What stands in the way becomes the way.”[1] Holiday draws from Meditations, Aurelius, and the philosophy of Stoicism to expand the central theme of the book, which is that how we respond to obstacles is what defines us.

[5] As he explains this framework, Holiday supplements each section with historical anecdotes and figures from politics, commerce, sports, and history including Theodore Roosevelt, Demosthenes, John D Rockefeller, Amelia Earhart, Laura Ingalls Wilder, Ulysses S. Grant, Barack Obama, Steve Jobs, among others.

…"[8] In the preface of The Obstacle is the Way, Holiday begins by setting up the scene in the year of 170 in Germania, as the Roman Emperor Marcus Aurelius wrote down the formula for getting through rough situations.

"[8] In the preface, Holiday discusses how this book studies how countless individuals took their struggles, flipped them around and eventually used it as a chance to enhance a virtue or skillset.

[10] After the book's release, the book slowly made its way through the community of professional sports, and are being read by a number of prominent athletes and head coaches including Joe Maddon of the Chicago Cubs, Marquette basketball coach Shaka Smart, tennis pro James McGee, NFL lineman Garrett Gilkey, Olympic gold medalist Chandra Crawford, and others.

[10][11] On the way to their 2014 Super Bowl victory, Michael Lombardi and Bill Belichick of the New England Patriots distributed copies of The Obstacle Is the Way to their staff and players.