What worked for me was to run my own servers and services. You have to learn how to manage things because there's no one else to call on - and if it breaks, you

What worked for me was to run my own servers and services. You have to learn how to manage things because there's no one else to call on - and if it breaks, you have to fix it. Hence why I have stories about how to recover a remote machine after PAM has been uninstalled. A background in customer services can be parlayed into technical support, which - if you can show competence - can get you in the door somewhere and get you commercial experience. I have no formal training or education, and I don't think I'm an uncommon case. This is a job you can learn by doing. If you have a development background, look into devops, which is the hybrid/crossover movement. Learn how to deploy your app, how to configure Apache (or the reasons why you might not use Apache at all). For your next weekend project, try getting a cheap VM/VPS and deploying to that instead of Heroku. The nature of sysadminning is changing, thanks to the flexibility offered by 'cloud' hosting solutions and automated deployment and configuration management tools. Learn how to use chef or puppet. Look up 'chef-box', which uses vagrant and VirtualBox to give you a virtual network that's configured using chef. You can use this to learn how a real network works. Learn about virtualisation, buy a cheap machine (I like the HP Microserver) and install Xen on it. Increase your swearing vocabulary by trying to use VMWare in production with no support contracts. I have no idea how you learn about Windows. Never owned a Windows box, never had to do meaningful support for Windows systems. Even if you're a Mac/*nix person, you should probably learn how to manage a Windows network, though.