I've worked in IT for about eight years, starting in help desk and desktop support before moving into infrastructure systems administration and engineering, with VMware as my main specialty. I've spent my entire career in cleared environments and currently hold a TS clearance.
My certifications include CompTIA IT Fundamentals, A+, Security+, VMware VCTA-DCV, and VMware VCP-DCV. I'm currently a senior systems administrator in the Washington, DC–Maryland–Virginia area, essentially acting as the generalist who handles a bit of everything. The job pays well, but I'm unhappy with several aspects of it. I also have to work onsite every day because of the classified environment, and the commute is becoming a major issue.
I've had difficulty finding another position with comparable pay, especially one offering remote or hybrid flexibility. The market also seems more competitive and there appear to be fewer roles focused on the type of infrastructure work I currently do.
I'm considering two possible directions: pursuing more advanced VMware certifications and moving toward architecture or consulting, or pivoting into cloud engineering by building on my on-premises background. For the cloud route, I'm considering learning AWS or Azure, earning relevant certifications, studying containers and Kubernetes, and creating hands-on projects to demonstrate my skills.
I'm not interested in moving into management. Given my experience, clearance, location, and desire for better flexibility, which path would you recommend? Are there other career directions I should consider?
3 Answers
You may not need to change specialties yet. A move to a different company could solve more of the problem than another major career pivot. Your TS clearance is valuable in the cleared market, so protect it if possible—contractors generally do not want to sponsor a new clearance when they can hire someone who already has one.
The remote-work requirement will be difficult for classified work, since employers cannot let sensitive information be handled through an uncontrolled home network. Hybrid roles may exist for the unclassified portion of the job, but fully remote cleared infrastructure positions are much less common. If changing employers does not help, reducing the commute by finding a closer office may be the most realistic compromise.
That’s probably my biggest obstacle. There aren’t many suitable positions near me, and moving closer would be difficult because I already own a home.
Choose the type of work that actually keeps you interested, then specialize in that rather than collecting certifications without a clear goal. If automation is the part you enjoy, focus on scripting, infrastructure as code, configuration management, and platform automation. If cloud architecture or reliability work is more appealing, build toward that instead.
Your existing on-premises experience would transfer well to cloud engineering, but employers will want evidence that you can work with real cloud services, not just certificates. A practical path could be learning one platform deeply, building a few projects, and adding automation and container skills along the way. Enjoying the work matters because it is much easier to keep developing when the subject does not drain you.
Both options are reasonable, but I would avoid treating VMware and cloud as mutually exclusive. The strongest next step may be a hybrid infrastructure or platform-engineering role: virtualization, cloud migration, automation, and container platforms. That lets you use your current experience while gradually moving away from work that requires constant onsite access.
Start by reviewing job postings you would realistically accept, identify the recurring requirements, and then build toward those. In many cases, demonstrable experience with Azure or AWS, Terraform, PowerShell or Python, CI/CD, and Kubernetes will help more than stacking another narrowly focused certification.
Even organizations outside the government space are becoming more cautious about fully remote work. Occasional flexibility is still possible, but insisting on completely remote work will narrow the options considerably.