Be a Nice Person, or Seem like a Nice Person?

A friend once said "I'm one of those people who seems like an asshole, but I'm a really nice person."

Of course my former-consultant-brain put this in a 2x2 matrix:


But the thing is, most assholes who seem like assholes end up getting ignored and marginalized; and most nice people who seem like nice people end up getting taken advantage of or steamrolled. (The exceptions are those who are born into power or have powerful friends that people don't want to piss off.)

And, I think, most successful people are either a) nice but seem like assholes, or b) assholes but seem nice.


The ones who are assholes but seem nice are the sociopaths and psychopaths in the workforce, who are much more likely than average to rise through the ranks, because they are ruthless but charismatic.

The ones who are nice but seem like assholes are the ones who mean well but aren't high on EQ, or the ones trying to practice radical candor. They try to do the right thing, and take care of people, but sometimes let their emotions get the best of them or put their foot in their mouth.

Flipping the script, what does it take to become successful? In my opinion, the common trait is that successful people are ruthless in some way. The way they're ruthless defines which category they fall into.

  • Are you ruthless in service of achieving a collective goal, or doing right by people? Is their moral compass (generally) unwavering? You are probably the Nice-but-Seems-like-a-Jerk person, aka the "Morally Ruthless" person.
  • Or are you ruthless to get ahead, no matter the personal cost to others? Can you sway others to go with your route, even if they have misgivings? You're probably the Jerk-but-Seems-Nice person, aka the "Charismatically Ruthless" person.

Here's how I these these people tend to behave as an archetype, in terms of trustworthiness:

  1. People who will stick their neck out for others (sometimes foolishly) at personal cost, to do the right thing (nice people who seem like jerks). Famous fictional example: Ned Stark.
  2. People who are self-interested, and never pretended otherwise. They won't go out of their way to hurt you, but you can't count on them either (assholes who seem like assholes). Famous fictional example: Gordon Gekko.
  3. People who want to please everyone, and as a result rarely take sides, or show conviction. In the absence of manipulation, they'll do the right thing, but if there's someone less-than-nice influencing them they're often complicit (nice people who seem nice but can be manipulated). Famous fictional example: Bilbo Baggins.
  4. People who only care about their own outcomes, and sometimes relish winning at the expense of others. Famous fictional example: Voldemort.

Obviously there is a ton of nuance here... humans are complex and usually don't neatly fit into buckets. But thinking about whether their intentions match up with their words, and what that means for how they'll treat me, is something I've learned from in the past (the hard way).

If you want to spend the rest of the day thinking about this more, check out the always-thought-provoking Tim Urban's post on this topic, which I read after writing this. So his categories map to:

  • Seem Asshole / Are Nice → Bad-Bad-Good + Bad-Good-Good (#4 + #2)
  • Nice/Nice → Good-Good-Good (#1)
  • Asshole/Asshole → Bad-Bad-Bad (#8)
  • Nice/Asshole - Good-Bad-Bad + Good-Good-Bad (#7 + #5)