Key Lessons From Cybersecurity Career Paths

If I could restart my cybersecurity career, here's what I'd do differently: I spent my first 2 years trying to learn everything about security. Firewalls, pentesting, malware analysis, cloud, GRC, incident response—all of it. Result? I was mediocre at everything and great at nothing. What actually worked: Pick a lane and go deep first. I chose cloud security and IAM. Spent a year becoming the "Azure security guy" on my team. Learned Sentinel inside and out. Mastered Entra ID and Conditional Access. Got really good at one thing. Then the other skills came easier because I had context. Stop chasing every certification. Early on I thought certs = career progress. They help, but they're not enough. Security+, AZ-500, and working toward CISSP? Great. That's a solid foundation. But the hiring manager cares more about: "Have you actually built a SIEM from scratch? Can you architect Zero Trust? Have you led an incident response?" Experience > certifications. Every time. Get comfortable with "I don't know... yet." Security is too broad for anyone to know everything. The people who succeed aren't the ones who pretend to have all the answers. They're the ones who know how to figure it out fast. Build in public (even a little). I wish I'd started sharing what I was learning earlier. Write a blog post about implementing Conditional Access. Post a KQL query that solved a problem. Share lessons from an IR. It builds your reputation and helps others. Win-win. Bottom line: Specialize first, generalize later. Get hands-on experience however you can. Stay curious. And don't compare your chapter 1 to someone else's chapter 10. What's one thing you wish you'd known earlier in your security career? #Cybersecurity #CareerAdvice #InfoSec #CloudSecurity #CyberSecurityCareers #ITSecurity

Most cyber advice is wrong. These mistakes cost careers. I see the same pattern every time someone tries to break into cybersecurity. Smart people. Motivated people. People doing everything they were told to do. And still… no progress. Not because they aren’t capable, but because they’re following advice built for a different era of cyber. Cybersecurity today isn’t about:  • collecting endless tools  • hoarding certifications  • waiting until you feel “ready” It’s about:  • understanding risk and trade-offs  • communicating clearly with non-technical teams  • showing how you think, not just what you’ve studied Most entry-level candidates fail not at the technical stage, but at the trust stage. Hiring managers are asking: “Can I rely on this person?” “Do they understand business reality?” “Will they reduce noise or add to it?” This carousel breaks down the 7 biggest mistakes I see career switchers make, and the simple shifts that change everything: 1. Tool Obsession: Focusing on tools instead of understanding risk ↳ Learn why controls exist before tools ↳ Understand risk trade-offs, not configurations ↳ Practice explaining security in plain language 2. Cert Hoarding: Collecting certifications without demonstrating applied capability. ↳ Use one cert to build examples ↳ Document decisions, not just completions ↳ Show learning through real scenarios 3. Copying Tech CVs: Using technical CV formats that hide business skills. ↳ Lead with outcomes, not responsibilities ↳ Translate experience into cyber-relevant impact ↳ Align skills to role risk areas 4. Ignoring Business Context: Treating cybersecurity as isolated from commercial and ops realities. ↳ Learn how organisations actually make decisions ↳ Understand cost, risk, and trade-offs ↳ Frame security as business enabler 5. Waiting To Feel Ready: Delaying action until confidence appears, instead of building it through action. ↳ Apply while learning, not after finishing ↳ Accept discomfort as growth signal ↳ Learn publicly, refine privately 6. Solo Learning: Trying to navigate cybersecurity alone without guidance or feedback loops. ↳ Learn from people already in-role ↳ Ask better questions, not more questions ↳ Get feedback early, adjust faster 7. Misunderstanding Entry Roles: Expecting senior responsibility without first building trust and exposure. ↳ Focus on reliability before visibility ↳ Learn systems, people, processes patiently ↳ Build credibility through consistency If you’re serious about entering cyber, clarity matters more than confidence. Mistakes are normal. Repeating avoidable ones is optional. ♻️ Repost to help a career switcher ➕ Follow Victoria Coker for practical, non-tech pathways into cybersecurity #AskVictoria Coker

