Evoking the woke and wayward wanderer

The phrase “evoking the woke and wayward wanderer” isn’t something you’ll find in the canon. It’s not Wilde or Baldwin or a lost line of Old English poetry. It’s a mash-up, a cultural experiment, a rhetorical collision. Which is exactly why I use it. Because like most of us, I live in contradictions. And nothing feels more of this moment than trying to hold them together without the safety of an easy answer.

First, the woke.

Once, the word meant vigilance: stay awake to injustice, alert to systemic wrongs. Rooted in Black vernacular, it carried urgency and moral clarity. Then came its afterlife: commodified, politicized, sneered at. Now it’s a mirror word. To some it signals enlightenment; to others, delusion. “Woke” reveals as much about who uses it as who it describes.

Then, the wanderer.

That figure is ancient. The lonely drifter, cast out or self-removed, tracing the edges of belonging. The Old English poem The Wanderer depicts him adrift, mourning a lost lord and lost order. His exile is both tragic and deeply human: he is awake to life’s impermanence, and for that awareness he suffers.

So what happens when we evoke them together?

The woke and the wanderer.

It feels like naming a cultural condition: we are hyper-aware yet profoundly unmoored. Loud in conviction, quiet in direction. Half marching, half drifting. Awake to injustice, alive to contradiction, but alienated all the same.

That tension matters.

Because awareness without compass leaves us in exile. And yet exile can be fertile: a place where old structures collapse and new ones might be imagined. The wanderer suffers, yes, but wandering is also a search — for meaning, for community, for a way to live awake without losing oneself.

And isn’t that the middle so many of us occupy? We are neither zealots for the extremes nor apathetic spectators. We feel the pull of both sides and the exhaustion of being told to pick one. We know things could be worse, but also better — if cruelty weren’t mistaken for conviction, if performance weren’t sold as progress.

The middle isn’t passive. It’s restless, questioning, often lonely. But it may also be where the future is made.

Marilyn Monroe once quipped, “If I’d observed all the rules, I’d never have got anywhere.” It was cheeky, defiant, and, read now, quietly radical. Because rules — political, cultural, social — are often written by those who benefit from absolutes. And perhaps the only way out of our current impasse is to break a few.

To wander, then, is not to be lost but to be searching.

To be woke, at its best, is not to posture but to remain awake. Together, they form a paradox worth inhabiting: the awareness of the woke, the restlessness of the wanderer, fused in the messy middle.

And the middle isn’t moderation. It’s radical clarity — the courage to resist being weaponized by either side, to stand in the grey long enough to see the human in front of you. In a culture addicted to outrage, that may be the most rebellious act of all.