8 Life Lessons From RedFin's Chief Economist
I interviewed Dr. Daryl Fairweather on her new book Hate the Game: Economic Cheat Codes for Life Love and Work. We talk about careers, leaving academia, love, terrible commutes, and housing.
Note: Today, I bring you an interview with
, chief economist at Redfin, the housing and real estate website. We discuss her new book Hate the Game: Economic Cheat Codes for Life Love and Work (University of Chicago Press, 2025). The conversation gets into her trajectory in and out of academia (including studying under Steven Levitt of Freakonomics fame), relationship advice, why terrible commutes are not worth it, and, of course, housing.The full interview has been transcribed below (lightly edited), along with pull quote video clips. The full video interview can be found on YouTube or at the end of this post. More information on the book beyond what we cover here can also be found at her
.#1 Find a Good Book (Or Role Model) for Career Inspiration
Ryan Allen: If we could start, your book's interesting in terms of how you talk about your own career, your own path, your own journey. Those are things that I'm consistently writing about here, thinking about here, talking to young students. So, maybe what led you into your PhD and then your interest in economics?
Dr. Fairweather: Sure. So, when I was applying for college for undergrad, I thought I was going to be an engineer. I put on all my college applications that I was going to study mechanical engineering because I liked math, I liked physics, it seemed like a good fit. I wanted to do something that was not so theoretical like physics but had real-world meaning. But then on the way to MIT, which is where I went for undergrad, my dad gave me the book Freakonomics. I read it on the plane, and by the time I had landed in Boston, I was sure I was going to be an economist.
Even though I had studied—I had taken AP Econ in high school—I didn’t really understand what the power of economics was, how broad the field was. Freakonomics was the thing that made it click for me, that it was really about people interacting with one another and the incentives that they have and how you can essentially predict human behavior if you understand people’s goals, their benefits, their costs. If you scale it all the way up, then you can understand the entire economy. So that really was interesting to me. I loved all the math that was in it, the statistics, but really the focus on human interactions is what drew me in.
College Towns: That’s great. It’s funny—Freakonomics, I read it too, probably around the same time, maybe a little bit after, and I was inspired as well. I went and got my PhD, not in economics, but just thinking more about the world in a scientific way. I wasn’t very focused on academics as an undergrad. I can feel that kinship in terms of this is a gateway drug to social science or something like that with Freakonomics. You were lucky—you actually got to study under the Freakonomics economist, author Stephen Levitt. Can you talk about being in that space and the intellectual—what it felt like to be around that University of Chicago and this mythical economics place?
Dr. Fairweather: Yeah. So I was very inspired by Freakonomics. Steve Levitt, he went to MIT for his PhD, and then he became a professor at the University of Chicago. I just basically modeled my trajectory. I was like, I’m going to go where he is since he did the kind of research that I wanted to do. I was also really getting into behavioral economics. I was in college during the foreclosure crisis, and I was actually doing undergraduate research on the foreclosure crisis at MIT and then at the Boston Fed with a behavioral economics emphasis because back then it was really controversial that economists didn’t see the housing bubble coming. They weren’t alerting people of it as much.
There were economists out there talking about it—Robert Shiller, for example—but people felt like economists had failed, and behavioral economics was viewed as the reason that they failed, that regular economists didn’t really understand the mistakes that home buyers were going to make. Liking behavioral economics and also just the time and the place got me into the housing market, but then I wanted to go to Chicago for Steve Levitt and also Richard Thaler, the father of behavioral economics, was at the business school. It just felt like the ideal place for me to be to learn the kind of economics that I wanted to learn.
#2 Don’t Be Afraid to Quit (Or Why She Left Academia)
College Towns: On your academic committee, you did study under both of those professors, but you tell a story in the book about how you submit your proposal for your research and they literally tell you, “Hey, this is interesting, but it’s never going to get published in top journals.” Is that when you told yourself, “Okay, maybe I’m doing this PhD, but I’m not going to be an academic”? Because I think you have a quote: “I want to do research that people outside the ivory tower found useful.”
Dr. Fairweather: Yeah, so the kind of research that I was attracted to—this kind of Freakonomics-style research where there’s an interesting fact and then you dig into the data and you have some theories about how it’s going to play out—you do a pretty simple economic analysis, regression analysis, to see if your hypothesis was correct. That was very popular in the ‘90s; Steve Levitt made it really popular. But then by the time that I was in graduate school in the early 2000s, it was already on its way out.