𝟑𝟎 𝐲𝐞𝐚𝐫𝐬 𝐢𝐧 𝐜𝐲𝐛𝐞𝐫𝐬𝐞𝐜𝐮𝐫𝐢𝐭𝐲. 𝐇𝐞𝐫𝐞 𝐚𝐫𝐞 𝐭𝐡𝐞 𝟔 𝐥𝐞𝐬𝐬𝐨𝐧𝐬 𝐞𝐯𝐞𝐫𝐲 𝐂𝐈𝐒𝐎 𝐥𝐞𝐚𝐫𝐧𝐬 𝐭𝐡𝐞 𝐡𝐚𝐫𝐝 𝐰𝐚𝐲👇. 𝟏. 𝐒𝐞𝐜𝐮𝐫𝐢𝐭𝐲 𝐦𝐮𝐬𝐭 𝐞𝐧𝐚𝐛𝐥𝐞 𝐛𝐮𝐬𝐢𝐧𝐞𝐬𝐬 If security blocks growth, it gets ignored. If it enables growth, leaders support it. 𝟐. 𝐓𝐚𝐥𝐤 𝐫𝐢𝐬𝐤, 𝐧𝐨𝐭 𝐭𝐨𝐨𝐥𝐬 Boards don’t care about your stack. They care about impact, scenarios, and trade-offs. 𝟑. 𝐋𝐢𝐬𝐭𝐞𝐧 𝐛𝐞𝐟𝐨𝐫𝐞 𝐟𝐢𝐱𝐢𝐧𝐠 The best insights come from: -Analysts -Engineers -Business teams Your job is turning their reality into strategy. 𝟒. 𝐒𝐭𝐫𝐚𝐭𝐞𝐠𝐲 𝐦𝐞𝐚𝐧𝐬 𝐜𝐡𝐨𝐨𝐬𝐢𝐧𝐠 You can’t fix everything. Protect what matters most. Monitor the rest. 𝟓. 𝐁𝐮𝐢𝐥𝐝 𝐩𝐞𝐨𝐩𝐥𝐞, 𝐧𝐨𝐭 𝐣𝐮𝐬𝐭 𝐜𝐨𝐧𝐭𝐫𝐨𝐥𝐬 Tools change. Strong teams last. 𝟔. 𝐏𝐫𝐨𝐭𝐞𝐜𝐭 𝐲𝐨𝐮𝐫 𝐨𝐰𝐧 𝐫𝐞𝐬𝐢𝐥𝐢𝐞𝐧𝐜𝐞 Exhausted leaders make bad decisions. Guard your time. Ask for help. Build support. Cybersecurity leadership is not about being heroic. It’s about being 𝐬𝐮𝐬𝐭𝐚𝐢𝐧𝐚𝐛𝐥𝐞. If you're early in cybersecurity: 𝐖𝐡𝐢𝐜𝐡 𝐥𝐞𝐬𝐬𝐨𝐧 𝐰𝐢𝐥𝐥 𝐬𝐚𝐯𝐞 𝐲𝐨𝐮 𝐭𝐡𝐞 𝐦𝐨𝐬𝐭 𝐩𝐚𝐢𝐧 𝐥𝐚𝐭𝐞𝐫? ------ Hi, I’m Harris D. Schwartz, 𝐅𝐫𝐚𝐜𝐭𝐢𝐨𝐧𝐚𝐥 𝐂𝐈𝐒𝐎 & 𝐂𝐲𝐛𝐞𝐫𝐬𝐞𝐜𝐮𝐫𝐢𝐭𝐲 𝐋𝐞𝐚𝐝𝐞𝐫. I help CEOs and executive teams strengthen their security posture and build resilient, compliant organizations. With deep expertise across 𝐍𝐈𝐒𝐓, 𝐈𝐒𝐎, 𝐏𝐂𝐈, 𝐚𝐧𝐝 𝐆𝐃𝐏𝐑, I focus on making security a business enabler, not just a control function. If you’re planning how your security program should evolve in 2026, this is the right time to start the conversation. #cybersecurity #infosec #CISO #cybersecurityleadership #riskmanagement #securitystrategy #infosecleadership #cyberrisk #securityculture #leadership

