The Information Technology field is one of the most rewarding and challenging career fields in the world today. It is one of the only career fields that changes almost on a daily basis, and requires you to be up on the latest trends in order to keep pace and stay relevant. I’ve been in the IT career field for 20 years and it has been an amazing experience to say the least. What I experience in my work now is not what I experienced when I first started 20 years ago, and it’s not just about the technology I was using, either. Everyone has to start somewhere, and since I’ve experienced the highs and lows of climbing the IT ladder, I want to share some tips with you. My hope is you can feel good about kick-starting a career in IT, or get an understanding of what you need to do to keep climbing and have success.

You Have to Start Somewhere

A wise old man once told me, a journey of 10,000 miles begins with one step…Okay, no one actually told me that – but it’s a good adage to think of as you approach a career in IT. How do you take that first step?  Let’s focus on a couple of different jobs you can do to get off to a good start in your IT career.

Bottom of the Ladder:  Help Desk Technician

The help desk technician is the first stop for almost anyone that is having trouble with their IT assets, printers, laptops, desktops, email, passwords, printers, printers, printers (ok, you get the gist). In most organizations, when there is an issue with an employee’s IT, they are either going to open a help desk ticket through their web interface or they are going to pick up a phone and call the help desk.  As a help desk tech, you are on the other end of that ticket, and you are answering the phone. Like a first responder in an emergency (hey, email is an emergency!) the help desk technician is tasked with triaging the issue. If it’s a password reset, it’s likely the tech can do it. If the issue involves a user needing a copy of their Exchange .pst file, you will send the ticket to the Exchange Admin queue. You are a traffic cop, keeping things moving and fixing small things where you can.

Disclaimer, this job generally doesn’t pay too well. But if you are just starting out, this is the job you want. You will learn if you pay attention to what goes on around you and ask plenty of questions. This is also a job where you might have some down time, which if utilized productively can prove to be a great time to study for certifications or read up on what you don’t quite understand.  This is exactly what I did 20 years ago, and it helped me get to the next step.  Don’t think of it as a dead end, it’s more of a stepping stone.

Entry Level Certifications:

CompTIA A+, CompTIA Network+, CompTIA IT Fundamentals, Microsoft Certified Professional, CompTIA

Middle of the Ladder:  Systems Administrator/Network Administrator

After you’ve put in your time as a help desk technician and obtained some good entry level certifications, you can likely expect to move on to a job as either a network administrator or systems administrator. A systems administrator is not going to be answering the phone as much as a help desk tech will be. As a sys admin, you will be expected to know how to install, configure and manage operating systems from the server level down to a desktop level. You might start to pick up some data center experience with virtualization technologies and various storage technologies. This is where you might start to build out a niche for a specific software or technology, and grow the rest of your career off of it. For me, this was where I learned VMware and it just took off and brought me where I am today. It could be networking or storage that piques your interest. If you find something that does, grab ahold of it and learn all you can.

Find a mentor that will help you understand the ins and outs of the technology that your organization is utilizing and sit in on any architecture or design meetings that you can. Take lots of notes and do your best to gain an expert level understanding of how the organization architected their infrastructure and also why they did.  Time spent as a system or network administrator will be where you gain the bulk of your experience and knowledge of IT, and it will help you advance to more technically challenging roles later on in your career. Expect to spend a good chunk of your career in systems administration, starting as a junior sys admin and working your way to a senior admin before moving on.

Mid-level certifications:

Cisco Certified Networking Associate CCNA, Cisco Certified Networking Professional CCNP, VMware Certified Professional-Datacenter Virtualization VCP-DCV, VMware Certified Professional-Network Virtualization VCP-NV, Microsoft Certified Systems Administrator MCSA, Microsoft Certified Systems Engineer MCSE, Red Hat Certified Professional RHCP, Red Hat Certified Engineer RHCE

Top of the Ladder:  Systems Architect, Design Expert

This is it, you’ve reached the top. To go beyond the top of the ladder would be to become a C-level executive, Director, Independent Consultant, Analyst or VP.  Some people work for 30 years and don’t get to the metaphorical ‘top of the ladder’.  That’s not a reflection on the quality of your work or career. I firmly believe you could be a Senior Systems Engineer up until you are ready to retire and be completely happy. Being a Systems Architect or Design Expert is not for everyone. You have to have a complete understanding of every aspect of a company’s infrastructure (networking, storage, virtualization, OS, security) to architect or design a solution that suits their needs. This is not an easy process but you can get there with years of experience and lots of knowledge.

To get here, you have to have had lots of hands on experience, both with successful deployments and failed deployments. There isn’t an architect out there who hasn’t dealt with failures or mistakes in their career.  At this level you are an influencer, trusted advisor and liaison between the decision makers and the administrators/engineers who will bring your design to life. It helps to have been an admin at one point in your career to understand what the team will go through with implementing a design.

Advanced certifications:

VMware Design Expert VCDX, Cisco Certified Internetworking Expert CCIE, Microsoft Certified Solutions Developer MCSD

The Ladder Doesn’t = Success

Don’t think that you have to be “climbing the ladder.”  You don’t… it doesn’t equate to success or happiness. In fact, “climbing the ladder” could frustrate you and create unnecessary anxiety. Success is being happy in whatever you are doing. If you love help desk and doing that job makes you happy, then do it and be the best at it. If you love design and architecture, then be happy doing it and don’t sweat trying to advance. The old idea that working hard and going above and beyond at work makes you successful is dead wrong. True success is finding joy in what you do from day to day.

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Greg Stuart is the owner and editor of He's been a VMware vExpert every year since 2011. Greg enjoys spending time with his wife and 3 kids. He has 20 years of IT experience and currently works as an IT Consultant both in the private and public sector. Greg holds a BS in Information Technology and an MBA degree. He currently resides in Southeast Idaho. You can follow him on Twitter @vDestination, read his blog ( and listen to his podcast (