This new kind of economics… structural economics, which is still pretty popular, was on its way in, which was more about creating complex economic models and then putting big data—not necessarily big data, but data—attached to it. I guess the difference is that economists became less interested in these kind of “aha” results that are un-intuitive but interesting, the kind of things that would go in a Freakonomics book, and they became more interested in things that were hard to do technically without really the results being that interesting to people who don’t understand the technical feat that it took to get the results. That was just not what I was interested in. I knew that I wasn’t going to be the best at that.
There were people in my graduate program who were really passionate about doing that kind of technical work, and at the same time, there were new kinds of economics happening outside of academia in tech. Tech was this place where all this data was being created, and they wanted to understand it better, and that’s what I ended up going into eventually. I think it was just a matter—I’m sure this happens to people in their career all the time—that the thing that they wanted to do, they get into it because it’s really popular, and then it starts to fade in popularity when they get their skills. You see this in a lot of industries, and you just have to adapt when that happens and find out what is the next thing that I could get into earlier.
College Towns: Was there a stigma when you were deciding to leave? I’m an academic—I have had colleagues that have talked about that, and you read any professor subreddit and people are saying, “Should I leave? Should I not leave?” It’s even called an “alt-ac” career for academia, leaving academia. Did you feel pressured to potentially stay?
Dr. Fairweather: There was social pressure to stay, but the kind of social pressure that you get in academia is about—so anybody who leaves academia is kind of seen as essentially a failure because the belief is that you couldn’t hack it, that you weren’t good enough to make it, and that the best are going to stay and they’re going to rise to the top. So telling my professors that I was leaving, it did kind of feel like I was telling them that I was accepting failure, and I think that’s—for them, all they know is academia too. So I think that they were afraid for me. They maybe thought that I was going to go become a consultant forever, which was the first job that I took, which is—I think some people think that consulting is a waste of intelligent people’s resources.
So I think that there is some of that stigma too, that I was going to go into the private sector and do work that wasn’t going to help anybody or be useful to the broader economy. So yeah, I definitely got that disappointment from professors. I remember Levitt actually asked me, “Is something going on? Is one of my family members sick? Why do I need the money?”—that kind of thing. So yeah, but really I was just coming to the realization that this place was not where I was going to succeed. So yeah, it was a tough thing to deliver, but I don’t know, you kind of have to get through it.
#3 Find a Second Skill to Couple With Your First
College Towns: You get out, you go to the tech world and then Redfin—but was there this sort of, “Oh, I still want to teach. I still want to pass on the knowledge or be kind of a teacher” when you were conceptualizing your career and then obviously with the book?
Dr. Fairweather: One of the reasons that when I was in graduate school, I wanted to be a professor was for the teaching part of it, not just the research part of it. I really do enjoy talking about economics. I enjoy teaching people who think that they don’t know economics something that makes them think that they do understand economics. One of the things I learned when—like in my first tech job—was that everybody I was working with was capable of understanding economic concepts. I just had to figure out what metaphors or what use cases they could connect to to understand these concepts. And doing that over and over again was what built this muscle to communicate with people—like, I know I can teach you basically any concept if I can just find out what are the metaphors that work for you.
So yeah, I really enjoy writing—writing is a part of my job as well—and just communicating in general. That is one of the qualities that set me apart in the private sector. When you’re an economist in academia, the only thing that you need to do to be successful is be a great economist—research, publish. That’s all you need to focus on. But in the private sector, it’s really valuable to be an economist and something else. Sometimes that’s being an economist and a software engineer, being an economist and, I don’t know, a financial analyst. You have a second type of knowledge that you can use with your economics. And for me, it was my communication skills. And I put a lot of effort into developing them after graduate school because I saw how important it would be in the private sector. And that’s kind of the niche that I started to grow in. And I didn’t have a ton of competition either. So that was a good niche to be in.
#4 What Does an Economist at Redfin Do? (Not Really Advice, but I Was Just Curious. I Guess I’ll Call This “A Job You Love Can Come From Unexpected Places”)
College Towns: You use a lot of housing examples, I presume from your work at Redfin, in the book. So can you maybe talk a little bit about what’s your day-to-day? Like, what exactly does an economist at Redfin do, actually?
Dr. Fairweather: We do housing research. Me and the other economists, we try to come up with research projects and questions that are going to be relevant to people buying, selling, or renting homes, which is really a very wide audience. And then also journalists who write about the housing market—we try to communicate with them—also our executives and our agents in the Redfin company. We’re communicating this research to them.
