So you want to DevOps? There’s no “right” path, but here’s my path.

Learn to Code at the Commandline

Automation is the language of the sysadmin. Embrace the keyboard. Code away what’s trivial, boring, mundane, and belittling



  1. Learn Windows PowerShell in a Month of Lunches, Third Edition
  2. Learn PowerShell Scripting in a Month of Lunches
  3. The PowerShell Scripting and Toolmaking Book
  4. Windows PowerShell in Action, Third Edition
  5. The Pester Book

Video Courses

Windows PowerShell

  1. Pluralsight: Windows PowerShell Essentials
  2. Pluralsight: Windows PowerShell Scripting and Toolmaking

Azure + PowerShell

  1. CloudSkills Azure PowerShell The Ultimate Beginners Course

Store Your Code in Source Control

Long gone are the days of relying on shell history and file shares to store your code. You need something better. You need source control.

Infrastructure Should be Code

Because clicking sucks.

Desired State Configuration


  1. become Ansible: Zero to Production-Ready <– My book
  2. Ansible for DevOps: Server and configuration management for humans


  2. Terraform on Azure: Infrastructure as Code from Scratch
  3. Terraform: Up & Running

Releasing Code Can’t be Manual

You’ve automated the sysadmin stuff. Now automate some more. It’s time to automate the build, deployment, and testing of your automation.

The Release Pipeline Model - Microsoft Download Center

Cloud, Insert Something clever

The industry is rebasing on a new skill set. And that skill set is cloud.

Reading List

  1. Practice of Cloud System Administration, The: DevOps and SRE Practices for Web Services, Volume 2
  2. Cloud Native Patterns

Level Up with Certs

Certifications matter. Each major cloud vendor has made a tremendous investment in their certification tracks. It’s simple, they want you to be able to use their cloud.

If you feel stuck. Or left behind in the cloud game, study, and crush some exams. It’s not the piece of paper that matters. It won’t make you an expert. But it will get you in the game and you’ll have something to show for it.

In other words, certifications don’t matter but they absolutely do matter.


  1. AWS Certified Cloud Practitioner
  2. AWS Certified Solutions Architect – Associate
  3. AWS Certified SysOps Administrator - Associate


Microsoft Certified: Azure Fundamentals Microsoft Certified: Azure Administrator Associate Microsoft Certified: DevOps Engineer Expert

I have a sysadmin background. And my recommendations reflect my background. I hold the AWS CCP, but then chose to pivot to Azure. I currently hold the AZ-103 & AZ-400.


Cloud Resume Challenge


DevOps as a Philosophy

What they mean by DevOps isn’t about tools. It requires a different mindset & somewhat of a philosophy.

Required Reading, (Not just for your manager)

  1. The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win
  2. Making Work Visible: Exposing Time Theft to Optimize Work & Flow
  3. Team Topologies: Organizing Business and Technology Teams for Fast Flow

More reading!