The Enlightened Asshole

(Note: This is a post on being mean. Or, realistically, a useful meanie. But I would be remiss if I did not mention Paul Graham’s essay Mean People Fail. He makes a solid argument about why you should not be mean, and it’s tempered by his entrepreneurial/startup experience with caveats regarding other industries.

If it’s not obvious yet I disagree with him a little bit. I suggest reading this blog post first then reading his essay, although this blog post is not a direct response to his essay so the order is not terribly important.

I also want to be clear that the title is tongue-firmly-in-cheek. I don’t consider myself an enlightened anything.)


The What Now?

The term asshole is generally thrown at mean people as a pejorative and that encapsulates the problem: being mean isn’t always bad.

There are plenty of situations where meanness is called for. I think what people actually intend is “unnecessarily mean.” And unnecessarily oftentimes translates to “never be mean.” Which is silly.

Allow me to elaborate.


I Defy Thee!

People aren’t really homogeneous with regards to how they interact and respond to other people. It would be inaccurate to say that always being mean is good, and that never being mean is good. “Tough love” is a phrase with a kernel of truth, but that can be carried too far as well.

Every piece of criticism, constructive or otherwise, is mean. I don’t mean stingy, shabby, or the usage of its first occurrence in this sentence – I mean MEAN. As in offensive.

That’s really the point of criticism, to point out something inferior and a lot of people will take that personally and badly. There really is no way to convey the idea that something could be made better without also implicitly conveying the idea that it is currently sub-optimal.

And that’s the crucial bit: the meanness is leveled at the inferior thing. In the same way that people should learn not to take criticism (of their work) personally, critics should learn how to level criticism appropriately.

Aside: Those of you who know me are screaming, “POT, MEET KETTLE!” I will address your concerns further down. You butts.

It may be appropriate to criticize someone directly, as an extension of his or her work, but it also may not be. There’s a degree of nuance here.


That Seat is Taken

Being outright mean and condescending and critical is easy. Some people use lines such as “I’m just calling it like I see it” to justify their sadistic tendencies. Why? What sort of reasonable person goes around calling it not like how they see it? The default assumption is that other people are not directly lying to  your face in most social interactions.

Aside: I’m aware of how often people casually lie – that’s not what I’m referring to. I’m speaking in the context of serious discourse and not, “I’m doing fine, thanks!” versus, “I need to take a huge dump and you are blocking the path to the bathroom; remove yourself or I will do it for you.”

As a person taking criticism you have to filter the meanness into two categories: malicious and non-malicious.

The people who are leveling criticism (especially at you personally) to waste your time, are not actually invested in your well-being or future performance, et cetera, are useless. Cut those people out of your life with ruthless efficiency.

Aside: With the advent of the Internet it can become difficult if not outright impossible to cut this toxic element out. I unfortunately have no good advice for those individuals, but at any rate I’m sure they have more experience and advice to give than to get.

You also have to filter the meanness into useful and not-useful. I don’t mean constructive. I mean useful. As in you have to be able to put it into actual use. “X is bad, do [completely impractical option] instead” may be constructive but it’s not useful.


Beg, Borrow, Steal

It is said that you should surround yourself with those better than yourself that you may learn to be better. This sounds good except that in reality the better people are, the higher the likelihood that they are doing the exact same thing.

You can see the problem if you’re just starting out and are not very good.

You need to beg, borrow, or steal some of their time and experience. Nicely. And with permission. Don’t be a run-of-the-mill asshole about it. A lot of people are more than happy to share their knowledge and experience with you as long as you just ask!

People who are good at stuff generally spend a lot of time doing that stuff. Their time is valuable. Your time is also valuable, but probably not as valuable to them or others. It really is incredible how much useful information you can soak up just interfacing with a really knowledgeable person directly for an hour or so. If you can one-to-one your time like that, that’s golden. If you spend an hour typing out a giant email and they respond with a succinct, but illuminating one-liner, that’s fine, too.

You should cultivate a garden of people explaining why what you’re doing is bad and how to make it better.

