Say "Woke" Like You Mean It

“You keep using that word. I do not think it means what you think it means.” — Inigo Montoya in The Princess Bride

Many years ago in an acting class, I watched a friend work on a scene from Wait Until Dark where he played a murderous drug dealer (Alan Arkin’s role in the ’67 film). My buddy did his best to be the baddest bad guy he could be. But Terry, our acting coach (and the voice of the Stormtrooper who said “These are not the droids we’re looking for”) stopped him mid-scene.

Terry could see he was playing the scene like a man who thought of himself as bad, being evil because he enjoyed it. But that’s not how bad guys work, Terry told us. Everyone is the hero of their own story. We all have moral codes and motivations, and even villains think of themselves as good people doing what they have to do.

This lesson has stuck with me for over 20 years. Sure, it made me a better actor, but the real gift was that it helped me view the world in new ways. It’s something I think about often when I see powerful moderate liberals like Scott Galloway (and Bill Maher and so many more) criticize people who are asking (sometimes clumsily) for social change.

I know Galloway and others see themselves as heroes defending institutions and public discourse from the excesses of the “regressive left.” But I see them as gatekeepers of the status quo — and therefore obstacles to meaningful change.

I don’t think these moderates have bad intentions, nor do I see them as bad people. I like Galloway’s work a great deal, listen to him regularly, and learn a lot when I do. But whenever he brings up “wokeness,” I hear ignorance. And I think I know where it comes from.

Dr. Robert Livingston in his excellent book The Conversation: How Seeking and Speaking the Truth About Racism Can Radically Transform Individuals and Organizations draws a distinction between two types of privilege: individual and institutional.

Individual privilege is accrued through work, study, and experience. For instance, I have university degrees and years in the business trenches. I’m also a voracious reader and prolific creator. This gives me a certain amount of access to resources and opportunities that many don’t have.

On the other hand, I’m white, male, cisgender, heterosexual, and tall. I’ve always had access to healthy food, quality medical care, and education. I look and sound like I belong in places where big decisions get made and big checks get cut. When I walk into a boardroom, no one bats an eye — unless I flash a tattoo (and even they get little attention these days). This is institutional privilege that comes to me through the accident of birth. It’s like playing the game of life at a low difficulty setting.  

Some of my unequal access to resources and opportunities is due to individual, or earned, privilege and some is due to institutional, or unearned, privilege.

When I first noticed that much of what I have in life is unearned, it was a hard pill to swallow. Life hasn’t been easy for me — it's not for anyone. I’ve had long struggles with depression and had my share of financial and personal troubles. On a few occasions, I’ve come close to taking my own life. I’ve worked hard to overcome these challenges and achieve what I have. So my default setting is to believe that these struggles mean that I’ve earned what I have and that I know how to help everyone else get theirs too. But it’s not that simple.

One of my goals in work and life is to leave the world better than I found it. I’m especially interested in creating a more equitable world, where more people have more access to resources and opportunities.

So when someone points out my unearned privilege or suggests I might be part of the problem, my first reaction is to be defensive. I notice a similar defensiveness, masquerading as helpfulness, from Galloway and other successful men from our generation.

Galloway is a professor at NYU, and a successful podcaster, author, investor, and business owner. One of his favorite pieces of advice for young people is that they should “Be Warriors, Not Wokesters.”

“Woke” of course, is a term that originated in Black communities that means to be alert to injustice in society, especially racism. In other words, it means being aware of statistical disparities in unearned privilege among various groups. In a 2021 advice piece to new grads, Galloway had this to say about the word:

“But the word has lost that original meaning. Beyond the media noise, an insidious pattern is emerging in academic and professional settings. The insistence on filtering everything through the lens of personal identity and experience. The prioritization of victimhood. The belief that to be offended is to be right.”

To my eye, it’s people like Galloway who have caused the word to adopt this new pejorative meaning. When someone points out the grossly uneven distribution of institutional privilege and the part folks on top play in preserving it, they get defensive and preachy.

I get it — it’s an understandable, and even natural, reaction. It can be hard to feel judged especially when the points made are wrapped in frustration and anger. I’m a successful, straight white guy of a certain age — and it can feel like we are everyone’s favorite villain recently.

But when I look a layer deeper into the anger and angst that Galloway calls “the prioritization of victimhood,” I see a new generation, many from marginalized communities, finding a voice with a lot to teach us older folks. Rather than quiet them, I’d like to elevate, amplify, and learn from them.

When I hear older successful men (and it’s mostly men in my experience) like Galloway use the word “woke” as a pejorative, I hear a gatekeeping for the status quo. I’d argue that subtle gatekeeping by well-intentioned moderates is a larger obstacle to real change than overt or violent opposition by authoritarians. The message seems to be that while change is good, we still want it only on our terms, and we don’t want it to be too disruptive. In essence we prioritize civility and our comfort over justice, equity, diversity, or inclusion.

But tension is an inevitable part of the diversity equation. There is always tension when we consider perspectives contrary to our own or when we learn that we aren’t the good people we thought we were — that we’ve missed something, hurt others, or excluded them. We, the folks with institutional privilege, need to embrace that tension rather than deflect it.

So here’s what I think we (older successful liberal men) need to do. We need to allow for more discomfort in ourselves. We need to expect the resentment and anger from others that naturally comes along with our unearned privilege.

We need to be willing to swim against the stream — even the stream of our own thoughts. Listen to the opinions of young people, people of color, and women with generosity and empathy, even (especially) when they are expressed with vehemence and anger, no matter how uncomfortable it makes us.

We need to be woke warriors and have thicker skins.

We won’t reverse the flow of injustice and inequality in our lifetimes, but if we do some hard work, we can leave things a bit better than we found them.

— Bob Gower

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