Starting Your IT Career with Noah Rosen | Where’s the Any Key Podcast Episode 10

The following is a transcription of an episode of our podcast, Where’s The Any Key? Feel free to reach out with any questions you may have in response to this recording. You can find our show on Apple Podcasts, Spotify, and wherever podcasts are available.

Ryan Bacon: Welcome to Where’s the Any Key? The podcast where we talk about anything IT related and even some topics that are IT adjacent. I’m your host Ryan Bacon, the IT Support Engineer at JumpCloud® Directory-as-a-Service®.

So, I have with me Noah Rosen, IT support technician here at JumpCloud. How’s it going, Noah? 

Noah Rosen: I’m doing great! How are you doing? 

Ryan: I’m doing well, thank you. So normally when I introduce our guest, I would ask them to give a little bit about their background and describe how they got to JumpCloud but really, that’s going to be the purpose of this whole episode: getting into IT. This is Noah’s first job as an IT pro, so we wanted to bring him on to talk to him about the various topics about getting into the field. So, to kick things off, Noah, why don’t you tell us: why IT? What made you decide this field, this industry?

Noah: I think there’s a lot of people who are in my situation, when I was first curious about moving to IT where I played with computers since I was 12. When I was in middle school, I really wanted to play video games, but I couldn’t afford the console, so I went on eBay and scavenged a bunch of random computer parts and I think there’s a lot of people in that situation who have a difficult time thinking of how they transition to turning that into a real career and turning that into a field that they can spend their life and I’m hoping that maybe I can give some advice to people who are in that situation and would be interested moving over. 

For me personally, like I said, when I was young I was always interested in computers and I poked around in a couple other fields for a while but always had technology in the back of my mind by I never really had a way in and for a lot of people, it can definitely be a, and I definitely felt this, a weird transition because unlike some other degrees like in college: business or science or whatnot… there’s a pretty linear pathway into other fields. In IT, there isn’t really a  linear, dedicated pathway. Everyone you talk to in IT started a different way. Many people have computer science degrees, but other people like myself, we’re really passionate about technology. I learned what I needed to do to make my mark. 

Formal Education vs. Certifications

Ryan: You mention education and stuff like that. There’s a pretty consistent debate amongst IT people about what is more important: education, like a formal education, or certification? I will go out there and say that, above all, experience trumps education and certain certifications in the vast majority of situations but when you’re first getting into the field… that experience thing, you really don’t have it. So we’re going to talk about the education vs. certification debate. Noah, where do you stand on it? Formal education or certification? 

Noah: Kind of interestingly, I fall on more on the experience side, like you were saying. But, for someone with no experience, and it’s obvious you can’t go in saying you have experience just because you have certifications. I think certification and education both are equally valid if you’re learning actually applicable skills, because anyone can memorize every test answer and get a degree and anyone can pass any certifications by memorizing all the answers online or one of the many other ways to do it. It’s not actually being able to apply these skills. All these certifications ask you specific questions to dig into the details of different protocols and different process and how different aspects of technology work… but really what they’re asking you is how to troubleshoot, how to think, and how to understand low enough level processes that you can work your way up and answer these questions. So I think that an education and a certification are both valid as long as you’re actually learning all the skills that they’re trying to teach you, and not just memorizing test answers. 

Ryan: Well said. Now, on my part of it: I am of the school of thought that education is important but it’s a long line to what you’re saying: as long as you can apply that education. Why I view education as important is that, if you go get a degree, there’s a lot more to it that comes into play than just being hyper focused on certain topics. So, the programs that I was in, you had to do public speaking. I had to learn how to write. I had to learn how to research topics. There’s a lot of stuff that went into a formal education. But that being said, formal education isn’t the cheapest thing out there. It might be more cost effective to just focus in on certain areas and to get certifications. I’ll put it this way: Education tends to be more broad; certifications will be more deep. Then again, something else with education is there’s that HR filter: ‘must have a degree to apply’ and those can get tough. I see the value of them both. I lean a little bit more towards education, but that’s me.

