For instance: In the 1920s, the black writer Elise McDougald wrote about the liberating aspects of paid labor in new fields for black women in Harlem; a decade later, the black lawyer Sadie Alexander eloquently laid out the many benefits of female work outside the home. Yet it was 30 years later that Betty Friedan, a white middle-class woman addressing similar arguments to a white middle-class audience, was credited with kicking off feminism’s Second Wave. (I’m not endorsing this model, but rather countering your notion that past advances have existed outside a context of wealth.)

Often, it has been financially comfortable people who are most able to lend their time to organizing and opining, and not to scraping by. And I don’t mean to simply tag women here: Karl Marx was middle class; Martin Luther King Jr. was middle class; the Port Huron Statement begins with a description of Students for a Democratic Society activists “bred in at least modest comfort, housed now in universities, looking uncomfortably to the world we inherit.”

Of course, movements have also been led by people whose experiences of subjugation shaped their activism—Frederick Douglass, Fannie Lou Hamer, Dorothy Hughes—and by those whose devotion to agitation over money-making has left them struggling. But the nation’s economic structures have changed. Shulamith Firestone died in 2012 in her East Village apartment, which she rented for around $400 a month. It is no longer possible to live in the East Village for $400 a month—or East Bushwick, for that matter.

Things are bad right now for millennials—the very people who are freshly invested in popularizing feminism. Young people enter adulthood hobbled by unprecedented student debt, facing a paucity of jobs and lowered earnings and even worse prospects should they forgo college; they’re living with their parents, are economically barred from many of the cities that make organizing more possible.

You’re right that the Internet permits a new form of gathering—I think now you’re making my argument about its usefulness back at me! But let’s consider the efficacy of noise-making without funding today. The Supreme Court has just gutted the Voting Rights Act and created a post–Citizens United world in which voting has become harder and literally purchasing representative power has become easier. The impoverishment of youthful agitators is not same-as-it-ever-was La Bohème–ism. It’s a structurally supported impediment to altering the dynamics of power.

So now who’s pessimistic? Though let me recover a smidgen of sunniness by saying that I believe that the restriction of freedoms for women, people of color, and poor people are the death throes of the old status quo. But it’s ridiculous to pretend that money and influence have been incidental to social movements: They’ve been pretty central. That’s partly why it’s important that we not throw the capitalists out with the bathwater.

Speaking of money and class, I’ve been thinking about policy advances: how they’ve worked in the past and about the likelihood that future concrete achievements will be offered up only alongside deeply destructive compromises. The 14th and 15th Amendments granted black men, but not women of any color, the franchise, creating a terrible rift between abolitionists and suffragists who had long worked in tandem. Fifty years later, Carrie Chapman Catt, the head of the National American Woman Suffrage Association, supported Woodrow Wilson’s entry into World War I, enraging her pacifist feminist allies, but probably ensuring the eventual passage of the 19th Amendment, which would allow them the vote.

Were we to imagine a future that included federal paid-family-leave legislation—to pick an example we both believe to be vital—we’d have to imagine the tolls that might be exacted in its passage. Consider that, when California recently passed its paid-sick-day legislation, it left out home health care workers. And remember that, when Social Security was created in 1935, it excluded domestic and agricultural workers. It’s not hard to envision a future paid-leave act that cuts out Americans who need it the most: shift workers, minimum-wage earners, home health care professionals. Such legislation could be a boon to gender equality for millions of Americans, but it could simultaneously crowbar open an even deeper class (and race) chasm between those it benefits and those it leaves out.

How do we move forward without simply walking straight into a repetition of history, in which victories tear apart the coalitions that make them possible? Is it feminist support of more economic populists like Elizabeth Warren? An intensive commitment to voting rights, to ensure that the government actually represents the diverse population it serves? How else can we realistically—and optimistically—prepare ourselves to get the work done without incurring major losses?

Dear Rebecca,

Let me tell you a story. During World War II, day care centers filled the land. You know why: America needed women to do the jobs formerly done by the men now fighting overseas. Newspaper stories about children left in cars and chained to trailer homes, along with the congressional testimony of female union members, convinced the government to fund the day care programs that would allow mothers to go to work. Congress passed the Lanham Act in 1940. It ultimately paid for 3,102 centers that enrolled around 600,000 children—not nearly enough centers, but nothing like it had ever been seen before.

