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How to Ask for More Money Than You Ever Thought Possible – The Cut

Anna Sale, host of the Death, Sex & Money podcast. Photo-Illustration: by Stevie Remsberg; Photo: Mindy Tucker

As the host of the award-winning podcast Death, Sex & Money, Anna Sale thinks (and talks) about money a lot. Over the past five years, the 38-year-old journalist has interviewed hundreds of people — including big names like Jane Fonda, Lena Waithe, and Sonia Sotomayor — about their anxieties around finances and relationships. And Sale comes from a place of experience: In 2011, she split up with her husband of four years and, in the aftermath, was forced to contend with her biggest fears about planning for the worst. We spoke with her about post-divorce financial angst, going to couples therapy with her current husband to talk through money issues, and what it was like to ask for a raise after her show became a surprise hit. She’s currently on maternity leave for her second child and working on a book, Go There: the Art of Talking about Hard Things. And no, she’ll never stop worrying about money.

Were you raised to be super-conscious of money?
My dad was a doctor and my mom was a physical therapist, so we had money, but we didn’t waste money. The Sale family, we are real value hunters. We never spent on things for extra luxury. We are very much a T.J.Maxx family.

When you first started your show, you had just gotten out of a previous marriage. How did your divorce affect your view of money?
I had the very rare experience of not taking a financial hit from a divorce. Statistics show the woman usually fares worse, but I didn’t really. My main financial memory of going through the divorce was how we had to boil down every moment from the marriage and look at the numbers. And then you figure out who owes who what and divide by two. I was in charge of doing those calculations on my laptop, and the date I had to go back to was the date of our wedding, which was sad.

I was very afraid about money in my first marriage. But once I was single again, I was like, “Oh! I don’t need to worry about anybody else anymore.” I didn’t have to compromise about anything, and it made me feel less worried. I started buying nice things for myself in a way that I hadn’t before.

What was an “I’m single” purchase?
Right when we were breaking up and he was moving out and it was sad, I was walking past a farmer’s market and I saw this little thimble cactus. I think it cost $25, and I was like, “I need this for my new apartment. I think it’s beautiful, and I’m going to buy it for myself.” I remember walking the few blocks home with it, being like, “This is what taking care of yourself feels like!” I know that sounds dumb. It’s a modest purchase. But I never would have bought it before. And then that thimble cactus totally thrived and grew like crazy, and moved with me to the next apartment and then the next one where I moved with Arthur, my husband. By the time we moved out of New York, it had gotten so big that we couldn’t take it with us. I loved that thing.

How did you cope with the money stuff better in your second marriage?
When I was falling in love with Arthur, the thought of having to navigate money in a relationship again — I really didn’t want to do it. I was like, “Ugh, all of my money anxieties are going to come back.” Part of the trauma of the divorce was that I lost trust in my ability to make relationships work, and my ability to solve problems with somebody else. Figuring out how we were going to move in together and handle our expenses and eventually combine our money was a long, slow process.

You and Arthur saw a therapist to sort out some of those money-related issues, right? How did she help?
When you’re trying to make decisions about money in a relationship with a partner, I think it’s about control, and whose worldview and whose sensibility is going to win the day. My husband and I have complimentary money worldviews, but they are not aligned. He’s very much, “Let’s step back, maybe we have a cash flow pinch right now, but in the grand scheme, we’re good.” And for me, the cashflow pinches are terrifying. They’re an assault on my money management skills. Patricia, our counselor, was very practical and would give us homework, and one of the assignments was to each make our own spreadsheets for what our dream lives would look like and how we should budget for them. Because I’m more of a stickler, I assumed that I was going to have the more prudent budget, and his was going to be just crazy.

Your spreadsheet was going to win.
Exactly. But then, as we were making the spreadsheets, we realized that they didn’t look that different, and his wasn’t crazy at all. It helped us separate out the dollars from the conflicts and make reality-based decisions. It also exposed that most of the power struggles were mostly coming from my fears. This is embarrassing, but when I was pregnant and we were in the process of deciding when to move out of our Brooklyn apartment, I was just really freaked out. I didn’t want to leave. And Arthur was like, “Okay, let’s write Anna’s fears on the whiteboard.” And one of them was that if we didn’t plan well, we were going to have a period of homelessness when I was 36 weeks pregnant. Arthur wrote that down, and then he was like, “Okay, who do you think might let us stay in their apartment if we needed a place to go? Let’s make a list.” And I was like, “Ohhhh. We’ll be okay. I don’t have to go to catastrophic thinking.”

