How to deal with a hard conversation about money

Podcast host and author Anna Sale wants you to help you have that money conversation that you’ve been avoiding or putting off—maybe for years.
Book Excerpt-Let's Talk About Hard Things
“Let’s Talk About Hard Things” by Anna Sale
Courtesy of Simon & Schuster

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In my work as a journalist, I talk with people about very personal, tender subjects. I interview people on a podcast called Death, Sex & Money, and I’m often asked, “What’s the hardest thing to talk about?” Death is certainly uncomfortable, because no one likes to linger long on the idea of losing loved ones or of life finally ending for themselves. Sex is tricky because it can bring up shame and embarrassment and questions about how close to the norm you are.

But money, I have to say, is definitely the most challenging to talk about concretely. So many of us have a limited public vocabulary for how money works in our lives. We trade personal finance tips, or we talk in very broad brushes about our personal financial values. This, of course, is what drives almost every political debate there is.

Anything in between, though, we largely stay quiet about. This distorts our understanding of how our society is working, and also prevents us from offering and asking for help. Money, whether we have what we need and how we got it, is a major plot driver in all of our lives. We ought to admit that, and share our stories about money with less trepidation.

Including stories about when you have much more than you need, as I explore in this excerpt from my new book, Let’s Talk About Hard Things (Simon & Schuster).

Anna Sale, author of “Let’s Talk About Hard Things.” She’s also the creator and host of “Death, Sex & Money,” a podcast from WNYC Studios.
Courtesy of Simon & Schuster

The way work is rewarded with money in this country does not reflect the worth of the work or the labor that’s gone into it. For preschool teachers, the national median salary in the United States is just over $30,000. I host a podcast and make more money than my husband, who spent seven years getting graduate degrees and usually puts in more hours a week teaching, advising, fundraising, and writing.

“There’s this weird thing that happens where we talk about money and its tie to work,” Chris Hughes told me in an interview. “Most Americans are working. It’s just that only a select few are getting very, very lucky.” He is one of those very, very lucky people. He was Mark Zuckerberg’s college roommate at Harvard and is a cofounder of Facebook. When he was 25, Chris got his first bank statement that showed a million dollars to his name. “That would have been 2008,” he said. At the time, he was working for the Obama campaign, making $65,000 year. It was still four years before Facebook went public, but he could sell some of his shares on a secondary market. “Most early employees did that as a way of taking out a kind of insurance,” he told me. “I sold a million dollars’ worth of stock then, and no one around me had any idea.”

He said this to me in the fall of 2017 when I interviewed him onstage at the San Francisco Mint at an event hosted by the Economic Security Project, a group that Chris cochairs that advocates for a guaranteed income for all Americans. The program billed our chat as “A Frank Conversation About Money.” And it was, though he demurred when I asked about his current net worth. “For three years of work at Facebook,” he did tell me, “I made about a half a billion dollars.” The audience in front of us gasped and laughed nervously. Chris continued, “Meanwhile, median wages are stagnated, and normal working people can’t make ends meet. And I think these things are related.”

Chris is the only child of a paper salesman and a teacher, and he told me that he still goes to his parents for advice about money. “It sounds crazy, because they never had an experience like this. But their relationship to money is so healthy,” he said. Chris and his parents can’t connect on the dollar amounts, but they have similar values about how they should manage what they have. “I still do all the things that they do. They tithed every single Sunday, and I do a lot more than that, but that kind of rigorous budgeting and accounting is something that I look to them for.”

That said, Chris did admit that in his daily life now, he is very frequently the richest person in any room he walks into, and he also doesn’t have much exposure to people making less than, say, $50,000 a year. “It’s really hard to get out of a bubble and to have disarming conversations that are honest,” he told me. Still, he tries, and for all his money, he doesn’t feel like he belongs in the tech gazillionaire scene. “I feel more like an interloper in the sense that, like, I have very much become part of the inside, but I still really relish challenging the conventional wisdom that poor people, working people, middle-class people don’t know best,” Chris said. “I find that that’s the status quo in a lot of the conversations that I’m in.”

In other words, in rooms full of people with money, they’re all pretty confident that they’ve figured out something essential that poor people simply haven’t. As Pew reported in 2017, compared with lower-income people, people with higher family incomes are more likely to believe a person is rich because they’ve worked hard, as opposed to any advantages in their circumstances.

Chris has tried to pierce that mythology of meritocracy by talking about how he became so wealthy, which is how he came to discuss his personal budgeting style in front of an audience with me. He said it’s not always comfortable, but it had gotten easier as he challenged himself to be more personally open. “I’ve learned that it’s just money, you know?” he said to me. “There’s a responsibility that comes with it, but you can talk about it in a way that recognizes its power and also helps people make collective decisions about how to move it.”

Minutes after our public conversation ended and we walked offstage, I found Chris alone in a corner of the greenroom, nervously looking over the trays of snacks. He told me he wished he hadn’t tossed off the line, “It’s just money” at the end of our conversation. He knows the risk of being seen as a clueless rich-guy donor, or, worse, a careless steward of immense wealth.

I assured him I got his point—that he was trying to articulate that money is a tool, but one that doesn’t confer worthiness on people. That didn’t seem to comfort him. I asked him if he wanted to elaborate on what it had felt like to talk so candidly and publicly about his money. When we connected again a few months later, he acknowledged a particular kind of loneliness. He felt compelled politically to detail what his personal story revealed about inequality, but being open about his wealth also highlighted a social distance he wished he could shrink. “With money, it can separate you from other people, and it’s something that you don’t want to be boxed into.” He knows it’s easier to just glide past that, but he believes that he has an obligation to sacrifice his social comfort for something bigger. “I think, on wealth, we haven’t really broken through on the taboo,” Chris told me, “of talking about how the economy works, who’s getting wealthy, why they’re getting wealthy, and what they’re doing with the money. We assume those who have it have worked hard for it, fair and square.”

We all know that’s not the whole story. So if you have more money than you need, talk about how that happened. We’re used to acknowledging the big rewards that came from risk or hard work, but don’t skip over your lucky breaks and inherited advantages. You’ll be telling a more honest story, and one that may make you feel less alienated from other people, because you don’t have to pretend that you are more worthy of comfort and reward than others to justify your wealth.

The social strain of wealth may not be something a lot of people without wealth have much sympathy for, but that doesn’t mean the strain is not real. A wealthy software developer named Vik described this to me on Death, Sex & Money in 2018, for a series we did about class in America. “You know, in fairy tales it’s a little easy because when Cinderella gets ahead, [she’s] surrounded by mean stepsisters and a mom and an environment that wasn’t helping, and it was unfair,” Vik said, continuing:

So when you arrive upon some really awesome destination, you’re supposed to sort of go, “Well, they deserve it, and the other people were mean.” And I think the reality is that, at least in my case, you find yourself here, but along the way there weren’t mean people. In fact, it’s because of all the people that were around you that you got here. And not everybody’s at the same place. And so you’re left wondering about that.

When you take opportunities to acknowledge when you’re doing well financially, you can talk about success in a way that also indicates what’s important to you. Do you feel grateful because you have enough to help out your extended family? Have you created job opportunities for others? Has it allowed you to contribute to causes you support? As you acknowledge all this, you are also drawing boundaries around what you want to spend your money on, and what you don’t.

Excerpt from Let’s Talk About Hard Things by Anna Sale. Copyright © 2021 by Anna Sale. Reprinted by permission of Simon & Schuster, Inc., N.Y.