Book Review: Hate the Game by Daryl Fairweather

Redfin's chief economist memoir/self help book

Daryl Fairweather, chief economist of online real estate broker Redfin.com, has a new book out called Hate the Game: Economic cheat codes for life, love & work.

Full disclosure: Ms. Fairweather is a friend of this blog and sent us a copy of the book for us to review.

It’s half memoir, half self-help, in which Fairweather matter-of-factly recounts the steps she took in her life and career to wind up where she is today, and analyzes those choices through the lens of game theory, a branch of economics that analyzes decisions in terms of the tradeoffs, rewards, and penalties incurred by players of various games. She presents this in an easily-digestible format clearly meant for a lay audience; the book is literally positioned as an “airport book:”

The title is a clear reference to the popular late-90’s phrase “Don’t hate the player, hate the game” (possibly originating from Hip-hop artist Mac Dre’s 1998 album). An equally suitable subtitle might have been: “life’s not fair, so what shall we do about it?”

(There’s a brief but important connection to Georgism at the end, which I’ll discuss in my conclusion.)

I like to judge media on its own terms—not against some abstract standard, but in relation to what a work itself is trying to accomplish. Fairweather makes this quite clear in the introduction by mentioning three other books that inspired her—Freakonomics, Lean In, and Never Split the Difference.

Freakonomics by Steven Levitt and Stephen Dubner was a bestselling book of the early 2000’s that described itself as, “a rogue economist explores the hidden side of everything.” Fairweather cites this book as specifically inspiring her her field of study as well as her choice of schools; not only did she major in economics, she eventually secured Steven Levitt himself as advisor for her PhD program at the University of Chicago.

Lean In was written by Facebook executive Sheryl Sandberg and was a bestselling book of the early 2010’s that essentially encouraged women to assert themselves more in the workplace in order to earn more and be successful.

Never Split the Difference by Chris Voss was a late 2010’s bestselling book about succeeding in negotiations, written by a former FBI hostage negotiator.

Fairweather is fond of Levitt and Freakonomics, but critiques Lean In and Never Split the Difference as oversimplifying the art of getting what you want.

Fairweather concludes that too many of these books are infected with an irreducible amount of “survivorship bias.” This is when we only hear stories from life’s winners, but not life’s losers. A concrete example would be listening to your grandfather explain how he managed to survive the allied assault on Normandy beach. It worked for him, but how many men now buried at Colleville-sur-Mer followed the same strategy?

Fairweather concludes:

I stopped reading career books for advice and resigned myself to reading them for what they truly were: memoirs and personal essays written by authors who didn’t understand the economic context that led to their success.

Fairweather has written just such a book herself, and the chief difference between hers and all the other books is that she’s honest about it. It’s also the chief reason I enjoyed the book. While a critic might say an individual’s life is highly particular and non-repeatable, limiting its generalizability, I would say that’s exactly what makes it interesting.

The other kind of book—the kind that’s not honest about what it’s doing—constantly over-generalizes its advice, spinning a tiny thread of amusing anecdotes into a puffed up sail that promises to guide your ship of life into a safe harbor of perfectly abstract prosperity.

Instead, Fairweather’s book charts a course through her own extremely specific and highly particular life, with stops along the way at every major life decision. We are taken on a long journey starting with which college to attend and what major to pursue, through early career choices at a certain “big tech company” that is never mentioned by name but which Fairweather is clearly happy to leave for greener pastures. (Amazon. It’s Amazon.) She gets married, works out division of labor and home vs. career choices with her husband, navigates multiple salary negotiations, pregnancy, maternity leave, a big career change, buying and selling a house, and coping with the pandemic.

For each milestone Fairweather recounts not only her personal decision making process, but also the relevant principles from economics and game theory that helped her arrive at an optimal decision. She’ll usually then bring in a concrete example from pop culture, and, with a slight nod to the genre’s demands for generalizability, suggestions for how you might apply the same decision making tools in your own life.

In an early section on negotiations and ultimatums, she uses the example of the popular late-90’s band Destiny’s Child. The band originally featured four members: Beyoncé Knowles, Kelly Rowland, LaTavia Roberson, and LeToya Luckett, and was managed by Beyoncé’s father, Matthew Knowles. Fairweather recounts how LaTavia and LeToya, upset that Beyoncé’s father was favoring his daughter at their expense, demanded Matthew’s ouster at a moment when they thought they had leverage over him. Unfortunately for them, they misjudged two things—the relative importance of Beyoncé to the group, and the amount of short term pain Mr. Knowles was willing to endure to ensure his daughter’s success.

Fairweather recounts her own “LaTavia and LeToya” moment in a failed salary negotiation at an early job in her career:

I completely misunderstood the CEO’s objectives. I mistakenly thought his primary goal was to impress the client. I knew the client would be concerned about seeing me leave after the other project’s economist left. But now I understood the CEO cared first and foremost about having complete control over his employees. That was the missing piece of information I couldn’t see, even though it was in front of my face the whole time.

