Covert operatives have a hard time dating. Even if you find someone who doesn't mind you won't talk about your past or that you carry a concealed weapon, they usually want more than your ready to give.
Selling stolen goods is all about discretion. You gotta be the kind of person who can keep your mouth shut. The kind of person that never ever shares the numbers that in their little black book.
Even the most careful spy leaves a trail that can get them burned. A patriot making illicit deals for his government looks a lot like a traitor making black market sales for his wallet. Somebody upstairs gets the wrong idea and suddenly your burned and out of a job.
When your giving 5 inches and over a hundred pounds to a well trained opponent, it helps to know the terrain better than he does.
A good cover identity is a team effort. If you want to meet someone it's a good idea to play a little hard to get. Put people between yourself and the target; make them come to you.
Just because someone believes you are who you say you are doesn't mean he'll do what you want him to do.
Clandestine meetings are never fun to arrange. It's a big part of the job for a covert operative but it's never pleasant. It's not so much the fear of death that bothers you, it's driving to the meet with a bag over your head. Sometimes they wash the bag, sometimes they don't.
The thing about security is that the very things that protect you can be turned against you by someone that knows what he's doing. It's tough to compromise a well thought out security system, but making someone think you can compromise it - well, that's much easier. Take surveillance cameras for example. You can disable it by shooting a laser at it and overloading the light sensitive chip. Cheap, easy, and exactly the sort of thing a sophisticated criminal gang would lots of resources would do. Leave around some tell tale signs of surveillance like cigarette butts or forgotten camera lens cap and the more security their is the more likely they are to think they have a very serious problem. Even the security team itself can be an opportunity. The more employees you have the more you have to worry about them. Deliver some vague threats and a few hundred bucks to a security guard. If he's honest he'll tell his boss, who then wonders who wasn't so honest. For the cost of a nice dinner you can get a whole security team canned.
One of the dangers of any kind of psychological warfare is it can be too effective and send the target into a paranoid tailspin. That paranoia can be useful... or deadly.
The key to good security is good systems, but those systems make you predictable. Where will you take your valuables? A bank you trust. How are you going to get there? With armed men in a big SUV. When will you go? When the bank is least crowded. All good procedure, all 100% predictable.
If you know someone's going to be at the bank at a particular time, it's not hard to make it look like they're robbing the bank. Knock out a few surveillance cameras, block off the street with a stolen car like they're preparing an escape route, fire up a spark gap transmitter to kill the security radios at the bank and they'll really look like they know what they're doing.
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