Sounding a lot like Tolstoy, I posit that all agreeable people are alike but difficult people are difficult in their own way. A rash of recent interactions with people I consider difficult lately has me wondering what it means to be a difficult person, whether there’s value in being categorized as such and finally, whether, I myself, am a difficult person (despite my disavowal).

According to one website, Difficult people:

• “tend to feel they are better than everyone else.  This type of person seems unapproachable when you’re looking to shake their hand.  They even seem disgusted when you approach, them as if you have some contagious disease. Then, when conversing with them, they talk down to you as if you’re inferior to them.
• have an aggressiveness about themselves.  They tend to be rude and sometimes hostile toward others.  This type of difficulty in a person is usually brought on by someone who doesn’t “mind their own business” and doesn’t seem to have boundaries.
• tend to be very distrusting of others.  They are very suspicious… and many of the thoughts, feelings, and expectations they have of others are very unreasonable.  You may even ask yourself, “Where do they come up with this line of thinking?” 
• have a tendency to be very selfish and make everything all about themselves.”

Of course not all difficult people have all of the above traits. One person I know has most of these above qualities, e.g., she calls a wide swath of people “fucking idiots,” even those who objectively aren’t, routinely says biting things about people behind their backs, is notably paranoid and embellishes/ flat out makes up other peoples’ conversations to support her arguments. But she has empathy when people she likes are suffering, e.g., she reaches out to me concerned when I am sick and I imagine she’d help a good friend in need.

Two qualities that many really difficult people possess: a stubborn and sometimes prickly resistance to helping themselves/letting others help them and a frustrating lack of self-awareness. I think every difficult person I know has these traits. (The person above alienates people over and over, clearly could benefit from intense therapy, but seems to have little awareness of her own complicity in her failed relationships).

Most of the characters in my favorite show Succession are indeed difficult in all the classic ways: they are selfish, aggressive, disloyal, condescending, arrogant and paranoid. Plus, they appear disinterested in therapy, self-reflection or psychiatric medication. These siblings jab at each other with the kind of admirably wry insults that I wish I could dish, e.g, Roman to his sister Shiv, “You look tired and your face is giving me a headache.” They have a knack for creative cursing e.g., Roman calling his brother Kendall “fuckchops,” as a term of endearment. (I love that!).

These characters don’t do inhibition or self-censorship; hear Shiv mumbling pretty loud on the phone with her father’s young mistress “we could hear you better if you took my father’s cock out of your mouth.” Watching Season 4, episode 5 tonight (directed by a clearly talented alum from my liberal arts Carleton College) that involves the entire crew embarking on a Nordic field trip to close a deal, I am salivating over what is to come– sibling treachery, eviscerating slings unfiltered by social mores and other asshole-ry that is scrumptious on TV but vastly less palatable in real life.

Watching this show, I am further convinced you can’t be nice if you want to succeed in business and many other competitive fields. Reading Death of a Salesman in high school, I learned that only someone delusional like Willy Loman would think being nice/well liked is a prerequisite for success in business/life..In Succession via the Mattson character and of course Logan Roy, it’s clear that at least appearing difficult/derailed in negotiations can be advantageous.

This has me thinking about my own negotiation style as an employment attorney. I remember at one EEOC mediation years ago, the attorney representing the corporate employer pulled me aside just to tell me he had taken acting classes because acting is an important asset for litigators. I thought his moment was odd and likely strategic in some way. But perhaps he was right. During my settlement negotiations, should I turn up the bat-shit- bonkers dial and morph into an arrogant, miscreant who is unpredictable and a shade creepy? Will I overcome considerable stereotypes of being a submissive, sweet Asian woman if I don an eye patch, spit sunflower seed shells onto the conference room floor and snarl at the opposing counsel at random intervals? Can such props and maybe some acting classes help me overcome my “kind, open” face and my overall preschool-teacher vibe? Is being inordinately difficult a boon for a litigator? Questions I’ve often asked but not yet answered.

Listening to me complain of the difficult people I’m juggling in my life, my therapist suggested I watch the movie, The Whale, about a morbidly overweight man (brilliantly played by Brendon Fraser) who refuses to take care of himself or let others help him overcome his failing health, depression and inertia. I can certainly relate to the frustrations of his nurse friend who watches the Whale’s caloric blitzkrieg in agony and ends up enabling him by feeding him pizzas and foot-long sandwiches. (Who among us hasn’t had a friend who makes terrible choices while you patiently empathize with them and dole out advice that is never heeded?)

The Whale highlights a common problem we encounter in dealing with many difficult people who are often both beguiling/charming and toxic; their highs and lows leave us with a woozy kind of whiplash. On one hand, we learn the Whale broke some hearts in leaving his wife and daughter to be with a man he loved, but turns out, he’s not a classic philandering demon as he tried to maintain a relationship with his daughter but gave up when his efforts were thwarted by his ex-wife. Indeed, we see the charming side of the Whale, e.g., his intelligence and tenderness when teaching English literature to his students via Zoom or when trying to woo his teenage daughter who has resurfaced in his life by helping her write essays for school that she refuses to complete.