The Lanham Act was not meant to be permanent, and in 1946, Congress ended its funding and most of the centers shut down immediately. In some places, however, the centers did not close. One such place was Philadelphia, because the mothers of that city wrote letters and petitioned and erupted in protests to keep at least 20 centers open. “If something isn’t done by next Thursday,” a woman declared at one City Council meeting, “we will have 200 women, with the children, in the balconies of the City Council’s chambers.” The women kept the centers alive for two more years. In 1948, when the city decided not to allocate any more money, 150 sign-wielding mothers buttonholed councilmembers at City Hall. The police kicked them out, but the women got a permit and returned. They had public sentiment on their side—“never before have readers exhibited such overwhelmingly strong support for a measure,” wrote Philadelphia’s The Bulletin—and by 1949, they had won an imperfect victory. The mayor agreed to fund the centers out of the budget from his own office. He couldn’t get the councilmembers to give public day care a single dollar out of the municipal budget. Nonetheless, ten centers operated well into the 1960s.

“Who were these women?” asks historian Elizabeth Rose, who tells this story in Mother’s Job: The History of Day Care, 1890–1960. “They always identified themselves as working mothers who used the child care centers ... and none of their leaders seem to have been publicly prominent in Philadelphia in subsequent years.” Rose speculates that they were recruited through the centers’ parents’ associations and met during pick-up and drop-off.

It would make a great movie, don’t you think? And it tells me that change doesn’t require professional middle-class activists. (Don’t get me wrong: I’m not saying they can’t be the ones leading the way. I’m just saying they don’t have to be.) More than middle-class approbation, change requires rage, persistence, and on-the-ground organization. A thriving network of civic associations available for mobilization doesn’t hurt, either.

This is one reason I do not agree that federally subsidized day care is far-fetched or idealistic. (We have already come so close to getting it—think of the Comprehensive Child Development Bill of 1971, which would have funded universal day care had Richard Nixon not vetoed it.) I feel fairly sanguine that we could secure maternalist, if not strictly speaking feminist, social welfare policies in this country. But getting such legislation passed will require shoe leather and grit and tapping into existing pressure groups more than it will depend on elites talking to elites. It will come from grassroots organizations being willing to make compromises and unlikely alliances to get the necessary votes.

What kind of strange bedfellows might these be? Maybe Hispanic Catholics. Maybe evangelical church groups. Maybe the Bob Caseys of this world, or other Democratic candidates who fall afoul of Emily’s List by not taking the right position on abortion but who are electable and have views about health care, day care, and family leave that could help millions of women. I don’t mean to give short shrift to reproductive rights; goodness knows my life has been predicated on them. But if we’ve got to choose for now, I choose health care, day care, and family leave. For now.

One bedfellow I personally can’t stand, but you can, because you realize, correctly, that we have to take our friends where we find them: the ever-present Sheryl Sandberg and her brand of Davos feminism. Even if the COO of Facebook sounds completely tone-deaf when she brags about improving parking for pregnant employees, even if the so-called Lean In movement is a sham dreamed up by her book publicist, if she highlights the problem of unequal pay for equal work, well then, OK. Would the exclusion of mostly minority home health care workers and others at the low end of the pay scale from paid-sick-leave legislation be grotesque, unjust? Absolutely. Should we take the legislation if we can get it? Absolutely. We build from there.

I wonder whether, in the end, we’ve met in the middle: You sounded a whole lot more Eeyorish in your last entry than when you started, and as we go on, I find myself developing a Charlie-Brown-like hope-against-hope for change in my lifetime. You chuckle at Elaine Showalter when she says feminists need an attainable goal that will unify us across all our dividing lines, but I think she’s right, and I think “caregiverism” might well be that goal. What do I want? Would I like women to stop having to pay that “mommy tax”? Would I like to stop paying it? Hell yes. Would I be satisfied, for now, with a deeply compromised version of a federal paid-leave bill or with state-by-state rather than federal funding for day care? Yes. (What is Bill DeBlasio’s universal pre-K if not New York City’s baby step in that direction?) We have to do what we can to make it possible for men as well as women to work and raise families at the same time, and we have to do it in the name of social equality and economic growth, not just in the name of feminism. This “is the big unfinished business of the women’s movement,” Crittenden once said. It’s a long way off, obviously, but yes, Rebecca, let’s get on it.