Milestone Blog

Reflections of Famous Failures

Posted by Milestone Leadership on Feb 7, 2019 4:39:41 PM




Milestone: a significant event which often causes a person to reflect upon where they stand in life.

Events of significance take many forms—sometimes with life-changing impact on many people, sometimes as a quiet and very personal episode. Defining moments like these, whether joyful, catastrophic, embarrassing, affirming or something in between, have the potential to shape future behavior and attitudes when paired with a healthy dose of self-reflection.

An ability to reflect is a key trait found among strong leaders, and it offers valuable opportunity to question why something happened, how one may have contributed to a situation and what positive (or negative) behaviors are likely to influence the future.

In a Business Insider article by Emmie Martin and Aaron Taube, “7 Successful People Describe the Decision That Changed Their Careers Forever,” several examples of milestone moments are cited that provided enormous influence on where some well known leaders have ended up today.

Deepak Chopra, internationally prominent author, speaker and one of the best-known and wealthiest leaders in alternative medicine, was kicked out of a Tuft University science research lab for losing his temper and dumping a folder full of papers over his advisor’s head. Chopra’s outburst led to him having to work in a Boston-area emergency room, which soon revealed he was much more interested in helping patients than remaining in a laboratory setting. He turned the negative and humiliating experience into an opportunity to pursue self-awareness—recognizing that it provided a path to overcoming fear, anger, doubt and trauma of the past.

After college, personal finance guru Suze Orman had dreams of entrepreneurship and opening a hot tub café, something she frequently told customers in the bakery where she worked. Willing to invest in Orman’s dream, a customer gave her a whopping $50,000 tip as seed money to start her own business. Uninformed about saving and investing wisely, the gift disappeared in little time and she was no farther ahead in pursuing her dream business. According to Orman, the experience was an excruciating lesson about being too trusting of others and personally uninformed. She came to realize that she actually had an interest in investing, which led her to eventually earning back all of the money she lost. This, paired with a passion for helping others, provided her the insight to help millions through her books, speaking engagements and television program.

Kevin O’Leary, businessman, author and current television personality on “Shark Tank,” got off to a very rocky start as a 16-year-old ice cream scooper. On his second day at the parlor, the manager asked O’Leary to scrape gum off the floor, to which he replied, “That’s not my job.” He then had the humiliation of explaining to his parents that he had been fired. His stepfather’s response to him was hard to hear, but O’Leary took to heart the assertion that he was hired not only to serve customers, but to also serve the business owner whether he liked that person or not. This self-reflection taught him that being in business means always serving someone—and that he wanted a future of being his own boss, which led him to a career in entrepreneurship.

At Milestone Leadership, we believe in the power of self-examination that results in personal awareness. Every journey is individual, but by recognizing and learning to enhance the traits that exemplify leaders worth following, we know it’s possible to grow and inspire the best in others at any stage of a career.


Kelly Hale Syer
Milestone Leadership


Topics: Leadership, Reflection, Failure, Heart, Bravery, Role Models, Criticism, Relationships, Values & Ethics, Personal Development, Deepak Chopra, Leader Worth Following, Suze Orman, Kevin O’Leary

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