How to Start a Career in IT

By on 07/16/2015.

On episode 27 of the Cisco Champion radio, I participated in a discussion about how to get started in an IT job.

Topics covered included:

  • Landing a first job
  • Developing a career
  • What hiring managers look for
  • Interview tips

I gave some input and decided it would make a good topic for a blog post. As a twist, I want to cover it from the perspective of someone who did not take a traditional route to get into IT. Some of the best engineers I have worked with were not computer science majors. Some majored in music. Some in philosophy. Some in English. It’s entirely possible to be a competent IT person without needing a 4 year degree and mountain of debt to do it. But it won’t necessarily be easy…

What is IT?

IT stands for “information technology.” If you were to try to explain IT to your mom, you’d say “I work in computers.” But, IT is much more. It can be help desk. It could be systems administration. It could be tech support. It could be programming. IT covers a lot of different areas. For me, IT has been help desk, systems administrator, tech support and, now, technical marketing.

A little about me

Before I became the @NFSDudeAbides, I took an unlikely path into my role in IT. I went to college with all intentions of going to design school and becoming a graphic designer. But some poor planning and indecision paused that track for a year. In that time, I realized I didn’t have to spend tons of money for supplies to get a design degree. Instead, I could get work experience and major in something else, something flexible enough to fit into my goal of graphic design/marketing/advertising. The major would also be flexible enough to allow me to change careers if for some reason design didn’t work out for me.

So, I majored in English.


Why English? Well, my thought process was that the writing aspect was invaluable in any and all career paths. Being able to convey your thoughts intelligently in written and spoken word plays across all career paths. And the creative writing aspect of English tied in nicely with the design portion of the stuff I wanted to do.

So, my career started in college, working at a non-profit part time, doing both web and print design work. Because it was a small non-profit, I was also asked to do other things, such as helpdesk/basic PC support. That’s where my IT career began – making about 10 bucks an hour doing the jobs of several people.

Eventually the non-profit shut its doors, but not before I had picked up a 2nd job at a startup that sold posters online. In that job, I was asked to do much of the same work – web design, print design and helpdesk.

I worked there for 2 years or so. In that time, the company grew and expanded. It became readily apparent that I was not going to be able to perform both design and helpdesk tasks, especially as the web design started becoming more demanding. I had to pick up ASP in addition to HTML. On the other side, the helpdesk role was morphing into a systems administrator role. And why not? They were paying me 36k a year to do the work of 3 people!

Plus, they made my continued employment contingent on getting IT certifications and I had to basically twist their arm to agree to pay for it, since they were forcing me to do it.

Eventually, they needed to make some cuts and I got laid off with a number of other people. That IT certification bill? They tried to saddle me with it in the exit interview and eventually we “negotiated” them not having to pay me for my accrued vacation. Illegal? Probably. But I was in my early 20s and kind of in shock from being laid off.

Didn’t realize it at the time, but it was the best thing that ever happened to me. I went from being severely underpaid to a new job where I was making just below average salary. It was a pretty sizeable increase – nearly a 100% jump!

It also taught me my first lesson…

Starting out in IT is not always about money

This is especially true when you took the route I took.

When you look for jobs, especially at larger companies, you see a lot of “4 year degree in computer science or equivalent work experience” in the job descriptions. That’s a problem for people who did not major in an IT-specific major. In reality, it’s a weed out by companies to discourage people who probably aren’t qualified from applying, as well as a filter mechanism for HR/hiring managers to filter out resumes. If you don’t fit a keyword, you don’t get picked for an interview. So, naturally, you can imagine how frustrating it is to apply to many, many jobs and never have even a phone screen.

It’s the classic age-old quandary of “how do you get experience without a job/how do you get a job without experience.”


Sometimes, you have to do things you don’t want to do in order to do things you want to do later. Call it “paying your dues.” Unfortunately, this is the reality you face. However, there are options…

Unpaid (or lightly paid) internships

If you are in college or looking to break into the IT field, you might look into doing some gratis work. It could be for a large company or it could be for a non-profit. It doesn’t really matter – what matters is being able to put information under “work experience” that isn’t your last gig at TGI Fridays (yes, I did some time there and wore my flair).


But you’re not there just to mark a check box on your resume’. You are there to gain valuable experience and knowledge, whether it’s in fixing computers or in working well with others. If not getting paid isn’t for you, then you might consider…

IT Recruiters

You can say whatever you want about recruiters (aka, headhunters) – they get results. In fact, my first few jobs after my first job were the direct result of IT recruiters. Having some experience up front is ideal, but they may be able to help you land some entry level contract work to help bolster your resume’. And contract work is better than no work.

Just keep in mind that recruiters are making a tidy profit off of you, so be sure you’re getting a fair share. Try to stick to more well known or established companies, if possible. They might even offer health insurance during your contract! Of course, your negotiating power will be solely contingent on your overall experience (and genuine desire for the offered job), so don’t push it. :)

IT Certifications/Tech schools

This is a tricky one – IT certs can be *very* expensive, as can tech schools that offer promises of lucrative careers in IT. If you’re trying to land a job, you’re probably not flush with cash and probably not looking to take on a heap of debt in the form of loans. So you have to carefully weigh your options and understand the real value of certifications and tech schools.

Certifications definitely can land you interviews and even jobs. But they don’t help you stay in those jobs, and if you manage to get a certification by cramming and memorizing answers, you will get exposed. Fast.

