Political Conversations With Family Are Hard. Here’s How to Make Them Easier

Navigating political conversations with family can be hard. Navigating political conversations with family in the middle of a period of historic polarization can be so daunting it may cause you to reconsider going home for the holidays.

So to help us prepare for this holiday season, we caught up with Robert and Sam Reich, a father-son duo who have each built impressive digital empires in very different parts of the internet, and who both have a lot to say about both politics and civility. Sam, on one hand, a 42-year-old veteran improv comic who dropped out of high school at 16 to “to do videos and put them on the internet” (as his dad puts it), bought the flailing CollegeHumor.com in 2019, renamed it Dropout TV, and now is the CEO of a booming subscription network, host to shows including Game Changers, Dimension 20, and Very Important People. Not only has his model become profitable — Dropout teases their shows across nearly every social media site but only offers them in full on their own platform — he and his partners offer profit sharing to some of their employees, making them one of the most coveted places to work in Hollywood.

Then there’s Robert, his 80-year-old father, who most people probably remember as the Labor Secretary for President Bill Clinton. Back in 1994, he made wild predictions like, “We are on our way to becoming a two-tiered society composed of a few winners and a larger group of Americans left behind, whose anger and disillusionment is easily manipulated,” and, “Once unbottled, mass resentment can poison the very fabric of society… replacing ambition with envy, replacing tolerance with hate.” He was a public intellectual back when people still used the term “public intellectual,” writing about things like “enlightened capitalism” and the dangers of inequality when that was still a dystopian future, not a crushing reality.

Over the past few years, with a little help from Sam, Robert, who is an emeritus professor of public policy at UC Berkeley, has become a TikTok star, with over 1.5 million followers. “I’ve been writing books forever, and Sam said, very politely and with a great deal of empathy, ‘Dad, if you want to reach my generation, maybe you should think about videos and films,’” Robert says. “And I didn’t know what Sam was talking about.” Now, Robert has his own company, Inequality Media, as well as a new documentary, The Work in Progress, which is being screened this fall at theaters across the country. The film pairs people from two different generations — 30-year-olds and 80-year-olds — to discuss what it means to be American, and, as Robert puts it, “What do we owe each other?” (“I’m the first child to set their parent up on social media to have their parent surpass them by millions of followers,” Sam notes. “This is truthfully reverse nepotism.”)

If anyone could offer advice for civil discourse among family, it’s these two. Over the course of our hour-long conversation, they alternately offered praise (“Sam is a master of laughter and humor”) and constructive advice (“Dad, I’ll coach you as an executive producer to say you should take complete credit”), while allowing room for alternate points of view, even if they seemed to agree on just about everything. To watch them interact is a great reminder that sometimes patience offers the best perspective.

“I have a theory I’ve been writing about for years, and that is that many of the things that divide us are not real,” says Robert. “They’re manufactured, sometimes by people or groups that want to divide us, want to keep us divided. People are basically good people. They want to connect with each other. They face many of the same problems together. And when we discover that commonality, we can begin to work on those problems. It’s when we cannot see that commonality [that] we have no hope of beginning to do the kind of work that’s necessary.”

Even past connecting with your fellow American, it can help you better understand and articulate your beliefs. “The best way of learning something is to talk to people who disagree with you, because that forces you to come to grips with what may be the weakest part of your arguments, your beliefs, your assumptions and also engage in a kind of listening process, which many people are not terribly good at doing,” Robert says. “It’s very closely linked to democracy, because I think that what we are in danger of losing in our democracy is the capacity to deliberate together about what’s important.”

With that in mind, here’s five tips on how to have those same sort of constructive conversations — true intergenerational dialogue — even when it can seem far off.

Having the conversation face-to-face — “person-to-person” — is half the battle.

As much as the internet has become real life, it still isn’t a good place for meaningful engagement. “The internet, specifically, has not helped,” Sam says. “It is such a poor excuse for connection that it makes us feel as if we are communicating with each other, and yet we’re all just down our own algorithmic rabbit holes.” Additionally, he points out, when we confront someone on the internet, we don’t have to live with the repercussions. “We can just comment on something in all caps and eject.” We might make our point, but we’re not actually communicating.

On the other hand, Robert notes, being in a room with a person forces us to see their reactions to our ideas and conduct ourselves accordingly. “One thing that the movie tried to do was create these safe environments,” he says. “If it’s a safe environment and you’re actually sitting there with somebody, you’re encountering them as a real whole person. It makes a gigantic difference.”

Robert remembers a moment in The Work in Progress where an older white woman and younger Black women discuss their lives. “There’s a dialogue in which a young Black woman says to an older white woman, ‘You don’t understand where I’m coming from, because I really have faced barriers you’ve never faced.’ And the older white woman, at first, is coming from a completely different mindset. She says to the young Black woman, ‘Don’t be defeatist, be positive. You’ve just got to have confidence in yourself.’ But gradually, the older white woman actually begins to see what the young Black woman is saying, and it’s very moving because you can actually see in the movie the point at which the older white woman [has a] kind of ‘aha!’ [moment] because they’re there looking into each other’s eyes.”

So how do you create a safe environment for open dialogue? That brings us to…

Remember that you have a respect for this person — and a real curiosity in what they’re saying — will keep the conversation grounded.

