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7 Freelancing Tips for Taming Your Friendly Neighborhood Psychopath

Photo by Al Shep

Let's discuss some strategies that you can use to cope with psychopathic behavior, whether it's coming from your client, your coworkers, your boss or your colleagues.

This post is about dealing with psychopaths. It’s more geared toward dealing with psychopaths in freelancing, but I feel the strategies contained herein can be used to handle psychopaths in any arena. I shouldn’t have to make any apologies about what I’m going to write here. It’s a fact that psychopaths exist, and that they’re not all axe murderers, and that we sometimes encounter them in everyday life. So if any of the things you’re about to read make you feel personally uncomfortable, you might want to take a good hard look in the mirror and figure out why that is.

I’m sure you’ve read articles entitled “10 Ways to Tell Your CEO’s a Psychopath” or the “Top 10 Jobs That Attract Psychopaths” (lawyers are supposedly #2, by the way) and so on. As a zero sum game, business makes top performers out of the most callous and ruthless players. But for the purposes of this post, let’s put aside our personal opinions about that argument and discuss some strategies that you can use to cope with psychopathic behavior, whether it’s coming from your client, your coworkers, your boss or your colleagues.

Detecting a Psychopath

We have a ton of clinical information out there that’ll help us detect psychopaths outside of that gut “I’m being manipulated” feeling. Obviously you should Google those. In this article, however, I want to focus on the PCL-R’s “Interpersonal/Affective Factors,” because in freelancing the brunt of psychopathic behavior I’ve encountered stems from these traits being bundled up all in one wonderful human package:

  • Glibness & superficial charm. On the surface, the psychopath will appear accommodating, friendly, open-minded, and even warm-hearted. This is, of course, is all part of the psychopath’s long-term predation. He wants you to get comfortable, because then you’ll lower your guard and he’ll be able to make your more susceptible to his unreasonable demands.
  • Grandiose sense of self-worth. Psychopaths are naturally egomaniacs. They have giant egos. They tout grand narratives and they want you to believe in these narratives because it inflates their sense of self and makes their goals seem superior to yours.
  • Pathological lying. It’s difficult to catch psychopaths in a lie, because they are powerfully manipulative (see below). My experience is that psychopaths tend to tell lots of little lies, over time, so you don’t notice them. They’ll lie on a spectrum, from misrepresenting things you’ve said in the past to flat out fabricating numbers in order to strengthen unrelated claims. If a psychopath assures you that the sky is blue, go outside and check for yourself.
  • Cunning / manipulative. Psychopaths are highly intelligent, in the D&D “Wisdom” stat sort of way. Their lack of empathy coupled with their egomania makes their glib charm all the more effective in winning you over and making you vulnerable to their desires. Because of this you will always be at a disadvantage when you negotiate with a psychopath.
  • Lack of remorse or guilt. This is the single most powerful attribute of a psychopath’s personality, in my opinion. No matter how sophisticated we imagine our sense of right and wrong to be, our wrong behavior is still mediated by feelings of guilt and remorse, and we can’t escape these feelings. Psychopaths are not at this disadvantage.
  • Emotionally shallow. This one’s pretty straightforward: the psychopath will certainly ask how your weekend was, or inquire about your children, but he really doesn’t care about your well-being. He only cares insofar as your being in good spirits and health helps him to accomplish his goals. Psychopaths lack sincerity.
  • Callous/lack of empathy. For a psychopath, the sword never cuts both ways. Psychopaths are selfish. Because they lack empathy, they’re never going to consider your end of the deal. In fact, they will prey on your capacity to feel remorse for taking a stand about what you want out of the relationship.
  • Failure to accept responsibility for own actions. Whenever a psychopath is caught dead to rights, he will deny responsibility for any harm that he’s caused through his lies and deceits, and claim that you’ve misrepresented the situation for whatever reason.

Dealing with your psychopath

Handling the crazy that comes out of psychopathic behavior is not easy. Ideally, we should just get the heck out of there if we have the opportunity. That’s not always an option, though, especially in freelancing. It takes a lot of willpower and patience to resist a psychopath’s charm and ego. In effect, you need to cultivate behavior that is almost completely opposite of the psychopath’s in order to stand your ground in interactions with him.

