The Billfold Takes On “Bad With Money”

Friday chatting about the podcast of our dreams

ESTER: I still have the Gaby Dunn theme song in my head from listening to the third episode of her podcast yesterday. It’s catchy!

NICOLE: Yes! “You’re a freak with a dark shameful secret.” And the music style’s like a show we used to watch when we were kids.

ESTER: I hadn’t thought that through but you’re totally right. That’s why it seemed immediately familiar. Like home. “Next up on TGIF: It’s ‘Bad With Money’!” Actually I wish something like her show had run in prime time when we were kids. Think how much better off we’d be if we’d gotten to learn from her experts, and her mistakes, instead of watching “Dinosaurs” and “Step by Step.”

NICOLE: I am sure “Step by Step” had a very special episode where one of the kids had to deal with wanting something they couldn’t afford. But yeah, except for “Roseanne” and a few episodes of other shows where teens had to do without name-brand sneakers, prime time TV didn’t really deal with money.

ESTER: Not at all. Oh, “the Simpsons,” some! But largely, no. Even “Fresh Prince,” which I loved, and which you’d think would be dealing with issues of class and finances all the time! I don’t remember money ever coming up. Maybe people thought it was too real. Too much of a downer.

But what’s your favorite of these Gaby Dunn episodes? They’ve each been pretty fascinating in their own way. In the first episode, she interviews her parents about the various ways they were bad with money in her childhood. In the second, she talks to a financial psychologist to understand the emotional scaffolding of her own problems. And in the third, she talks frankly with her boyfriend about their different situations and attitudes.

NICOLE: I thought the financial psychologist episode was the most interesting because it invited us to think about our own perspectives and emotions re: money. Which — I agreed with some of what the psychologist was saying, but I got really bristly when he was all, “And you can’t upgrade your lifestyle ever because you need 1.5 million dollars to retire.” The idea of living in reduced circumstances, as it were, is “rich person thinking,” and lifestyle creep is “poor person thinking,” and I had a super-visceral emotional response to that.

ESTER: I heard you discuss that before I listened to the episode, so I was braced to be indignant too, but I actually experienced it differently. I thought he was pretty gentle about it, that he was trying to help her course-correct, because she hadn’t thought along these lines before. She keeps dreaming of windfalls — that’s been a recurring theme, the idea that some lump sum would materialize and solve her problems — and he was helping her understand that 1) odds are there will be no magic lump sum, and 2) even if you do get one, if you immediately and accordingly adjust your lifestyle up, your bills will rise to meet it and it won’t feel like more.

NICOLE: I hadn’t thought of it that way, and it makes A LOT of sense. Especially when you listen to that conversation between Gaby and her mom, where her mom says, “You’re our retirement fund.” So Gaby is her mother’s windfall. Also this is where it starts to feel weird to discuss real people and their financial issues.

ESTER: We can pretend they’re characters in a soap opera! Ones we care about, since I’m already super invested in this story and how it will play out.

NICOLE: Do you think we’ll ever know “how it ends?” As much as I hope “Bad With Money” runs for years, I can’t imagine it running long enough to see Gaby — or her parents — retire. But it does make me think “okay, what would be a good outcome for these characters,” which is a way to indirectly think about our own long-term financial choices.

ESTER: Yeah, I’d settle for her opening an IRA. Already she’s shown openness to change! I loved the conversation she had with her sister about the time, recently, when her sister asked her for money, and Gaby complied, infuriating Gaby’s boyfriend and also, later, annoying Gaby herself, because she started judging the choices her sister made with that money. (Sushi!!) Her sister was unrepentant: she said that, largely, she was very responsible with the funds, but, you know, first she needed to eat.

The thing is, when you get money like that from a sibling or someone close to you, it can feel like a windfall. Free money! Of course you take free money and go out to get sushi. But I already had the sense that Gaby’s sister wouldn’t necessarily ask again anytime soon, that if she did ask and get she’d make smarter choices (at LEAST forego Instagramming the meal), and that Gaby might say No. Which is all progress!

NICOLE: I have never asked family for money, although my parents have in the past given me money, and I totally get the “what if they see me spending it in a way that appears irresponsible” feeling. (Actually I don’t think Gaby’s sister had that feeling, which was part of the point.) I even get a little anxious about doing Friday Estimates sometimes, because I know The Billfold knows exactly how much I earn and I don’t want them to think I’m frittering away my resources!

ESTER: I think readers may be more likely to feel judged than to judge — not everyone is nearly as organized about and on top of their finances as you are! Over 40% of people our age aren’t even saving for retirement at all (yet?) — though maybe that’s my mistaken assumption. But yeah. The worst part of asking for money is it comes with scrutiny, and very few of us enjoy being scrutinized.

NICOLE: Even asking for help. I started meeting with a new CPA, and I’m really pleased with our conversations, but I went in terrified that someone was going to scrutinize both my money and my business.

ESTER: You’re super independent. And I get the sense that Gaby is too. She hasn’t spent much, or any, time patting herself on the back for what she’s doing so far, but in a lot of ways, she has made good choices. She hasn’t let herself go completely off the rails in terms of debt or spending, right? She isn’t dependent on her parents; she doesn’t seem to have assumed someone would step in and pay her bills (even if she does dream of windfalls).

🎤 Don’t go chasing windfalls! Please stick to the rivers and the lakes that you’re used to … 🎤

NICOLE: What about the part where Gaby admits that sometimes she puts stuff on credit instead of telling friends or family that she can’t afford it? That was another huge resonant point for me. I don’t do that anymore because I earn more money now, but that was a big part of my life at one point, and I kept thinking, “Well, I’m investing in relationships now, and I’ll pay it off someday.”

ESTER: Yeah, it is really hard to resist YOLO culture, especially in big cities like LA and when you’re hanging out with people who seem to have unlimited funds. That’s why it can help to cultivate like-minded communities, friends to whom you don’t have to explain why you can’t go out for the 3rd or 5th time this week, because they get it and they can’t either. Those “live in the moment!!” types can be exhausting company, anyway. They seem to need constant stimulation.

Gaby seems to have found her people now: her partner, who’s a bit calmer and more focused on the future; her boyfriend, who’s very financially practical.

NICOLE: And her audience.

ESTER: Yes! We’re cheering for you, Gaby. Keep it up. You can do it.

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