“There is nothing either good or bad, but thinking makes it so.”
―William Shakespear

In his book, The Obstacle Is the Way, Ryan Holiday (2014) shares the wisdom of Stoicism* (a Greek philosophy) and ancient Stoics to help readers “accomplish the very specific and increasingly urgent goal we all share: overcoming obstacles. Mental obstacles. Physical obstacles. Emotional obstacles. Perceived obstacles” (Holiday, 2014, p. 5).

*Stoicism is “about acknowledging our emotions, reflecting on what causes them, and redirecting them for our own good. It is about keeping in mind what is and what is not under our control, focusing our efforts on the former and not wasting them on the latter. It is about practicing virtue and excellence and navigating the world to the best of our abilities, while being mindful of the moral dimension of all our actions” (Pigliucci, 2017, p. 2-3).

“The Stoics realized that we have considerable flexibility in how we frame the situations we experience. They discovered, more precisely, that by thinking of setbacks as tests of our character, we can dramatically alter our emotional response to them. We can, in particular, develop our ability to stay clam, even in the face of very significant setbacks, and this in turn can have a dramatic impact on our quality of life” (Irvine, 2019, p. 17).

Holiday’s book teaches us: “How to turn the many negative situations we encounter in our lives into positive ones—or at least to snatch whatever benefit we can from them. To steal good fortune from misfortune” (2014, p. 5).

“We’re dissatisfied with our jobs, our relationships, our place in the world. We’re trying to get somewhere, but something stands in the way. So we do nothing. We blame our bosses, the economy, our politicians, other people, or we write ourselves off as failures or our goals as impossible. When really only one thing is at fault: our attitude and approach” (Holiday, 2014, p. 2).

But not everyone is stuck like this. Some people are able to turn their obstacles and trials into triumphs. What’s more, many of these individuals faced unimaginable challenges and frustrations and despite those obstacles, or perhaps thanks to those obstacles, they overcame and succeeded. Great individuals, like great companies, find a way to transform weakness into strength. They are able to take what should have held them back and used it to move forward (Holiday, 2014).

“Like oxygen to a fire, obstacles became fuel for the blaze that was their ambition. Nothing could stop them, they were (and continue to be) impossible to discourage or contain. Every impediment only served to make the inferno within them burn with greater ferocity” (Holiday, 2014, p. 4).

There are a few things to keep in mind when faced with a seemingly insurmountable obstacle. We must try (Holiday, 2014, p. 18):

  • To be objective
  • To control emotions and keep an even keel
  • To choose to see the good in a situation
  • To steady our nerves
  • To ignore what disturbs or limits others
  • To place things in perspective
  • To revert to the present moment
  • To focus on what can be controlled

“This is how you see the opportunity within the obstacle. It does not happen on its own. It is a process—one that results from self-discipline and logic” (Holiday, 2014, p. 18).

Take Helen Keller, the first deaf and blind person to ever graduate from college. Can you imagine losing one of your senses, let alone two? Many people know about Keller’s successes and accolades, but not many are familiar with the struggles she had to overcome to get there. For instance, Keller was such a temperamental, wild, and unruly deaf-blind child that even family and close friends didn’t think she could be taught. It took Helen’s mother, Kate Keller, and her unrelenting quest for a teacher (one who would be willing to travel to rural Tuscumbia, Alabama to teach Helen), and a teacher (Anne Sullivan), who was both qualified and willing to travel to Alabama. Under Sullivan’s tutelage, the young Keller thrived ― learning how to fingerspell, read Braille, and write. Helen Keller eventually graduated from Radcliffe College. Keller could read English, German, French, Greek, and Latin in Braille! She also learned to speak (McGinnity, Seymour-Ford, & Andries, 2004).

“Keller hit, pinched and kicked her teacher and knocked out one of her teeth. Sullivan finally gained control by moving with the girl into a small cottage on the Kellers’ property. Through patience and firm consistency, she finally won the child’s heart and trust, a necessary step before Keller’s education could proceed” (McGinnity, Seymour-Ford, & Andries, 2004).