Looking back on my own career I see several times I’ve had this exact experience, and could have greatly benefited from reading this chapter immediately before heading into negotiations.

One part of the book that particularly struck me was how frank and open Ms. Fairweather was when it came to a particularly taboo feature of American work culture—talking about money. There are many sensible reasons for being coy about salaries and living expenses, either to avoid coming across as arrogantly flaunting one’s success, or to avoid the shame of being less well off than your peers. But there’s another reason, and it’s not in the average person’s interest: employers always know what their employees are earning, but the employees don’t, and this gives the boss the upper hand in negotiations.

Fairweather bluntly points out that getting what you want in negotiations is not so much about saying the right magic words as it is about carefully weighing your options and knowing how to muster power. You must understand what your “inside” and “outside” options are (the value of staying versus the value of leaving, respectively), as well as the position your counterparty is negotiating from.

A great example of this is a particularly pivotal moment in Fairweather’s life—the moment a recruiter from Redfin reached out to her while she was still at Amazon “the big tech company,” asking her to apply for the position of chief economist.

One might say it was luck, or alternatively that Fairweather “made her own luck” by intentionally fostering serendipity (a real phenomenon). Wherever you land, it’s what happens next that made this moment the centerpiece of the book for me, as Fairweather applied her methods to optimize the impact of a life-changing decision:

The number had to be believable and be below the recruiter’s budget for the role. So I needed to estimate the recruiter’s budget. Unfortunately, there wasn’t much data for chief economist salaries online. However, I discovered directors could earn $250,000 to $400,000 per year. So I estimated a chief economist could make as much as a director. So, I settled on the high end, $400,000 as my opener, to avoid overthinking.

The recruiter countered with $360,000, which she accepted. For context, Fairweather’s previous salary at her old position was $230,000. If she hadn’t done her research, she would have missed out on a $110,000 raise. If she had led with her current salary or modestly picked the bottom of the range at $250,000, she’d have left money on the table, and if she had made an unreasonable request like asking for a million dollars, the recruiter would have just balked and ended the negotiations early.

Her old salary is higher than anything I’ve ever earned, but there’s still a valuable and relatable lesson for me here: a single negotiation can change your life.

Does this mean I’ll get a big raise if I try the exact same trick at my next job interview? Not necessarily, and I doubt I’ll be getting any surprise offers to be Redfin’s chief economist anytime soon (I hear the position’s taken, for one). But this is advice I can actually use, even as I contextualize the vast differences between Fairweather’s life story and my own.

The main message that prevails throughout is that life isn’t fair and the game is in many ways rigged. So what are we supposed to do about it? Instead of waiting for a revolution, Fairweather offers two suggestions.

The first is the main narrative thread of the book: don’t hate the player, hate the game. There are rules, you can learn them, you can and should better yourself, and there’s nothing wrong with that.

The second is that if you do find yourself the winner of an unfair game, you have a responsibility to pay your success forward in leveling the playing field for others.

One of the clearest examples of this is Fairweather’s obsession with solving the housing crisis, which features most prominently in her online advocacy. The book contains a short chapter at the end that uses Lizzie Maggie and the history of the Landlord’s game/Monopoly as an obvious metaphor for the unfairness of the housing market. Fairweather recounts her own good fortune in being able to buy at the right time and riding a rising housing market to large windfall games when she sells her house.

I collected hundreds of thousands of dollars in wealth not through hard work, but by owning my home. And I did this while tens of thousands of Seattle residents went homeless. I arguably deserved the money I made working, but I had nothing to do with the value of the land I owned. That came from scarcity…Every time a new person moved to Seattle for a fresh start, the value of my home’s land went up. Every time a tourist booked an Airbnb that could have been rented out to someone needing a permanent home, the value of my home’s land went up. Every time a NIMBY prevented land from being developed into new housing, the value of my home’s land went up.

She concludes this last chapter of the book with a brief call for fixing the rigged game by implementing Henry George’s Land Value Tax.

If I have one criticism of the book, it is that it spends too much time succeeding at its own stated goal of being a highly readable and educational self-help book/memoir that teaches economics through the lens of pop culture, and not enough time being a nerdy polemic dedicated exclusively to my personal niche policy interests. Who wants to sell a bunch of copies at airports and bookstores when you could sell one and only one copy to me?

More seriously, while I acknowledge the book is a solid entry when judged on its own merits, I personally was left wanting a bit more about how we can actually fix the “rigged game.” For instance, I would have loved an analysis about how worker power is affected by the need to pay ever-escalating rent, and how this diminishes a worker’s “outside option” in any negotiation with their boss. The only thing is that if Fairweather were to keep following that thread, she would inevitably wind up writing a whole new book.

All in all, I found Fairweather’s book easy to read, highly engaging, and refreshingly specific and pragmatic. If you enjoy books in this genre you will likely enjoy this one.

And if she does get the chance to write that second book, we will be happy to review it right here at Progress and Poverty.