DO THIS Before Trying to Break Into Cybersecurity

If you’ve been chasing certifications but still can’t land that cybersecurity job, you’re not alone. I’m here to share my two cents as someone who’s been deep in the cybersecurity job market for the last six years, tracking hiring trends, chatting with recruiters, and talking to hiring managers. In this article, I’m breaking down the biggest mistakes beginners make when trying to break into cybersecurity in 2025—and what you should do instead. Let’s dive in!

Mistake #1: Starting Your Career in Entry-Level Cybersecurity

Now, hear me out on this. If you’ve read my previous articles, you know I broke into cybersecurity through an entry-level cybersecurity rotation program designed specifically for beginners. I landed that job offer back in 2018. But it’s 2025 now—seven years later—and a lot has changed.

Why Entry-Level Cybersecurity Jobs Are Tougher to Get Now

Back then, yes, even just seven years ago (which sounds like forever but doesn’t feel like it), it was much easier to snag an entry-level cybersecurity job. This was before the chaos of 2020, before the massive tech layoffs, and before AI exploded onto the scene. Nowadays, when people talk about entry-level cybersecurity jobs, you’ll hear things like:

• “They don’t exist!”
• “You can’t get an entry-level job in cybersecurity!”
• “There are no jobs available!”

First off, I want to say that’s not true. Jobs are out there. But I’ll be real—it’s significantly harder to start a career in cybersecurity as an entry-level professional in 2025.

What to Do Instead: Start in IT or Help Desk

I know, I know—not everyone wants to hear that their dream career is one door behind another career. But stick with me. IT and help desk roles are some of the most entry-level jobs in tech, and they’re still very technical. For example:

• Helping customers troubleshoot issues
• Learning to configure firewalls
• Managing user permissions or identity access management

These skills are directly transferable to cybersecurity jobs. Starting in IT or help desk isn’t wasting time—it’s boosting your chances by multiple degrees. Why? Because:

• You’ll gain real work experience.
• There are way more entry-level IT jobs than entry-level cybersecurity jobs, making it easier to break into the job market.

Instead of chasing the few and far-between entry-level cybersecurity roles on job boards like Indeed or Monster.com (more on those later), start in IT, networking, or help desk, and then pivot into cybersecurity.

Recommended Resource: Upskill for IT Success

To kickstart your IT career, I highly recommend checking out the beginner IT courses on Upskill. Upskill is a platform where you can learn a variety of skills through free and affordable paid courses. One standout is the CourseCareers IT course by Josh Madakor—a hands-on, practical program where you’ll work with Active Directory, ticketing systems, and troubleshoot real IT issues. It’s designed to take you from zero experience to hired. Plus, they offer a free intro course! Head to Upskill’s IT training programs to explore this course and more to level up your skills.

The Bigger Picture: Cybersecurity Is Still Hot

If you’re worried it’s too late to break into cybersecurity, don’t be. According to the World Economic Forum’s Future of Jobs 2025 Report, the fastest-growing skills by 2030 are:

1. AI (no surprise there)
2. Networks and cybersecurity

Globally, cybersecurity is the second fastest-growing skill in terms of demand and skill gaps. From a governance, risk, and compliance (GRC) standpoint, the need for cybersecurity professionals is just beginning, especially with AI tools, big data, and new tech flooding the scene.

Mistake #2: Getting Stuck in the Job Application Loop

The second biggest mistake I see beginners make is falling into the trap of cold-applying to jobs on massive job boards like Indeed or Monster.com. Let’s be honest—we don’t even know what percentage of those listings are real versus ghost jobs.

The Problem with Big Job Boards

I recently spoke with someone in the hiring space who spilled the tea on how recruiters and headhunters operate. Here’s what they do:

• Post job listings to collect candidate info and store résumés for future jobs.
• Create listings to gauge interest in a role, even if it’s not open yet.
• Leave listings up for weeks or months after the job’s been filled.

It’s a shady practice, and I’ll be real—I’ve sent out hundreds of applications on these platforms and never heard back. Those “easy apply” or “one-click apply” buttons? They’re bait. Thousands of people apply to a single job, and your application probably never gets seen by a human. It sucks.

LinkedIn’s Pros and Cons

A lot of you ask me about LinkedIn. I’ve used it to look for jobs, but their search feature is honestly terrible. I can filter for cybersecurity jobs, and it’ll still show me tutoring roles or other irrelevant gigs. You end up digging through ten listings to find one that’s actually relevant. Plus, those jobs often have hundreds or thousands of applicants too.

But here’s the good part about LinkedIn: sometimes, a hiring manager or recruiter attaches their profile to the listing. If you find a cybersecurity analyst role with a recruiter’s name, here’s what to do:

1. Click on their profile.
2. Send a connection request with a personalized message (not a novel, just a few sentences) about:
   • Who you are
   • A bit about your background
   • That you’ve applied to their job

This makes your name stick in their mind. When they’re sifting through résumés, they’ll remember you. Trust me—hardly anyone does this, and I’ve seen it lead to job offers. One person followed this exact strategy, thanked the hiring manager for the opportunity, and landed the job after a few interview rounds.

Better Alternatives to Big Job Boards

Instead of wasting time on Indeed or Monster, try these:

1. Massive

Massive is a job board that pulls listings directly from company portals, so you know they’re real. Plus, it has an AI tool that customizes your résumé for every job you apply to. It can help you apply to 200 relevant jobs a month—way more than most people manage manually. (It takes me 10-15 minutes to send one tailored application!) This service isn’t free, so only go for it if it fits your budget, but it’s worth checking out on Upskill’s career resources.

2. Smaller, Tech-Focused Job Boards

I’m a big fan of Built In. It’s where I found my last cybersecurity job, so I’m biased, but it’s awesome. They list jobs from startups to bigger companies now, though senior-level roles outnumber entry-level ones. Still, you’ll find a few relevant listings. Explore Built In and other career tools on Upskill’s job search tools to level up your job search game.

Mistake #3: Getting Too Many Cybersecurity Certifications

You might be thinking, “Is there such a thing as too many cybersecurity certifications?” Yes. Yes, there is.

The Certification Trap

I get tons of messages daily on Facebook, TikTok, and Instagram (shoutout to our community—join us via Upskill’s community hub!). The people struggling the most often have alphabet soup behind their names—three, four, five certifications—and they’re still not landing jobs. Why? The cybersecurity industry does beginners dirty by making us think piling up certifications will get us hired. Spoiler: it won’t.

What Really Gets You a Cybersecurity Job

To land a job, you need a mix of:

1. Certifications (but not too many)
   Aim for Security+ and maybe one or two more. That’s enough to start.
2. Technical Cybersecurity Projects
   A lot of people skip this, thinking certs are enough. They’re not. Build a portfolio of hands-on projects to show you can apply your knowledge.
3. Networking
   This could be at conferences, on LinkedIn, at BSides, or even in our community channels. Engage with the community, meet people, and put yourself out there.

Certifications alone won’t cut it—not 100%, not 90%, not even 60% of the time. You need projects and connections to back them up.

Building a Strong Portfolio

I highly recommend creating a cybersecurity technical project portfolio. I’ve written articles on this, including one on building your own cybersecurity home lab—a great starting point. Check out these guides and more on Upskill’s project portfolio resources. Hands-on experience is what impresses interviewers. In an interview, don’t just parrot foundational knowledge. Talk about:

• How you’ve implemented concepts
• Projects you’ve built
• Tools or skills you’ve learned and applied

That’s what grabs their attention.

Wrapping It Up

That’s it for this article—I’ve yapped for a while! If you’ve got questions, drop them in the comments below. Made other mistakes as a beginner in cybersecurity? Share your story! If you’ve broken into the field recently, I’d love to hear your experience and any advice for the community.

All the resources mentioned are available on Upskill’s learning platform, where you can explore free and low-cost courses to level up your skills. If this article was helpful, please consider liking and sharing—it really helps spread the word. Stay connected with me on Facebook, TikTok, or Instagram (find links on Upskill’s community page). I’m on those platforms almost daily, and I post new articles weekly. Hopefully, I’ll see you in the next one—stay curious and keep learning!