Noah: Exactly. A huge part of learning a technological skill, anything in the IT world, it’s such a deep field and jumping right in it can be really… in some fields there’s kind of an easy way. In some parts of IT, there’s no easy jumping-off point. No matter where you start, you’re always going to be drowning a little bit, and in a formal environment where you going to school for it or whatever your formal education is, you have someone there, a mentor to guide you and answer any silly questions so you don’t spend five hours to figure out something that you don’t really need to know. It’s just stopping you from completing one task. 

Building Your Resume Effectively

Ryan: Agreed. Also, a good education program should include certifications, or at least get you to the point where you’re ready to take different certification exams, so there’s that. Again, going back to if you’re in the right program, something that you can really help you are internships. So, there’s that. I found mine to be really valuable, so that’s the way to kind of get that little bit of experience, maybe enough to to get your foot in the door. Or, you have something to add on to your resume if you can manage to get an internship. Then again, there’s not a ton of IT internships out there.

Noah: Yeah, absolutely not. I’d even revise what I said earlier about saying the education versus the certification pathway of learning things. I’d say from the perspective of resume material and actually breaking into the industry, having certifications and formal education on your resume are both really important, but I feel like both of them are really a validation of skills that you have, as opposed to just being an HR checkbox, which they are in many cases, but it becomes obvious if someone doesn’t actually understand the skills their resume says they do. So I believe your education and certification should show that you actually know these things are not that just you went through a program. 

Ryan: Right, that’s very true. You have to have certain things to get past those HR filters but you know, hopefully, the people interviewing are doing a thorough job and will really test your knowledge. The way I go into it, especially looking at entry level field — you can attest to this — it’s not necessarily what you know. I’m more interested in how you think and your personality. We can teach you how to do certain things, but that critical thinking and that troubleshooting ability and that sort of thing… that’s a lot more difficult to teach. 

Noah: Yeah, of course. Memorizing huge numbers of ports, ports numbers for every possible service going through a network. Many certifications will help you do that kind of thing but they won’t necessarily teach you how to troubleshoot a network the day when something isn’t getting through. When one service isn’t traversing a network, even if you know what ports it’s going across, it isn’t necessarily going to troubleshoot it. And, it’s something you can look up, so again like you were saying, someone who can learn is much more important than someone who can memorize a lot of information. 

Testing Skills with Homelabs

Ryan: Exactly. So, going on, like both of us said: experience is key. But, what do you do with having that experience before you get your first IT job? That can be tricky, but then again, as opposed to other fields in IT, I feel it’s made a little bit easier because of the nature of what we do. A popular thing, and something that I strongly recommend anybody who’s trying to get into the field, is a homelab. It’s very easy to find old enterprise-grade gear on eBay or something for really cheap and put together a lab where you can test this stuff out — destructively even — in a safe environment. My homelabs, mainly because I’ve lived in small apartments for a long time, have been a lot of virtual stuff, such as Cisco’s Packet Tracer and stuff like that, where you can build virtual networks. There’s a ton of other resources out there for it. What about you, Noah? What is your experience with homelabs and cobbling together technology to give yourself experience before you had a chance to get professional experience?

Noah: I’d say, despite the number of networking classes and certifications I’ve gotten, by far the most I’ve ever learned about networking was the couple weeks I got four or five Raspberry Pis and a couple switches and just did every possible combination of everything I could think of. You know, it’s fun! A setup like that cost a couple hundred dollars but if you have any laptop lying around built in the last 15 years, you can run VirtualBox on it and basically create an entire virtual network, all on one system right there. 

Ryan: Exactly, you don’t have all of this, have multiple husbands of dollars worth of hardware in order to do this, and frankly you don’t even have to invest a couple hundred. You go out to… if you’re lucky enough to live in a college town, a lot of these schools will have a supply depot where they’re getting rid of old computers or laptops for dirt cheap or you going places like Craigslist, I’ve seen people giving the stuff away. While this system may not be great for running Windows 10 or whatever, you throw a lightweight Linux distribution on there and you are set. 

