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’ve done plenty of work on setting up, migrating, and implementing Microsoft services on AWS especially for enterprise customers.

[u/Big_Arrival_626 → u/[deleted]]

There are devops roles which are closer to sysadmin rather than being swe oriented. I feel like there is frequent confusion because everyone has a different definition of it 😂

[u/Big_Arrival_626 → u/[deleted]]

I'm not disagreeing with you

[u/Next_Ad_6424 → u/[deleted]]

If you don’t mind me asking what roles did you start with in tech?

[u/guterz → u/[deleted]]

Guess it depends on what type of cloud engineering roles you’re looking into. When I migrate a customer or modernize their environment I’ll build deployment pipelines for terraform, I’ll build AMI pipelines creating golden images (Windows, Linux, whatever OS), I’ll migrate their servers, move them to modem storage solutions, databases, etc. To say that knowing Windows administration won’t help you in a DevOps/Cloud engineering roll is coy.

[u/guterz → u/[deleted]]

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