My First Attempt at Breaking Into IT — Why It Was Harder Than I Thought (Full Series)

A 20-part series sharing every struggle, failure, and breakthrough I faced trying to land my first IT job — so you don't have to go through it alone.

I've been there if you're stuck trying to break into IT — applying to jobs and hearing nothing back.

In this series, I'm sharing my raw, honest journey — from tagging clothes at my sister's dry cleaners to finally landing a job in tech.

Because I wish someone had told me what I'm about to share with you.

I didn’t wake up one day and randomly decide to get into IT. Looking back, I think it was always a part of me — I didn’t know it could be a career.

As a kid, I was always curious about how things worked. I used to take apart VCRs, radios, and anything electronic I could handle. Sometimes, I put them back together; sometimes, I didn’t, but I always tried to figure out what was inside.

Later, when I got older and finally had a little money, I built my computer — mainly to play games—but putting it together, troubleshooting, and learning what every part did lit a fire in me. I loved it.

So for me, IT was a passion before it was about money.

First Steps Toward an IT Career — Self-Taught Hustle

When I finally decided to take IT seriously as a career, I did what many people do — I started studying for certifications. Back then, the CCNA was "the" certification to get if you wanted to get into networking or IT. Everyone was talking about it.

I didn’t have much money for school, so I taught myself. I used Udemy courses and YouTube videos—whatever I could find online. This was around 2007-2008, when the internet started to explode with content, right around the time the economy crashed.

I studied hard. I sat the first CCNA exam but failed the second part. That crushed me at first, but I didn’t stop. I returned, studied harder, and eventually passed, getting my CCNA and passing the first test of CCNP.

At that point, I thought, “Okay, I’m ready. Someone’s going to hire me now.”

But that’s not what happened.

Reality Check — Misconceptions and the Job Hunt Wall

I thought getting my CCNA meant doors would open, but they didn’t.
I kept applying for jobs, but nothing was happening.

Meanwhile, I was working at my sister’s cleaners.

Tagging clothes.
Handing customers their orders.

But behind the scenes? I was running all the tech stuff:

• Fixing computers

• Managing their network

• Installing security cameras

It wasn’t glamorous, but looking back, it was real IT work, even though it didn’t feel like it then.

Still, I felt stuck.

I would look around and see other people breaking into IT, getting jobs, moving up — and there I was, still working in a cleaners, feeling like I wasn’t getting anywhere, even though I was doing all the right things:

• Studying

• Certifying

• Applying

Frustration and Doubt

I’m not going to lie — it was frustrating.
I had poured so much time and money into getting the CCNA, and nothing was happening.

And when you see other people succeeding while you’re struggling, it makes you start to question yourself:

• Am I even good enough for IT?

• Maybe I’m just not smart enough.

• Why is it working for everyone else and not for me?

Support System — But Still Feeling Alone in the Fight

My sister always supported me, and later, when I met my wife, she also supported me, but even with their support, I still felt like I was fighting this battle alone.

Because no one understood how hard it was to break into IT when you’re starting from nothing — no degree, no connections, no fancy experience.

Coming Next — When It Got Worse Before It Got Better

In the next part of this series, I’ll share how I struggled—even after getting my foot in the door with small IT jobs.
It wasn’t what I expected, and I almost gave up for good.

I've been there if you’re reading this and you feel stuck.
Keep following this series because I’ll show you exactly how I went from working in a cleaners to eventually landing a job at a Big Tech company — and what I did that finally worked.

If You’re Struggling to Break Into IT, You’re Not Alone

If you’re grinding, studying, applying, and hearing nothing back, I see you.
I’ve been there, and I know how hard it is.

But don’t give up.
If I made it through, you can too.

Start Here: My Journey to Breaking Into IT — Full Series

Stay tuned for Part 2: The First Jobs I Took To Survive

Want a step-by-step guide to landing your first IT job?

I've been there if you're tired of sending resumes into a void and second-guessing yourself before every interview. That's precisely why I wrote these books — to help you break into tech faster and with fewer mistakes than I made.

Break into IT: Witout Losing Your Mind(Kindle & Paperback)

Breaking Into IT: The 16-Step Roadmap to Land Your First Tech Job

They're honest, relatable, and built for people like you — no degree or fancy background required. Just clear guidance from someone who's been through it.

Check them out — and if they help you, I'd love an honest review. It means more than you know.

Want a simple, step-by-step guide to get started in IT?

Download my free 5-Step IT Career Roadmap

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