Noah: I will warn you that it becomes addicting. There’s this subreddit called the home lab subreddit (/r/homelab) where people have like entire racks in their garage with like 40 NAS, so be careful. Don’t go too deep. 

Ryan: Now, I don’t know if I’d say don’t go too deep. My wife and I are looking at houses, so I’m like ‘you realize we’re going to have an office and I’m going to have a full rack in the office.’ She just sighs and says, ‘yeah I know.’ 

Noah: Along the lines of getting equipment; I’ve looked at this myself a couple times. You can go on eBay and buy two or three year-old Opticor Blades, like actual servers, and put in, they don’t come with drives, but you can get them a hundred and fifty bucks and they have a quad-core processor. They’re all set up for some serious virtualization work. 

Ryan: It doesn’t take that much searching to go and find this stuff. If you really want to build a really robust homelab, it takes just a small investment but the more important thing is that you have your setup, your lab whether it’s physical or virtual, and that you work on different things. Go look online, look on Reddit. There’s various IT subreddits out there, I mean like that homelab one. There will be discussions there of what people are doing in their home lab so that you can get an idea of what to do. Or, if there’s a particular field that you’re interested in getting into, look at what skills are required in there and go at it. You can recreate all these things in a lab environment and guess what, if you mess up, that’s part of learning! There’s very few things that you can do, especially in a virtual environment, that will make it so where you just lose your investment. So you, like I said, you can do some really destructive testing in there and if you end up completely, you know, pancaking your lab, you just start over again and that’s part of the learning process.

Noah: One of the best parts about home labbing is that you don’t have to follow a particular process. You should go out there and find something that’s interesting to you, but no matter what you’re doing you’re learning something valuable. All that work you’re doing in homelabs, whether it’s setting up NAS, media servers, anything you’re doing is going to be applicable to basically any job you’ll be doing in the IT field. 

In a previous life I was an inventory manager, so I just explained how I’d, on my own, kind of go out to make my job easier. In my previous role, I wrote a small Python script. Super simple, you know, it took a couple days but it cut down a workload process that took maybe 5 hours a week down to three minutes. Anything like that in your current role is something you can learn and put towards a future in IT.

Ryan: Yeah, and that’s the thing: the fact is that, getting something like that to work or frankly even attempting to do it, shows a motivation and the drive and desire to learn and try new things which I think are vital for any successful IT career. There’s ways that you can leverage your aptitude and your knowledge and your passion for IT in a role that isn’t exactly an IT role and use that to help you get into an IT role. So always be looking for those opportunities. 

Taking Your Skills and Finding Your First IT Job 

Ryan: So moving on, you want to get into IT. You’re working on an education. You went through certification, both or neither. You put together a home lab to hone your skills and get some form of experience on there. Now, you’re looking for a job. I will have to admit, my first IT job, I was lucky enough that I got to try to shoehorn myself into it. I was working at a print shop, not as IT. Those print services were transferred over to a small business print shop and so all three of us in the shop went over with it and when I got there, it was one of those things where it’s like ‘oh, you know how to do computers. You could do computer stuff for us!’ and I’m like ‘well, can I make it part of an official duty?’ So, Noah, how did you go about searching for and pursuing opportunities to find that first IT job?

Noah: For my first IT job, I think I did what many people do and sent out as many resumes as I possibly could and at least gave everyone who responded to me a chance. I wanted to talk to them and see what they were about and there were quite a few people who, after I met with them, I realized that it would not be a pleasant place to work. So, I decided to wait ‘til I found a really, really great company like JumpCloud.

Ryan: I think you ended up taking a really good approach. You can cast a really wide net and you can stick with whatever the first bite, the first thing that comes in, but honestly with that, if you’re not going to be picky about it,you’re going to run the risk of burning out and getting disillusioned with IT.

