Ever since the start of Donald Trump’s second term, I’ve been doing the impossible. I’ve been having increasingly productive, illuminating and even fun conversations about politics — as someone who feared Trump’s presidency — with someone who was way more optimistic.

These discussions have gotten increasingly better, I’ve come to realize, because we avoid two big traps that occur when fear enters the fray. Instead, two critical questions can strengthen us.

Avoiding the fear traps

It all started because I was freaking out.

Once Trump was in office, he wasted no time launching an aggressive agenda on everything from immigration and climate change to health and diversity programs. Its pace and force tested not just political norms but, as far as I was concerned, constitutional ones too.

I was angry and scared, and because of that, uncertain. Doing the work that I do, I know that political fear and rage can save us, if they’re channeled right. I also know that these same intense emotions can blind us, contorting into the violence, hatred and destruction we all fear most.

I want to get better at expressing my views while also getting better at joining my fellow Americans in a collective search for the truest ones.

I needed to check my fear. And to do that, I needed to talk to someone who didn’t share it. Someone who had respect for both me and themselves — enough to save us from two traps I see people fall into over and over that make it impossible for us to actually understand each other.

That meant, first of all, respecting me enough to hear me out on what scares me and not laugh at it or dismiss it, even in a well-meaning attempt to defuse what’s hurting me. The latter is one of the most damaging mistakes any of us make in a political conversation.

And second, they had to respect themselves enough to be honest with me, and not hide or deny their actual beliefs for the sake of my perceived fragility. I don’t want to be fragile. I want to be heard, then learn whatever I need to know about other perspectives I dislike. This is what I’ve found helps me stay grounded and clear-eyed in a world whose deformities I refuse to let deform me.

That is how I ended up reaching out to Travis Tripodi.

Opposite sides, same side

Travis is a friend I met through our work at the grassroots nonprofit Braver Angels. He is an engineer and independent business consultant in New Hampshire who considers himself a “pragmatic libertarian.” We are on opposite sides of the political divide, but on the same side of a movement to keep those divides from poisoning us.

That first conversation lasted over an hour. Then, we followed up again and again in subsequent phone and Zoom calls, each time bringing topics in the headlines that bothered us most and having it out — interrupting, arguing and challenging at will.

This is a far cry from what many people assume is “healthy dialogue.” But that’s where they’re missing something important. Dialogue at its most mature form can and maybe should include a sharing of honest frustrations and even a pressing of each other.

When I train people to disagree better, I like to point out that when you have a conversation with one other person, there are actually three conversations happening at once: the conversation you’re having with each other, the conversation your partner is having with themselves and the conversation you’re having with yourself.

2 questions you can ask

Every time Travis and I ended our calls, the conversations we each had with ourselves kept going. That included doubts: “Did I explain my views on socialism right?”; meta-questions: “How well am I listening when voter fraud comes up?”; and plenty of processing: “I never thought of it that way before, but what he said about ICE makes a weird sort of sense…”

So we started checking in the day after we talked, prompting what we called our “debrief” with two questions: “What do you feel you understand better about the other person’s perspective now?” and “Are there any new questions, insights or concerns that surfaced after the conversation, whether with regard to the subject matter, or to the way the conversation went?”

Bringing each other answers to those questions turned what was a collection of political debates into an ongoing project with benefits well beyond the political. I wasn’t just understanding Travis’ views better. I was understanding myself better. And vice-versa with Travis, who thanks to the friction our clashes generate has found plenty of his own edges to explore.

All of this has revealed, to me, my most audacious goal not just in political disagreements with Travis but also with anyone who doesn’t see things my way — one that’s more fun than checking my fears and more ambitious than trying to persuade someone that I’m right.

Namely this: I want to get better at expressing my views while also getting better at joining my fellow Americans in a collective search for the truest ones.

Want to listen in?

My discussions with Travis have felt so candid and constructive in a moment so clearly starved for those things that in a new episode of the “A Braver Way” podcast, we take exactly what we’ve been doing in private and make it public.

View Comments

“I congratulate you on having a productive conversation across difference, and modeling how constructive and satisfying it can be,” one viewer texted us.

“My only frustration was that I couldn’t join the conversation!” wrote another.

Keep in mind: We’re not pundits or experts. We’re just two people who get something out of letting our perspectives collide, and want to inspire our fellow liberals, conservatives and independents to try and do the same.

Curious? Check it out, and let me know what you think at abraverway@reclaimcuriosity.com.

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