So yeah, basic days are coming up with research ideas—what we can do with the data that we have, which is pretty extensive. We have all of the data that’s created by the website and the app, plus all the purchase history and county records for all the home sales—basically all the home sales in the United States. So it’s really rich data, and we’re just trying to come up with new interesting questions to write about that are relevant. We do really try to prioritize relevancy to the time, whether that’s talking about how tariffs might impact the supply of housing or talking about what mortgage rates are doing to the housing market, but also broader research about, like, how does the legacy of redlining still impact home prices today? Just trying to get people to understand the housing market better.
#5 AI + Uncertainty Means Young People Should Follow Their Own Passions
College Towns: What is some advice to young people right now who are about to graduate into a possible recession, or some thoughts that you have there?
Dr. Fairweather: Yeah, I think the economy is difficult right now. It’s weirdly strong when you look at the metrics like unemployment and GDP growth. But the uncertainty is extremely high. Like, there’s the economic uncertainty index that looks at how much recession is being mentioned, and it’s—I think just today it got as high as it was during COVID. So I talk about uncertainty aversion in the book a lot and ambiguity aversion, which is this idea that people really don’t like uncertainty. If they had the option between picking a ball out of an urn where they know half the balls are black versus half red versus an urn where they don’t know the mix, they would rather go with the certainty, even though the probabilities are actually the same. When you know nothing, it’s still 50/50, but people will go for the situation where more information is known, even when that information is not useful to them.
So I think the advice I would give to people is to try to embrace uncertainty as much as you can, to not be afraid of it. I think that because there’s so much uncertainty with the way the economy is going, but also with AI and what jobs could be created, you should probably listen to yourself more than anything else—like, follow your own passions, develop your skills, and have some faith that if you develop your skills, those skills are going to be useful to you in the future. I never could have imagined being a chief economist because when I started studying economics, that role didn’t really exist. So I think that I don’t know what careers are going to be most in demand, but I know that having skills—especially ones that can’t be done by an AI, like judgment, for example—is something that you should develop because it’s going to be useful.
#6 A Good Life Partner (In a Different Line of Work) Is Good Economics
College Towns: I was watching a viral video of a woman going through the dating apps and kind of like hitting X—she’d tap on the screen, “I don’t like this, X on that, X on that.” I was just thinking, “Wow, I got married right before the app craze got really popular.” And so I’m like, “I think I got the last lifeboat on the Titanic.” It seems very difficult right now for people in the dating market and just being a young person trying to navigate this—or I guess any person, really, trying to navigate this. So can you walk me through the importance—I think you talk about finding a partner and making decisions and this kind of thing?
Dr. Fairweather: Yeah. So in the book, I kind of break down all the different economic reasons for marriage or the different economic factors that go into marriage. There’s a lot of research from Gary Becker or modeling about the economics of marriage, how there’s a production aspect to it—you’re producing household productivity. Sorry, that’s a weird way to say it. You produce children, for one, you do dishes together, you invest together, you make decisions together. So in a way, a family is like a firm. I think Emily Oster has a book about this.
But there’s a lot of research about things that could be more likely to lead to divorce. One interesting piece of research shows that when two married people have correlated incomes, they’re more likely to get divorced than when their incomes are negatively correlated. And the reason why is that when you have a negative shock and you’re highly correlated, you’re going to be in a worse situation than if you’re negatively correlated. The example I use is a real estate agent who specializes in luxury housing and a real estate agent who specializes in foreclosures. In that situation, assuming that homes are being sold, both types of agents will be doing—or one of the agents will be doing well—no matter whether the housing market is up or down. So that income within a couple would be more stable than if they were both luxury agents and their income is really good when the housing market is good but really bad when the housing market is bad.
So it seems kind of heartless to consider something like that, but I think knowing that can help you plan. If you do decide to marry somebody in the same exact industry as you, maybe try to work on slightly different areas that aren’t so correlated or save more so that when you’re both experiencing a negative shock, you have more in savings so you can ride that out a bit better. But yeah, there are a bunch of examples I talk about with marriage.
#7 Terrible Commutes Aren’t Worth It
College Towns: Can you talk about the importance of a commute and how it affects us and how having a choice maybe can lead to some positive outcomes?
