During my MBA program we were required to take a class in leadership. One assignment required us to reflect on our past experiences and self-asses our own leadership journey. In particular, we needed to understand how we managed change in our work and lives. Unlike writing a resume or cover letter, this assignment forced me to take a critical look at my reaction to life events and how they shaped me.

 

That assignment resonated with me. It brought me a great deal of clarity. I'm reproducing it here (with a few slight edits) because I believe it is the best narrative of my professional "course of life" to date, more so than the bullet points above. It's a bit of a long read, but provides more insight than a simple resume ever could.

 

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Leadership Philosophy:      Leadership images-in-use through iteration

Personal Motto:                      “The thing that gets us to the thing.”

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Over the course of our Leadership course, I re-watched one of my favorite television series, Halt and Catch Fire. Nominally, the show follows five people building tech companies between the early 1980s and 1990s, the decade when personal computers and the Internet were born. More important than the actual businesses were the growth of the individuals, their leadership styles, and their pursuit of the next “thing.” In the series pilot – and in the finale – one character sets his ambition to chase “the thing that gets us to the thing.”

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The show resonates with me because it reflects the iterative process of leadership. Regularly reevaluating, reassessing, reinventing and coming up with the next “thing” to chase. Success and failure don’t come in black and white categories, but build upon themselves in my experience.

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Iteration #1 – Education (Learning to be a Director – Controlling Intended Outcomes)

 

Graduating high school as a valedictorian, I earned a full four-year scholarship to the University of Colorado where I completed two degrees (a B.A. and a B.S.) and three majors (Economics, Political Science, Finance) within four years. I believed I could plan for the outcomes I wanted in life. With enough sheer will and hard work, any eventuality could be overcome.

 

Iteration #2 – Bad Timing (Learning to be a Caretaker – Controlling Unintended Outcomes)

 

Immediately out of college, I moved to Washington D.C. to find a job working for an elected official. I saw this as my first step toward a career in politics and policy-making. I worked on a congressional campaign in college and had prepared myself with multiple policy related degrees. I had a plan and I was executing it.

 

The week I arrived, Sen. Jim Jeffords switched parties. Because it flipped control of the U.S. Senate, it caused upheaval on Capitol Hill. The same jobs I planned to seek were flooded by veteran staffers suddenly in need of a landing place. Despite my best laid plans and hard-work, I found myself in a scenario where unintended, external changes were so powerful that no amount of planning or work could overcome them. I had to evolve and change my own course. After several unsuccessful months, I moved back to Colorado.

 

Iteration #3 – Rebuilding (Learning to be a Navigator – Controlling Partially Intended Outcomes)

 

During college, I worked as the Deputy Campaign Manager for a losing congressional candidate. Part of a small, but dedicated team, I ran the volunteer and outreach program. In my role I planned out every detail of every event, but had to understand that many of the outcomes could only be partially intended – voters have a mind of their own!

 

Returning from Washington D.C., I rebuilt on that framework. I returned to campaigning and worked on both a successful congressional primary race (that ultimately elected a congresswoman) as a field director and as the campaign manager for a state treasurer candidate. During the treasurer’s race, I had responsibility over every aspect of the campaign. Contrary to popular belief, down-ballot political campaigns do not have vast resources. Working directly with the candidate and a few staff members day-in-and-day-out, I became an expert in navigating the political waters of an election. From communications and outreach to fundraising and debate preparation, I did it all. Because the candidate I worked for was very driven and prone to micro-managing, I learned how to understand where he wanted the campaign to go and how to allocate my time and resources to get there. Winning on Election Night gave me my first sense of real, professional achievement.

 

Iteration #4 – Illness, Setbacks & Steps Forward (Learning to be a Nurturer – Shaping Unintended Outcomes)

 

A month after electoral success, I collapsed with stroke like symptoms. Rushed to the hospital by my registered nurse mother, by the time I reached the emergency room I had lost all feeling on my right side and the ability to speak. After days of testing, a medically induced coma, and life-threatening seizures, doctors diagnosed me with two massive infections of my brain tissue: meningitis and encephalitis.

 

I spent the next year re-teaching myself everything. I had to re-learn to speak, re-learn to walk, re-learn all the things I had taken for granted before. I spent hours and hours reading “The Illustrated A Brief History of Time” by Stephen Hawking just to re-wire my own critical thinking skills. All I could do in the face of circumstances I couldn’t control was attempt to build myself toward a time when things would change.

