Question:

How to transition from a self-taught IT generalist to a professional Sys-Admin?

I have been working in IT for 30 years, mostly in a small family business and as an Android app developer. I have never had a formal IT job or worked in a large enterprise environment. I have a computer science degree, but it is outdated and does not cover many of the modern technologies and tools that Sys-Admins use today.

I have been trying to update my IT skills by setting up a lab with virtual machines, Active Directory, Intune, and other services. However, I feel overwhelmed by the amount of information and skills that I need to learn and master, such as virtualization platforms, MECM/MEM, PowerShell, Azure AD Connect, Group Policy, and more. I also have trouble remembering everything that I have learned and applying it to real-world scenarios.

I want to pursue a Sys-Admin job on-premises, but I am not sure how to prepare for it and what are the key areas that I need to focus on. I am also worried about how I will perform in an interview and on the job, and whether I will be able to adapt and assimilate to the existing domain environment and the tasks at hand.

What are the essential skills and knowledge that a Sys-Admin should have in order to succeed in this field? What are the tools and technologies that you use every day and that I should learn and practice? How can I overcome the feeling of being overwhelmed and underprepared, and gain confidence and competence as a Sys-Admin?

Your insights and feedback are greatly appreciated.

Answer:

If you are a self-taught IT generalist who wants to become a professional Sys-Admin, you might feel daunted by the amount of skills and knowledge that you need to acquire and update. You might also wonder how to prepare for the job market and the work environment, and how to overcome the impostor syndrome and the fear of failure. In this article, I will share some tips and advice on how to make this transition successfully.

1. Identify your strengths and weaknesses

As a self-taught IT generalist, you have a lot of experience and expertise in various aspects of IT, such as app development, networking, Windows systems, and more. However, you might also have some gaps and blind spots in your knowledge, especially when it comes to the modern technologies and tools that Sys-Admins use today. Therefore, the first step is to identify your strengths and weaknesses, and to assess your current level of proficiency in the key areas of Sys-Admin work.

Some of the key areas that you should be familiar with are:

• Active Directory: This is the core service that manages the identity and access of users and devices in a Windows domain. You should know how to create and manage users, groups, organizational units, domains, forests, trusts, and policies. You should also know how to troubleshoot common issues and errors related to Active Directory.
• Virtualization: This is the technology that allows you to create and run multiple virtual machines on a single physical server. You should know how to use popular virtualization platforms, such as Microsoft Hyper-V or VMware ESXi, and how to configure and manage virtual networks, storage, and resources. You should also know how to migrate and backup virtual machines, and how to monitor their performance and availability.
• MECM/MEM: These are the acronyms for Microsoft Endpoint Configuration Manager and Microsoft Endpoint Manager, which are the tools that allow you to manage and secure the devices and applications in your organization. You should know how to deploy, update, and patch software, how to enforce compliance and security policies, how to inventory and report on devices and applications, and how to use features such as co-management, cloud management gateway, and desktop analytics.
• PowerShell: This is the scripting language and shell that enables you to automate and streamline various administrative tasks. You should know how to write and run PowerShell scripts, how to use cmdlets and modules, how to work with variables, arrays, loops, and conditions, and how to handle errors and exceptions. You should also know how to use PowerShell remoting, workflows, and desired state configuration.
• Azure AD Connect: This is the tool that synchronizes your on-premises Active Directory with Azure Active Directory, which is the cloud-based identity and access service. You should know how to install and configure Azure AD Connect, how to choose the appropriate synchronization options and methods, how to troubleshoot synchronization issues and errors, and how to use features such as password hash synchronization, pass-through authentication, and seamless single sign-on.
• Group Policy: This is the mechanism that allows you to apply settings and preferences to users and computers in your domain. You should know how to create and edit group policy objects, how to link and enforce them, how to use group policy preferences and item-level targeting, and how to troubleshoot group policy issues and conflicts.

To assess your level of proficiency in these areas, you can use various resources, such as online quizzes, practice tests, certification exams, or self-evaluation tools. You can also ask for feedback from other IT professionals, such as mentors, peers, or online communities.

2. Fill in the gaps and update your skills

Once you have identified your strengths and weaknesses, the next step is to fill in the gaps and update your skills. You should create a learning plan that covers the topics and technologies that you need to master, and that aligns with your career goals and interests. You should also set realistic and measurable objectives and milestones, and track your progress and achievements.

