How to Break into (and Succeed) in IT

At a crossroads? Want to make to the move to Information Technology? You can, whether you’re fresh-faced from high school or a mid-career changer.

Any career change is challenging, however, you will find that being smart, teachable, and clear on your strengths will help you transition to the world of tech. Strap yourself in- here are some practical steps you can take now.

Step 1: Do it for the right reasons.

Before you start your I.T. journey, do some introspection and consider whether the industry is right for you. You are the only one who can answer that, and you should go into IT for your own reasons, and no one else’s.

DON’T enter I.T. because someone said you can make a bunch of money at it. You can in fact make a great income, but if money is the only motivation, you will be disappointed. As author Dan Miller says in his bestselling book, 48 Days to the Work You Love says, “…money is never enough compensation for investing one’s time and energy.” Don’t start down this road just because a parent or a trusted person did. You have to have a love for technology at a minimum, because otherwise, you will hate it after a short time.

…money is never enough compensation for investing one’s time and energy. – Dan Miller

DO join I.T. if you keep coming back to it. If you like tinkering with computers and learning, researching, talking, sometimes being wrong and making mistakes (and owning them), this field might be for you.

Step 2: Find an employment model that works for you.

There are many ways to work in I.T.- employee, contractor, freelancer, temporary- and the list goes on. This is a question about how you like to work.

If you like having structure, you can work as an hourly or salaried employee, but your income can be limited to an extent. Bear in mind that this model is shrinking, and has been for some time. Don’t think of it as a bad thing- it’s a actually an artificial model, and quite unsustainable. Only recently, with the advent of factories, has time been traded for money. This is probably how you will start out, especially if you have limited work experience.

If you are a self-starter and make connections easily, working as a contractor or a freelancer can really uncap your income potential. This model based is on compensation for production, rather than hours spent or a set salary. A big plus is that you get to gain control of your time and aren’t beholden to just one company. This actually is more secure in a lot of ways than if you are an employee. You will also have to know what you are doing, and possess some business acumen, but the big secret is that a lot of people with varying levels of expertise do this successfully. More on that later.

Step 3: Learn!

To get into I.T., you will need to learn, learn, and then learn some more. You never stop learning in I.T.- it’s the nature of the business. New tech hits the streets continuously. If you do stop learning, you will quickly find yourself with outdated skills and probably unemployed.

Part of this learning is having a natural curiosity about how technology works. If you have that curiosity or a love for IT, you will find the learning easier. Notice I didn’t say it is easy- but very doable. Loads of free and low-cost information out there can help you. Think YouTube, Spiceworks, Tom’s Hardware, and more. But what about structured training?

You don’t need to spend a fortune to learn like a million bucks.

Structured training is excellent, and will get you subject-matter expertise quickly, but not all training programs are created equal. In general, Experience beats Certification which beats College. This is likely to make you sad if you are spending a pile of money on college. Let’s unpack these starting with that one.


College is great, but it’s also been incredibly oversold as a cure-all for any vocational woes. Many people falsely believe that a degree (or another or more advanced degree) will result in a job, but for most professionals, I.T. included, it’s just not the case. PLEASE don’t fall into the trap of borrowing money for a degree, thinking you’re going to get a huge salary so you can pay it off. Degrees are nice and some companies require them, but they are not necessary in the world of I.T.

This is not to say that IT degrees are worthless. If you already have one, or are close to finishing one, great. Keep going. If you are not in the process, however, think long and hard before getting one. College is absurdly expensive, and you are also going to spend a lot of time and money learning things that won’t always transfer to IT. You certainly learn to become well-rounded at college, but you should not go if you are questioning why you are going. If you want a better bang-for-your-buck, you should consider…


Ahhh… certifications. Many a dream in IT has started with a certification, which, simply put, is a credential obtained by passing some kind of test. Certifications do not mean you know what you are doing, but it’s a great foundation. In IT, certifications abound, but they are not all created equal.