Noah: I’ve definitely been in the position of, where the first job offer comes in and you come really excited you’re like ‘wow, a new field!’ but you just take a little bit of self-discipline to make sure that you realize that interviews aren’t just them evaluating you, you have to evaluate if you want to work there and if you’re going to enjoy working at that company. So, it’s definitely important. It’s a good way to avoid burning out really quickly in the IT field. You want to make sure you have a good relationship with your employer.

Initially, I was really interested in networking stuff and I feel like many burgeoning IT people, at least when they’re younger, want to be ‘I’m going to be a hacker!’ So, then you go read the first forum post on how to become a hacker, an elite hacker, and they tell you to go look at networking stuff. I think a lot of people at that point decide, ‘wait, I think I don’t want to actually do this,’ but I actually kind of fell in love with the networking and I actually even enjoy the administration side of networking. No longer am I really just into the penetration testing side, but the security side and the administering and making sure a large network runs smoothly and everyone has access to their resources. That side of IT interested me from the very beginning and I still spend a fair amount of my time learning about that on the side. 

Ryan: That’s another very good thing; I’m glad you had mentioned that. Even if that first job that you get doesn’t necessarily align with that thing that you’re really interested about in IT, there’s nothing saying that you can’t still do stuff on the side. Again, we go back to that homelab.

Starting Your First Day of Your IT Career

Ryan: Okay, we’re moving along. You have your IT job, you are officially an IT pro. Now what? Noah, tell us a bit about your experience and your feelings and everything when you started your first day at JumpCloud, your first actual job as an IT person? 

Noah: I’d say, the very first step is take a breath and relax. It’s definitely a really stressful time. I know it was for me, and I’m sure it is for most people. There’s two really important things that I think a lot of IT people need to hear. I definitely am glad I heard it from Ryan. The two things are don’t be afraid that you’re going to damage something irreparably, and if you think you might damage something irreparably, definitely ask someone else before you do it. As long as you keep those two things in mind, there’s very little that can go wrong. As long as you can apply the skills you know, it’s a fight against imposter syndrome for a while. You feel like you’re in over your head constantly and slowly, you begin to realize that you know things, basically.

Ryan: To add onto that, it’s also part of the responsibility of your manager and your team members, whoever it is that hired you, to understand that you’re new at this. There are expectations, but it’s also on them to hand you, to feed you tasks and duties that you can handle. The ideal ones where you’re like where they come to you to be like ‘can you do this?’ You’re like ‘I’m 75% comfortable that I can do this,’ where there’s that bit of uncertainty or nervousness… that’s how you grow. You never want to be 100% comfortable with certain tasks when you are trying to learn. Obviously, you’ll have the ones that are routine, but when you’re given a new responsibility, you know it’s a good growing step if you have some confidence but you’re not completely confident about it. Obviously, it needs to be something that you can do, maybe with a little bit of research and asking questions, but you definitely want that room in there where you could learn and grow. Do you have anything like that, Noah, that you can share?

Noah: I definitely had to learn to basically accept that whenever I start a new project or jump into a new part of IT that I hadn’t done before, especially on the job, is that if you wait until you know everything about it before you start, you’ll never start because you can never know everything about it. So, the best way to learn is always just to start on it and learn as you go and basically don’t be nervous and be willing to learn and to try things… non-destructive things, but experiment as you go and that’s how things get better and that’s how you learn and improve processes.

Ryan: Any good setup when you’re trying to implement a new system gets tested first. That testing environment is there to allow you to mess up. That’s there to be like ‘Oops, I actually deleted all of the users.’ That’s something that you learn in the testing environment. That’s where you make your mistakes and honestly, you should be making mistakes because that’s how you learn to avoid and fix these mistakes, so that when you get into the final product, when it’s in production, you can avoid, or if something does happen, quickly fix it. 

To add what Noah’s been saying, don’t be afraid to ask for help. This is where you should be really picky when you’re finding those job opportunities and for teams out there looking to grow in those people where you need to keep this in mind if you’re going to put out an entry-level position. First off, an entry-level position that requires three years of professional experience in the industry is not an entry-level position. Just saying. 