What’s perhaps more remarkable is that Anne Sullivan (Helen Keller’s teacher) herself experienced much more extreme hardships growing up. When Sullivan was about five years old, she contracted trachoma, an eye disease caused by bacteria. Trachoma causes repeated, painful infections, making the eyes red and swollen. Over time the recurring irritation and scarring of the cornea causes severe vision loss. Sullivan dealt with the effects of trachoma throughout her life. After her mother died (Anne was eight years old), her father struggled to raise the family and soon abandoned his children. Anne and her younger brother Jimmie were sent to Tewksbury Almshouse, a home for the poor. Sadly and very tragically, the conditions there were so deplorable that three months after they arrived, Jimmie Sullivan died. Early in her stay at Tewksbury, Anne realized that her best chance at a better life was to get an education at a school for blind children. This became her central focus. She heard about a commission coming to investigate the conditions at Tewksbury, and on the day of their visit, she followed them around waiting for her time to speak up. As the tour was wrapping up, Anne approached one of the inspectors and told him she wanted to go to school. That moment changed her life. On October 7, 1880, Anne Sullivan entered the Perkins School for the Blind (McGinnity, Seymour-Ford, & Andries, 2004).

And even after she got into the school, many of the other girls (most from wealthy families) made fun of her because, at the age of 14, she was unable to read or write her name. And she had never owned a nightgown or hairbrush. “Anne Sullivan’s recollections of her early years at Perkins were mainly of feeling humiliated about her own shortcomings. Her anger and shame fueled a determination to excel in her studies” (McGinnity, Seymour-Ford, & Andries, 2004).

“Not everyone looks at obstacles—often the same ones you and I face—and sees reason to despair. In fact, they see the
opposite. They see a problem with a ready solution. They see a chance to test and improve themselves. Nothing stands in their way. Rather, everything guides them on the way” (Holiday, 2014, p. 178).

Anne Sullivan’s life experiences, like so many of the great history changers and makers before and after her, were “tested in the crucible of adversity and forged in the furnace of trial” (Holiday, 2014, p. 178).

“People seldom see the halting and painful steps by which the most insignificant success is achieved.” ―Anne Sullivan

“Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, vision cleared, ambition inspired, and success achieved.” ―Helen Keller

Takeaway: “You will come across obstacles in life—fair and unfair. And you will discover, time and time again, that what matters most is not what these obstacles are but how we see them, how we react to them, and whether we keep our composure. . . . [T]his reaction determines how successful we will be in overcoming—or possibly thriving because of—them” (Holiday, 2014, p. 16).

Written By: Steve Nguyen, Ph.D.
Leadership Development Advisor


Holiday, R. (2019). The Daily Stoic. What Is Stoicism? A Definition & 9 Stoic Exercises To Get You Started. https://dailystoic.com/what-is-stoicism-a-definition-3-stoic-exercises-to-get-you-started/

Holiday, R. (2014). The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph. Portfolio.

Irvine, W. B. (2019). The Stoic Challenge: A Philosopher’s Guide to Becoming Tougher, Calmer, and More Resilient. W. W. Norton & Company, Inc.

McGinnity, B.L., Seymour-Ford, J. and Andries, K.J. (2004) Anne Sullivan. Perkins History Museum, Perkins School for the Blind, Watertown, MA. [Also from https://www.perkins.org/history/people/anne-sullivan]

McGinnity, B.L., Seymour-Ford, J. and Andries, K.J. (2004) Helen Keller. Perkins History Museum, Perkins School for the Blind, Watertown, MA. [Also from https://www.perkins.org/history/people/helen-keller]

Pigliucci, M. (2017). How To Be a Stoic: Using Ancient Philosophy to Live a Modern Life. Basic Books.

Originally published on WorkplacePsychology on March 17, 2020 by Steve Nguyen, Ph.D. Used by kind permission of Dr. Steve Nguyen. Please visit WorkplacePsychology.