The Career Game

Anita Brick:

Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth to help you advance in your career. Today we're delighted, well, I would say more than delighted to be speaking with Daryl Fairweather. She is the chief economist at Redfin where she analyzes US housing markets and consumer behavior and is a member of the Advisory Council of the Federal Reserve Bank of Dallas. Prior to that, she was a senior economist at Amazon, and she's the author of a really extraordinary book, which I will tell you I read cover to cover called Hate the Game: Economic Cheat Codes for Life, Love, and Work, and a regular contributor to Forbes. Daryl has been featured in 60 Minutes, Today, the New York Times, and Bloomberg, among many other outlets. I must complete this intro by saying that Daryl is also a PhD in economics from the University of Chicago.

Daryl, thank you so much for making time for us today.

Daryl Fairweather:

Thank you for having me.

Anita Brick:

I would say that you are probably more determined, more focused, and maybe even have a deeper level of curiosity and creativity than most, even within the listeners. Because of the things that you did, and you covered a lot of different topics, we're going to focus mostly on career. We'll start there. And here's our first question from an MBA student at Booth. "I am pursuing a highly competitive role at a top-tier consulting firm. What advice can you share so that I can realistically assess my odds and which factors truly matter most? Market demand, school brand, test scores, internships, network, or something else? And by the way, I'm coming from a tech background, if that helps.

Daryl Fairweather:

Yeah, for that specific question, I think the hardest part about getting a job nowadays is getting past that initial screen, especially now with AI tools and people being able to send out massive amounts of resumes and cover letters. Firms are just being inundated with applicants. It's really hard to break through all the other applicants. I think the best way to do that is to have an inside connection, use your network, figure out who you know, who works for the firms that you're trying to apply to, or who might be those second connections, like people you know who might introduce you to people that work for these firms, so that there is somebody looking for your application when it's submitted. Now, once you get past that initial screen, you're actually able to talk to a human. All of the things like what school you went to or what your test scores were, those don't matter anymore.

It's about impressing that person in the room or on the phone, convincing them that you are enthusiastic, competent, and ready to work. The thing that a lot of employers want is just somebody who is going to hit the ground running and be enthusiastic about all the challenges that are going to come their way. It's not so much that your school doesn't matter. I think your school can matter a lot in terms of giving you that network that will get you that first interview. But once you're in the room, it really is about making sure that you shine of your communication and demonstrating your competence.

Anita Brick:

Well, I know you had a role in consulting because he was talking about consulting. Consulting is not for everyone. I see people when they are working to break in, and I also see them when they've decided it's not right anymore, and sometimes it's hard to move from consulting to industry because of the implications on their compensation. So here's a question from an alum, and she said, "What advice would you give to someone who chose a career for money status or excitement and now feels like personal costs are way too high and wants to redefine what success looks like?"

Daryl Fairweather:

I mean, I think that you should constantly be introspecting and trying to figure out what success means to you. And when you're early in your career, you're not going to have it figured out, you just don't have enough experience to know what you like and what you don't like. And this happened to me. When I was first applying for jobs, I really just focused on the compensation because that was something easy for me to see and compare jobs across. I didn't know enough about myself or about different firms to really be able to distinguish on things like culture. And so I guess the first thing is that there's nothing to be ashamed about in terms of picking a job based on factors that you discover later are no longer important to you. When you're making that transition, what can make that transition easier is to build your kind of life raft before you actually quit.

So your life raft might be the skills that you have. Even if a job's not right for you, there are still a lot of skills that you can acquire and things that you can add to your resume that will position you to get that next job. So focus on opportunities that give you those skills that will take you to that next place. You can also save money so that when you're in that in between period between jobs, you're not in a situation where you feel really pressured to take another job based on money alone. And you can also start networking and reaching out to people, doing informational interviews, finding out what other opportunities might be out there before you really start the process of applying. Focus on right now, don't get down on yourself for picking a job that you discovered wasn't right for you.

That's totally normal. And when you're early in your career, you want as many experiences as possible so you can learn more about yourself.

Anita Brick:

Well, and you had that dilemma.

Daryl Fairweather:

Yeah, the first job that I took out of graduate school was in consulting, mostly litigation consulting, a little management consulting. It was just the easiest job for me to get straight out of grad school. Banks hire a lot of entry-level workers, consultant firms hire a lot of entry-level workers. They have the infrastructure in place to take somebody from not having any job experience to giving them the tools to be productive on the job. It's not someplace where I think you should get stuck. I've seen a lot of people get stuck in those consulting jobs because the pay is so good and because they're afraid of making a change. The job is really attractive at first, but then slowly over time there are probably better opportunities out there for you that you might be reluctant to take because you've just gotten comfortable or it's a status quo bias, you don't want to shift.

So I think if you're going to take one of these consulting jobs, you should just give yourself a hard stop date for when you are going to seriously pursue outside opportunities, probably at the two to three year mark because the longer you stay, the harder it is to leave, the more firm specific skills you will develop that aren't so easily transferable to other firms. Every place is different. I think when I was younger, I used to think that all jobs were the same, but that's definitely not true. There's a big variety in terms of culture, hours and the type of work that you do. It's fine to take those jobs, but just make sure that you are exploring those other opportunities. And if you're unhappy, listen to yourself. I was unhappy in that job and I felt kind of like a failure for not meeting the standards that they were expecting of me, but really it just wasn't a good fit and it's fine.

It takes a while to find that good fit.

Anita Brick:

You mentioned before about having people who can help us both in terms of giving us information about how things are done in an organization. How did that come into play when you moved to Amazon?

Daryl Fairweather:

Well, I had a friend from graduate school, another U Chicago alum who was already working at Amazon. So I called him up and he told me all about the job and I had a bunch of questions for him and he told me about the culture. He told me about what the application process would look like and what they would be looking for. So just having all that information definitely gave me a big advantage when applying because I knew what Amazon was looking for and I also knew how to position my experience to fit what they were looking for. But it also helped in terms of learning about the culture, making sure ahead of time that I wasn't just going to go to another job that wasn't going to be a good cultural fit. Of course, Amazon, there are things about the culture that aren't ideal or that might be a no-go for some people, but I felt like the things that I was hearing were things that I could deal with or I could thrive with in terms of the fast-paced culture and independent culture that they have for their employees.

So the more you can talk to other people who have job experiences that are different from yours, I think the more informed you can be and the more you can learn about what you might like and also ask people what they don't like about their jobs. Sometimes people are a little bit reluctant to say those things because especially if they're still working for the company, they want to have a self-perception that they like their job. But if you ask them what are the worst parts of your job, I think that's where it becomes very telling and where the culture really might have frictions with your own personal preferences.

Anita Brick:

Well, you found enough things that matched for you. How did you bring what you knew about yourself and what your friend told you into the interview so that you could authentically position yourself but be savvy about it?

Daryl Fairweather:

Yeah, so the tip that he gave me, and I think that this applies to nearly any job, is to frame my experience in the values of the company. So almost all companies will post on their website what their company values are. Now, some companies take their values more seriously and they adhere to them really strictly, and for some it's just nice words that they put on their website, so it's another thing to ask about, but at least it's a good place to start. So if a company's value says that we value people who speak up and say what's wrong, then you should give examples in your interviews of times that you spoke up and went against what other people were saying. But if the company says, "We really value teamwork and collaboration," then give examples of times that you were a good team member and you were a good collaborator.

I think there's ways to frame the exact same experience according to different values, but you should try to match it up to what your potential employer is looking for as much as possible so that you're speaking the same language. I think that's another thing to look at is look at the kinds of words that are used on the website, that are used in the job requisition and repeat those words back because that's a way to show that you are going to be a good cultural fit, that you're already speaking the same language.

Anita Brick:

How did you balance that with being authentic? Because it's very clear to me, I mean, we've never met before, but I felt like I learned things about you reading your book. You are very determined, focused, and you know what you want and you know what you don't want. How did you retain the authenticity also matching what the company needed?

Daryl Fairweather:

Yeah, I mean, I think that one of my skills and also one of my faults is that I am a chameleon and I am very good at giving people what they want. The people pleaser in me is just good at detecting when I'm doing an interview, what that interviewer wants me to say and giving them what they want. But at the same time, I need to pick a job that's going to be right for me that I'm going to thrive in. Part of that depends on what stage you are in your career. When you're early in your career and all you want is a job because it's so hard to get a job in the first place, you can't be picky. You have to take whatever job you can get and you have to mold yourself into whatever they want. When you're later in your career and you have a lot of options, that's when you can be the most selective and you can just say no to opportunities that you know aren't going to be a good fit.

And when you're in the middle of your career, you have to balance both, be accommodating enough to have the opportunities that are out there, but also you don't want to get yourself in a situation where you're going to fail. So you kind of have to have two minds about interviewing. Part of it is impressing the person who's interviewing you, and the other part is interviewing that interviewer and figuring out what the job is really going to be like, where is the job going to potentially not be a great fit for you? But it's a difficult balancing act because you don't want to come off as inflexible or as somebody who isn't able to adjust to whatever the culture of the company is. I think especially when you're in the middle of the career, you have to be flexible and know what you're willing to adjust in yourself and what is really just a boundary that you can't cross.

Anita Brick:

That's really important because sometimes even beyond that first, in this case it would be post MBA job and alums they're clearly further in their careers, it is very, very difficult, especially if you have pressures. And I'm curious, and this actually came from an alum, and he said, "You often talk about marginal benefit and marginal cost." How can someone apply that thinking to career decisions when the trade-offs are not just financial, but also emotional, relational, and personal?

Daryl Fairweather:

You really do not want to ignore those marginal benefits and marginal costs that aren't easily quantifiable. It's easy to quantify pay. It's easy to quantify the number of hours you're going to be working if that's transparent to you. It's much more difficult to quantify the way that you feel about a job, how your interactions with your colleagues are going, all that stuff. It's difficult to quantify, but incredibly important is probably the most woo-woo thing an economist would say, but I think it comes down to just the way you feel internally.That's how I've been guiding my career lately, is trying to focus on doing work that feels good to do because then I know the marginal cost is very low to me if the work feels good. If the work feels bad, the worse it feels, that's the marginal cost. I mean, there's the pay differences.

Focusing too much on money can be misleading because money is really just a conversion for these other things that you might care about. When you have money, you can buy vacations, you can potentially buy more leisure time, but some things you can't buy easily and the way you feel day-to-day in your job is not something that you can trade for money. I think that's the thing that I've been focusing on more and more and less and less on the money. Well,

Anita Brick:

It makes perfect sense. I don't know if this is an economic issue or if it's a psychological issue, but whatever the money is, at some point it becomes the norm and now that really enough? The goalpost keeps changing. You're absolutely right. If you don't have the other things in play, no matter how much money there is, it will probably never be enough.

Daryl Fairweather:

In economics, there's something called the Easterland paradox, which finds that once you go past a certain level of income, somewhere between $75,000 a year and $125,000 a year, that increase in money doesn't make you happier. I think once you get past that point of having enough money for your basic needs, it does come down to how you feel because the money isn't going to make you happier. It's the work that you're doing or your relationship to your work that determines how you feel.

Anita Brick:

Totally agree. Here's a question, and I find this to be an interesting question, and I think about it because I moderate a fair number of panels and they certainly include consultants. You speak about asymmetrical information and that asymmetric information can be an advantage, but in the world where AI gives everyone greater, greater and greater and greater access to more information, sometimes it's not accurate, I know we need to be careful of that, how can someone still create an edge in how they prepare and make decisions even before they walk into the interview?

Daryl Fairweather:

Yeah, artificial intelligence knows a lot, but there's plenty that it doesn't know. When you're walking into an interaction with somebody, the artificial intelligence isn't going to be able to tell you what that person's goals are, what they care about, who they are trying to impress, or who they dislike. That interpersonal information becomes a much more important piece of information in terms of the asymmetry, because the artificial intelligence, it really only knows what's been written down and what's been put on the internet. It doesn't know what's in the minds of the people that you're interacting with. And the way you learn that is by talking to people and paying attention to what they say and asking them straight up, "What do you care about? What is your biggest problem right now?" Or, "What are your goals?" They might not have written that down and been published anywhere that the AI can internalize, but you can get that information one-on-one.

Anita Brick:

With that, one of the questions is aligned with that, this was from a student, how do you actually pull out the truth about what someone cares about? How can you tell if someone is being candid or just speaking the party line? How do you discern that?

Daryl Fairweather:

I think you really have to take in everything that people are saying. When people lie, they're usually only lying for part of the time, and there are places where the truth will start to seep out. Paying attention, figuring out when people are being inconsistent, that's the way to determine when somebody might be being deceptive. But yeah, I think for the most part, people are not great at being deceptive. They're not great liars, and the truth will seep out. And then you might say, "Huh, that's interesting. I remember that they said that." I feel like backhanded compliments, they set off a light bulb for me that somebody is maybe being deceptive with me because I feel like the backhanded compliment, it's like they're trying to say something nice, but their negative thoughts, they can't help but let them seep through. So that's one that I would pay attention to if somebody is giving you a backhanded compliment or saying a backhanded compliment about somebody else at the company or the leadership or whatever it might be, that's something to hone in on.

Anita Brick:

Well, that's really good. I don't think anyone has ever said that to me before. I don't mean the backhanded compliment, but the way you phrase this, because it makes a ton of sense. Most people are uncomfortable, and so they are thinking about what they're going to say next rather than listening at the depth that you really mentioned, and that those inconsistencies are great clues. So thank you for that. That was really good. Thank you.

Daryl Fairweather:

Thanks.

Anita Brick:

Another MBA student who says, who's working full-time, by the way, "Career changes can sound rational in theory, but feel deeply emotional in real life." How have you seen people successfully work through doubt, fear, and pressure from family or peers when they're considering a pretty big move?

Daryl Fairweather:

Any transition, any move can bring up a lot of uncomfortable feelings. Maybe it's just my personality, but the uncomfortableness, the anxiety, for me, it's not even about the move itself. It's about the realization that whatever situation I'm in is unsustainable. And then it's like, "Oh, I'm so anxious because now I have to figure out what I'm going to do next because I have suddenly realized that I can't stay and be successful." Yeah, I think that's completely a normal feeling to have. Take a step back and look at it more objectively as the choice isn't necessarily to stay or leave. It's out of all the options available to me, including staying, what is going to be the best for me personally? And I know that parents are very risk averse. I mean, I'm a parent and it's just something about being a parent, you're always thinking about the risks to your child.

So your parents are always going to want you to take the safe situation. I think most people assume that the status quo is safer, but the status quo sometimes could be the most dangerous thing. Staying in a job where you know you don't have opportunities to move up or maybe in a job where the employer might be going under, employers come and go, firms come and go, staying put is not the safest choice. The safest choice is to make sure that you have the skills to survive in any situation and at any job that you might pursue next. Staying put can sometimes be even more risky.

Anita Brick:

It's interesting because you have a PhD in economics and the University of Chicago overall is kind of a quant focused environment. How did you develop the interpersonal wherewithal to have those skills that actually in many ways can be a lot more important, whether it means building rapport with people who are very different than us or alternatively standing up for ourselves? How did you develop the other skills beyond the quant?

Daryl Fairweather:

Well, to me, I don't see them as being so separate. When I was getting my PhD, my concentration was in behavioral economic. Having this understanding of psychology was always something that I was deeply interested in and was trained in. And then also I've always been deeply fascinated by game theory. The book Hate the Game, it means a play on game theory itself. When you zoom into just those one-on-one games, these interpersonal factors are actually greatly important. Things like understanding what the other person knows and what they don't know, that's a huge part of game theory, that's asymmetric information. And the only way you can understand what your opponent or what your negotiating partner might know or don't know is to really get into their head and have that empathy and see things from their perspective. So to me, it's a necessary skill to be able to see things from the perspectives of other people if you're going to understand what decisions they're going to make and what decisions you might want to make in return.

Anita Brick:

It's a really good point. I mean, aside from having that deep interest in behavioral economics on the psychological, the behavioral side, how else did you do it? If you think about an experience that you had, whether it was at school or whether it was in your internship and banking or the consulting, what is something that you developed that you still carry with you today as, dare I say, even a superpower?