If I could go back and talk to my younger self when I first started in cybersecurity… I’d tell him a few things that would’ve changed the entire game. Now that I’ve been in the RMF and cybersecurity space for 5 years, I look back and realize there are lessons I wish I’d learned sooner lessons that could’ve helped me navigate this field faster and smarter. 1. You can’t do it alone. When I started, I thought if I just worked hard enough, I could figure it all out get the job, build the resume, and break into the right rooms. But everything I’ve accomplished came through community people who shared opportunities, reviewed my resume, or taught me what to look for. The truth is: collaboration gets you further than isolation ever will. 2. Network early and often. In college, I wish I’d gone to more cybersecurity events, joined more orgs, and interned more. Networking isn’t optional it’s the fuel that moves your career forward. Most of your biggest breaks will come from people, not job boards. 3. Build your personal brand. Your brand is your reputation in digital form. I wish I started earlier on LinkedIn sharing my projects, documenting my journey, and connecting with professionals in my space. That changed everything for me later on. 4. Stay ahead of the trends. I once wrote a paper on Bitcoin before it blew up… and didn’t invest. Lesson learned. The same applies in cybersecurity if people are talking about AI, Cloud, GRC Engineering, or Quantum Security, learn them now. Be early. Expertise in emerging areas will keep you employed forever. These are things I wish I knew when I started. If you’re trying to break into cybersecurity or move up in RMF learn from my mistakes, apply these lessons, and move with intention. You’ll thank yourself later. #CyberSecurity #RMF #CareerGrowth

If I had to restart my cybersecurity journey from zero… this is exactly what I’d do. No BS. No 20 certs. No “learn everything.” No endless YouTube rabbit holes. Just a practical, step-by-step path that actually works 👇🏽 1) Pick your lane (so you don’t waste months) Cybersecurity is not one job. Choose a starting lane: Blue Team (Defense): SOC, incident response GRC (Governance/Risk/Compliance): policies, risk, audits Cloud/Security Engineering: AWS/Azure security AppSec: secure coding, web app security If you’re unsure, start with Blue Team or GRC — easiest entry points. 2) Learn the fundamentals like a normal human You only need 4 foundations: ✅ How the internet works (basic networking) ✅ How accounts/logins work (identity & access) ✅ How data is stored & moved (endpoints + cloud basics) ✅ How attacks happen (common scams, phishing, malware) If you can explain these to a 12-year-old, you’re ready to move on. 3) Build a simple home lab (don’t overcomplicate it) You don’t need fancy gear. One laptop VirtualBox (or any VM tool) A Windows VM + a Linux VM Practice: updates, users, permissions, firewalls, logs Your goal: get comfortable touching systems without fear. 4) Learn security by solving real problems (not theory) Do these weekly: Spot phishing attempts (email examples) Set up MFA everywhere Secure a home Wi-Fi router Review permissions on your phone Practice incident basics: “What would I do first?” Security is a habit, not a textbook. 5) Pick ONE beginner cert (not five) If I was restarting today, I’d choose ONE: ISC2 CC (great foundation) Or Security+ (widely recognized) One cert + real practice beats 6 certs and no skills. 6) Create 3 portfolio projects (this is what gets interviews) You don’t need a job to build proof. Examples: A “Home Network Security Checklist” with screenshots A “Phishing Spotter Guide” with real examples A “Incident Response One-Pager” for small businesses Put them on LinkedIn or a simple portfolio page. 7) Start showing up on LinkedIn the right way Don’t post “I’m excited to learn cybersecurity” 50 times 😅 Post what you’re learning like this: “Before you click a link, do this instead…” “How to secure your email in 5 minutes…” “What I learned from a scam attempt today…” Consistency builds credibility. 8) Apply for realistic entry roles (don’t aim too high too early) Start here: SOC Analyst (Tier 1) IT Support with security focus GRC Analyst / Risk Analyst Security Coordinator Identity Admin (IAM support) Security careers often start adjacent to security. 9) Find a mentor + community (this speeds everything up) One good mentor can save you a year of guessing. Join communities, ask for feedback, and build relationships — not just resumes. 10) Be patient, but aggressive This journey rewards consistency. If you do the basics daily for 90 days, you’ll be shocked at the progress. Share this with someone considering a career transition 🙂