They basically fall into 2 categories- vendor specific (think Cisco CCNA, Microsoft MCSA/MCSE) and vendor agnostic (CompTIA A+, Network+, CISSP). You can self-study with videos online, YouTube, and books. You can also do group study with others (this is awesome), and you can also opt for paid training. All of these options will require a huge commitment of time and money, but you get a lot of very specialized information, much of which will be handy on the job. This beats college because overall it’s cheaper and faster, and you don’t have to take that Eastern Studies in Contemporary Basket Weaving class that will likely be wasted.

College says, “I learned about that”, certification says “I played with that”, and experience says, “Yes, I have actually done that and (may) know what I’m doing.

The downside to certifications are also real. It’s a LOT of work, and most certs require that you re-certify every so many years to stay current- not necessarily a bad thing, but just be prepared to keep learning and spending on it. It will probably pay for itself many times over, but it’s something to think about. Also, if you get certifications, but have no practical experience in that job, you run the risk of being called “Paper (insert_cert_name)” which just means that you got the paper, but may not know how to apply it in the real world.

The value of certifications varies depending on who issues it, and whether or not you have…


Hands down, the most valuable thing to have in IT is real-world, actually-worked-on, yes-I-touched-it-and-broke-it-and-fixed-it-again, good old fashioned experience. College says, “I learned about that”, certification says “I played with that”, and experience says, “Yes, I have actually done that and (may) know what I’m doing.”

A common complaint about experience is this: “I need experience to get a job, but no one will give me a job to get experience.” It’s a classic catch-22.

If you combine certifications, college, and experience, then you will be a force to be reckoned with. You will be competent, people will trust you, and you will probably make some money, too. A common complaint about experience is this: I need experience to get a job, but no one will give me a job to get experience. It’s a classic catch-22, which I will address next.

Step 4: Get to work. Right now.

Do you still want in? Good! Now get to work. The best way to get into IT is just to, well… get into IT! “But I don’t have experience!!1!”, says you. Not a problem, says I. There are actually a number of ways to get started.

Volunteer some place.

People may not be willing to pay you, but might be willing to take a shot on you breaking their stuff in a low-risk environment to get your feet wet. Start reaching outwell-known non-profits or churches to see if you can help them. You can put that on your resume as actual experience.

Start small.

Entry-level IT jobs, like Help Desk, are easy to get, especially if you have some certification or college under your belt (although you don’t need those to get in). This is probably the most sure-fire way to break into IT, but don’t expect to make much money out of the gate. It’s ok, though- if you manage your expectations and can bear the pay, and are pretty sharp, you can move out of Help Desk into other roles pretty swiftly.

Look at Small or Medium Businesses to get into on Help Desk. This way, you’re more likely to touch other IT things. If you get into an Enterprise Help Desk, your job is more likely to be “siloed”, which is a jargon-y way to say very specialized, meaning you will probably do the same tasks repeatedly. The upside is that you will get very good at them, and you will have various specialists at your place, exposing you to other IT roles.

For heaven’s sake- build a home lab!

Once you get your learning going, one more piece you can add to your experience is to build a home test lab. You can use inexpensive hardware and get evaluation versions of software from the major vendors to get some experience. This one really is a no-brainer. Information abounds on SpiceWorks and the internet on how to make one. Bear in mind that you should start small. You don’t need to spend a fortune to learn like a million bucks.

Consider freelancing.

You don’t need to make a career of it (but if you do, it will probably be awesome), but freelancing (read: consulting) is another good way to get IT experience. Think of it as being an IT Mercenary. You may find that people you know or friends of friend may be willing to take a chance on you and let you learn on their dime. This is beautiful because you get to learn with less risk on someone else’s equipment- and make some money to boot! Just be careful to not get into too much that you don’t understand, and make sure that you clearly communicate with the people you work for.

Step 5: Now that you’re in, keep going!

Once you get into IT, it can be a rewarding career, but won’t always be easy.Avoid burnout by giving back to others. Write articles, contribute to forums, help mentor and coach other IT people. Also, never stop learning.

Don’t give up, set goals and keep chipping away at them, and make sure you visit great industry resources like SpiceWorks and others to stay on top of your IT game.

If I helped inspire you to get into IT, please let me know and keep me posted! You can connect with me on TwitterFacebook, and LinkedIn.



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