 

A year after my illness I became the Deputy Campaign Manager for a U.S. Senate primary campaign. I worked for a smart, well-spoken, and ultimately unsuccessful congressman. Campaigning against the scion of Coors Brewing, I taught several green staffers how to run a campaign. Almost fifteen years later, two of them are among the mostly highly regarded political consultants in Colorado, but still ask me for advice. While we lost the campaign, I believe the skills I learned re-building myself served my friends well when I helped to nurture their political talents.

 

Iteration #5 – Education, Again; Another Campaign; A New Career (Interpreter – Shaping Partially Intended Outcomes)

 

After my candidate lost his primary race, I enrolled in the University of Colorado School of Law. It shouldn’t come as a surprise that I associate the practice of law with the role of an Interpreter; effectively, attorneys are interpreters of the law. They help shape clients’ futures by planning for expected outcomes while understanding that not everything can be predicted. At least that is what I learned: how to balance between known outcomes in the law and unknown outcomes driven by both internal and external forces.

 

That perspective helped me when I graduated law school a semester early and decided to use my time to move to New York and work for Rudy Giuliani’s presidential race. One of the first twenty hires, I served as a senior research analyst in the 27th floor campaign headquarters overlooking the Brooklyn Bridge. As such, I taught other analysts how to conduct research, how to apply it, and how to use it when we needed to react to an unexpected event. One of my proudest moments came when former United States Solicitor General Ted Olson argued for our campaign to take a policy position he supported and our research team opposed. We went toe-to-toe with a giant in the legal world and won because our team had put in the time to prepare ourselves and worked together seamlessly.

 

That campaign ended before we wished, but I met some amazing people. Among the friends I have to this day are the former chief-of-staff for NY Gov. Andrew Cuomo, the former White House Political Director, several presidential campaign managers, and the  former editor for the Daily Beast and a current CNN host. I can honestly say that there is no better crucible for leadership than a presidential campaign.

 

After the campaign, I went to work at one of Colorado’s preeminent political and election law firms. For nearly three years I mentored under a master litigator and the future Secretary of State. When he left, I took over his book of business and helped interpret laws for many of the state’s largest nonprofits, trade associations, businesses, and campaigns. I argued and won seminal decisions before the Colorado Supreme Court. I quickly earned recognition as a “Rising Star” and “Super Lawyer” in my area of expertise.

 

Iteration #6 – Advocacy & My Own (Non-)Election (Mixing and Matching)

 

My reputation as a zealous advocate earned me appointment to the 2011 Colorado Reapportionment Commission by the State Senate Minority Leader. One of eleven members, I spent the better part of the year engaged in hearings and the process of re-drawing the state’s political lines. My fellow commissioners included elected officials and chief executives. In fact, one journalist turned me into a raccoon in a newspaper article after a lost a bet to former Denver Mayor Wellington Webb.

 

Working on a commission with those individuals forced me to learn how to use different leadership models in different situations. While drawing maps with my party’s commissioners, I often adopted a Director role, controlling the strategy and planning for each district down to the individual house. I became the “de facto” leader for Republicans on the commission. However, for the elected officials our maps affected, I often had to act as an Interpreter so they understood the effect the proposed maps may have on them, their constituents, and how they could work with us to create a positive environment for the outcomes we hoped to achieve.

 

One year later, I helped found a conservative group advocating in favor of civil unions for same sex couples. Reflecting now, the leadership approach I took during that time period most closely reassembled a Coach – I knew what the change would be and the outcome we planned to achieve, but had to gradually educate others and bring them onto our team. In fact, it was my intervention that ultimately swayed the pivotal swing vote that led to the most dramatic end to a legislative session in Colorado’s history. While we lost that night, I won awards for my advocacy and would later become a signatory on an amicus brief with 300 prominent conservatives across the country in the landmark Obergefell v. Hodges marriage equality case.

 

By 2013-14, I was running for election to the Colorado State Senate. If I thought running campaigns had been hard, being the candidate is exponentially more difficult. Not only did I have to run the campaign myself (state legislative races are almost entirely candidate/volunteer driven), I had to make all the appearances and dedicate my life to the race. While I worked 12-16 hours a day, every day for over a year, I eventually lost a primary election over my prior support for civil unions. Losing that race taught me both resiliency and how to hold on to my own ideals even when surrendering them would be most expedient. While I lost in a landslide because of those ideals, I believe I learned exactly the same skill any leader needs to drive a vision, whether for a political race or in a business.