Some of the resources that you can use to learn and update your skills are:

• Online courses: There are many online platforms that offer courses on various IT topics and technologies, such as Microsoft Learn, Pluralsight, Udemy, Coursera, and more. You can choose the courses that suit your level, budget, and schedule, and that provide interactive and engaging content, such as videos, quizzes, labs, and projects.
• Books and blogs: There are many books and blogs that provide in-depth and up-to-date information and guidance on various IT topics and technologies, such as Microsoft Docs, TechNet, PowerShell.org, Petri, and more. You can use these resources to supplement your online courses, or to explore specific topics and scenarios that interest you.
• Podcasts and webinars: There are many podcasts and webinars that provide insights and tips on various IT topics and technologies, such as RunAs Radio, The SysAdmin Show, Microsoft Mechanics, and more. You can listen to these resources to keep up with the latest trends and developments, or to learn from the experiences and best practices of other IT professionals.
• Labs and simulations: There are many labs and simulations that allow you to practice and apply your skills in a realistic and safe environment, such as Microsoft Virtual Labs, TestOut, Boson, and more. You can use these resources to test your knowledge and skills, or to prepare for certification exams or job interviews.

3. Build your portfolio and network

As a self-taught IT generalist, you might not have a formal IT job or a work experience in a large enterprise environment. Therefore, you need to build your portfolio and network to showcase your skills and knowledge, and to connect with potential employers and colleagues. You should also update your resume and LinkedIn profile to reflect your current skills and achievements, and to highlight your value and potential as a Sys-Admin.

Some of the ways that you can build your portfolio and network are:

• Projects and case studies: You can create and document projects and case studies that demonstrate your skills and knowledge in various IT topics and technologies, such as setting up a virtualized domain environment, deploying and managing software using MECM/MEM, automating tasks using PowerShell, and more. You can use your own lab or simulation environment, or you can use cloud-based services, such as Azure or AWS, to create and host your projects. You can also use GitHub or other platforms to store and share your code and scripts.
• Certifications and badges: You can obtain certifications and badges that validate your skills and knowledge in various IT topics and technologies, such as Microsoft Certified: Azure Administrator Associate, Microsoft Certified: Modern Desktop Administrator Associate, VMware Certified Professional – Data Center Virtualization, and more. You can use online courses, books, blogs, podcasts, webinars, labs, and simulations to prepare for the certification exams, and you can display your certifications and badges on your resume, LinkedIn profile, and portfolio.
• Communities and events: You can join and participate in online and offline communities and events that are related to IT topics and technologies, such as Reddit, Stack Overflow, Spiceworks, Meetup, and more. You can use these platforms to ask and answer questions, share and learn from others, seek and offer advice, and network and socialize with other IT professionals. You can also attend and contribute to webinars, podcasts, conferences, workshops, and hackathons that are related to IT topics and technologies.

4. Apply for jobs and prepare for interviews

Once you have built your portfolio and network, the final step is to apply for jobs and prepare for interviews. You should look for Sys-Admin jobs that match your skills, interests, and goals, and that offer opportunities for learning and growth. You should also tailor your resume and cover letter to each job application, and highlight your relevant skills and achievements.

Some of the resources that you can use to apply for jobs and prepare for interviews are:

• Job boards and websites: There are many job boards and websites that list Sys-Admin jobs, such as Indeed, Glassdoor, Monster, Dice, and more. You can use these platforms to search and filter jobs by location, salary, experience, and keywords, and to apply online or directly to the employer. You can also use these platforms to research the company and the role, and to read reviews and ratings from other employees and candidates.
• Recruiters and agencies: There are many recruiters and agencies that specialize in IT jobs, such as Robert Half, TEKsystems, Randstad, and more. You can use these services to find and apply for Sys-Admin jobs, and to get assistance and guidance throughout the hiring process. You can also use these services to get feedback and recommendations on your resume, portfolio, and interview skills.
• Interview questions and tips: There are many interview questions and tips that can help you prepare for Sys-Admin interviews, such as GeekInterview, Interview Cake, CareerCup, and more. You can use these resources to practice and improve your technical and behavioral skills, and to learn how to answer common and challenging questions, such as “What are the benefits and drawbacks of virtualization?”, “How do you troubleshoot a slow network connection?”, “How do you automate tasks using PowerShell?”, and more.

Conclusion

Becoming

a professional Sys-Admin is not an easy task, especially if you are a self-taught IT generalist who has never had a formal IT job or worked in a large enterprise environment. However, it is not impossible either, if you are willing to learn and update your skills, to showcase your skills and knowledge, to connect with potential employers and colleagues,