I’ve kept blog posts here primarily technology related, offering how-to or problem-solving topics. However, I thought it would be time to review my IT career over the past dozen years and try to offer advice or perspective on what has led me to where I am now and what I learned along the way. By sharing this, I hope that it might help someone just starting out or considering what to do next.

From Music to Computers

I was originally a music performance major out of high school. Three semesters later, I realized that, while I was a decent musician, there was very little chance I would make a living doing this. I looked around at my peers who were in their early 30s (or in one case 50s) working on a doctoral degree that would lead them to a teaching position. I realized that I did not want to be in school that long only to end up teaching. To those that are going this route, no disrespect to your decision, but I just realized it wasn’t the path for me.

I “transferred” to a community college and starting taking computer classes. I wanted to work on building, troubleshooting, and repairing computers. Growing up, my dad worked at Seagate, so I had a computer from an early age (this was in the early 90s, computers in homes were not that common, Internet access was through dial-up). While I didn’t program or doing anything beyond being a user, I did grow up using the command prompt a little, dialing into bulletin board systems (BBS) to play games and order books from the library. I still remember my dad telling me to type “win” at the DOS prompt to load Windows 95 (hotdog theme anyone?). But I didn’t know how they worked or what was inside the box and I wanted to learn.

I started on some classes to prep for the CompTIA A+ Certification as well taking management information system and programming courses. This is where I discovered I really loved programming, but I didn’t see that as my future in IT (looking back, I wish I had pursued programming). I felt my future was in systems administration in some capacity as I wanted to be hands-on. I finished my associates degree and managed to land a job before graduation.

Entering the IT Profession

For my first “grown-up” job, I started out doing phone support for Dell assisting home users with parts replacement and operating system reinstalls. While I quickly found out that I had no desire to do frontline support like this (especially over the phone), I had to develop the ability to troubleshoot issues quickly while maintaining a conversation with the person on the phone. I also learned my distaste for performance metrics, like resolution rate, average call time, repeat dispatch rate, among others. While I understand the importance of needing to measure job performance, I’m a firm believer in looking at someone’s whole performance that metrics can’t measure. In preparation for advancing my career, I completed my A+ and Network+ certifications.

Deciding that just talking people through issues wasn’t going to cut it (and not actually touching a computer), I starting applying for helpdesk positions. My thought process was that this was my entry into corporate IT to work my way to a sys admin. I applied and interviewed at a particular place, and while I didn’t get the helpdesk job, the company actually offered me a junior sys admin type role instead. Success! I bypassed the entry-level position to get the job I really wanted. I knew nothing about Active Directory, Exchange, SCCM, scripting, workstation imaging, servers, or printers (which are the devil by the way) but I got to learn on the job. The almost five years I spent in this role laid the foundation for the rest of my career as I learned the basics of enterprise IT.

Next I moved to a company where I was also a general sys admin. While the company was smaller, it was extremely well organized and had procedures and processes to follow. I learned about creating documentation for systems, virtualization, and getting free meals from vendor lunch-and-learns. During this time I completed the MCSA for Windows Server 2008 and 2012 as well as VMware’s VCP in Data Center Virtualization.

Gaining New Skills

It was at this point in my career that I decide in order to maximize my value (translation: compensation) I should specialize in something. I had been a generalist and my knowledge was “a mile wide but an inch deep”. I felt that gaining expertise in 1-2 technologies would lead to a consultant or architect type role. I got a job at a large company supporting Exchange and Lync. I knew very little about these technologies, so I lucked out again and got to learn on the job.

I spent the next 3 years immersing myself into these technologies and learning how to work with other groups in IT who had their own specializations. Coming from smaller environments, I was used to having full control to do whatever I wanted. Not the case anymore. Now there was change control and project planning. And meetings. I had never used my Outlook calendar this much before.

Exchange and Lync being the technologies they are, it was expected to learn and master PowerShell. Along with using PowerShell on a regular basis came script writing. I already had basic programming knowledge from school as well as previous VBScript scripting experience, so picking up PowerShell was natural. I also had some great mentors who took the time to teach me scripting norms and the right way to do things (remember, Write-Host kills puppies). During this time I completed the MCSE for Communications and Messaging as well as MCSA for Office 365. I also started this blog, publishing my first post in May 2014 and completed my bachelors degree at WGU.

Moving Even Higher

Finally, I had a specialization, now onto the next step of maximization (translation: compensation). I was contacted by a recruiter for a Skype for Business consulting position. I didn’t get it the job the first time, but I kept in touch with the company. When another position came open several months later, I followed up with the recruiter. This time it worked out, and I got the job. I had achieved my goal set four years earlier: maximize what I was worth by gaining specific skills and landing a consulting position.

Another goal for consulting was the opportunity to be exposed to multiple environments. I felt that the best way to gain expertise was to be exposed to different environments and scenarios. I viewed being in one environment would make you an expert in one thing: that environment. Gaining this additional experience and expertise eventually led to my current position as a field engineer with Microsoft. I specialize in Skype for Business and Microsoft Teams and assist customers with maximizing their environments to fulfill their business needs. I think it’s pretty cool to be working for the company that created the product that I specialize in.

What’s Next?

As I started writing this, I intended to say everything I wanted to say in one post. Writing this out, I realize this is going to be a multi-post affair as I have a lot more to say! Check back in a few days as I release more articles on what I learned through my career and advice to any one new to the landscape. This post will be updated will links to the rest of the articles in the series.

So You Want to Work in IT? My Career Journey – Part 2

So You Want to Work in IT? My Career Journey – Part 3

So You Want to Work in IT? My Career Journey – Part 4