I’ve run this little meditation a few times in this space over the years.

I keep coming back to it—and when I do, I’m compelled to bring you back to it, too.

I think it’s especially poignant in times of real social change—and especially valuable to people in midlife, people with mortgages and jobs and raggedy families and a growing sense of finite remaining years of life who wonder all the time (and usually in secret) if they are being as useful as they can.

And I think it’s especially useful now, as we each break for a rest after a hard and disorienting year—and to ready ourselves for what will inevitably be one more.

It’s by my first publisher Larry Ragan, one of the most influential stylists I ever read. In a little Catholic newsletter sometime in the 1960s, Larry wrote:

There are the insiders and the outsiders. Two kinds of people. Two ways of looking at life. Two ways of making things happen.

The outsiders raise hell. they demonstrate; they organize marches. They issue reports that excoriate the establishment, challenge the status quo, appeal to all who thirst for justice.

The insiders? Often dull. The insiders speak a different language: they know the tax tables, the zoning variations, the assessment equalizers, the square-foot cost to educate the kids. You’ll find them on the school board, city government, on the village board. Ordinarily not word people, they have mastered the art of the platitude.

Outsiders are often wild. At first, they don’t seem to make sense. The first black kids who sat at a lunch counter and refused to move were outsiders. The first marchers to Selma were outsiders. Surely it was an outsider who first proposed the shocking idea that the generic “he” is a sexist word. Dorothy Kay, who in the 1950s stopped Manhattan traffic to protest atom bomb tests, was an outsider.

Please God, let us always have outsiders and give me the grace, in my better moments, to know how to be one. But I’m torn because I want to be an insider too. The insiders resist the first answer that comes to them: they have heard it before. They are offended when they see the world’s complexities reduced to slogans shouted into a microphone or preached at a town hall meeting. They are saddened when they hear someone argue that God is on his or her side, and they wonder why God doesn’t speak so clearly to them.

Sometimes you’ve got to feel sorry for the insiders. When they win, few know of their victory. When they go wrong, their mistakes are branded as evil. Often they share the goals of the outsider but continue to say, “things aren’t that simple.”

The world is filled with people who like to feel they are right. Insiders are not always certain they are right. They are unhappy when they must resist the simplicities of popular sloganeering. So when we tip our hats to outsiders, as so often we must, let’s not do so with such vigor that we fail to give two cheers to the insider.

It’s this line that seems even more relevant than when it was written: “Please God, let us always have outsiders and give me the grace, in my better moments, to know how to be one. But I’m torn because I want to be an insider too.”

I live in a world where a Black gay woman ran for mayor of Chicago a few years ago and I was getting notices from some friends to my left not to vote for her because she was using her creds—as a Black gay woman, in Chicago—to conceal her brutal establishment agenda. In that scenario, when I supported Lori Lightfoot, was it as a progressive or a conservative, an agent of change or a defender of the status quo—an insider or an outsider? (In any case—these days, those folks are saying, “I told you so.”)

Everyone feels like an outsider this year—especially Trump voters. And everyone behaves like an outsider—throwing words like rocks. No one wants to take responsibility for being an insider; no one wants to take that rap. And yet many of us are insiders in one or more important aspects of our lives—people working within powerful institutions or industries, always deciding how far to push it, and how fast. And often wondering where to begin, and what to say. No wonder why the speechwriters I look at on these Zoom calls these days look back with eyes that are tired from more than overwork.

Last week I thought to send Larry’s prayer to one of these tortured insiders and outsiders—a close friend, who seems to me under the most terrible pressure, as a chief communicator at an educational institution beset by young agitators for urgent change—change that he and the leader of the institution believe in, but don’t know how to implement overnight. The communicator sent Larry’s prayer to his boss. She called it “beautiful.” And the communicator told me, “It’s utterly perfect for where she and I are right now.”

Where so many of us are right now.

Insiders, and outsiders.

In America.

What differentiates a kook from a contrarian from a cultural critic?

Yesterday, I was following these Senate hearings where the social media moguls were being grilled about, among other things, whether they are suppressing the distribution of conservative posts. Good hearings to have, it seems to me. I’d like to know how the bloodless bastards who run these companies decide who sees what. Maybe we should have these hearings about once a week.

But on the very same morning, I was on a Zoom call with a self-admitted eccentric, who was complaining that he worries the social media platforms are censoring his admittedly out-of-the-mainstream views. His expressed views begin with alleged scientific evidence that undercuts the value of masks in suppressing the spread of COVID. His views escalate to: The larger problem here is that people are overly afraid of their own death—and we sentimentalize lots of the dear vulnerable old people who are actually mean assholes, truth be told.

