My Story

I’ve told pieces of my story in recent posts. You know, the ones about Homebrewing being a salvation, and moving to a role in Customer Success at DigitalOcean. I don’t think I’ve ever posted about the long, circuitous route that my career has taken. Perhaps it’s time to tell you the story. So sit back and grab a cup of joe…this ride is known to cause whiplash. Trust me, the trail from aspiring academic to customer success engineer is not exactly the smoothest.

The Younger (Wonder) Years

My single-prop Cessna carrying supplies to a remote African village hit a patch of turbulence, sending my stomach lurching…or at least that was the dream I had when I was a kid. All I wanted to do was be a pilot. I was going to go to school like all good kids do, graduate, and be a bush pilot. Things changed when I realized that the school I wanted to attend was planning on closing.

In the mean time, I had taken a trip where we traced the 101st Airborne’s route through Europe during World War II. It was the trip that forever kicked off a desire to learn foreign languages (specifically German). I returned from the trip in the Summer of 2002, met with my guidance counselor, and had her completely rearrange my sophomore class schedule just so that I could learn German (I had also been taking Spanish up to that point). Over the next three years, I did everything I could possible do to learn German. As a sophomore in high school, I’d aced the county German exam (and found 3 grammatical mistakes), taken the national German exam (scored a 96), and was invited to participate in the American Association of German Teachers Summer Study Program. Not to mention, I was the first person from TN in 12 years to be selected for that program.

Until this point, I had thought that I was going to spend the rest of my life and career in Germany, with a German wife, happily speaking German. All roads led to Rome…er, Berlin, in this case.

College (Or, The Real World Sets In)

I graduated in 2005 having kicked the proverbial pants off of my high school’s German program. Along with two friends, we’d forced the school to start providing German AP classes, had all scored high marks on the German AP exam, and were going to continue our German studies in college. In fact, I’d waived up to senior level courses, completed the required classes, done another exchange stent in Leipzig during the 2006 Weltmeisterschaft (World Cup), and was merrily on my way to being a career academic. All the while, I’d somehow acquired a bit of technical acumen (designed a website for a local non-profit, fixed computers for friends, etc.)

Here’s where the path gets a bit wonky. While I’d completed the German degree requirements, I was at a four-year institution that required me to complete the whole four-year stent in order to earn my degree. I was two years in, and had no idea what I was going to do. Me being the chatty dude that I am, I picked up another degree in Speech Communication. What better combination? I could ramble in German, and put a bit of communication theory behind it. “How to Be Persuasive in German” should have been my senior project…

Oh, did I mention I met an amazing woman along the way? We knew each other since high school, but started dating in college. Our relationship had blossomed to the point that the thought of pursuing further German studies was going to take me far away from her. We’d spent 2006-2009 dating long distance, and I wasn’t keen to be further away from her (we also began our relationship by starting to date each other two weeks before the three-month exchange trip I took to Leipzig). I decided then that I would pursue further studies in Communication, and enrolled in the MS of Communication and Information program at the University of Tennessee.

Communication is Cheap…Literally

After Ashley and I graduated, we both ended up back in Tennessee. I had started my Master’s program, and she was studying to be a forensic pathologist. While searching for a job on campus that didn’t involve spending my days at the local Chick-fil-A breading chicken, I started applying for assistantships. My department’s assistantship paid ~$300/month (which was NOT going to cover rent), so I looked to other departments. After 13 rejections, I landed a job at the Office of Information Technology at the helpdesk.

Over the next two years, I worked on just about everything related to desktop support and have the horror stories to prove it. Professor-dad screaming about how his non-student daughter’s desktop got infected by malware and we’re not helping him? Check. Crazy cat lady’s ancient, dust-bunny infested desktop that has barely enough resources to run notepad? Check. The student who has a completely disarticulated hard drive and wants us to ‘fix it?’ Oh yeah, check.

Graduation was looming, as was my marriage to Ashley. I decided that a $1000/month job wasn’t really going to cut it for a young family (and neither was surviving on the rest of my student loans), so I met with my then manager, beefed up a resume with her help, and eventually ended up with a contract job at Pilot/Flying J where I re-architected their desktop deployment process as contractor in their QA lab. It’s safe to say that the deployment process was…archaic. In the first two months of my contract, I was able to reduce the number of ‘golden images’ from ~30 to two, decrease the average deployment time from two weeks to four hours, and decrease the total space taken up by the images from ~100gb to < 16gb. At the end of the contract, I moved next door to a small MSP–I wasn’t going to be able to get them to use WSUS (which would have brought its own challenges) and was still going to be a contractor with no benefits.