1. Understand what he wants. Kurt Vonnegut said it best (and I’m paraphrasing here): Everyone wants something, even if it’s a drink of water. Your friendly neighborhood psychopath, despite all his unreasonableness, is after something, whether it’s to impress his boss, rake in sales from a shiny new website, or defeat his competitor. Figure out what that central desire is. It means you’re going to have to do a lot of listening and a lot of careful probing. Being egomaniacs, psychopaths are more than willing to share about themselves. And when you total up the lies they espouse about the quality of their character, you’ll find a nugget of truth about how they have constructed their identity that will undoubtedly help you understand what they’re trying to accomplish.

2. Acknowledge but do not buy into his worldview. Almost every psychopath I’ve encountered has a “grand narrative,” which is to say a story he tells to prospective victims that makes his mission in life and/or his belief system so admirable and adoptable as to be irresistible to any reasonable person. It’s possible the psychopath’s grand narrative is sensible–oftentimes it is, because it’s just an exaggerated version of a grand narrative you’ve heard before. But like many cult leaders, the psychopath rarely behaves in ways that live up to his transcendent message. It’s important to understand the psychopath’s narrative because it gives you insight into his central desire, but it’s equally important to never buy into it, especially if it’s agreeable to you. The story is there to disguise the psychopath’s real attitudes with more palatable ones that he will never actually act upon.

3. Put your ego aside. Many of the psychopath’s tactics rely on getting you worked up in the moment, whether by appealing to your emotions or by threatening your integrity. The psychopath will try to tangle you up in arguments that present your behavior as a contradiction, by belittling you, or by trying to make you feel unworthy of his praise. Remember, because the psychopath is constantly constructing his own identity out of lies, he will also try to reconstruct your identity with his storytelling power to suit his purposes. Whenever your heart skips a beat because of something insane your psychopath says, take a deep breath and keep your counterargument to yourself.

4. Give him the illusion of control. Psychopaths don’t like to be constrained. Whenever you impose a boundary on their freedom (scopes of work and deadlines come to mind), psychopaths tend to do their best to minimize the importance of these boundaries or outright reject them. The most common tactic I’ve witnessed is playing dumb about your impositions and/or willfully disregarding them, only to blame the consequences of their ignorance on you later. You can’t reign in a psychopath, but you can certainly overwhelm him with options. You have to build a framework for the psychopath to operate inside of so that you maintain control of the overall process. If the psychopath can construct their course of action a la carte, he’ll feel like he’s in control of the situation. As long as the options you provide him with are viable for you, it doesn’t matter which one(s) he chooses. All roads will lead to acceptable outcomes.

5. Never accept promises or gifts. In the beginning the psychopath will do whatever is necessary to butter you up. He may shower you with gifts or make big promises about the future of your relationship. He will almost always insist on handshakes instead of formal agreements. The psychopath will say anything to put you into a receptive mode. Politely decline the gifts, listen to but do not reciprocate the promises, and get everything in writing. Which ties directly into…

6. Document everything. Once it’s apparent you’re dealing with a psychopath, you need to start creating a history for yourself you can refer back to, in much the same way as a clinical psychologist will keep notes in her case study. Psychopaths prefer to hash out agreements over the phone and through in-person meetings, and will even request that you forgo the paperwork afterwards so they’re not pinned down by the details. While there’s nothing wrong with getting things resolved face-to-face, don’t act impulsively in these meetings and remember that “verbal agreements” with a psychopath carry zero weight. Document everything and get confirmations in tangible formats.

7. Don’t be afraid. Alternatively this could be called “have a good contract.” Psychopaths, like T-Rexes, can smell fear and prey on your lack of confidence. The old Teddy Roosevelt motto, “Speak softly and carry a big stick” is crucial here, because in order to appease a psychopath in short-term interactions, you must act compliant, even-tempered, and mild-mannered but have the power to completely disarm him if the time comes. Your “big stick” needs to be a nuclear option: the option to walk away or the option to revoke the value you’re offering, even if it’s at a substantial cost to yourself. If your big stick unambiguously threatens the psychopath’s central desire, you’ll be surprised how quickly he’ll change his behavior to keep his carrot in sight.

With these strategies in hand, it’s still unlikely you’ll come out of a negotiation with a psychopath unscathed, but then again, getting out of the negotiation at all is usually a good thing when you’re dealing with this kind of behavior. Challenges to your personal integrity are one of the psychopath’s greatest weapons to use against you, especially if you try hard to hold yourself up to a certain standard. So whatever you do, don’t take it personally and try to practice as much emotional detachment from the situation as your psychopath does.

Good luck!


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