Ellen—the protagonist of In the Wake, Lisa Kron’s play about the early ’00s and the accompanying George W. Bush presidency—is a common type of white idealist American. Righteous free spirit, not-for-profiteer, writer, and believer in art and American democracy, Ellen lives in New York among her makeshift family: Danny, the man she loves but won’t marry; Danny’s sister Kayla and her wife, Laurie, a chef at a restaurant near the World Trade Center; an older friend, Judy, who spends most of her life working in refugee camps; and Judy’s niece Tessa, a conservative southern teenager who is the only non-white character (“mixed,” not “Black,” as she points out to Ellen when Ellen, of course, whitesplains race relations).

Ellen (Beth Thompson) is insufferable. To some extent, it’s by design: The play wants to know why we are so surprised by our own failings, both as individuals and as a nation, and that’s what Ellen wants, too. See, Ellen falls wildly in love with a woman, Amy (Jamie M. Rea), complicating her relationship with Danny (an affable Chris Murray). Thompson is at her compelling best when Ellen is faced with the painful prospect of losing either relationship. Unfortunately, the actress is given less to work with in the play’s other soliloquies, which propose questions like “How are you supposed to see your own blind spots?”

By the time Judy (Jane Bement Geesman) finally does what we’ve wanted to do for two hours and slaps Ellen with a speech about the unspoken privilege of American exceptionalism, we’re ready to make Geesman the lead. (And she would deserve it: Judy’s gruff standoffishness is stretched broad enough to see the fragility and fear it covers.) When Ellen asks her, “How much farther do I have to fall?” Judy answers, “That’s a question of someone who never considered that they might fall.”

Ellen’s flaw is her assumption that she, by virtue of never having questioned her own goodness, is capable of perfect empathy. She believes she knows exactly what Danny wants, exactly what Laurie (played by a genuinely funny Alissa Jessup) felt on 9/11. Unfortunately, empathy offers nothing to a person who needs sympathy.

Yet the play doesn’t care if she learns that lesson. Ellen’s character arc amounts to “checking her privilege,” and it’s hard to call that heroic. The play ends with Ellen literally transcending an imagined boundary on the stage, into yet another spotlight of self-congratulation that no other character need enter.

Josh Hecht, in his director’s note, laments that he’s often told he’s “preaching to the choir.” And truly, theater audiences in Portland are full of old rich liberals, young drama students, or jaded—and, in my case, white—critics. “The choir,” he says, “needs more convincing than we like to think.”

The big lie of In the Wake is the one it tells itself: that it is possible for us dispassionately map our blind spots. But you can’t see yourself from the outside any more than you can experience someone else’s life. When the hubris of self-examination is not itself examined, nothing meaningful results from it.

To preach—to, alone at the pulpit, claim to offer salvation—is not an honest act for an artist. But neither is singing a rangy, indulgent solo to the choir, no matter how enjoyable its individual notes.