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My Leadership Journey (A Work in Progress)

Next week, I will present my leadership journey to a gathering of assembled peers. We are to focus on three takeaways that we have learned from the various leaders in our lives over the course of our leadership journeys. I have a long list of exceptional leaders in my life, so I thought it valuable to put the full list somewhere as I prepare what I will share there.

Below is a timeline view of sorts that represents my leadership journey. Notes:

  • The timeline itself is fuzzy, including "dates" like Childhood, College, etc. I did my best to group situations that occur within the same timeline, though there is overlap.
  • The Event/Idea column represents shorthand for a lesson or experience I believe to be integral to my leadership journey.
  • The +/Δ column is a part of the exercise; not everything can make a positive impact, but those times can still be impactful.
  • The VIP column is a list of who taught me a given lesson; I used "myself" for situations where I reference an experience that did not specifically include someone else.
  • The experiences and takeaways referenced in the narrative are noted in the table as asterisks; this is the most important part of the exercise.
  • Unlike most of my blog posts, this is all a work in progress. This post will change frequently until the end of the week.
Date Event/Idea +/Δ VIP
Childhood Access through Education + My Parents
Childhood The Importance of Communication + My Mom
Childhood Standing for Social Justice + My Dad
Childhood The Strong One, Advocating for Others + My Sister
Childhood Faith, Community, and, Church + My Parents
Childhood Perseverance Through Loss + My Grandmother
High School Academic Center Admittance + Myself
High School Future Problem Solvers + My Teacher
High School The Hard Geometry Class Δ My Teacher
High School Leading in the Theatre + My Teacher
Undergrad Perseverance to Complete a Degree Δ My Parents *
Undergrad Shifting focus to technology + My Mentor *
Grad School The Road to Never Use that Degree Δ Myself
Indianapolis New City, New Opportunities + My Mentor
Indianapolis New Baby, New Pink Slip Δ My Employer *
Indianapolis Being a Stay-at-Home Dad + My Daughter *
Madison Moving to Madison Δ My Family *
Madison My Dream Job at UW-Madison + My Boss *
Madison Advocating for Yourself + Myself *


I come from a family of educators, social advocates, and activists. My mom has spent her life in education at the Chicago Public Schools, my dad is a pastor at a neighborhood church in Chicago, and my sister has spent her life fighting for social change through leadership, advocacy, and financial coaching. This is the tenor of the home in which I grew up and my personality was formed.

At each step of the way in my life, my family has been ever-present, supportive, and defining. My childhood lessons were defined by the importance of communication, humor, grace, and faith, juxtaposed with the needs of a broken world: advocacy, social justice, access, and acceptance. These ideologies have only grown at each stage of my life, but all of them have been strengthened by strong female leaders and the lessons I have learned through both routine and challenging experiences.

Note that I have decided to focus my takeaways mostly on what I would consider low points or deltas in my journey where hindsight has shown they were some of the most impactful lessons in my journey.

Perseverance through difficulty

Although plenty occurred beforehand, I will start my focus in my college years at Valparaiso University, where I can only describe the Spring semester of Sophomore year in the Engineering program as a weed out timeframe. Some of the most difficult content, coupled with a full schedule, a technology help desk job, and a new relationship with my future wife, meant that I was ready to leave the program and become a statistic. I had learned the value of perseverance before, sticking with instruments, activities, and sports I had lost interest in as a child, but I had never felt this level of stress before in my life.

In a conversation about my concerns and prospects, my mother was yet again the leader who helped me to push through a difficult situation. Although she remembers the conversation specifics better than I do, I apparently talked about shifting majors to something I had never before shown a remote interest in like business or psychology, the ones that seemingly always got Fridays off of classes. She asked just the right questions at just the right times to get me to realize I could still do this. Fast forward three years and I graduated with a degree that had taught me not Engineering concepts but how to learn anything. But it was also a degree I would never directly use because I had found my passion in technology support.

Takeaway: When the going gets tough, a leader asks the right questions to help others keep going.

