The High Cost of Keeping It Real

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It’s always nice when you take a risk and hit paydirt.

My wife and I – natch – have a lot in common, but there’s obviously some history and experiences we don’t share, what with us being from different countries and her being a woman and whatnot. She’ll never get the Three Stooges, for instance. Her loss.

But we can remedy some of our missing shared experiences. A few years back I cautiously introduced her to the comedy / documentary Idiocracy, and my punt paid off smashingly. Now we have a rich library of allusions to share from that one movie alone.

Recent events kept bringing me back to a comedic sketch I saw some time ago, one that captured the spirit of many people nowadays. 

With some trepidation, I introduced my wife to the best of Dave Chappelle’s “When Keeping It Real Goes Wrong” (R-rated language, and most certainly not suitable for work):

(Sidebar: I did consider whether this piece was appropriate to share right now, as it explores how Chappelle’s character fits in an office full of white men. That certainly adds a layer of complexity, but I think that was always Chappelle’s intent and actually makes it timely. He’s a great comedian, but he’s also a keen social observer.)

This was another winning bet. Now, instead of a detailed description of the inappropriateness of someone’s righteous indignation over a small matter, we can simply allude to someone “keeping it real.”

A popular definition of “keeping it real”, per Urban Dictionary, is:

“Not being fake or influenced. Being true to yourself and your values, but more importantly, being true to innate values that all people acknowledge as respectable.”

Inspired by my Chappelle Muse and in honor of the way many people have perverted this term, I’m making my glossary definition:

Keeping It Real:

\”Seeking out major confrontations over small, insignificant matters under the facade of ‘being true to one’s values’ and ‘not being fake’. Drawing an unnecessary line in the sand over a perceived slight or injustice. Being antagonistic to others due to one’s own extreme inflexibility.\”

People who are keeping it real look at a situation that could go either way, and they strap up for war. They hear Sun Tzu’s famous line, “The greatest victory is that which requires no battle,” and they ask, “Where’s the fun in that?” They don’t just respond to actual slights; they will dig and probe to see if they can find a slight where there wasn’t one initially. And they are masters of comments and actions that serve as the opening gambit in a fight that should never have happened.

When people refer to “Karen” and her wild behavior, she’s just keeping it real. Why on earth would she let a small thing slip when it’s a matter of principle?

I won’t link to all of the videos and stories of people keeping it real. You and I know they are everywhere. It seriously stresses me out to watch them. Folks create fights out of thin air when the barest whisper of social skills or consideration – or just minding one’s own business – could have avoided conflict.

Is This the Hill You Wanna Die On?

It’s quite rare to truly need to keep it real in social interactions. When the safety of a child is involved, for instance. When there’s a true injustice occurring that can’t be easily remedied later. But the times that demand a principled stand are few.

Most of the time, people are in full-on, keep it real, rage mode over things so petty, so inconsequential, that it’s laughable. And it’s become the world’s entertainment. 

Some worry we live in a “cancel” culture. They’re worried that people who make a “momentary” mistake captured in writing or on film lose their jobs, their business, their reputation, and more. (It turns out that the internet masses are far better at keeping it real than any one individual.)

I’m not quite there. I guess there’s a chance that someone caught in the act is delivering their very first rage-filled invective, or is being racist for the very first time, or is just caught up in a perfect storm of stress that will never happen again. But it’s not likely. And while the punishment can be heavy-handed, it should hopefully serve as a deterrent. We should all act like we’re being filmed, because it can guide our behavior and control our more base impulses. (Also because we actually are being filmed, all of the time.)

When someone is caught and called out for keeping it a little too real, the often fake apologies are as predictable as they are pathetic. “These words and actions are completely out of character and not who I am.” “I will be taking time to heal and consider the pain caused by my actions and start the process of becoming a better person.” And so on. (“P.S. What I’m sorry about most is that I got caught.”)

If you are dead set on always “keeping it real”, the costs can be huge. Not just financial – assuming you’re caught by the internet masses, and they’re quite good – but for you as a person. Going through life as an inflexible, narrow-minded, combative person sounds like a living hell to me. Every day would be a battlefield, and most interactions with others would be win-lose affairs. Even if you win most of the time, you’re trapped in a vicious and ugly world. Sadly, some people are going to roll that way, but we all have a choice. 

Whenever I find myself at risk of picking a fight over something meaningless, or if I’m just in the crosshairs of someone who’s keeping it real, I try to use empathy. Considering someone else’s situation and whatever problems or insecurities are driving the conflict can go a long way to defusing it. And if that fails, I just try to shut my mouth and smile…

There’s probably a lot of battles I could have won that I never even got to fight. But at least now, when it happens, I can allude to someone who was keeping it real, and the missus will share a giggle with me 🙂


I’d be remiss in referencing Dave Chappelle if I didn’t link to his commentary on recent events. If you have the time, you should watch his special “8:46” (also has R-rated language not suitable for work)

4 thoughts on “The High Cost of Keeping It Real”

  1. Is this face covering related? Considering rolling this grenade under the door on Facebook – if you’re pro-life and anti-mask, is that inconsistent? If not, why not?

    1. Oh yes. Face covering is squarely in my sights. Screaming about your Constitutional right to have an uncovered face is keeping it a little too real in my book. So is casually reminding us that people dying from coronavirus are mostly old or have pre-existing conditions (i.e., they had it coming). If you’re low risk why should you worry about it at all? Keep It Real!

      But there’s a lot more. Seeing someone with a different color skin and telling them to go back to where they came from (ummmm…I was born here) or calling the police on them? Nice work keeping it real. Sorry you lost your job, tho.

      Reminding us that all lives matter? Thank you for keeping it real – we were about to forget that, and your valuable perspective really helps.

      Even within the little personal finance community (in which I realize I’m a peripheral member at best), there are some brave souls keeping it real.

      I know people have been “keeping it real” throughout history, but the ubiquity of smart phones and the open platforms like Twitter are giving them a global stage they didn’t have before. And it is eye-opening!

  2. Chris Bullock

    Thanks for sharing this insight…. its those little mind shifts that go a long way to a better life. I find I get less judgemental and appreciate other perspectives more as I get older…. although sometime observing these things can rile me up internally somewhat. This insight will help.

    1. I hear you. I can get pretty riled up too (I feel just like Chappelle when they freeze the scene and he’s about to go off!), but I try to remember it’s an unnecessary luxury most of the time to act on it.

      I’m finding myself less judgmental as well as I age. I wonder why some folks go the opposite way?

      Thanks for the note

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