⚠️ If I had to start over in 2026, this is exactly what I’d do. ⚠️ Every career starts somewhere and mine started in the trenches as a Helpdesk Technician. Printers. Password resets. “Have you tried turning it off and on again?” That role didn’t feel glamorous but it sparked curiosity. Curiosity turned into skill-building. Skill-building led me into cybersecurity. I’m still a firm believer in earning your stripes. Cybersecurity is not a shortcut career. It’s built layer by layer. If I were starting fresh in 2026, here’s how I’d approach it 👇 1️⃣ Master the IT Fundamentals (Still Non-Negotiable) Before security, you need systems knowledge. Start with CompTIA A+ (or the equivalent hands-on learning): • Hardware & operating systems • Troubleshooting methodology • How users actually break things Why this still matters in 2026: ➡️ AI didn’t remove the need to understand systems, it made it more important. ➡️ You can’t secure what you don’t understand. 2️⃣ Learn How Things Connect (Networking Is Mandatory) Next: Networking. Study Network+ or CCNA to learn: • How data moves • Common protocols & ports • What “normal” traffic looks like Why this matters more than ever: ➡️ Cloud, zero trust, and remote work all sit on networking fundamentals ➡️ Security alerts make zero sense without networking context This is the point where many people try to skip ahead. Don’t. 3️⃣ Build a Security Foundation (Not Just a Cert) Once the fundamentals are solid, move into Security+ or equivalent learning: • Threat types & attack vectors • Risk management • Defensive controls & security concepts But in 2026, here’s the upgrade: ➡️ Pair Security+ with hands-on labs, cloud basics, and exposure to real tools ➡️ Certs open doors but skills keep them open 4️⃣ Get Comfortable With Learning Forever This is the part people don’t talk about enough. Cybersecurity changes constantly: • New threats • New tools • New expectations The most successful people aren’t the smartest, they’re the most adaptable. TRUST THE PROCESS. Cybersecurity is not overnight success. It’s: • Time • Repetition • Failure • Small wins stacked consistently Be patient with yourself. Celebrate progress—even when it feels small. I’d love to hear your story 👇 What path worked for you? What would you do differently if you were starting today?

As a member of L0pht Heavy Industries in the late 1990s, we shook up the cybersecurity world by exposing systemic flaws in software through full disclosure and advocacy. Testifying before the U.S. Senate in 1998, we weren’t just hackers. We were catalysts for change, pushing for accountability and transparency in a world that often ignored vulnerabilities. Those experiences shaped my approach to cybersecurity, and they hold critical lessons for today’s professionals navigating an AI-driven, hyperconnected threat landscape. In my recent Forbes article, I reflect on how the clash of hacker culture with industry norms sparked a revolution in software security. From adversarial beginnings, we learned that collaboration beats confrontation. Working with Microsoft in the late '90s, we helped shape coordinated disclosure policies and methodologies like threat modeling and fuzzing, practices now foundational to secure development. For today’s CISOs, engineers, and tech leaders, the takeaway is clear: security is a human endeavor as much as a technical one. Build a culture where uncomfortable truths are welcomed, and empower your teams to raise issues without fear. Embed security early in the development cycle to balance speed and innovation. Foster partnerships with researchers and the open-source community to drive resilience. As AI accelerates vulnerability discovery, create pathways for responsible disclosure and red-teaming to stay ahead of machine-speed threats. The spirit of L0pht, curiosity, principled dissent, and democratizing knowledge, remains vital. Hire for creativity, promote truth-tellers, and build psychological safety so your teams can think like attackers to protect what matters. Read more about how these lessons apply to today’s cybersecurity challenges: https://lnkd.in/ei_PnYPz #Cybersecurity #SoftwareSecurity #Leadership #Innovation #L0pht

5 lessons from a cybersecurity journey no one tells you about. Most people think cybersecurity careers start with degrees, certs, and perfect résumés. This episode will destroy that myth. Kevin went from fast-food worker → NYPD → IT → Senior SOC Analyst… and his story is one of the most honest, practical breakdowns of how real careers in tech actually happen. We got into the stuff nobody talks about: → Why restaurant workers can make better IT pros than engineers → How “nobody cares unless it’s broken” is the most important lesson in tech → Why communication skills can beat technical certs → How to talk to executives so they don’t buy a cappuccino machine instead of your security tool → Why fundamentals matter more than any security buzzword → And the brutal truth about entry-level cyber jobs you don't know If you’ve ever wondered what it really takes to grow in IT or cybersecurity, this episode is a playbook. I sat down with Kevin Apolinario of Kevtech Academy on The Keyboard Samurai Podcast Kevin’s journey is insane, inspiring, and painfully relatable. And the insights apply to anyone trying to break in or level up. 🎧 Listen to the full episode: https://lnkd.in/eESyrway 💬 What was your first “real” lesson in IT or security? 🔄 Repost to help educate others 📲 Follow Wil Klusovsky for wisdom on cyber & tech business