 

Iteration #7 – New Careers; More Education

 

After losing the primary, and knowing that I likely did not have a future in electoral politics, I sought out new challenges.

 

First, I began to write regular opinion columns. Originally asked by the sadly defunct Colorado Statesman's editor to write about the law, politics and public policy, my columns quickly garnered a significant following. By January of 2017 I had a bi-weekly column in Colorado's largest daily newspaper, The Denver Post. I wrote about everything from healthcare reform to the death penalty to puppy mills and former First Lady Michelle Obama’s powerful message to women.

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In April 2018, I joined several other columnists in an open "rebellion" against the paper's hedge fund owners and the death of local journalism. Our actions garnered national acclaim.

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A few months later I followed several former Denver Post writers to the journalist-owned startup, online only Colorado Sun. My columns began appearing weekly and in April 2020, the Society of Professional Journalists recognized my work as the the third best "News Column" across Colorado, New Mexico, Utah and Wyoming in their annual Top of the Rockies awards.

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Just as I began writing professionally, I also became tired of the mercenary lifestyle of a law firm. I lived in 6-minute billing increments and needed a change. Consequently, I sought an in-house counsel position.

 

Serendipitously, in January 2016, I found a role as General Counsel for Colorado’s largest post-acute and long-term care provider. With 30+ facilities, 2,400+ residents, and 3,500+ employees, that role gave me an opportunity to take my life in a whole new direction. While I still worked with the law on a daily basis, I contributed to building something. Every day I helped to create environments for staff to succeed and to improve the care for residents. Most of the time, I acted as a Coach, helping to plan the outcomes our company wanted to achieve, but doing so by recognizing and enhancing the skills staff members already had.

 

After about a year, I began my Executive MBA with an emphasis in Health Administration. Two years of intensive study in a class with leaders in the healthcare field (including hospital CEO's, heart surgeons, CFO's, and similar dignitaries) only increased my passion for blending the law with business.

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Iteration #8 - My Own Law Firm (KBNlaw.com) (Explorer)

 

A semester before I completed my MBA, I found myself out of a job after a company reorganization. Out of work but stuck with plenty of bills, I fell back on the law firm I created several years before to do good works for friends, family and causes I believed in. 

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As an accidental entrepreneur, I've been on a new course of self-discovery aided by my leadership lessons of the past.

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Not only have I enjoyed re-connecting with former clients thrilled I could suddenly represent them again, but I've found a whole new set of clients to help. Throw that into the freedom I enjoy as the "boss" - and the responsibility that comes with it - and I have learned a whole new set of lessons.

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During the 2020 election I served as the Lead Legal Counsel for The Lincoln Project, the leading advocacy organization for conservatives, Republicans and former Republicans working to defeat President Trump and Trumpism. I filed multiple amicus briefs across the country for The Lincoln Project and continue to advise on a range of ongoing matters.

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At the beginning of 2021, I took a position as General Counsel for COVIDCheck Colorado to help combat the COVID-19 pandemic. As a philanthropic organization that grew rapidly in response to the greatest shared threat in a century, I knew my background in law and healthcare would be a useful compliment to the dedicated, talented staff already working to provide relief to Coloradans. 

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While the leadership images I referenced above do not include "Explorer" as an option, I felt this best expresses my current leadership journey. I have been thrust into a position to explore my own strengths (and weaknesses), explore new opportunities, explore different models for success. It requires a sense of adventure and vision, if not a specific plan. 

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Iteration #9 - Guest Teacher  (All the Above)

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Through the coronavirus pandemic, my middle school literacy specialist spouse kept telling me about the struggles faced by educators and the overwhelming feeling of burnout. After we were vaccinated, she urged me to apply to guest (i.e. substitute) teach in order to help our schools. I did and I loved it. I taught middle and high school students, primarily in English and Social Studies. Walking into differing classrooms really helped me to understand how much impact educators have every day. 

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I plan to continue teaching as long as my schedule remains flexible enough to do so!

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Iteration # Next

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Who knows? But I'm sure it will be fun ...

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