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How can you actually get a system administrator job in 2026? Guys, in this video, I'm going to take you from zero to actually landing that system administrator job. We'll talk about what the job really is, the skills, the labs,
Learn how to land a sysadmin job in 2026 with a full roadmap covering skills, certifications, resume tips, and career growth advice.
Key Takeaways
- Sysadmin roles are diverse and evolving but remain essential in IT infrastructure management.
- Strong troubleshooting and communication skills are critical for success.
- Certifications and hands-on labs significantly improve job prospects.
- Persistence through early challenges leads to confidence and career growth.
- There are many lucrative and varied career paths after becoming a sysadmin.
What the video covers
- Distinguishes between Linux sysadmins and Windows in-house IT sysadmins, focusing on the latter.
- Jake shares his career journey from IT help desk to sysadmin and beyond, emphasizing certifications and hands-on experience.
- Explains the evolving sysadmin role including server management, networking, cloud, security, and end-user support.
- Highlights the importance of troubleshooting, communication, and context switching skills.
- Discusses typical sysadmin salaries ranging from $65,000 to $125,000 with growth through experience and job changes.
- Encourages persistence through the initial learning curve of 6-8 months before gaining confidence.
- Outlines certifications like A+, Network+, Security+, CCNA, AZ-104, and SC-300 as valuable for career progression.
- Shares practical advice on job searching, resume building, and lab practice resources.
- Describes potential career paths beyond sysadmin including system engineer, network engineer, CTO, or startup roles.
- Motivates viewers by emphasizing the demand for sysadmins and the rewarding nature of the job.
Chapters
- 00:00Introduction and Career Background
- 00:54Training Others and Early Career Advice
- 01:42Building Confidence as a Sysadmin
- 02:31Sysadmin Job Overview and Misconceptions
- 03:25Career Success and Opportunities
- 04:13Mindset and Problem Solving
- 04:54Salary Expectations
- 05:38Essential Skills and Context Switching
- 06:35Soft Skills and Communication
- 07:27Hands-on Labs and Learning Resources
Full Transcript — Download SRT & Markdown
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the certs, the resume, and then that exact roadmap that I would take if I were starting today. Now, right at the gate, something that I think is important to distinguish is that there are kind of two types of system
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administrator. There's the Linux system administrator, and then there's the typical in-house IT Windows Server type system administrator. So, who am I and why can I talk about this? Guys, I am Jake. I've been in tech for a couple of
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years. I started at IT help desk. I was a tier one for four months, and I moved up very quickly to system administrator, and I did that job for about a year and a half. I used to be a teacher, and I
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wanted more money, more purpose, more responsibility, so I got A+, Network+, Security+. That got me into IT, and then I got CCNA, and again got promoted to sysadmin. Once in as a sysadmin, I got the AZ-104 and the SC-300. Now, I
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grinded. I also became the system administrator trainer. I trained seven people, I believe, to be sysadmins, and I trained a lot of tier ones as well.
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Now, I say all of this not to brag, I say it just to show you that I've done the job and I understand it. Now, eventually, I actually moved into developer relations at a startup out in San Francisco. And now I get to learn
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about even bigger systems. And when I was a sysadmin, we supported banks, financial institutions, credit unions. I think we had over 300 companies, and we had companies that had five people, and we had companies that had hundreds and
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even thousands of employees. So, there was a lot of on-prem, cloud, hybrid stuff, and I felt like I really became a jack-of-all-trades. I was touching cyber, touching a bunch of networking things, I was touching infrastructure, I was doing server updates and all of the
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above. It was awesome. And one thing that I wish somebody had told me when I started as a sysadmin was that you're going to feel like an idiot for like six to eight months, and the time is coming
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where you will start to feel confident. And I think that that feeling is coming for you, too. And I don't want you to quit before the confident feeling comes.
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So, let's get into it. So, what does a sysadmin actually do? As mentioned, there are two types of sysadmins. There is the Linux system administrator, and then there is the Windows in-house IT type system administrator. The Linux lives in a different world. They do more
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software-related stuff. There are fewer of these roles, and you're deeper into the world of ensuring that Linux servers are continuing to serve software correctly. In this video, I'm going to focus on the in-house IT type Windows server sysadmin. Even though you will
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touch some Linux stuff, it's not just a Linux guy. The person that I'm talking about administers systems. You keep servers running. You keep Windows servers running. Now, this also means print servers, file servers, routers, switches, firewalls.
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Plus, you're keeping the internet up and keeping everything highly available as it should be. There's a little bit of cloud in here. There's some cyber.
