Anna Sale talks about hard things

When I was thirty years old, words failed me.

I couldn’t stop my marriage from unraveling, despite going to couples counseling and church, despite buying new relationship books and rereading passages I’d underlined in old ones. We’d been together since I was in college and had learned how to be adults together. We were best friends who loved each other. And then we were two people who couldn’t be in the same room together.

At first the breakdown happened by such small degrees we didn’t notice. Or rather, we noticed, but we didn’t know what we were noticing. Each argument felt specific and isolated, but one by one they built up a lingering resentment that tore at our friendship. We tried to talk about it. We analyzed each individual argument and did our best to smooth over hurt feelings. I spent months trying to say everything I could think of that would recommit me to our marriage, re-endear me to him, and keep my life in line with what I thought it ought to look like.

That didn’t work. Because, all the while, the underlying conflict went unsaid. Quite simply, we didn’t want the same thing anymore.

Ours was a boring divorce. There were no real scandals. We had no children, no pets. My ex-husband and I mutually agreed to end the marriage. But it was still devastating and confusing. I couldn’t explain what had happened, either to myself or anyone else. It would take years for me to make any sense of it.

This was new for me. I grew up with a certain faith that I could find the right words to navigate whatever life threw at me. I had two older sisters in college by the time I was in fourth grade, and they were always offering the long view on my pressing questions as I grew up: about friendships, drugs, sex, music. I just had to ask the right questions, and I could harvest their wisdom. I also kept notebooks scrawled with quotes from poetry, music lyrics, speeches, and books—scraps of insight to stow away for future use. When I became a political reporter at twenty-four, it was partly out of that same underlying belief, that with enough phone calls and stacks of documents—and the pitch-perfect question—I could uncover the truth and set the world right.

Sure, I knew it was a rosy view, but for a long time all my studying and digging and researching kept me feeling on track. That is, until I needed to decide whether to stay in my marriage, and what the hell to do if it was actually over. The answer was not something I could google. (I tried.) The truth was that no one else could tell me what to do. I needed to figure out my own choices and face the trade-offs that came with them.

What ultimately helped me to find a sense of clarity, little by little, was talking to other people about the choices they’d made when they’d felt lost. I had conversations with family members, friends, coworkers, and older mentors. They told me about their mistakes and where they got help when they needed it. They made me see how normal it is to find yourself grappling with uncertainty and despair. Theirs were messy stories, without neatly packaged lessons or aphorisms ready to be copied down in a journal. And, crucially, they made me feel like I wouldn’t be alone as I began to figure out my next steps.

The stories stuck with me. Once I stumbled away from my marriage and began to put my life back together, I decided I wanted to keep having those deep conversations. I decided to make that my job.

I pitched my idea for Death, Sex & Money to my bosses at WNYC, New York City’s public radio station, as a show about the things that mattered most in life but that we talked about least: how death and loss, sex and relationships, and money and work shape all of our lives. I came up with the name for the show while I was out walking my dog, and I smiled at its boldness. Then I thought, What could be better? We flinch from these topics in public conversations, but they make up the most animating details of our lives! As I got the show started, I noticed that when I explained the idea to my interviewees, they leaned in. I told them that I would be asking about the hardest, loneliest things all of us go through, in the hopes that others might listen and feel less on their own. Our conversations became open, collaborative, and honest. It was like uncovering a buried passageway to unexpected emotional connection.

For seven years, the show has given me permission to explore who and how we love, how we survive and scrape by, and, of course, the urgency of it all, because we don’t get to be here forever. Many of us have fight-or-flight responses when uncomfortable things come up, but we also have a deep need to share. We all want to be understood, and we all want to look like we are handling setbacks, pain, and alienation gracefully. But life is not so simple, and it doesn’t help to pretend that it is. With every episode on the show, my goal has been to give all of us a little more permission to try, mess up, and try again.

Hard conversations in real life, however, are a lot trickier than they are on a podcast. For one, they don’t take place in a radio studio, between strangers, with an editing crew at the ready. They occur in real time, with the people we love, when our emotions are tangled and raw. When tensions are high, a single conversation has the potential to solidify a relationship into a lifelong bond, or to send it spiraling toward doubt. In that sense, there’s a reason we like to spill our guts to bartenders and podcast hosts. Because it’s downright terrifying to discuss the things that are most important to us with the people who are most important to us. Even so, the most meaningful moments of our lives hinge on the hard conversations we have with our family, friends, coworkers, and partners.

Living fully and honestly depends on stepping toward these conversations despite the risk. Hard things happen to all of us: family discord, illness, romantic rejection, missed opportunities, sudden loss. We each have different sets of resources to deal with these challenges—and for that matter, hardship is not evenly distributed among us; pain is often compounded by more pain. None of us, however, can navigate our way completely around life’s difficult moments, especially on our own. Talking more openly about what we’re facing helps us understand what is specific about each of our circumstances, and how our experiences fit into broader patterns that we can learn from and take solace in.

In these pages, I address five sweeping categories that contain many of the hardest conversations we’ll have in our lives—death, sex, money, family, and identity. These subjects are all inescapable, and each is also challenging in its own particular ways. Over the course of each chapter, I’ll share the stories of people who’ve

lived through—and learned how to talk about—the challenges and pitfalls each subject presents. Throughout, I’ll also share the most pivotal conversations I’ve had in my own life, and what I’ve learned while struggling to find the right words. All of the conversations you’ll encounter as you read are drawn from original interviews conducted for the book, though I also sprinkle in a few moments from the Death, Sex & Money archives when they resonate with the discussion.

I want this book to feel, chiefly, like a companion. My goal is to open up that buried passageway between us, to let us connect and understand our lives more clearly. Through the stories of others who’ve been there, you’ll see how to navigate life’s rocky territories. You’ll see how people came to express what they needed to say, and how to begin translating that to your own hard conversations. These stories, taken together, remind you that you’re not doing this on your own. The rest of us are going through all this right alongside you.