Woke, Entropy, and Confusion: When Terms Take Sides

Ira Warren Whiteside

Alright, so, today we're gonna dive into something a little different, but honestly, it's everywhere: the whole evolution of the word “woke” and how it turned from a simple awareness into, well, this crazy culture war where everybody’s either waving it like a flag or using it as an insult. And look—I’ve, um, seen a lot of terms drift and shift over the years working in tech and governance, but "woke" is a real case study in terminology taking on a life of its own, way beyond its roots.

Ira Warren Whiteside

So, let’s back up for a second to the origins. "Woke" actually started in African-American English, long before Twitter and 24-hour news cycles. It wasn't even just about being politically correct—it was, I mean, a call for vigilance, especially around issues of racial prejudice. Folks trace it all the way back to Marcus Garvey in the 1920s shouting, "Wake up Ethiopia! Wake up Africa!" And Lead Belly—yeah, that old blues legend—he sings “stay woke” in his “Scottsboro Boys” ballad from, what, 1938? Basically warning Black folks to keep their eyes open to threats and injustice around them.

Ira Warren Whiteside

By the 60s and definitely by that ’62 New York Times Magazine piece—William Melvin Kelley, that was the author—“woke” started meaning, you know, well-informed, tuned-in. And there’s this great line from the 1971 play "Garvey Lives!": “I been sleeping all my life. And now that Mr. Garvey done woke me up, I’m gon’ stay woke.” It really speaks to that shift from ignorance to awareness, which, I mean, you see in a lot of social justice lingo but not always with the same depth.

Ira Warren Whiteside

Then, fast forward a bit, and here's where it just launches—music, social media, all that. Erykah Badu, 2008, she drops “Master Teacher” and the phrase “I stay woke” suddenly has a whole new generation repeating it, then Badu herself tweets #staywoke in 2012 and it’s off to the races, tied into movements like Black Lives Matter after Ferguson in 2014. Now, “woke” doesn’t just mean racial justice—it’s expanded to cover, I dunno, sexism, LGBTQ rights, you name it. Suddenly, it’s a catch-all for progressive ideals, and everyone’s got an opinion about what it means.

Ira Warren Whiteside

That's about where things kind of, uh, take a sharp turn. So around 2019, “woke” gets taken up—not lovingly—by critics, right? Politicians and pundits start using it in a sarcastic or just flat-out nasty way. In the U.S., you got Florida’s governor talking about making Florida “where woke goes to die,” passing stuff like the Stop WOKE Act, and apparently President Trump—wait, did I read this right?—he did an executive order to ban “Woke AI in the Federal Government.” I never thought I’d hear “woke” and “AI” in the same sentence, but, you know, it’s 2025 and here we are.

Ira Warren Whiteside

And it’s not even staying here—France is all “le wokisme,” the UK has “Wokewatch” on GB News. Even India, Australia, Canada—they’ve all grabbed this term, twisted it for their own political conversations. It’s wild watching a word go global, especially one with such specific cultural and historical meaning.

Ira Warren Whiteside

But what stands out to me, especially working with data and, well, trying to label things without bias, is how real-time digital conversations can totally flip a term. Like, labeling data for AI models—sounds dry, but if you don’t keep up with how people are actually using words online, you risk building in all sorts of bias. Woke is a prime example. It means one thing in one context, something totally different somewhere else, and honestly, sometimes it’s used just to muddy the waters. And now we even have “woke right” folks, using their own language policing and cancel culture tactics, or companies doing “woke-washing”—ad campaigns about, you know, “inclusion” while ignoring real workplace change.

Ira Warren Whiteside

So, to tie that up, “woke” is basically a masterclass in how language evolves—sometimes in shocking, unpredictable ways. And from where I sit, managing terminology, data, even AI annotations, it’s...well, if you’re not paying attention, you’re probably missing something important. And, like, it’s not going away anytime soon.

Ira Warren Whiteside

So let’s pivot—sort of naturally, I think—into how this whole “woke” debate is, uh, playing out inside leftist and progressive circles. Because here’s where it gets really, honestly, messy. It’s not just haters on the other side tossing "woke" around. You’ve got deep arguments among folks who all consider themselves left or progressive. And this isn’t new—if you look back at history, the left has always wrestled with what comes first: is it identity, or is it class?

Ira Warren Whiteside

One side—usually referred to as “class-first”—says, look, the biggest force in oppression is capital, it’s economics, it’s the class system. Adolph Reed or Walter Benn Michaels, their book “No Politics but Class Politics” pretty much lays it out: focus on solidarity, not splintering over identity. Their argument is that identity stuff, while real, can get people chasing their tails instead of addressing material conditions that shape everybody’s lives. But even saying that, I’m thinking—wait, there’s always a risk of, you know, erasing genuine oppression that crosses class lines. The classic example that’s always brought up is high-income Black women still being at higher risk in childbirth than their white counterparts, no matter how much money’s in the equation.

Ira Warren Whiteside

The counterpoint—sometimes labeled as “identity-first,” though I admit that term’s a little loaded—is more like, okay, but if you overlook identity, you’re missing targets of specific oppression, like trans folks or racial minorities, that need focused attention even if the end game is, you know, fight the whole system. I mean, there’s a tension here—between being broad enough to build coalitions, but sharp enough to recognize when someone’s getting hammered in a way that’s not about class.

Ira Warren Whiteside

Then there’s this big thread about “elite capture”—a term Olúfẹ́mi O. Táíwò and Catherine Liu really unpacked in their books. The gist is, there’s this sort of professional-managerial class, the “PMC,” that swoops in, grabs the banner of social justice, and uses it more to polish their own image or keep their seat at the table than to actually shift power to marginalized communities. Liu, for example, basically says academia’s critical theory folks have lost touch with both reality and with any kind of real, data-driven economics.

Ira Warren Whiteside

But—and this is, like, the merry-go-round of leftist debate—Adolph Reed, who’s all about class-first, even calls Táíwò’s critique the “quintessence of neoliberal leftism,” basically accusing it of just making peace with elite capture and big, flashy radical language but no actual change. It’s performative, at least in his words.

Ira Warren Whiteside

Part of what’s wild is when you go back to the original “identity politics” from the Combahee River Collective, the intent was genuinely materialist. They saw identity as the launchpad for real coalition and analysis—a “process of becoming,” not just “I am X, so I get Y.” But now, modern discourse sometimes gets twisted into, I dunno, “who has it worse?” competitions and an endless focus on subjectivities, leaving class on the backburner.

Ira Warren Whiteside

I’ve read—or tried to read—a bunch of the critiques people point to: “Elite Capture,” "Virtue Hoarders," the Adolph Reed and Walter Benn Michaels stuff, Kenan Malik on solidarity, even pieces by Nancy Fraser and Mark Fisher’s “Exiting the Vampire Castle.” They all, in different ways, pick at the same scab—how do we build a politics that’s universal enough to address shared exploitation, but also responsive to lived realities and not just, you know, grand theory?

Ira Warren Whiteside

It kind of ties back to what we talked about in previous episodes, especially when we dug into business glossaries or the real-world consequences of terminology in governance. Whether you’re talking data, social justice, or even AI, words matter—and who gets to own them, well, that might matter most of all.