Dr. Fairweather: Yeah, for me personally, I feel like there is an extremely high correlation between how long my commute is and how miserable I am. Because, like, my first job, I had the worst commute. It was in San Diego, and the traffic was just terrible, especially right at rush hour. And I would have to drive because there was no public transit. Once I got to Seattle, I started taking the bus to work, and that was so much better because I could work on the bus and then leave the office a little bit earlier. I could listen to podcasts or read or something, at least. And then working remote was like the pinnacle because now I don’t have a commute at all.
Yeah, I think people maybe don’t appreciate how costly commutes are because you’re just literally taking time out of your day. But also that cost is not just for you—it’s for the entire economy. So much productive time is lost to traffic. And if we had better transit and better housing policy, we could have a more efficient economy, and people’s lives would be better off—at least if they hate commutes as much as I do.
College Towns: Yeah, that same experience—I changed jobs but didn’t move, and so I was living a lot further away, and I’m in Southern California as well, not too far from San Diego, a little north. My mood was just awful when I had to commute and sit in traffic, whereas now I moved closer—it’s like a 10-minute drive. I can even bike sometimes, and it’s just—I feel so much better all the time.
Dr. Fairweather: Yeah, yeah. I talk about the commuting paradox in the book—how when people’s incomes go up, they don’t actually reduce their commutes because it’s even more valuable to them to get to the office. It’s a little bit unintuitive, but yeah, people endure these commutes. When people buy homes, they’ll oftentimes trade off a longer commute for a bigger home. I think it’s just an underappreciation of how much commutes can impact you negatively.
#8 Advice on Home Buying as Redfin’s Chief Economist (Become a YIMBY)
College Towns: What advice do you have on buying a home or what to think about? That’s a huge question, but is there any nuggets in the book that can help someone alleviate kind of the concern or consternation that maybe this entire generation has?
Dr. Fairweather: The general advice I have is that you shouldn’t worry about buying a home until you are ready to commit to staying in that home for around five years—that’s a good rule of thumb—because the transaction cost of buying homes is high. You have to pay your real estate agents, you have to pay taxes. If you’re not ready to really lay down roots, then you’re probably not ready to buy a home. That was my mistake that I made—that I bought a home before I was really committed to staying there long-term. I ended up selling it at a slight loss, but all’s well that ends well because I got to a better place in my career.
I think that’s also something that people underappreciate—that if you can’t afford to buy a home, the answer is not necessarily that you need to limit your budget or you need to sacrifice something. Sometimes the answer is that you need to figure out a way to earn more money so that you can buy that home. There’s a trade-off there because the cities that have the best job opportunities also have some of the highest housing costs. So I think if you’re at a stage in your life where you’re just trying to focus on increasing your earnings, then you should not feel bad about falling behind on homeownership because you’re probably living in a place where it is extremely unaffordable to buy a home. But then once you earn enough money, it won’t be as challenging—or you might be in a place in your career where you can work remotely and then go buy a home somewhere more affordable.
But I think renting—well, renting is becoming more and more common now. I think we’re starting to lose our attachment to the American dream. So if you are buying a home later, you’re really just part of that overall trend. Now housing policy obviously is to blame, and if you are upset that you can’t buy a home, then may I suggest YIMBYism as something that you could put some time into or learn more about. Because it’s really not any one person’s fault—it’s a failure of policy.
College Towns: Do you have any kind of final words, final thoughts? What do you want people to take away? What’s a pitch to go read this book, buy this book for the audience?
Dr. Fairweather: Yeah, well, one of the themes in the book is that the economy is unfair, but you should still try to win because you can win if you just understand how the economy works. I think that is the overall pitch for learning economics in general—that if you understand the economy, you’ll be able to navigate it better. I think a lot of young people, when they start learning about economics, the first thing they understand is the failures of capitalism—and capitalism does have a lot of failures—but it also creates a lot of opportunities.
And I think the best feature of our economy is that you have choice—that there are millions of games in the economy that you could be playing. So I think just going into the economy or the industry with the attitude that you will find the thing that you are best at can help you because it means that you’re not going to get stuck in opportunities or in places where you’re limiting yourself. I think just keep trying—you’ve got to keep playing new games and have confidence that if you’re building skills, you will get to the place that will feel like success for you.
College Towns: Wonderful. Thank you. Well, the book is Hate the Game by Dr. Daryl Fairweather. Thank you for joining College Towns. This has been great.
Dr. Fairweather: Thank you for having me.
Note: See the full interview below.