Strategies for Success in Defense and Intelligence Careers

I was recently asked what I would do today if I were in the military and made the decision—or had the decision made for me—to transition out before retirement. Whether you’re in the Army, Marine Corps, Navy, Air Force, Space Force, or Coast Guard, my advice is the same. Here’s what I’d focus on to set myself up for success: 1️⃣ Eliminate Debt: I’d make getting out of debt a priority—everything except a mortgage. If possible, I’d pay that off too. Debt limits your options and can force you to compromise on critical decisions. Freedom from financial burdens creates flexibility. 2️⃣ Max Out My TSP Contributions: I’m a fan of Roth, but whether you choose Traditional, Roth, or a combination, the key is to save aggressively. Your future self will thank you. 3️⃣ Leverage Tuition Assistance (TA): If you don’t have a degree, get one. If you have a bachelor’s, pursue a master’s, and focus on something value-added to your goals. For those in tech, chase certifications with the same determination. TA covered 100% of my BA and MS when I was in the Marine Corps—take full advantage of it! 4️⃣ Network Relentlessly: Create a strong LinkedIn profile. Post 3+ times weekly about the field you want to enter—cybersecurity, business, defense contracting, etc. Attend seminars, trade shows, and any networking opportunities available. Respond when people reach out, and always follow up with a thank-you note. Networking isn’t just online; it’s face-to-face too. Build a large, strong network to maximize opportunities. 5️⃣ Document Everything: Complete and document your medical, dental, vision, and hearing appointments. Keep a copy too. 6️⃣ Protect Your Reputation: Finish strong. Nothing is more important than your last name and professional reputation. Stay 100% committed to your assignment. Dropping your pack in uniform will hurt your endorsements and recommendations. Excellence until the end sends a message: you’re someone worth investing in. 7️⃣ Weigh SkillBridge Thoughtfully: This is personal. I wouldn’t choose SkillBridge because I’m not interested in working for free. Instead, I’d save my leave and use those 60+ days to focus on my transition. PTAD/PTDY can also provide valuable time to reset. 8️⃣ Learn from Fellow Veterans: Reach out to those who’ve transitioned successfully. Ask questions, seek advice on resumes, interviews, starting a business, consulting, contracting, or government roles. Follow up and implement what you learn. 9️⃣ Plan Time Off: Whether you served 4 years or 20+, you’ve earned a break. Take time to decompress, reflect, and think clearly about your future. Be proud of your service—it’s a foundation for what comes next. What Did I Miss? This list reflects what I’d do, but I’d love to hear your thoughts. What would you add? Where do you disagree? To all of you who have served: thank you for your service and sacrifice.

Surprise is an intelligence team’s top adversary. Here are several methods to reduce its likelihood. While surprise appears to come from external events, it more often results from our own limited thinking. These six methods help to reduce the likelihood of surprise: 1.     Get your head out of the current. Intelligence teams can get stuck reacting to the latest news or reporting, cycling from one event to the next. You must create time to look at broader and longer term issues and not get trapped in the current. 2.     Talk to others. Discuss your assessments and thoughts with people outside the immediate team. This should include operations teams as well as other intelligence teams and functions. They won’t see things exactly the same way, and even a 10% difference uncovers new lines of analysis. 3.     Look into other areas and topics. Developing an analyst’s subject matter expertise requires time and focus. However, this can turn into tunnel vision. With increased interconnectivity, analysts need to anticipate the quick adoption of techniques and technologies into their area of expertise. 4.     Structured analytical techniques that test assumptions or generate multiple scenarios force an open mind. Red hatting is an obvious choice. But the important point is using them routinely, not only when something happens. 5.     Ongoing monitoring after an assessment is published. Production is often detached from collection. An intelligence report captures a point-in-time assessment but must then be monitored against new information to see if it holds or must be updated. One intelligence cycle produces a report, the next cycle monitors. 6.     Narrow down your focus. This appears counter-intuitive at first, but breaking down the general picture into specific things to look for makes intelligence work easier. How narrow is context dependent, but for example, identifying surprise in the next week is an easier problem than looking at the next 5 years. No single method is sufficient, and even all six together can't guarantee zero surprise. What matters most is building a proactive culture. This is done by planning out analytical sessions, conscious reviews, and a deliberate approach to seeking new information. Surprise thrives when we accept the status quo. A proactive culture encourages all team members to continuously scan ahead and challenge assumptions as standard practice. #intelligenceanalysis #intelligenceleadership #intelligencetraining

Years of playing strategy games growing up has led me to love career strategizing. After pivoting from geopolitical intel to CTI, I started to mentor others on how to make similar transitions. Here’s a high-level strategy I use to help people pivot into a new role. Long-term aspiration; medium-term goals; short-term objectives. Long-term aspiration: → Start with the end-goal in mind by working out the job specialization you want → Check your assumptions about that specialization and research the daily reality of that job to ensure you will be happy doing it Medium-term goals: → Find job descriptions for the role you want (if cyber: check the NICCS NICE framework) and go through them line-by-line with a highlighter → Highlight green if you have that skill/experience/knowledge; yellow if you partially have it; and red if you do not at all → Use the yellow and red highlights to identify your priority gaps Short-term objectives: → Develop a list of achievable objectives to turn your gaps from red to yellow, then from yellow to green → These objectives can include doing a course, training yourself on a new tool, job shadowing, reading textbooks, publishing analysis, etc. → Set up a schedule to consistently work on one objective at a time Strategies rarely offer quick fixes but if you can persistently tick off the objectives, the rest will follow in suit.

