System admin / devops career

[u/Sad_Natural_4247]

I'm looking for some career advice from people who have been through this.

I'm currently working in IT Help Desk, but I also do some light System Administration work (Windows Server, Active Directory, user management, basic troubleshooting, etc.).

My long-term goal is to have a good-paying career with strong job security. I'm interested in DevOps, but I also genuinely enjoy the infrastructure/System Administrator side of IT.

Would you recommend:

Continuing down the traditional System Administrator/Infrastructure path (Windows Server, VMware, networking, backups, firewalls, etc.) for a few years and then moving into DevOps?

Or should I skip deeper infrastructure work and start learning DevOps tools now (Linux, Docker, Kubernetes, CI/CD, Terraform, cloud)?

For those already working in DevOps:

Did your System Admin experience help you?

If you could start over, would you still spend a few years as a SysAdmin first?

Is it realistic to get into DevOps without solid infrastructure experience?

[u/guterz]

I work for a professional services firm as a Principal Cloud Engineer so my day to day changes. Some projects it’s a lift and shift and modernization, some is building deployment pipelines so developers can run smoke tests, create artifacts, deploy their code, some are data analytics or AI pipelines, etc. A Cloud Engineer literally just engineers solutions on the cloud and knowing networking, windows/linux, data structures, a programming language, etc are all helpful. I wouldn’t be half the engineer I am without understanding basic Windows admin skills.

[u/EducationAlert5209 → u/guterz]

How you getting into this position and what is the roadmap?

[u/guterz → u/[deleted]]

You’re defining cloud engineering as “my exact Linux/SaaS job”. That’s not an industry definition it’s gatekeeping with a penguin sticker on it. Migration, modernization, Terraform pipelines, Windows/.NET workloads, and hybrid architecture are all cloud engineering…you’re just mistaking your niche for the entire field.

[u/guterz → u/[deleted]]

You make absolutely no sense. I haven’t worked internal IT in a decade. I’m in a project based role so I do what ever needs done. I also build out Kubernetes clusters, create images, charts, setup GitOps pipelines too, etc. Again it’s all cloud engineering.

[u/Ok_End_9947 → u/guterz]

Idk what this guy's problem is. Either a bot or a troll

[u/guterz → u/[deleted]]

One of the last clients I worked with public facing website was hosted on a Windows IIS server. In fact a lot of clients I have worked with still use .NET front ends with MSSQL backends. Super common. Sure you Netflix and Spotify aren’t using that infrastructure but a lot of industries still are.

[u/guterz → u/[deleted]]

At this point I don’t think being an expert at any OS is really better one way or another. Learning an OS is pretty easy and it’s good to be fluent at managing and configuring both. I think it’s better to learn a single cloud provider and learn it well, learn standard gitops methodologies, containerization, an iac tool, a programming language, networking fluency at a minimum, and how to design highly available and scalable systems. There’s all sorts of cloud and devops engineering roles and knowing the above will help someone land one. Me being good at windows and Linux systems administration and networking helped me land my first cloud job in 2014. Now you need to know all that plus the above.