Learning How to Learn: From Special Operations to Cisconian

Computer science professor and author Cal Newport claims meaningful employment is related to one’s ability to perform a “rare and valuable skill.” Adding that commonly, the rarer and the more valuable, typically the more lucrative. In 2010, I found myself two semesters shy of an undergraduate diploma having a hard time matching any of my interests to the short list of rare and valuable skills that might belong on a resume. So, I decided to enlist in the Navy with the goal of becoming a SEAL.

In retrospect, I was somewhat ignorant to what becoming a SEAL required, a benefit I don’t think many of today’s trainees experience. Immediately, the need to learn new processes and adopt new skills proved to be the predictor of success or failure. Many of these new skills are rare in their own rights and some valuable, but what I know now is that learning how to learn efficiently would prove to be the rarest and most valuable skill – a skill that I would call on consistently in the years that followed, from special operations to Cisconian.

As trainees progress through the dozen or so training blocks, standout performance in previous blocks holds no weight in the current block. The ability to ride the wave of past performance doesn’t exist, an inconvenient truth that follows you your whole career. The training taught me how to manage pressure and how to perform in the face of enormous impacts for failure. I learned how to acknowledge and quickly let go of failures as well as successes. Before the military, I approached each new skill with the same mindset, “How do I do this?” That question was evolving into, “What does this challenge require of me to achieve a successful outcome?”

When I checked into my first command, excellence was an unspoken expectation. The ability to make complex decisions dictated success, and learning opened up the subjectivity that exists in leadership and strategy. Conflict requires understanding, empathy, and integrity as much as precision, technology, and automation. The most impactful leaders I knew in the military managed to find the ideal combination of those skills.

Nearly a decade later, I was contemplating leaving the Navy when I decided to try my hand at business school. I thought it might lessen the effects of being in the military for nine years while my peers built momentum in the private sector. It was there that I first acknowledged the payoff of learning how to learn. The program consisted of what I would describe as semester-long crash courses in the different aspects of business: accounting, finance, marketing, etc. – just enough to not truly master anything. I learned to pick out the three to four main ideas from each subject (which isn’t much of a task as most textbooks include a section that says “Main Ideas”) and view the process with the goal of becoming a well-rounded business leader. It was hardly any different than military training. It all revolved around the same core question, “What does this challenge require of me to achieve a successful outcome?”

After leaving the Navy, I took a finance role at a small real estate private equity firm. Until this point, my success was generally measured in pass/fail metrics. In finance and fund management, this couldn’t be more opposite. For money managers, percentage points rule the day, fonts matter, pennies matter, and the words that make up emails and reports have tremendous impact. Details were everything, and the measure of success changed, but the question did not, “What does this challenge require of me to achieve a successful outcome?”

One year ago, I joined Cisco focused on cybersecurity in the public sector. I think my colleagues would agree that staying on top of the latest in information security and cybersecurity is an enormous task. There’s a wealth of knowledge that already exists on the teams at Cisco, but for me, learning how to learn, has proven the most valuable. In my opinion, that’s why we’re seeing and will continue to see an emergence of veterans in tech. In a world where the threat landscape is evolving by the minute, my sense is that we’ll be seeing vets add value for years to come.

At the end of the day, from special operations to finance leaders, CISOs to CIOs, while their focuses may differ, the question will always be, “What does this challenge require of me to achieve a successful outcome?”  

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