Sears Was the Amazon of Its Time—Until It Made Preventable Mistakes

A customer enters the closing down Sears store is shown in downtown Vancouver.

Derek Thompson’s article for CITYLAB describes the rise and fall of Sears, and a cautionary tale for Amazon.  As the retail climate continues to shift, Sears’ properties, along with real estate holdings liberated by Macy’s and others during  the retail meltdown, offer prime opportunities for sprawl repair that can lead to complete and walkable communities.


“There are four broad lessons that Amazon can glean from the story of Sears’s decline.


  • First, retail is in a state of perpetual metamorphosis.
  • Second, even large technological advantages for retailers are fleeting.
  • Third, there is no strategic replacement for being obsessed with people and their behavior.
  • Finally, adding more businesses is not the same as building a better business.

But it’s important for Amazon to stay aggressive about experimenting with new platforms, in case one of today’s underdeveloped technologies—like ordering through AI assistants, delivery-by-drone, or virtual and augmented reality—turns out to be the next big thing that transforms retail, all over again.”

Like retail, it is important to be agile and creative in designing new communities and repairing suburban sprawl to meet the changing needs of Millennials and Baby Boomers.