Starting Support, Leaving the Southeast

The move to the MSP I worked at was my introduction to a proper ticket queue (often hundreds of tickets). I started beefing up my support chops there, where I supported everything from random line-of-business applications for doctors, to Outlook, Exchange, MSSQL, and everything in between. You read correctly–I was a Winows admin at one time (shudders). But honestly, without that job (or really any of my technical positions), I wouldn’t be where I am. It was there that I also beefed up my technical chops. I took the little that I knew from my job at the University of Tennessee’s helpdesk, and the bit that I knew about Windows and applied that in this job.

Eventually, I realized that if I wanted to grow technically, it wasn’t going to be as a Windows admin in the Southeast US. I’d come to find out that if you’re not in Atlanta, Georgia, and not in/around the research triangle in North Carolina, finding a technical job that pays well and wasn’t one of those ‘purple squirrel’ type positions was nigh impossible. If I was going to get anywhere, I needed a mentor. Thankfully, one of my best friends took me under his wing. For around 6 months, we met every Tuesday night at a local coffee shop talking Linux, operations, and everything in between. He even gave me a project that was designed to incrementally teach me more about the basics of being a Linux admin.

At around the six-month mark of our coffee shop meetings, I started applying to companies outside of Tennessee. Usenix, AWS, NIST, and Rackspace were the companies on my list, and amazingly, I got interviews with each one. The mentorship had paid off, even if I was a bit green and hadn’t worked on any Linux production infrastructure up to this point. In the end, I ended up getting turned down from AWS, NIST moved too slow, Usenix didn’t have a competitive offer, and while I had been turned down from Rackspace initially, they offered a position (Linux Technician) that would allow me to learn, work on customer production infrastructure, and provide the space for me to grow and learn more about being a Linux admin.

Texas and Beyond

Loaded Uhaul The move from Tennessee to Texas was the hardest thing I’ve done in my adult life. My wife and I moved 16 hours from all we’d ever known, to a town where we knew two people (my aunt and uncle, who have been our surrogate parents in the time we’ve been in San Antonio). The drive was hard, and the first 6 months of being in Texas almost broke us. We missed the mountains, the people, and our homes. Ultimately, we found a home at Rackspace. Some of our dearest friends were made there as we met for the first time at the Tamale Festival in sub 40F weather (unusual for San Antonio).

The time I spent at Rackspace grew me immensely. I went from knowing only what I had learned in the project my mentor had provided me, to working on projects that affected a number of customers, writing automation to take some of the pain out of support as well as reduce the number of hours we spent supporting customers, and mentoring other greenhorn admins.

While Rackspace was an amazing opportunity, I realized that the need I have to keep growing and learning wasn’t getting satisfied, and I was getting burnt out staying in the same place. I then started looking for a new role. I needed something that would allow a bit more creativity, as well as further growth. In March, I took a role with DigitalOcean, which you can read more about here. It’s been an amazing chance to grow technically, and touch more cutting edge technology than I would have at Rackspace.

Looking back, I can say that each new role and phase of my career led to the other. The path to support (yes, Customer Success is support, at least at DigitalOcean) hasn’t been a straight one at all. It’s been a bit caddywhompus at times, and has entailed making decisions that I never thought I’d have to make (like moving). But I can see that the roles built upon each other, whether it be developing new technical skills, or improving the ways in which I communicate and relate to customers. I also see the direct and tangible results that being in a mentoring relationship has had on my career. I’ll leave with a couple of thoughts: 1.) Unless you know 100% for a fact that support is the career you want to have, starting a career in support is never a straight path. Those of us in the Support Driven community know this, and come from various and sundry backgrounds that have led to where we are. 2.) If you’re starting out in a support role, I can’t stress enough how important it is to be in a mentoring relationship. It’s the difference in say, using two sticks to start a fire, and pouring some jet fuel on that fire. It made all the difference for me, and is something I actively try to pass on as I mentor other admins.