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There's a lot of Microsoft administration, email, Teams, conditional access. And there's a lot of help desk work, too. You're doing things that are helping end users be successful with technology. Now, I think the big misconception is that people think that
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you just live in servers. Yes, you do a ton of stuff in servers. You live there backstage a lot. But you're also in software, firewalls, networking, troubleshooting, conditional access, security. You're doing all of it. And yes, the job is definitely evolved with
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cloud and AI and automation, but I think sysadmin is still the title. So, why does this path still matter? I think a lot of people are saying that tech is dead, that you shouldn't even try to go in, you shouldn't even bother. I just
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don't trust the naysayers. I'm going to be honest, I've worked with a lot of people who are frankly quite incompetent. I've worked with a lot of extremely competent people as well. But I just still see how there's so much
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demand and there's so much opportunity in the space. Like I genuinely think if you work hard, if you're honest, if you're conscientious, and you communicate, there's a spot for you in IT, and you can be a sysadmin and be
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super successful. Again, not to brag, but I feel like my career is kind of evidence of this. Like I got in, I moved up quickly, I started making videos for what's now become almost 30,000 people, which is insane for me to say, and it
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opened up doors for me that would never have been opened if I had not just taken these chances. And there's a real wonder to this job of sysadmin, as well. You're just sitting in the backstage and ensuring that billions of dollars of
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infrastructure is still running. And that's pretty cool. It feels really purposeful. It's also genuinely fun.
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You're doing error log analysis. You're talking with ChatGPT a lot. You're figuring things out and putting together these pieces to a puzzle. You're teaching people and you're learning things all the time. So, who thrives in this position? Well, I think somebody
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who's confident, somebody who solves puzzles well, somebody who is there and ready to learn, and somebody who just never gives up and always thinks that the answer is at the edge of their fingertips. And you're just going to
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find it. It doesn't matter how long it takes. It might be 3 days, it might be 2 weeks, but there is an answer and you will find it. You have to have that mentality. Now, what's possible down the
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road from sysadmin in 2, 5, 10 years? I genuinely think there's so many opportunities that this role opens up for people. The world is your oyster.
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You could build generational wealth. You could become a CTO. You could start your own company. You can move up to a system engineer, to network engineer. You could go to developer relations at a startup like I did. And on the other hand, you
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can also just live a chill life. You can make decent money. You can make sure that infrastructure is up and running.
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You can learn slowly. You can take it slow if that's your jive. You can have job security and provide for your family. As long as you keep working, you stay honest, and you stay conscientious.
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I think that's beautiful. So, how much money do sysadmins make? Well, in my opinion, and from what I've seen, sysadmins make anywhere from 65,000 to 125,000.
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You may find sysadmins that make less. They're definitely out of the norm. You may find sysadmins that make more.
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They're also definitely out of the norm. Most people land right around 90,000. When I was a system administrator, I made $87,000 in my one full year as a sysadmin. Obviously, this climbs with experience, but oftentimes you have to
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jump jobs in order to get those big pay bumps. Now, what skills do you need to actually move the needle as a sysadmin?
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Well, the number one skill is going to be troubleshooting, gathering data, and being able to synthesize that data into a coherent problem, and then obviously a solution. After that, it's communication. You're going to be communicating with a lot of internal
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people and with other IT people and with end users. The reality of this job is there's a ton of context switching as well. You're in a router, then you're in a switch, then you're in a firewall, then you're doing some end user thing,
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then you've got some after-hours server updates, and then a priority one ticket comes in in the midst of all of it and you have to drop everything. So, being able to context switch and gather data and communicate that data is very
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important. Now, on the technical side, the core skills are understanding how an Active Directory domain works. You have to understand Microsoft administration at a deep level. That's Exchange, Teams, compliance or Purview, I forge
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those things, 365 of course. Then you have networking, DHCP, DNS, how a router, switch, firewall works, how, you know, network traffic moves along your network and how things are set up, VLANs and IP addressing of course. Now, if I'm
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ranking what to learn in this path, I would say learn Windows and Active Directory domain stuff first, then learn networking, and then learn Microsoft administration. And then after this, obviously sprinkle in some Linux and cloud as well. Cloud is really just
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learning all of these principles and then applying them to somebody else's data center behind a GUI. Now, the soft skills that people underestimate, I think is just communication, you know, proactive communication and being able to send messages confidently. You got to
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know when to keep people in the loop. You have to know when not to loop people in because you haven't done enough research yet. Now, as a beginner, I also think that you should be touching AI and automation tooling. You should
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understand CICD, you should understand how infrastructure works, how a a web server works, what actually happens when you visit a website, like what are all the things that are behind it, you know, DNS, probably a load balancer, probably
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maybe a reverse proxy, some other back end stuff that's going on and how this content is served. Very important. And what labs should you do preparing to be a sysadmin? I would start Active Directory lab. I have a free one at
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Jake's Tech Labs.com. Put in your email and you can get it for free. From there, you're probably going to do some networking labs, something like Jeremy's IT Lab CCNA Labs. David Bombal has some really good ones as well. I've linked
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all of these in the description. Now, all of this hands-on stuff is what's really going to make you dangerous, but to be honest, a lot of it you just can't learn until you go onto the job as well,
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which is tough. But the idea is you get that tier one IT help desk job and you just grind it until you learn the stuff necessary to get the sysadmin job. Now, which certs are actually useful for this
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job? I'm going to be very honest here about the certs with highest ROI. And when I say ROI, that's return on investment. I'm not going to tell you to buy a thousand dollar cert with very low return. If a cert is $50 and has an
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outsized return, I'm going to recommend that. So, first I would start with the Google IT Support Professional certificate. And people always tease me for recommending this, but it's cheap.
