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Redefining Success In the Winner-Take-All Economy

Haley Paskalides  |  May 1, 2024

Naomi Cahn explains why in our winner-take-all economy, “lean in” doesn’t always work out.

Eleven years ago, Sheryl Sandberg’s “Lean In” hit the shelves and became an instant hit. Her feminist manifesto encouraged women to stop holding themselves back from working to reach positions of power and instead lean on other women’s experiences to help them. As a mother of two young children when she wrote the book, Sandberg’s message was yes, you can have it all —  if you want it bad enough. 

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It’s undeniable that the book, at least in part, moved the needle — for the first time in the Fortune 500 list’s 68-year history, more than 10 percent of the companies are led by women. 

However, eleven years later many women are pushing back on the “lean in” approach that placed so much responsibility on individual women rather than the societal and economic structures around them. They’re also questioning if they really want to have it all in the first place. 

LISTEN: An Economist Weighs In On Being A Woman

Naomi Cahn has dedicated her life’s work to studying how we can fix the systems that hold women back in the workplace and how feminist theory intersects with the law. Her new book with co-authors June Carbone and Nancy Levit: “Fair Shake: Women And The Fight To Build A Just Economy,” explores why our “winner takes all” economy is the root cause of women’s continued economic inequality. 

“We’re using the term ‘winner take all economy’ to describe the critical shift in the new economy as the ability of those at the top to take a much larger share of institutional resources,” Cahn says. “The ‘winner take all’ world is a zero-sum game that produces negative sum consequences. There are internal competitions in workplaces, and the higher the stakes in the internal competition, the more likely it is that women will be pushed out.

She says this is especially prevalent in the financial services industry, where we’ve moved away from looking at company health as a whole to focusing on individual financial success. What used to be ‘my company produces better products than yours’ is now ‘my bonus is bigger than yours,’ which is a system women are less comfortable fitting into. 

Cahn argues that while we can’t fix this system overnight, there are things we can do to make changes in our immediate environment. First, she says to build a network of allies and mentors that you can turn to for questions and support inside and outside of the workplace. That way, if you’re asked to do something at work that completely goes against your values “then it’s time to draw on your network of allies and mentors and figure out another place to be where you don’t have to cheat to get ahead,” Cahn says. 

In Mailbag, we hear from a listener who’s feeling burned out in the healthcare field but knows her coworkers are already short-staffed and doesn’t want to leave them in a bind, and Jean’s daughter Julia answers a listener’s question on where to find friends that are as career-oriented as she is. 


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All advisory services offered through Financial Engines Advisors L.L.C. (FEA), a federally registered investment advisor. Results are not guaranteed. AM1969416

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