Wait, a whiteboard? Do you use them often?
Yeah. We use them during family meetings. I also keep a column where I write down everything that comes to me in the middle of the night that we haven’t gotten done. Like, life insurance, oil change, send that one email, make a will. It gives me a place to put that stuff. We have a couple of whiteboards. One is wall mounted and then we have smaller ones too.

Do you still use the spreadsheet?
Yeah, we fire it up whenever we’re making a major spending decision. I’m someone who thinks I can be vigilant and have control over my money anxiety by looking at the numbers. The problem with that is when you become a parent, and even just going through life, the numbers don’t always fix the anxiety.

When you started your show, it was a big hit pretty much right away. Did you ask for a raise?
I didn’t immediately ask for a raise, but I did later. The timing of the show was really fortuitous because we came out six months before Serial hit the world and people started discovering podcasts. All of a sudden, there was a much more competitive employment market for people who had my skills. My colleagues at WNYC were leaving for other opportunities at places like Gimlet and Slate and all over. I never anticipated that. But I’m really glad it happened because now you can take care of your family by making a podcast, and that’s great.

So what happened when you did ask for a raise?
I did the thing that people do, which is sniff around to find out what you can about what other people are making. I talked to other podcast people and radio people and colleagues at WNYC. And I thought, “Okay, if I could get this amount of money, I would feel satisfied. If I could get this amount of money, I would feel really taken care of. And if I got this amount of money, that’s more than I ever thought I could make.” Through those conversations with people, both men and women but particularly in conversations with men, they were like, “Just ask for what you don’t think you can get and see what happens.”

I definitely had the fear of, “Is this going to make me be seen a certain way?” But what you do is just step through that fear and you ask for it. And then you have a conversation and figure out what feels like a good deal for both of you. At the end of it, I felt really invested in and taken care of by my company, and that’s a rare feeling to have. The emotional work was to push myself just to ask. I’ve always been a public radio reporter, and you don’t start off in public radio thinking you’re ever going to make more than a lower-middle-class wage.

The “more than you thought you could make” amount — did you get it?
I’m not going to comment on that. But it led to a conversation about a contract for a longer period of time at the company. And for sure, I’m making more money than I ever thought possible. So I guess the answer is yes.

Have you lightened up about money at all?
Arthur does help. We still have our battles, but I’ve also learned from him. It turns out that some things that I was so uncomfortable about buying, like a nice rug in the bedroom that you step onto when you get out of bed every morning, are great. Or if we’re going to have a date night, we go to the nice restaurant and get cocktails and dessert. It’s just better if he pays the bill at the end. Even though it’s going on a shared credit card, I don’t want to look at what the total is. And we know that about me, so we don’t let it ruin the night. I don’t think I’ve lightened up necessarily. It doesn’t change me, but it’s helped me enjoy things.

These days, it seems like successful podcast hosts get all sorts of lucrative deals to do tours and sponsored content. Do you ever look around and think …
Can I have what they’re having? Yeah, I do have that part of my brain that’s like, “Should I be developing a one-woman show that’s going to tour across 18 states?” But I also have two little kids. So it’s more about making the show and doing strategic strikes based on available energy and time on top of that. I did sign up to write a book, which has been fun but very hard to actually write. I feel like every working parent goes through that process of, “Oh, here are the things that I used to be able to do, when I just ran on coffee and the fuel of my ambition.” You can still get a lot done when you have little kids, but not in the same way.

Have you ever had a moment when you were like, “I’ve made it. Everything’s going to be okay”?
Yes. But it wasn’t about money. As much as I worry about money, that’s not actually what calms my existential angst. For me, the moment of feeling like I’d made it was early on, the week that Death, Sex & Money launched. A version of our first episode ran on This American Life. I was standing in my living room, listening to the show, and I heard Ira Glass come out of the end and say my name and give Death, Sex & Money a really generous plug. I physically felt this wave, a huge exhale. As a person who’s creative, it was so satisfying to make exactly the kind of thing I wanted to put into the world. And then to see it get elevated by one of my heroes was just the best.

As far as making it financially, when did I stop worrying about money? That hasn’t happened. When I feel myself worrying, I try to use that as a thought exercise to be like, “Anna, this is just where you go when you have anxiety.” Right now, I worry about money just as much and with the same amount of energy that I did when I was working for $45,000 a year at Connecticut public radio. It’s part of my personality that has nothing to do with the actual numbers.

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