At 22 years old, I was promoted to a position of quasi-management in the restaurant industry. (“Quasi” because I was given the responsibility of management, but not the pay to coincide with the title).  It made an enjoyable gig much more challenging than I had ever expected. To many of my co-workers, especially those who were hired long before I arrived, I became “The Man.” A spirit of camaraderie was replaced by an him-versus-us mentality that eventually led to a less than desirable situation. The fact that I was only 22 probably had a great deal to do with this.

By the time I owned my own business in my late twenties, I had had the opportunity to reflect on the “failures” of my past and had a much more defined idea and philosophy on what being a truly solid leader. Part of this growth process was based in the accepting of my weaknesses and past failures.

In Episode I, we witness a young Obi-Wan go from apprentice to mentor with one brunt thrust of a lightsaber. This incident places Obi-Wan in an impossibly challenging situation, as Obi-Wan himself was still under the tutelage of a mentor when he became a mentor himself.

As the saga progresses, viewers witness the struggles of Anakin, the often wayward padawan, and a mentor straining to reel the learner in. While Anakin is challenged by the lure of the Dark Side, we see doubt, fear, anger, and mistrust eventually erode the mentor-mentee relationship until Obi-Wan himself proclaims his failure with training Anakin. The result is not just the failure of Anakin to become a Jedi, but the very death of Anakin himself (from a certain point of view…).

Jump to the original trilogy, where an aged Kenobi emerges  from isolation to once again begin a mentor-mentee relationship. This time, with the offspring of his life’s greatest failure. Though we have glimpses into the years between Episode III and IV, thanks largely to Marvel, we can only imagine what those eighteen or so years of self-reflection brought to Obi-Wan.  Whatever personal demons the Jedi dealt with during that time, he eventually came to a place of acceptance and readiness to atone for his failures.

As we track the 2.0 version of the Kenobi-Skywalker relationship over the course of the original trilogy, the difference in Kenobi’s approach to mentoring is apparent. His instruction is calculated and methodical, and becomes the voice that only experience can bring. While age itself is certainly part of this equation, there is little doubt Obi-Wan spent years under the twin suns replaying the events of the past – hoping to uncover those moments in which his role of mentor fell short.

Undoubtedly, future Star Wars installments (Obi-Wan standalone, anyone..?) will bring more enlightenment to this period of the Jedi’s life. Until then, we witness a glowing example of how one takes the mistakes and missteps of the past and uses them to redefine his role and influence. It is through this process, we embrace the character of Obi-Wan – a character whose ability to accept and overcome his flaws ultimately propel him to the legendary status his deserves.

-DK