Daryl Fairweather:

Breakthrough for me really came when I was working at Amazon and I was working with all these incredibly smart people who were not trained in economics. My job at Amazon was basically to help other people reach their goals. I was the economist who would help them understand the data, but understanding the data doesn't really do you any good unless you know what that other person that you're talking to, what their goals are, what they're worried about, what success means for them. The way I became successful at Amazon was really to focus on understanding the people that I was working with, where they were coming from and what their goals were and was holding them back from reaching those goals. And once I started to always go into an interaction with somebody, put the data to the side for a moment and just have a conversation about what their job is, what their goals are, that was the breakthrough for me when I really started to be successful and I took that into my career today.

Now I talk to journalists a lot as part of my job. I'm always talking about the housing market to different journalists. And again, journalists are incredibly smart people who might not be trained in economics at the level that I am, but I've learned how to get to the root of what it is that they're trying to figure out. With journalists, it's usually like what is the story angle or just focusing on the other person in the room, that's something that really was a breakthrough for me. Maybe even the first time I started thinking this way was when I took a writing class at U Chicago. I think it was in the Little Red Schoolhouse, the writing program for academics, because that program, it really focused on the reader, framing whatever argument you're making in a way that is going to resonate with the reader. That's the same thing that I do when I'm talking to people at work.

I'm trying to really understand them and how they're reading the information that I'm giving them because it's not just about the information, it's about fitting it into their communication style, their language style, what goals they have and making sure that it really resonates for whatever it is they're trying to get out of the interaction.

Anita Brick:

Well, I like that. Two things that come to mind, both related to when you are already in the job. So now you're in the job. One of these came from an alum, the other came from a student. The alum said, "Many talented professionals are held back not by ability, but by organizational politics." How would you advise someone who's not naturally political, how would you advise them to protect their career and still stay authentic? Yeah,

Daryl Fairweather:

I mean, this is something that I've always struggled with too. I feel like every time I start at a new company or there's a change in the leadership, there's always a culture shock element that happens for me where I've gotten used to speaking a certain way or delivering documents a certain way or interacting with leadership in a certain way and all of that is kind of thrown out the window when I have to relearn an entirely new system. It's really important to understand the organization and to understand that the organization is really just made up of individuals. All those individuals, they have their own goals, they have their own worries, and when you get them all in a group, all of those individuals interact in a way that builds the company culture. But what's been useful for me in terms of navigating that is just finding somebody at the company who's been there for a long enough time who can explain to you these cultural norms that are foreign to you.

It helps to find somebody who they themselves might struggle to with the company culture, so they're probably more aware of it. Ask them just all the questions that you might have, like what is the norm for sending emails? What's the norm for talking to executives inside your department versus outside your department? All of these things might not be written down anywhere, but there are people who know and who will be able to teach you about it. And another thing is that company culture, it does vary a lot company to company. So if you're at a place where the company culture is just terrible for you personally and you cannot find success there, that's okay. It just means that you need to get the skills that you can out of your job for as long as you feel like you need to stay there and then go to another company where the culture does match your working style better because that's where you're going to end up being more successful.

Anita Brick:

Of course. And it makes a lot of sense because you can only fake it for so long and it starts having so many damaging things, psychological makeup into our health and all of those things. I think it took a lot of courage when you made the move, although it was pretty evident that you needed to make the move from consulting somewhere else, absolutely somewhere else. Do you have time for a couple more questions?

Daryl Fairweather:

Sure.

Anita Brick:

Okay, great. So an MBA student said, "If you know that a recommendation you're making to leadership is the right way to go, but the power dynamics are working against you, how do you decide whether to push, build rapport quietly and go back to it or let the issue go completely?"

Daryl Fairweather:

Yeah, I think a lot of people have this misconception that if you have an idea that is obviously going to be beneficial to the company's bottom line, then it will get or it should get implemented, and that's just not true. And this kind of goes back to what I was saying before about how companies are made up of individuals. So you have to put yourself in that head space of whoever is the decision maker here, what are their goals? What is holding them back from taking your advice? I mean, what I found is that most people, they just don't want their lives to get harder. They don't want their jobs to get harder. So if your recommendation is going to make that person's job harder, they're probably not going to take it. And so then it's on you to figure out or how to reposition the idea in a way where that person starts to believe that this recommendation isn't going to make my life harder, it's actually going to make it easier or it's going to make me look better or it's going to make things easier in the long run.