People often approach me and ask how to get started in an OSINT career. Let’s discuss. The first answer is “it depends”. People have different ideas of what OSINT is and isn’t. Some prefer to work in an institution and others want to be independent. While there are some differences for each of these, there are a lot of things that are universal. 1. Surround yourself with people who are much smarter than you. This is how you learn and challenge yourself. 2. Be bold in the attempt. We learn fastest through trial and error. This is not the same as failure. There is no failure in the activity of OSINT except not trying and not stretching. 3. Take some courses. There are many fantastic certificates you can get for free. Keep an eye on Amy Brooks, weekly roundups. She posts about interesting trainings. Or take one of Angie Gad's trainings! 4. Volunteer - Many excellent organizations that really need help. You have the skills — help them. 5. Be humble. Back in the day when I was a theatre major in college, I had a professor who used to say “humble yourself to the work”. That means check your ego at the door and focus on the task at hand. You aren’t better than anyone — everyone has different strengths. 6. Be a generous peer and team member. It costs you nothing to share your experience, tradecraft and advice. Uplift each other. That’s how this community thrives. 7. Find a workflow that works for you — and then iterate over and over until it is not just “good enough” but excellent. This will make you faster and more accurate. 8. Read widely. People are always surprised when I say I don’t generally read OSINT books. What I do read is books that make me or bring joy. Dean Baratta posts often about things you would not think align with intelligence work but they do. Why? Because nothing exists in a vacuum and we all exist in the world. 9. Find excellent mentors who are willing to take you under their wing. This can be more formalized or it can be that person who is always willing to help give guidance when you need it. (see No. 6 about uplifting each other) 10. Find a way to remain open even when you have to watch your security posture. Your life will be better for it. 11. Be curious about everything. Return to that four year old self who asked question after question after question about life, the world and the nature of things and people. 12. Don’t stop at the lowest common denominator. If you are tasked with doing something, don’t just do the bare minimum. Always bring your A game. A reputation is the easiest thing to lose and once gone, there is no getting it back. 13. Be passionate. 14. Be hungry for knowledge. 15. Be balanced — You must have balance in your life. If you don’t have many real-world friends find them. Be a part of the world — not apart from it. [to be continued... ]

As an intelligence specialist that got farmed out to different organizations, one of the first personal objectives is building good relationships (rapport and trust) with the supported/supporting element. Some of the things I would do is truly learn how things are done within that organization, be smartly helpful, and project "asset not liability" by being humbly competent in the things they cared most about, which often meant just being great at my specialty and using that to make them more successful than if I was not there at all. When I say smartly helpful, what I mean is occasionally I would do things that weren't really my job, but would demonstrate I was a team player, competent or familiar in things they cared about, and was just in general a person they saw as value add. I say "smartly," because you don't want to make them think your job is something that it isn't; you don't want to be the forever hero that compensates for systemic shortcomings, etc. It can be hard to thread the needle between "helpful team player" and "toxic heroics." Overall, organizations are made up of people, people form opinions, and whether their opinions are based on misperception or not, your success as an individual is often about whether or not you have built the trust with the organization you are riding alongside. It can be challenging, but it's part of the job. This advice is good for all, but it's something I strongly encourage CTI people to focus on, since that's a primary audience for this channel.

If you’re still waiting for AI to hit your job — it already has. Now’s the time to lean in and lead. And it’s moving faster than most people realize. Here’s what’s really going on: 1. The Adversary Advantage AI is already being used by nation-state actors like China and Russia to launch cyberattacks that are faster, smarter, and harder to stop. • Attacks adapt in real time. • Defenses struggle to keep up. • The old playbook is obsolete. The Department of Defense knows this. They see the gap. They’re not waiting. 2. The DoD’s New Playbook AI is now a must-have, not a nice-to-have. The DoD is building AI skills into every layer of its cyber workforce. • Human expertise + machine speed = the new standard. • Detect, respond, and anticipate threats before they escalate. • Cybersecurity is now proactive, not just defensive. 3. The Workforce Is Changing AI isn’t just changing the tools. It’s changing the jobs. The Pentagon plans to fill 225,000 cyber roles. The fastest-growing areas: • Data science • Machine learning • AI-adjacent skills But here’s the key: Not every job is technical. Every professional is now expected to understand how AI impacts their mission. 4. What This Means for Your Career. AI isn’t just for engineers. If you’re a program manager, operations leader, or transitioning military professional, your future depends on using AI in your workflow. This looks like: • Automating reports • Using machine learning for better decisions • Leading conversations about AI risks and use cases Ignore this, and you fall behind. Embrace it, and you become the leader others follow. 5. How to Get Ahead Look at where AI is already showing up in your field. Learn the tools that make you faster, sharper, and more valuable. Add one bullet to your resume or LinkedIn: • Used AI to automate a task • Improved a report with AI • Sped up a process using AI This sends a clear signal: You’re paying attention. You’re evolving. 6. The Big Picture The DoD admits it: Right now, AI is used more effectively for attacks than defense. That’s a problem. They’re fixing it by training everyone — not just the techies — in AI. • Policy, software, operations — all getting AI training. • Partnering with private sector innovators to move fast. This is the model every organization should follow. The future of defense is here. It’s AI-powered. It’s workforce-driven. If you want to stay relevant, start now. I'm Randall, a Navy Veteran using AI-Enhanced Career Coaching to help job seekers get noticed by getting results that took me 18 months in less than 15 days. ★ LinkedIn Top Voice for Career Coaching ★ AI-Enhanced Career Coaching Your Career, Advance It. +Follow me +Tap the 🔔 on my profile P.S. The right job search strategy works for you—even when you're not online. DM me to find out how I can help you get this.