The cybersecurity field offers an exciting array of career paths, each with unique challenges, skills, and rewards. Whether you're intrigued by ethical hacking, compliance, threat analysis, or engineering, there's a role for every interest. But with so many options—penetration tester, government risk compliance (GRC) professional, SOC analyst, cybersecurity engineer—it’s easy to feel overwhelmed.
As a full-time penetration tester, I know the complexities and nuances of this field. After six years in cybersecurity, I’m here to help you navigate the journey with some practical strategies and insights that can set you on the right path.
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The First Step: Let Go of Analysis Paralysis
In cybersecurity, there’s a significant overlap in foundational knowledge across various positions. Your first role won’t define your entire career, and it's common to switch paths even after years in a particular position. The skills you learn as a SOC analyst, for example, will serve you well if you decide to transition to a penetration testing role later. So, don’t let indecision hold you back—get started with a focus on the basics. By diving into introductory courses and entry-level certifications, you’ll build a solid foundation that applies to all cybersecurity positions.
Tip: The most significant mistake is not starting at all. Overthinking and waiting for the "perfect" career path will only slow you down.
Cybersecurity is also a gateway to other tech domains. If you realize it’s not your passion, you’ll find that foundational cybersecurity skills can lead you to programming, cloud engineering, networking, or other roles within the tech industry.
Strategies for Choosing Your Cybersecurity Path
1. Explore TryHackMe Learning Paths
Platforms like TryHackMe offer a structured way to explore different cybersecurity careers through dedicated paths, including:
Penetration Tester Path: Ideal if you’re interested in ethical hacking and learning how to find vulnerabilities in systems.
SOC Analyst Path: Provides insight into monitoring and defending networks, ideal for those looking to protect an organization’s infrastructure.
Cybersecurity Engineer Path: Focuses on designing, implementing, and maintaining secure networks.
As you progress through these paths, you’ll discover which tasks you enjoy most and gain clarity on your ideal role.
2. Connect with Professionals in the Field
Networking can be instrumental in gaining insider knowledge on various cybersecurity roles. Most cybersecurity professionals are passionate about what they do and willing to share their experiences. Consider reaching out on LinkedIn or attending cybersecurity meetups. Conducting informational interviews with professionals from diverse roles—such as penetration testers, SOC analysts, and engineers—can give you a realistic view of day-to-day responsibilities, pros, and cons.
If reaching out feels intimidating, tune into my podcast, The Hacker’s Cache, where I interview experts working in offensive security. Each episode dives into their day-to-day tasks, career paths, challenges, and insights on entering and advancing in the field. It’s a great way to learn without directly reaching out.
3. Attend My Live Streams
Every Thursday and Sunday, I host a live stream where I tackle challenges on platforms like Hack The Box. These sessions offer a real-time look at what ethical hacking entails, showing you the actual process of testing, analyzing, and troubleshooting security issues. It’s a hands-on way to learn, and you can ask questions in the chat if anything isn’t clear. And if you can’t make it, the past broadcasts are available on my YouTube channel.
4. Go to Cybersecurity Conferences
Networking in person at cybersecurity conferences can be a powerful tool. Many cities host conferences like BSides, and larger events, as well as smaller meetups, are held regularly. These gatherings offer opportunities to connect with professionals, attend hands-on workshops, and listen to industry experts discuss the latest trends and techniques. Attending a conference can be a big investment, but the knowledge and contacts you gain are invaluable for your career.
Tip: Beginners are especially welcomed in these spaces. Cybersecurity professionals love helping newcomers because we’re passionate about growing and strengthening the field.
5. Pursue Cybersecurity Certifications
Certifications can be transformative for your career. They cover essential concepts and offer hands-on skills training, exposing you to a range of cybersecurity domains. I hold 13 certifications, and they’ve been instrumental in my career growth. Entry-level certifications, in particular, provide a broad overview of cybersecurity and can help you identify the areas that most appeal to you.
Check out Top 4 Certifications For Cybersecurity Beginners to see my recommended certifications for beginners.
If you’re unsure about a specific path after exploring these certifications, consider starting with a SOC analyst or cybersecurity analyst role. These positions are among the most accessible entry points in cybersecurity and offer a gateway to many specialized roles. While no position in cybersecurity is easy to break into, SOC analysts are in high demand, and the role provides broad exposure to security practices, making it a great foundation for other career paths.
Why I Chose to Become a Penetration Tester
For me, the path to penetration testing was driven by the appeal of ethical hacking. The “cool factor” of the role and the rewarding challenges it promised were major influences. Penetration testing isn’t easy; it requires thousands of hours of study and practice. But the satisfaction of identifying vulnerabilities, helping secure systems, and protecting clients is unmatched, and I find tremendous fulfillment in my work every day. It’s a journey I’m glad I undertook, and if ethical hacking appeals to you, I highly recommend exploring it.
Final Thoughts
If you’re drawn to cybersecurity but don’t know where to start, remember that taking the first step is more important than having all the answers. Dive into entry-level courses and certifications, connect with people in the field, and explore different domains like SOC analysis, engineering, and penetration testing. Cybersecurity offers flexibility, and you’re not locked into a single role—your career can evolve as your interests and skills grow.
If you found value in this guide, make sure to check out my YouTube channel for more cybersecurity content. And for an in-depth look at my journey, be sure to read From SysAdmin to Penetration Tester: My Path to SkillBridge Internship. The cybersecurity field is waiting for you, so get started today!