Eighteen years ago this August my first child was born. Just this month she graduated from The Bryn Mawr School in Baltimore, MD. This fall she is set to attend Wofford College in South Carolina to study medicine and play for their women's lacrosse team. As I write this she is wandering around the house looking for her wallet so she can go off and do whatever it is soon-to-be-adults do on their last true summer vacation. Unfortunately I have not seen her wallet so I cannot help her find it, and so I will continue writing this post.
It is an odd thing to have pride in someone else. Pride is something typically one feels for their own accomplishments but as a parent it comes as a mix of "I made that" and admiration for the person they are. It's still pride, I guess?
What makes me exceptionally proud of my first-born in this case is that not only has she graduated from a prestigious and academically challenging school, but she has graduated at all. I am proud of this because I myself did not graduate from high school.
I should have graduated with my peers from Stephen Decatur High School in Berlin, Maryland in 2001. Unfortunately I had a bit of an attendance problem in my junior and senior years which meant I was due to enter thirteenth grade in September of 2001. I never went back.
Remember that song Money for Nothing? Well I was in a band with two brothers whose uncle was in Dire Straits. I took the message "I should've learned to play them drums" very seriously so I played drums. I was a natural. It's still what I would consider my strongest skill. Our band was good. Really good. It seemed inevitable that I would become a rock star one day, so what use was high school?
After formally dropping out of school I obtained a GED but the music career was still my ambition. This ambition faltered when facing the reality of life independent of parental support. Never one to sit around and depend on others I made my own way in the world as soon as I turned eighteen and was no longer in school. Having to work two or three jobs at a time to make ends meet while also balancing band practice with scattered band mates meant little if any time to truly pursue my "inevitable" career in music. That's not to say there weren't successes.
In the summer of 2005 I had worked my way into an internship at a radio station in Towson, MD. Around that time, the legendary WHFS (HFS) rock station—a DC/Baltimore alternative rock staple since 1983—went off the air. Fan demand and Baltimore's desire to host the famous HFStival brought HFS back on 105.7, broadcasting from the very station where I was interning. Meanwhile, my band had just secured an opening slot for the national act Sailva at the Recher Theater, also in Towson. Everything was lining up perfectly—I had direct access to industry connections while my band was positioned to prove ourselves on a real stage.
Unfortunately things did not go as planned. While we played a good show, events unrelated to me led to the demise of the band that same night. It was clear the band was done and as a lone drummer I saw no path forward. Just two weeks later I was bumping elbows with The Foo Fighters (among others) in the press box at M&T Bank Stadium as I escorted VIPs around at the HFStival, but I lacked any foresight or confidence to pursue my career aspirations despite the ample opportunities to do so. I did my job that night and went home.
That fall I decided to move to Florida and reconnect with my father and find my own path post-band. Shortly after the move an old friend of mine from Maryland came to visit. That friendship turned spicy on that trip and that friend eventually became my wife. Courtney and I fell in love on that visit and within a few months she moved down to Florida so we could start a life together. After about a year we learned our family was going to unexpectedly expand....Caroline was on her way.
This was truly unexpected but welcome news! At the time I was working as a tech support agent at a QVC call center in Port St. Lucie, Florida, however the position was temporary. As the months passed work became harder to find.
Just after we learned of Caroline's pending arrival I started an Associates program at a certain online university (whose mascot is a burning bird). You see I know tech. I always have known tech. It's intuitive to me. And with a kid on the way and the world changing the way it was I knew I had to get into tech in some way and the only way in was to get an internship. A foot in a door. Being a student would provide that opportunity in that field.
I started school to learn to do things I already knew how to do so I could get a job doing those things. Those jobs were not readily available in Florida at that time...no job really was...it was 2007 and the next year the whole Floridian economy would spiral out resulting in the 2008 financial crisis.
Side note: I actually wrote an English paper forecasting the disaster based on what I was seeing all around me (and that the pattern forming was a repeat of crashes in the 1920's, but would be felt differently due to remediation of disintermediation). I got a B on the paper.
Anyway, the only job I could secure was waiting tables at a Carrabba's in Stuart, Florida. It was a good job for a kid in their twenties, but not nearly good enough for someone who needed to support their family. Plus I wasn't very good at it. By December of that year we were being evicted from our apartment with a newborn.
As a Hail Mary I spent the last money we had to attend a Dice.com job fair in DC. Unfortunately a snow storm delayed my flight and I arrived at the job fair as it was closing. There was exactly one table still setup and it was The Iowa Foundation for Medical Care. There was one man alone at the table and so I went right up to him with full confidence and my resume and we had a great conversation.
He asked if I knew CMS--which I took him to mean Content Management System like Drupal or Joomla!--and I said, "Absolutely, I know all about CMS!" He offered me a paid internship position working on a Centers for Medicare/Medicaid Services project based on my enthusiastic CMS experience...
Despite the misunderstanding we moved back to Maryland as a family and I went into the new job with grit, determination, and an undeniable talent for tech. Within a few short months the company offered me a full time position as a PL/SQL developer working on the Measures Engine program at CMS and my career in tech was off and running.
From there I've seen a lot in my tech career. After IFMC I went to work for a small cyber security firm called Ciphent and came up with a system remarkably similar to tokenization just before the firm was acquired by a larger firm Accuvant.