Cybersecurity Career Tips #1 If you want to enter the cybersecurity field, it’s not enough to just pick a list of courses, complete them, generate certificates, and think the job will come naturally. And it’s definitely not just about adding certifications to your resume that’s only one step in the process. It’s essential to learn what is applied in real work contexts. You don’t need to study C if you’ll never use it in your daily tasks. Your studies should be aligned with your actual needs. My first recommendation if you want to become a cybersecurity professional is to understand what the market is looking for. Analyze open positions in your region or remote roles, define the requirements for each position, and identify the practical skills you need. Platforms such as HackTheBox, TryHackMe, PortSwigger Academy, PentesterLab, and Root-Me are excellent for hands-on learning. I strongly recommend investing your time in acquiring real-world skills. Write write-ups, share your journey here on LinkedIn or other networks, build personal projects and publish them on GitHub, connect with other professionals, and expand your network both online and at industry events. Also, develop your soft skills. Communication is critical, even in a job interview. Being able to translate technical issues into business impact is just as important as technical knowledge. A common way to start a career is by working in consulting firms. There are many opportunities at different seniority levels. It may not be your dream job, but it opens doors. Prepare your resume for the positions you aim for and highlight the key points that match the role especially if specific knowledge is required. A resume will only be considered if it demonstrates the right skills, relevant training or certifications (to validate your expertise), and professional autonomy. And don’t limit your job search to LinkedIn. It’s great for networking, but when it comes to landing jobs, explore alternatives. Target companies that interest you and check their career pages many positions are never posted on LinkedIn. Above all, stay focused. Don’t try to learn everything at once. Concentrate on what will land you your first job, and then expand your knowledge base to increase your seniority or pivot to other areas. But the real secret lies in how you communicate and sell your work your knowledge, your problem-solving mindset, and your ability to handle situations consistently. #CyberSecurity #InfoSec #CareerAdvice #Hacking #TechJobs #SoftSkills

A friend of mine recently transitioned into cybersecurity, and only a few months in, she's already feeling the frustration that comes with navigating what seems like an oversaturated field—especially for those just starting out. It's easy to feel disheartened when it looks like there's a sea of talent all competing for the same roles. But here's the truth: while cybersecurity is growing rapidly, with more professionals entering the field, there are still countless opportunities for those who know how to stand out. If you're starting out like my friend, these tips can help you rise above the noise. 1. Don't Be a Generalist: Cybersecurity is incredibly broad, with many specialized areas. The earlier you identify your niche, the better. Avoid the temptation to learn everything all at once. Instead, focus on discovering your areas of interest and strength. 2. Share as You Learn: Many people fall into the trap of thinking they need to be experts before they can share knowledge. This is imposter syndrome at its finest! You don't have to wait until you're a seasoned pro to share what you know. By sharing your journey and the things you're learning, you not only solidify your own knowledge but also build credibility within the community.   3. Be Authentic: Don't see your lack of a technical background as a disadvantage. Instead, use your previous experiences to your advantage—they can be your competitive edge. For example, a colleague transitioned from Mass Communication to VAPT. She was able to leverage her communication skills as an asset in her cybersecurity career. 4. Have a Visibility Strategy: Visibility matters no matter how good you are. Especially for introverts, the idea of visibility can seem daunting, but it's crucial. Create a strategy to showcase your work and your progress. This could be through networking, attending industry events, contributing to forums, or being active on professional platforms like LinkedIn. The goal is to ensure that people in your network and beyond are aware of your skills. 5. Be Persistent: The journey isn't always easy, and facing rejection or feeling like progress is slow is common. But persistence is key. Keep applying, keep learning, and keep expanding your network. Every rejection brings you closer to the right opportunity. 6. Stay Current with Industry Trends: Cybersecurity constantly evolves, with new threats, technologies, and strategies continually emerging. My strategy for this is to subscribe to industry newsletters, participate in webinars, and follow thought leaders to remain informed and keep my skills relevant. 7. Ask for Help: Cybersecurity is a community, and you're not alone in your journey. Reach out to others for advice, guidance, or mentorship. Don't be shy—building connections with others is essential to growing in the industry.