But it’s important to know which certifications are worth their time. For example, certifications like CompTIA A+ and Net+ are good for some jobs (like a cable technician/internet installer/low-level help desk), but they won’t necessarily land you that six figure gig as a systems architect. But certs from Microsoft and Cisco will be much more lucrative. They will also be way more expensive, as well as harder to achieve. So it becomes a balancing act – do you want to spend a ton of money, get a certification and hope you land a job later? And if you land a job, hope you don’t figure out later that you hate working in IT?

Same goes for tech schools. Yes, you can make decent money by getting trained at a tech school that specializes in IT jobs. But you might also find that many companies won’t even call you for an interview if they see your only IT experience is at a tech school, or even one of those for-profit online universities.

A cheaper, safer alternative? Community college. Some offer IT courses and tracks that cost way less than tech schools and allow you to really evaluate what you want to do. Even cheaper and safer? Highly accredited schools like Stanford and Michigan are actually offering online courses for FREE.

Do a little research ahead of time and save yourself some money. Or…

Learn on your own

Believe it or not, but there is an entire Internet out there, full of all sorts of docs, manuals and information you can get for FREE. There are operating systems you can run FOR FREE. And now, with container technology like Docker, you can use platform as a service (PaaS) as an educational tool. Know how much I learned by trying to get systemd to work with a Docker container. A ton.

Plus, you get to put stuff like “Docker” on your resume’. Hiring managers and HR folks aren’t always IT savvy, so they have keywords they use. Think Docker isn’t in some keyword searches these days?

But, education is not enough. You also have to market yourself. The main way you do that is via the resume’ and cover letter…

Marketing yourself

The cover letter and resume’ are the gateway to the soul of the gainfully employed.

This is your one chance to make an impression on your prospective employer. So, don’t be lazy about it. There are plenty of resume’ writing guidelines out there, so I won’t re-hash here. But one piece of advice I’d give is to customize your resume’ for each and every company you really are interested in. Change skills around, add or remove keywords, etc. Anything to get the interview. Same for the cover letter. And for the love of all that’s holy, don’t lie. Don’t call yourself an “expert” unless you really are an expert. You won’t like the interview questions if you claim to be an expert at something you are not. And try to avoid spelling mistakes or typos.

The resume’ can be a Word doc or posted on a job site like Monster. In fact, post the resume’ as many places as possible. And, of course, don’t put stuff like your address/phone number on it. Some sites even let you go incognito. This is a perfect way to weed out discriminatory employers, such as ones who won’t hire minorities or women, for whatever reason.

Keep in mind there are other routes to getting interest in employment outside of the traditional resume’ and job hunt. For instance, blogging about IT can land you some interest and is useful to add to your resume’. Being active in social media, IT forums, etc can also help. It’s also a double-edged sword. You need to be cognizant that everything you say and do on social media can be mined by future employers. They will Google you. Make sure they don’t find anything that disqualifies you.

And remember: the goal of a resume’/cover letter/blog is not to get the job, but to get…

The interview

You have to realize that getting an interview for a job in IT is a pretty major accomplishment. So treat it as such.

I’ve conducted plenty of interviews in my time in IT. I used to come up with a list of questions and read off of that. What I realized is that the people I interviewed had often looked at the same sites I used to cram for the interview. That didn’t make for effective interviews.

These days, when I interview, I go free form. I ask questions that are pretty basic and then I dig deeper and deeper into the subject to test two things: how much the candidate knows and how well they react to not knowing. I’m not necessarily looking for someone who knows it all – I’m looking for how resourceful they are and how well they react to stress.

That doesn’t happen in all interviews. Some are stock questions. Some are long logic problems. Some are just plain weird. Sites like Glassdoor actually have people posting about interviews, which I think is kind of lame, but for someone starting out in IT, it might be useful! And as I previously mentioned, if you said you were an expert on something on your resume’, you better be an expert.

As for dress code, etc… that stuff is all covered elsewhere on the internet. Use your Google-Fu.Yoda Google Fu

Hopefully, you nail the interview and land…

The job offer

If you got picked for a job out of multiple candidates, great! But you’re not done…

Now you have to negotiate. This, for me, is the hardest part of the process because I never know how much to ask for without pissing off whoever I’m dealing with. As I mentioned before, sites like Glassdoor exist to try to level the playing field a bit. They list salaries, job titles, etc. So you can get a ballpark idea of what you should be asking for. I’ve been lowballed several times in my career and likely will be again. But at least I know I’m being lowballed. :-P

The job itself

When you land a job, you want to ensure you do the best you can at staying employed. But don’t kid yourself – the first (or 2nd or 3rd) job you get probably won’t be the only one you ever have. Nor should it be… you want to move around, learn new technologies and diversify your skillset. You also want to make more money. In my personal experience, I have always gotten more money at a new job than I was able to get through raises at my previous job. It’s just the way things work – employers can’t necessarily give large merit increases (especially in down years) to employees. And new employers need to pony up to lure talent away. You will eventually find your “ideal” company, but it may take some time. Before I landed at NetApp in technical support, I never spent more than a year or two at a job. I’d either get bored or realize I didn’t like the company’s culture (or their pay). When I got to NetApp, I realized that I had found a home and was able to learn more there than I ever learned elsewhere. 7 years later and still going strong…

Bringing it back full circle

I’ll cover how I learned to adapt and advance in IT in another post. Hopefully, this post has been helpful for some looking to get into IT. To complete the circle, I’ll reference my English degree and post this Robert Frost quote: