you’re really going to be getting a quick lesson).

Depending on just what kind of a pickle you’re in, you may need to get creative. Abagnale didn’t have the internet so if it wasn’t in a book, as with pilot lingo and slang, he had to get creative. When preparing to be a Pan Am pilot, he called up Pan Am pretending to be a student journalist for a high school newspaper and asked to speak with a pilot who he riddled with questions. If you’re at a party or with friends try using “I’m just curious” type questions to catch up on the fly. Say you’re sailing on your friend’s boat and he asks you to sheet in the jib, ask something like “where DO YOU keep that line?” Depending on the size of the boat, the line (sheet) may not be immediately obvious even to an experienced sailor. In any case, the question is asking about their habits/boat rather than confessing your lack of knowledge with a “how do I do that?”.


4) Turn on the charm
Look, there’s a good chance you’re gonna goof up at least once or twice. But, class is universally admired; nearly any mistake or crime will be judged less severely if there is some class involved.

Abagnale treated everyone from the janitor to the boss with respect, charm, and class. This made them less likely to suspect him and also much more willing to help.

If you’re an annoying boor and you keep messing up, people aren’t gonna put up with you for long. But with enough charm, people will give you second chances and the benefit of the doubt.

5) Shut up and pay attention
Whenever you speak, you’re running the risk of giving yourself away. More importantly, you aren’t paying attention, missing a chance to catch up. If you’re at a fancy dinner party, but don’t know which fork to use (hint: start outside and work your way in), keep quite and watch what others are doing. When you speak, try to focus on asking questions, this will help you play catchup, but since people love talking it’ll also help you turn on the charm; two birds, one stone!