Aside: Results based thinking is not, on an objective level, always the best route to follow, but in a sea of uncertainty and inexperience it’s the best bet. “I went against the grain and it paid off!” stories are few and far between and often a tissue of lies and revisionism. Until you get some experience under your belt you are in no position to even ask the correct questions or to evaluate what is corrosive groupthink versus solid conventional wisdom.


Assholing For Dummies

Don’t be, generally, especially if you’re a dummy. But there’s a pretty straightforward checklist of conditions to go through if you’re thinking of increasing your level of mean:

  • Does the recipient seem to deflect any and all other forms of criticism delivery?
  • Is the interaction public or private? Public humiliation is a poor tool for learning – at least for learning the thing you most likely want to teach. A private talking to can give a much more intimate feel and make a greater, correct impression.
  • Is the recipient a challenge seeker? A contrarian? You need to maneuver obstinate people more carefully.
  • Are there observers who might be on the fence? Being an asshole can be an “all hands, evacuate” button; sometimes you can’t convince someone, but you can convince others.
  • Are you sure that your desire to help is actually a desire to help? As opposed to say, a sadistic streak? A power tripping drill instructor is a bully, not a teacher or a mentor or anything good.

I know a lot of the “always be nice” crowd don’t believe that there are people who respond (well) to meanness, but that’s patently false. I’m one, for example. It’s quite literally the proverbial “I bet you can’t do that, loser!” – “OH YEAH? WATCH THIS.”

Conversely there is the crowd of people who believe that any and all criticism should be bare, stripped of nuance, and dedicated completely to the most offensive facts pertinent to a particular situation.

Both mentalities are toxic. There is an entire spectrum of people and associated reactions and convincing them requires different tools.


“He said WHAT?”

Negativity bias is a significant force. I know I just spent a few paragraphs explaining that people were individuals, but I’m going to go to a broad stroke now because it’s hard to argue against empirical evidence when it comes to a mostly hardwired psychological state.

Humans remember insults. They remember negative encounters. They do so significantly more than positive encounters both in range, duration, and intensity.

The literature suggests that humans, as a group, instinctively believe that negative information is more accurate than positive information. In other words, “Tom is a nice guy” has less weight than “Tom is a shitbird.” Higher intensity if you are Tom.

Perhaps unfortunately negative reinforcement and loss aversion are powerful tools.

Aside: I bet you thought this blog post was free and clear of games relevancy, eh? Loss aversion is particularly effective in the mobile gaming sphere. “Here’s your +7 Hammer of Pot Smashing! Oh no, pay fifty cents to keep it or it will disappear!”

The short version is creating an immediate negative encounter can result in increased memorability of said encounter.


Be Mean to Be Nice

There is something to be said about the time scale of niceness and meanness. It’s the whole teach a person to fish versus giving her a fish thing. You definitely don’t want to be put into a situation where you gave people bad advice to avoid hurting their feelings. Or at least you shouldn’t, from my point of view.

Saying nice things has benefits and perks – there’s no denying that. In the long run most people want a fun, happy, safe environment to live in where meanness does not spiral out of control.

There is every possibility if you’re mean when trying to persuade people that it backfires. They might dig their heels in out of personal principle, decide you are wrong (mean people are always wrong, right?) or for some other reason.

Being mean also generates friction, and many people are conflict-averse. Some people simply cannot handle criticism on any level, and until they learn to any meanness would simply be counter-productive. Some people simply love the criticism and attention (yes, these people exist.)


Reputation and Anecdotes

My general reputation is of an asshole. It’s one I promote, with the caveat that I also sincerely want to help people. It’s effective for all the reasons I mentioned above, but also because I can offer praise that is taken seriously. That last is a very nice selling point.

It really is remarkable how often I get asked in private how I feel about such and such a thing largely because that person feels those too close will not be honest.

I realize I’m conflating niceness and lies (as nice lies!), but this has become so common recently that I think it happens much more often than many people, myself included, think it does.

Final comment on being an Enlightened Asshole: If you read or hear something you think is completely off the rails, imagine someone you love and respect had said that. What would your reaction be? Employ that as a yardstick for measuring your meanness in the most useful way you can.

Use your inner asshole for good, not evil.


Thanks for reading,
Mister Bums

You can contact me at [email protected]Twitter, or leave a comment below.