The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph

Amelia Earhart overcame sexist discrimination to train as one of the first women pilots, and was the first woman to fly across the Atlantic solo and non-stop. Holiday argues that if Earhart had been offended by her first offer, in which she accompanied two men across the Atlantic and was unpaid for the gig, she would not have enjoyed the same success. Holiday claims that people should take advantage of any opportunity they can and make the most of it, rather than passively waiting for the perfect situation. Holiday claims that having the confidence to take initiative is an essential part of making progress. He uses the example of German army marshal Erwin Rommel, who had great success on the battlefield by maintaining constant momentum. Holiday claims that people should create their own sense of momentum and productivity by taking action, rather than waiting for perfect conditions.

Ulysses S. Grant is an example of how persistence can lead to success. In the US Civil War, Grant refused to give up on his goal of capturing Vicksburg, Mississippi in spite of months of failed strategies. While Lincoln was prepared to replace him with a new general, Grant persisted by embracing more risky strategies and defying conventional military practices, such as leaving supplies behind and living off the land. Similarly, Thomas Edison continued working on his lightbulb invention through continued failure and frustration, which included testing six thousand possible filaments. Holiday coaches the reader to adopt Stoic philosopher Epictetus’s mantra, “Persist and resist,” when facing obstacles in life and at work (80).

In Silicon Valley, many startups release simple versions of their product, which they call their “Minimum Viable Product” or “MVP,” in order to test their product on the market without risking catastrophic failure. New businesses see the MVP as a way to gauge whether their invention is going to be embraced by consumers. If their MVP’s fail, they are able to evaluate why and learn from the experience, taking these lessons into their next ventures. Holiday claims that if people can change their perception of failures, they don’t have to be failures at all, but lessons for future success. He writes: “Failure shows us the way—by showing us what isn’t the way” (86).

Holiday lauds football coach Nick Saban, who invented the training method known as “the process.” Saban believes that envisioning big picture success, such as winning a championship, is not a pragmatic way to achieve a goal. Instead, he trains his players to focus on excelling at the minutiae of everyday tasks, which will ultimately help them achieve the larger goal of winning games and tournaments. Holiday suggests that the reader could also benefit from this perspective. He advises that one focus energies on “finishing the smallest task you have right in front of you and finishing it well” (88). He shares how meteorologist James Pollard Espy learned to read as an adult after being inspired by orator Henry Clay, who encouraged him to simply begin the task and learn bit by bit. Espy was soon literate and began college the following year.

Holiday argues that focusing on excelling at work is a choice which will always yield personal and professional benefits. He rejects the notion that anyone can be above a certain task or job, and argues that when people embrace humble beginnings and work hard they can overcome obstacles. For instance, former president James Garfield overcame poverty by working as a janitor for his college instead of paying tuition. Garfield soon proved himself academically and began teaching at the school as well, and later became the dean. Holiday argues: “Wherever we are, whatever we’re doing and wherever we’re going, we owe it to ourselves, to our art, to the world to do it well. That’s our primary duty. And our obligation. When action is our priority, vanity falls away” (94). By applying themselves to their jobs people can “find the meaning of life” and turn “every obstacle into an opportunity” (96).

Holiday argues that when facing unethical or bureaucratic obstacles, people will need to be creative and strategic. He points to early 20th-century fruit company owner Samuel Zemurray, who happily paid twice for one plot of agricultural land rather than try to understand which seller truly owned it legally. Zemurray overcame a ban on bridge-building by building wharfs instead, and connecting them with temporary pontoons when necessary. In a very different example, author Richard Wright overcame Jim Crow discrimination in the South by pretending to pick up library books for a white boss while really taking them out for himself. This gave him the freedom to explore literature, which helped him ultimately become a novelist.

While none of these strategies were perfect, they helped each man make progress in their situation. Holiday contends this should be everyone’s focus: “Start thinking like a radical pragmatist: still ambitious, aggressive, and rooted in ideals, but also imminently practical and guided by the possible […] Think progress, not perfection” (101).

Holiday challenges the stereotype that wars are won through decisive victories in open battle on the opponent’s main army, citing historian B. H. Liddell Hart’s analysis that most wars are won by other means. While former president George Washington has a reputation for being a “brave and bold” general, most of his strategy involved small, defensive attacks and evading larger confrontations with the British (103). Using this strategy, Washington was able to win victories in spite of being short on funds and troops in comparison to the enemy.

Holiday argues that facing obstacles such as these can “force us to be creative, to find workarounds, to sublimate the ego and do anything to win besides challenging our enemies where they are strongest” (106). He argues that this approach also works when it comes to the obstacle of someone else’s disagreement. Rather than trying to attack their position openly, Holiday suggests emulating Danish philosopher Søren Kierkegaard by raising the topic from a new angle.

Holiday claims that there are many ways to take action against problems, including peaceful action or restraint. For instance, in agitating against British colonization in India, Gandhi led a campaign of civil disobedience which challenged the British through peaceful action or nonaction. Rather than try to challenge the British through military means, Gandhi strategically embraced the fact that he and his followers could not match the police or army’s brute strength. With his peaceful campaigns, such as marching to the sea to collect salt, Gandhi.

“leaned into that weakness, exaggerated it, exposed himself […] knowing that it placed authorities in an impossible dilemma” (109). Holiday explains: “Opposites work. Nonaction can be action. It uses the power of others and allows us to absorb their power as our own. Letting them—or the obstacle—do the work for us” (109). He claims that this strategy requires humility and patience but can be more successful than struggling using traditional methods.

Holiday instructs the reader to see their frustrations or anxiety as energy which they can channel into their work. He points to the tennis player Arthur Ashe as someone who learned how to limit obvious emotional reactions on the court, instead allowing his frustrations to manifest as physical energy and propel his game. Holiday advises the reader to reframe resentments against their own obstacles as mental energy which they can expend productively. He compares such energy to water which is dammed up and released when necessary.

Holiday claims that by not shying away from potential failure people can “seize the offensive” and turn difficult or vulnerable moments into new opportunities (118). For instance, in former President Barack Obama’s first presidential campaign, he took advantage of a controversy surrounding his former pastor to speak on the issue of race and racism in America. In a speech, Obama embraced the media’s spotlight on the issue and called it a “teachable moment” (118). According to Holiday, this allowed him to harness the energy and attention of the scandal and redirect it to good use, ultimately helping him to win the presidency. Holiday suggests that the reader can use the same approach in their own lives by interpreting vulnerability or loss in a new way.

Holiday concludes Part 2 by acknowledging that some obstacles will be “impassable,” and that failure happens to everyone (123). He coaches the reader to interpret things that stop them from proceeding down a certain path as “a new path with a new part of us” (123). For example, people may lament being hurt or having a failed venture, but could see it as a chance to practice acceptance or forgiveness. Holiday reiterates that risk is a part of life and that people must be “willing to roll the dice and lose” (124).