But, when you’re looking out for a true entry-level position, you need to realize that it is going to take some time on the team’s part to bring this person up to speed. Part of finding the right person is where they have the conference that they will get up to speed quickly and end up being a net positive to the team. How you handle that ramp up period is going to be critical to the success of this new hire and to this entry-level person. You can get to the point like where I am now with Noah. Frankly, when new stuff comes to me, I look at what I’m doing so I can make room for this so I can hand stuff off to him and be confident in his ability to do it. Props, Noah.

That’s the thing. It’s kind of like playing the long game here. For the new hire as well as the team that they join, the end result is the new hire gains more experience and the rest of the team gains more bandwidth to do what they need to do. It’s a give and take. The new person needs help and frankly the more senior people also need help. That’s why they hired the new people: to give the stuff that will help the new person grow and give time for the senior people to do other things and grow as well. It’s a symbiotic relationship. 

Dealing with Imposter Syndrome

Ryan: Going back to you, Noah, after I’ve rambled on for a while. With your first IT job, your responsibilities have grown and you brought up imposter syndrome, which is a real thing a lot of people experience. What did you do to get past that, and frankly, do you still feel it sometimes?

Noah: Yeah I definitely still feel imposter syndrome. I think that anyone that doesn’t probably isn’t pushing themselves hard enough. Overcoming it is kind of a slow process of chipping away at one of your own mental blocks. It’s not just about learning that you have the skills, it’s about learning that you can always acquire the new skills and no matter what it takes to complete some particular task or goal, you already know a lot. So whatever it was you have to learn to fix or to get to that next step or finish that big project, it’s an attainable skill in a reasonable amount of time. Basically, impostor syndrome, for me at least, came down to becoming less scared of learning new things and becoming comfortable with new processes. It’s not about becoming more acquainted with what I knew, it’s about learning new things and being comfortable with diving into new projects. 

Ryan: I feel it. That right there is really the core of a successful IT career: It’s being able to think on your feet and learn new skills. A bit of advice that I heard a while ago about getting over imposter syndrome: a good way to do it involves a bit of trust. You get into this new experience and you’re like ‘how did I manage to slip through the cracks and get into this?’ You have to trust that the people that hired you hired you for a reason. They did their due diligence. They didn’t just grab the first person, the top application off the stack and hire that person. They went through a process of vetting you. They had something they were looking for and you were the best fit for that. So you have confidence in that and once you’re in the job and you are being handed new tasks and stuff, you have confidence in the rest of your team or your manager, whoever is assigning you these tasks, that they’ve seen you work and they know what you can handle and that they would not give you something that is so far out of your grasp that you’re bound to fail. A good manager wouldn’t do that. Good team members would do that. They’d give you something that you’re capable of with a little bit of reaching. So that’s another way to look at imposter syndrome is that you have trust in the people that hired you and the people that you work with that they have a good idea of your based off of observation and that they don’t want you to fail. 

Closing Remarks

Ryan: So we’re getting close to wrapping up. Is there anything else that you feel would be valuable for this discussion, Noah, that you’d like to bring up? 

NoahL I say that if you really really want to get into IT, it is a really great field, and that it’s definitely one of the hardest fields to jump into. I think it’s really competitive, especially right now, there’s a lot of people who are deciding recently that they want to join IT like I did, and it’s definitely an uphill battle for a while, but in my experience it’s definitely been worth it.

Ryan: That is very true. I don’t regret getting into IT one bit and I highly recommend it to anybody who’s looking for a challenge, because it can definitely be a challenge, but also a lot of creativity and a lot of diversity and experience because it is something different every day. Thank you very much, Noah, for coming on and in chatting with me and sharing your experience.

Noah: Thank you very much for having me on, Ryan! It was great talking to you. 

Ryan: Thank you for listening to Where’s the Any Key? If you like what you heard, please feel free to subscribe. Again, my name is Ryan Bacon and I work for JumpCloud Directory-as-a-Service, where the team here is building a cloud-based platform for system and identity management. You can learn more and even set up a free account at

So until next time, keep looking for that any key. If you find it, please let us know.

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