From there I worked for a small insurance company in Timonium, Maryland that served the entertainment industry. I was brought on board to implement and maintain a SAAS product the company had licensed, but I quickly urged them to reconsider and let me lead an effort to develop a custom solution. The company ownership and leadership agreed to my suggestion which allowed me to further expand my work with semantic pairings in Bayesian calculations and algorithms.
Despite the company's unconventional operations and eventual regulatory troubles, this period taught me valuable lessons about leadership and showed me I had skills that went beyond typical software development. I found myself working internationally, including traveling to West Africa for cyber security consulting after a political transition there--that sounds unrelated and out of left field, and it was, but it wasn't...I'll write up a full post about that another day. The experience demonstrated that I could adapt and perform effectively in challenging, unfamiliar environments - a capability that would prove valuable throughout my career. When the company was eventually seized by state regulators due to financial irregularities, I once again faced the prospect of starting over.
Following the sudden collapse of the insurance company I found myself again facing a perilous moment. It is hard to start from the bottom and secure the type of financial stability needed to support a family. My seemingly secure job had been lost right as we were building our family's first home. Once again we faced the prospect of homelessness, though this time there were two children in the family. Neither were newborns, but both needed not just a roof over their heads but in my eyes deserved any and all opportunities in this life I could give them.
After two years of scattered work that took me around the globe, on the receiving end of not one but TWO FBI Raids (the insurance company was raided, not me personally), laid off after a merger, and frazzled from all of the drama, I landed a more stable position as a federal contractor working on EnergyStar projects for the EPA. We were able to move into our new home with only a minor delay.
Of course nothing is as stable as it seems in this world. My time at EnergyStar started with the company SRA which merged with CSGov and became CSRA. Shortly after that CSRA was acquired by GDIT...In less than ten years working in tech I was involved in four mergers, half of which resulted in the eventual termination of the development teams.
But this journey began out of a need to provide for my new family. As my career grew so did our family adding Caroline's younger sister Luciana in 2010. By the time Caroline was seven years old she knew she wanted to be a neurosurgeon one day, and by the time she was ten she showed her talent at the goalie position on the lacrosse field. When she was offered a place at The Bryn Mawr School entering her sixth grade year it was clear she needed to accept. Not only was it a chance to attend a prestigious and historic institution but the school promised to challenge her and truly push her towards her goal of helping others in medicine one day. This opportunity comes at a cost, of course, and so once again Caroline inspired--no demanded--I push myself further.
My time working on EnergyStar was one of my most cherished periods in my career. I loved my team, the work, and the stability (despite all of the mergers). Unfortunately GDIT was fairly rigid on pay scales, and with a new tuition expense on the horizon I needed to move on to support my family. It didn't take long for me to find a new opportunity with a much needed pay bump, and that opportunity brought me back to where it all began: The Center for Medicare/Medicaid Services.
This time I knew what CMS meant and my role was not limited to database management and development. My return to CMS marked the beginning of modernization efforts within the agency and I was privileged to join one of the most knowledgeable development teams I've ever been a part of. Together we successfully modernized a major CMS system for the first time, and that was just the beginning! Ever since our initial success on the MPSM project there have been a number of successful system modernization efforts under the MPSM initiative from a range of teams. I left MPSM after our initial success, but have been a critical if not crucial component in many other efforts at CMS since then, including pioneering AI use at CMS under the SEAS-IT project.
My work with CMS was never just about a pay raise. Caroline showed me what it meant to pursue an ambitious goal that helps others over a lifetime. She's never wavered from her desire to pursue medicine from the time she was seven years old. She put in the work in the classroom to match that ambition and as I joined the MPSM project I saw my opportunity to use what talents and knowledge I had to help others. In addition to my work at CMS I began volunteering with Code for Baltimore.
For me working on civic tech projects like MPSM and others was not just about a job: it is the best I can do to make critical functions of our country better for everyone. If universal healthcare is ever going to be realized in this country then CMS and its information systems need to be ready, and that's something I can help with.
Drawing inspiration from my beautiful and gifted children I have done my very best over the years to be a positive force of change to the benefit of my country while also providing for my family what they need to be successful in their pursuits. The job's not done, but we've passed some major milestones.
And so now Caroline will move on and need less direct support from me as she follows her path. Her sister Luciana is not far behind her. With my first child graduating and moving away for college there is a lot of emotion to process as a parent. That "bittersweet" feeling. That pride and sadness. I'm not ashamed to say I've shed more than a few tears.
Just as Caroline is moving on I myself am moving on. While always willing to help where I can my time with CMS has come to an end for now. It's time for me to apply my experience and effort towards a wider goal: to bring a level of tutelage and attention to learning previously only available to the richest of us to all of us. I'm building to that aim with my partners at ConversaDocs.
When arriving at an end (of sorts) to such a journey that defined your life's path I think it's good to reflect on that journey. To go back and look at the pictures, the videos, the code, and take stock. To that end I've begun an effort to capture my lessons learned in case studies so that I can share what I have learned with others, but also revisit those lessons myself. I hope you have enjoyed my post and that you keep an eye out for future case studies.
It's been a wild ride so far, there's lots to cover, and the journey ain't over yet...