Though he lacks the hallmarks of many difficult people, e.g, nasty temper, condescension/arrogance to most people, blistering potty mouth and grudge-holding, his self-sabotage is destructive to his family members and friends. (Indeed, the film seems to be a study in difficult people; the Whale’s daughter is not your average surly teenager; she’s vengeful, provocative, volatile and loathe to help herself or accept the Whale’s help. Ditto her mother).

My father-in- law, in my mind, is the definition of a difficult person. The ultimate whale. I’ve lived through many abusive outbursts seemingly reserved for me and no one else. I recall the time my kids, in laws and I waited on one of those please- kill-me-now-labrynth lines for Jungle Safari in Disneyland. When we finally reached the front of the line and were motioned forward to board the car, my father-in law returned on the scene with an ice cream cone for my toddler son. After a Disney employee shook his head in my FIL’s direction, indicating no food on the ride, I turned to my FIL and said, fatigued and sun stroked, “Can you throw it away so we can just get on the ride!” His response: to glare at my angrily and yell “Get the fuck away from me!” in front of my kids and a line of people. Upset, I tore through the park sobbing. (But I soon forgave him–my memory erased like Finding Nemo’s Dora).

Fast forward to 2020; during the height of COVID, my immediate family and I rashly decided to escape NYC and move into my in-laws suburban house—eschewing isolation in a city apartment for isolation in a large suburban home. Though now, I can see that having us all invade his home for many months derailed my father in law, it doesn’t take away the pain of being his victim. For I did much to be a good house guest; I paid for groceries, bought my in laws a much better juicer after breaking their old one, worked in a way I don’t in my own home–getting on my hands and knees to get every crumb off the kitchen floor at night and vacuuming frequently.

As with most Whales, he has a gentle, generous side, which makes the aggressive conduct, hurtful. (Some examples: once he drove a U-haul of his skillful hand-made furniture for my kids from the South to NYC. Most importantly, he supported my oldest child when he came out as non binary years ago and rushed him to cut his hair short when I protested like a backwards idiot and he did things like give me some patient driving lessons that I appreciated).

One day, while living with my in-laws, I was overcome with a bad toothache. I appreciatively accepted a ride with my father in law to a dentist and climbed into the passenger seat. Starting his car, my FIL turned to me oddly enraged. His teeth clenched, he growled that I treated his wife “like a slave.” He accused me of waking her at 11:30 a.m. to watch my children, when in reality it was my husband who had knocked on her door at this respectable time by accident. (I should add, the very confident belief that I have never treated my mother “like a slave”.) I said to him sternly (but not yelling), “If you want to start a fight, that’s a great way to do it.” His response: abruptly slamming the car brakes in the middle of the road and glaring at me so angrily, my flight instinct emerged. Though the car was in the middle of a road, I opened the passenger door, trembling and ran back to the house. To this day, he has never apologized to me.

Years later, my grudge is firmly in tact. I know that as someone who isn’t spending time analyzing himself and his behaviors, he’s not going to change. Is it crazy to want an apology? I’m waiting, arms crossed. In the meantime, my kids can see him where he lives but he’s not welcome in my house. Does this possibly make me a difficult person? Maybe. But to me, given the repeated largely unprovoked, hostile outbursts to me, being difficult is self-preservational and thus, I now believe, a positive. As someone who leans towards being steam rolled by strong people, I am proud of my middle-aged resolve to not smile this away.

What other times is being difficult a good thing? Sometimes i get an intake call as an employment lawyer from someone who claims to be a whistleblower–fired or otherwise disciplined for complaining of employer’s illegal/other rule-violating conduct. I imagine reporting wrong doing is not for the faint of heart and not for the conformists of this world. I’ve never had to but I question if I would have the guts to rattle the beast (employer). Whistleblowers are difficult people who benefit society.

When I think of people I admire and love, a fair share of them are difficult. They are truth tellers, complainers and/or agitators who can be exhausting. They don’t let things slide when others do. They are hyper- exacting with words and/or know-it- alls who are compelled to correct you at all times. They are fiercely independent people set in their ways who reject your help in curt, sometimes hurtful ways. They have plenty of critiques about other peoples’ weaknesses but rarely or never turn the mirror on themselves. They are people who live by the Nixonian mantra: “Trust but verify.” On the purely positive side, they are almost never boring. Plus if you wade through the abrasive/roughness,they can challenge you to look at yourself and become a better person. So kudos to the difficult of the world for not being floor mats!

If you want to know how difficult you are, take this test . (I scored 21.43% difficult when I took the test on my own but when, curious, I asked my teenage son to take the test for me, I scored 45% difficult, which goes to show you we’re all delusional when it comes to ourselves). Never fear if you score high. You can always be a whistleblower or an off-kilter, wealthy CEO.

See below photos of my difficult score when I completed the questions and the photo of the score when my son took the test for me.