He also told me he’s frustrated by others’ unwillingess to “punch back” at these views, when he expresses them in shops and on Zoom calls.

So I asked him why he felt it unjust that he not be able to easily find a wide and high platform to air his sanguine attitude toward herd immunization by accelerated mass global death.

I asked him to think of another time in history when the broad distribution of extremely unfashionable ideas was socially supported, or a nation where it was constitutionally guaranteed.

And I asked him to think about how he would try to express a contrary opinion 100 years ago.

Like, say, during Spanish Influenza, you thought that masks didn’t prevent spread and people who wore them were a bunch of sniveling cowards not manly enough to face down unblinkingly their likely random death.

And say you wanted to spread that opinion around. What were your options, 100 years ago? Well, you could print pamphlets and pass them around on street corners. You could start your own newsletter. You could write a little letter to the editor of one of the daily newspapers, like so many cranks so often did. Or you could stand on the street and shout your opinion into the wind.

If you lived in Chicago, on a warm night you could go to a place called “Bughouse Square,” which was the nickname, slang for a mental health facility, of Washington Square Park on the near north side. There, orators called “soapboxers” would hold forth on every subject under the moon, competing with poets, religionists, anarchists and Industrial Workers of the World (known as “Wobblies”).

Bughouse square became world-famous, actually—a tourist attraction.

“Many speakers became legendary,” according to the Encyclopedia of Chicago History, “including anarchist Lucy Parsons, ‘clap doctor’ Ben Reitman, labor-wars veteran John Loughman, socialist Frank Midney, feminist-Marxist Martha Biegler, Frederick Wilkesbarr (‘The Sirfessor’), Herbert Shaw (the ‘Cosmic Kid’), the Sheridan twins (Jack and Jimmy), and one-armed ‘Cholly’ Wendorf.”

Ever heard of one-armed “Cholly”? No, I didn’t think so.

Never heard of most of those folks, I bet. That’s because what they were saying wasn’t popular. And what’s not popular isn’t as well known as what is popular. Almost, you might say, by definition.

Now, I’m sure The Sirfessor was pretty bent out of shape that the Chicago Tribune or the Chicago Daily American wouldn’t give him a regular column to expound on his Nietzscean ideas about Egoism. I’m sure the Sirfessor didn’t see himself as a crank any more than you see yourself as a kook.

The Sirfessor would have been good on radio, too! Wikipedia tells us he once took part in “a non-stop talking contest in New York in 1928. Although he dropped out on the second day, he attracted attention by describing himself as the ‘coiner of more new words than any man in the world,’ and as ‘transcending the wit of Shakespeare.'”

But did the Sirfessor have a legitimate claim that the newspapers and radio stations were criminally and fascistically preventing him from carrying his message to the masses, in all the great capitals of the world?

No, newspapers and radio stations weren’t about to do that, because they wanted to maintain economic viability by maintaining public credibility, and the way you do that is to keep within shimmering sight of the solid land that is mainstream public opinion.

You’d have to be ignorant or purposely obtuse (as many of us are these days) to believe that such a fundamental fact of capitalist society has changed. Twitter and Facebook aren’t against conservatism. They’re against social instability. And they’re against the widespread perception that they are endangering the society in which they do business by enabling the spread of social madness.

I am not saying it’s madness to believe that there’s a chance masks don’t work as well as we think they do, though I think focusing on that possibility seems misplaced. And over a bottle or two, I would love to discuss people’s evolving attitudes about death, and how they might play into public policy regarding a pandemic; I actually have a few things to say on that subject myself.

Much more absurd than those conversations is the one that says, “I deserve to have my ideas heard by the masses, no matter how grating or odd they may sound to the mainstream ear. And anything that keeps me from doing that is a sign of creeping totalitarianism.” That really is a kooky thing to say.

If you want to get truly disagreeable or disruptive ideas heard, you either need to make them seem more mainstream—or you need to organize, and make enough noise and collect enough signatures that even the Power Guys have to listen. Because the numbers you gather begin to make your ideas socially legitimate—again, by definition. But that takes a hell of a lot of work and a lot more than inventing new words and saying them with power and wit.

Everyone knows that—except some people I know. Maybe some people who aren’t used to having their views marginalized.

But as I told my aggrieved friend, the good news is that Bughouse Square is still there, and it still looks very much like it always did, and every summer they hold the Bughouse Square Debates, where you can still say whatever words you want, and if you’re up to it, you can talk for two days straight.

There’s also the newly popular social media platform Parler, which bills itself as “The World’s Town Square,” and promises its users a place to “speak freely and express yourself openly, without fear of being ‘deplatformed’ for your views.”

That seemed to interest my friend even more.