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It's $50 a month and you learn so much and you get to do hands-on labs and you get to put this stuff on your portfolio.
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Again, I have a link in the description. That's an affiliate link, so I make a little bit of money at no extra cost to you, but this is the path that I took.
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And of all the things that I've analyzed, this is genuinely what I recommend starting with. After that, get your Network Plus, your Security Plus, and then your CCNA. The CCNA is massive.
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In my opinion, it's the highest ROI cert you could ever think about. AZ-104 is good, too, if you want to go deep thinking about this Microsoft ecosystem.
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And if you're going to be doing identity and access management stuff, the SC-300 is also a useful cert. But to be honest, a cert itself is not just going to get you a job. You have to have the labs,
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you have to have the experience, and you have to have that grind set and that ability to communicate, and obviously interview well as well. Now, on the note of getting hired, you're going to need a resume. In terms of how to have a good
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resume, I have a lab for that as well. It's free as well at jakestechlabs.com.
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Highly advise that you check it out. It'll take your resume from probably being pretty bad to being decent to pretty good. Again, with the Google IT Support Professional certificate and your other cert, you're probably going to have some labs that you can put on
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there. You're probably going to have a GitHub portfolio, and you're going to use AI to really optimize every part of your resume. And then in terms of actually hunting, well, my recommendation nowadays is actually just to spin up an AI agent like Hermes to do
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it for you. Uh look for actual instead of job boards like Indeed or LinkedIn, which is kind of just a waste of time.
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You can look online and you can look at actual companies' sites, jobs that they have listed. So, whatever company it is / careers, usually. Apply on company sites, you're going to have a way higher hit rate. You're going to be way more
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likely to get a job. Now, it's funny, the best job board that I've been able to come up with, to be honest with you, is just straight up Google. It's odd, but you can actually just find jobs on
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there and there's not as much slop. Now, one of the biggest mistakes that I see beginner tech people doing is trying to decide too early what it is that they want to do. And this is why I so
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vehemently recommend the sysadmin path. If you think that you want to do cybersecurity, like everybody else does when they first start, just start with learning the fundamentals and then networking. Because from fundamentals and networking, you can branch out
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anywhere. You can branch to cybersecurity seamlessly. If you hone that's your only choice. It's harder to transition from cyber to networking and sysadmin than it is to transition from sysadmin and networking to cyber. And this applies to a lot of different jobs
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as well, whether that's DevOps, you know, software engineering, things like that. You can always branch out from the sysadmin path. So, don't decide super early that you want something. Just try and get those basics really good and then you can branch out. So, the honest
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road map for getting a sysadmin job, Google IT Support Professional Certificate, Network Plus, Security Plus. Then you get a tier one help desk job, a help desk job, a desktop support job. You just become an absolute monster at that job. You take more tickets than
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anybody else. You work harder than anybody else. You try and get into abstract situations where you have to learn new things and you feel uncomfortable. You understand how a domain works. You understand how Microsoft works. You understand how a
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VPN works and how local accounts work. You've got the networking. You soak it up like a sponge. During this time, you get your CCNA. And this is exactly what I did. I think it's the best way to do
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it. It took me four months. It was while I was a tier one. It was really hard. It was a lot of work, but it was useful.
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Then you apply for sysadmin roles in your company or at another company far before you're ready. You're never going to feel ready to be a sysadmin and you're never going to be ready.
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Sometimes you just got to get thrown to the wolves and learn to survive and you just got to confidently interview.
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You're going to get the job and you're going to be successful. And then after a year of tailoring your craft as a sysadmin, you could start thinking, "Hey, where am I going next? Am I going to be a system engineer? Am I going to
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be a network engineer?" Maybe you don't know. Maybe you just apply to a bunch of different jobs and you see where it lands and you take your career to the next step. So, I'm rambling a little bit. Here's the truth. A lot of people
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say that they want something, but they don't do the necessary things to actually get that thing. At the end of the day, I've laid out exactly what you have to do in order to get this job and it is possible and I've seen tons of
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other people do this as well. So, go do it. Tailor your resume, get the certs, apply for the jobs, get the jobs, do the labs that you have to do, get the next certs that you have to get and have a
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successful tech career. Become a sysadmin and then see where that takes you. Guys, what I really want you to take from this video is that there is absolutely hope and it is absolutely possible. There's so many jobs out there
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and companies that genuinely need good talent. Don't let the naysayers, you know, talk you out of potentially living a dream life. Many the people who talk negatively on the internet have a vested interest in the world being chaotic and
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there being these things. Some people do it for YouTube views. You may have noticed, I try not to be negative on this YouTube channel. I try to always look at the positive. I'm honest about the things that are tough and the things
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that are difficult about certain jobs, but if you go out and take the world head on, it's astounding what you can accomplish. Guys, I appreciate you if you made it to this point sitting to the end of this video. Be safe, be smart,
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make some good decisions. Good luck getting those certs, doing the labs, tailoring the resume and getting the sysadmin job. We'll talk to you in the next one.
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Bye.
Topics:sysadminsystem administratorIT careercertificationsWindows ServerLinux sysadmintroubleshootingcareer roadmapjob searchtech skills