When Sam was growing up, he remembers, his dad had a friend, Alan Simpson. Simpson was a Republican, a senator from Wyoming, but he was also a dear family friend. There was the comical height difference — Simpson was 6-foot-8, Robert clocks in at 4-foot-11 — that led to a PBS talk show called The Long and Short of It, but also a respect that showed his sons you didn’t need to agree with someone politically to care for them deeply. “I am not ashamed to say, I just loved the guy,” says Robert. (Simpson died last year at 93.)

“Dad would always talk about this friend, this Republican senator from Wyoming, and it was just sort of impossible for us to grow up imagining that Republicans were the enemy, when Alan Simpson was so close by,” says Sam. “Wonderful guy, by the way. Unfortunately, when you distill people down to their politics, all personality is taken away, and when personality is taken away, humanity is taken away.”

It’s also a matter of remembering that there’s an opportunity to be had when encountering people who might not agree with you. “We’re so very much in our bubbles these days that when you actually run into someone publicly who believes something very other than you, it can feel like you’ve stumbled onto Mars,” says Sam. “Like, I’m interacting with a true alien. I think broaching that person, that interaction, with real curiosity is helpful. Which is to say, I rarely get this opportunity to talk to the other side, [but] if I think of it as my immediate social responsibility to try to change this person’s mind, I’m probably setting myself up for disappointment.”

Come in with a sense of humor, if you can.

Humor is disarming, and finding things that you can laugh about together can be a great step toward someone opening up to you in other meaningful ways. “If you can laugh with somebody, that’s it,” says Robert. “That’s ball game. You’re with them. You’ve created the path.”

Of course, as Sam points out, this can be tough — especially when the things we’re disagreeing about aren’t funny at all. “So many of these issues are so important, and we’re all so dug in. If you ask the vast majority of [Dropout’s] audience, for instance, these issues are simply too important to compromise on. I would venture to say that a lot of young people are so angry that even to engage in the debate feels insulting.”

Start with with with things that you have in common — that you like, and that you dislike.

Robert has a character he likes to bring up when talking about difficult family interactions, someone he calls Uncle Bob. “That is the person who is a Trumper, or let’s say, who really is just almost impossible to talk with because their brain is already wired in a particular way.” Robert explains that the best way to start talking with someone like that might be to try humor, or to just gripe about the things that you’re both experiencing equally. “I think you start with the most common everyday irritations that you both feel, or the most common everyday enjoyments you both share.” Gas prices, maybe, or the cost of groceries. “You don’t start with Trump. You don’t start with taxes. You don’t start with abortion. You don’t start with you know the things that are just going to let everybody just going to trigger everybody. You start at the opposite end. Things that people have in common.”

For Sam, growing up in the 1990s meant that he wasn’t raised to see the country as polarized factions. “To me, everyone feels worth reaching out to,” he says. “And [it’s] a matter of trying to connect with someone before you try to change their mind, trying to find commonality with them before you try to change their mind. The other subversive thing that you can do — a lot of what we’re doing at Dropout — is we’re really trying not to be preachy, because in my experience, preaching doesn’t convert anybody but the already converted.”

Avoid buzzwords

Just like the internet flattens conversation, buzzwords can flatten meaning. To drive this point home, Sam brings up a book his father wrote in 2015, called Saving Capitalism, which explored a financial system that Robert talked about a lot when Sam was growing up. “What he’s espoused throughout his career is capitalism with strict limits,” Sam says. “You don’t want billionaires on one side, and you don’t want people to be impoverished on the other side. Meanwhile, recently in a podcast, [New York Mayor Zohran] Mamdani was asked what socialism means to him, and he had almost the exact same definition.”

Speaking about the specifics of what you believe, rather than using imprecise terms you’ve heard repeated on talk shows, will help you connect with the other person. “Everything has moved right enough that now what young people think of as the definition of socialism is in fact what used to be the definition of sensible capitalism,” explains Sam — or, as Robert puts it, “enlightened capitalism.”

Sam remembers talking with a person a few years ago who insisted they were pro-life. “In the context of that conversation, they said, ‘I am anti-abortion. I wouldn’t hold it against anyone what they want to do, but I’m pro-life,’” Sam says. “And I was able to seize upon that as an opportunity to guide them gently to the realization that they weren’t [pro-life], by our shared definition of what that means. What they actually believed is it should be anyone’s privilege to do what they want to do, and just didn’t understand that that’s what those words meant.”

This isn’t necessarily an accident, Robert points out. Conflict is good fodder for entertainment, and people often mimic what they see on TV. Years ago, he says, he was on a debate show, talking with a conservative Republican. “We were actually discovering that we were agreeing on many more things than we were disagreeing on,” he says. “And in my earbud, the producer said, ‘Be angry.’ I was not going to be angry, but when we came to a commercial break, I exploded at her. Telling me that I should be angry to create more gladiator-type entertainment struck me as the essence of social irresponsibility.”

In the end, Robert explains, the point is not that we should all agree on everything. Differing opinions are a good thing, and important in a thriving democracy. “What we’re seeking here is not everybody holding hands and [going] kumbaya,” he says. “People do have different ideas. We should not repress differences. But there is a serious danger of neo-fascism in this country. And I might try to understand why they feel the way they do, but you know, I have limits in terms of my tolerance.”