A lot of people are short-term thinkers, so they might not be thinking about the long-run consequences or maybe they're on the way out and so they aren't concerned about what the long-term consequences are because they know internally they're not even going to be at the job a year or two from now. Talking to the person who is the decision maker and also identifying who the decision maker is, maybe you're recommending the idea to the wrong person

Anita Brick:

And

Daryl Fairweather:

They don't feel empowered to take that recommendation because they're not the owner of the decision. So understanding all of those things I think can help you better convey that recommendation. And if they still won't take it, then you're at an organization that isn't really set up to take recommendations well, and that's not a place you probably want to be in long-term.

Anita Brick:

Very good point. I think sometimes people who would like to pretend that they have the power to make the decision push back really hard because they don't have that power, and I think that's important to discern that as well.

Daryl Fairweather:

Yes, yes, that's very true.

Anita Brick:

Thank you for everything. And the way we like to close is to get very practical and very actionable. So what are three actions that you would recommend someone take and coming from your perspective as an economist to manage a successful career? And you can focus as little or be as broad as you want, but let's be practical and actionable.

Daryl Fairweather:

The thing that I would recommend is really being honest with yourself about what kind of job you want. I think sometimes we ignore our own impulses because we feel like it's too unrealistic. When I was first starting out my career, I definitely always had this inkling that I wanted to have a career that was in media in some way. One of the reasons I applied to Amazon was that I though, oh, well, Amazon, they have a books department, they have a film department. Maybe I could start off in one department and over time I could work my way over to these other departments that are related to media. That didn't happen, but nowadays I do interact with the media all the time. Like I said, I get interviewed by journalists all the time. But then once you have that kind of abstract idea of where you want your career to go, you can start thinking about, well, what skills do I need to develop to be successful in this career once I get there?

So for me, it was communication skills, public speaking skills, things like that. I mean, this is something that we talk about in game theory, working backwards, starting with your end goal. Even if the end goal seems ridiculous or out of reach, just go through the exercise, taking it seriously and then thinking about the skills that you would need to get there. And then it becomes about, well, how can I get those skills on my resume so that when eventually I am applying for my dream job, I am the best candidate possible? And you can get those skills even in the jobs that are not perfect, or you can take volunteer opportunities or you can do side projects that allow you to attain those skills that will get you to that place you want to one day go.

Anita Brick:

And anything else you'd like to add to that?

Daryl Fairweather:

I'm not sure.

Anita Brick:

But I do have one, I said that was the last question, but one final question. Is there a question that you are hoping I would ask you that I haven't yet?

Daryl Fairweather:

Well, yeah, just in this conversation, I feel like one thing we didn't talk about is we talked a little bit about navigating people who might be deceptive or who might be giving you bad information. Any organization, there are going to be people that you have conflict with. And sometimes, I think a lot of times actually the conflict really boils down to having conflicting goals. Within an organization, there are teams that are going to be focused on driving revenue and teams that are dedicated to cutting costs. And those teams are going to be in conflict with one another, and that might lead those teams to have poor interactions with one another where they fight with one another or they have personal spats with one another. Just accepting that as a part of working within an organization can be helpful. And also breaking things down into these goals that I have goals that might be conflicting with other people's goals takes out the personal.

It's not about this person doesn't like me or I don't like that person. It really just comes down to the goals that we have, and then you can see things a little bit more objectively.

Anita Brick:

I think that makes a lot of sense. And what you said today and what is in the book has this balance between logical and say in air quotes, a little bit more objective. And it's also deeply personal. I mean, you share a lot in the book and it shows where the depth and credibility in your life lies. So thank you for being forthcoming and I would say even vulnerable in the book. And it's all foundational with economics. So that's a little bit different spin and thank you. I thought it was really interesting when you said most advice is more of a memoir, and I would totally agree with that. It's about one person's experience. Although you shared your experience in the book and today, it's grounded in something that goes beyond personal experience. So thank you for writing the book and thank you for spending time with us today.

Daryl Fairweather:

Yeah, thank you so much. This is great.

Anita Brick:

Thanks again. And thank you all for listening. This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.