Shifting gears, from Engineering to Technology Support

I shifted to technology support through my job line up in my undergraduate career and opportunities that presented themselves after graduation. I started working for Apple during the summer after my first year of college because of my love for the brand and I started working at the technology service desk at Valparaiso University's main library during my second year because the work sounded interesting and I needed a job. I grew in both those roles throughout my undergraduate years, but never thought they would amount to a complete change in my career path. But my three supervisors over the course of that growth all instilled in me a sense of purpose, a desire to help others that I found was sorely lacking in my studies up to that point.

That shift in career path can be summed up by a single interaction with one of my supervisors. It was during an interview for a promotion to become a student manager and I remember it vividly even now. I, wearing traditional college student grab, gave a good interview and at the end received feedback about the interview "off the record," which was a common approach for learning within this unit. The feedback I internalized that day was this: "The pool for this position is competitive and your peers have all walked into this office in suits. You are wearing flip flops. Jay, we know you can do this job and do it well, but you also need to present yourself as being prepared for the next level." I was embarrassed and I had to take the time to ask the difficult question: how much do I care about this position and a future in this field? I realized that I did care and I thanked God the day that I received the promotion, but I used the situation as an opportunity to grow, assess my priorities, and move forward.

In the end, I started a graduate degree in technology and an unexpected move to Indianapolis to pursue work with a non-profit technology firm, focused on helping government agencies and higher education institutions push the boundaries of what technology could do for them in the early days of support outsourcing, colocation, ubiquitous high speed Internet, and web streaming. I was hooked.

Takeaway: Leaders accept growth in any form; the growth you expect is not always the growth you get.

Storm clouds and their silver lining

Next up, I have another young woman leader in my life: my daughter. She is eight years old, going on twenty, but I bring her up because her birth marked another low point in my leadership journey. I had been working with the Art Institute of Indianapolis for almost three years; I was starting my paperwork for paternity leave; and I had just finished my graduate degree in Information Systems and Technology with a focus on Information Architecture and Design. All was well in my life, until it wasn't. The day my wife was due to give birth to my daughter, I was laid off of my job, along with 20% of my employer's staff across the country. My daughter was born one week later and I had two job offers from employers unwilling to wait until after my paternity leave for my start date.

In that moment, I had a very important decision to make: take the job and the job security or take the time I needed with my first born child. Long story short, I became a stay-at-home dad that day. I took the time and was able to greet my daughter into this work with open arms, knowing I had made the right decision. I was able to do some consulting work in the technology space on the side. Four months later, I found a posting for my dream job in my wife's home state of Wisconsin at a higher education institution. I have never looked back.

Takeaway: When life gives you lemons, leaders find happiness in being a stay-at-home dad (or a new context).

New Beginnings Provide Opportunities for Advocacy

And finally, I have my move to Madison, WI, the start of the current leg of my leadership journey, and definitely not the end. I mentioned that four months into my daughter's life, I found my dream job. What I didn't mention was the fact that because money was so tight, I took that job before my young family could come with me. My wife and daughter stayed behind in Indianapolis while I struck out on my own to start building our new lives. I stayed with my wife's family near Madison, looked at new houses, dealt with the early days of video calling, and spent five hours in the car each way every weekend for the majority of three months.

We have now been in Madison for eight years. We were able to make it through those early days with the knowledge that Madison would be a great fit for us, worth the wait and worth the initial heartache, but one of the biggest takeaways from this time comes instead from my current supervisor, who helped me to understand that leaders advocate for themselves and others when needed. I have found my passion in advocacy through engagement within the libraries and across campus in diversity, equity, and inclusion efforts, strategic planning, and leadership. Below are a handful of times in my eight years that required advocacy:

  • Trips to and from Indianapolis in my early tenure to still be with my family consistently.
  • Understanding personal and team capacities and asking for assistance through staffing and delegation.
  • Defining new roles within the structure of technology support within the libraries.
  • Strategic planning—both within diversity, equity, and inclusion and the general libraries—and facilities master plan efforts.
  • Defining new titles within a campus-wide retitling process.

Takeaway: When others are not given voices or go otherwise unheard, a leader conscientiously and proactively advocates for change.