Land Your First IT JobMilitary or career changer
Whether you're leaving the military or changing careers, here's the roadmap I wish I had: which certs to get, in what order, how to translate your experience, and how to actually get hired.
“I failed Security+ the first time because I skipped the fundamentals. Went back, earned A+ and Network+ first, then passed. Everything in the Playbook is built from getting it wrong before I got it right.”
What people are saying.
I have been in education for almost 12 years and I have a degree in CIS and wanted to do something with it. I obtained my Security+ in December of 2025 and began my career transition. I joined the Your First Stack Discord and after a few months of conversations and meetings with Derek and the rest of the Discord members, I figured out that my issue was my resume. Derek helped me get it looking right, and that night I used it to apply to a few jobs. I was getting callbacks by the next day. That led to my first interview, which is where I had struggled before. I've since had 4 callbacks and made it through 3 rounds of interviews with a company, and I've been offered a role with them as an IT Specialist.
Derek was instrumental in helping me get into the IT field. His knowledge and expertise made the learning process much easier to understand, and he was always professional and approachable. He took the time to explain concepts clearly, answered all of my questions, and provided guidance that gave me the confidence to move forward in my IT career. I truly appreciate his patience, support, and willingness to help. I highly recommend Derek to anyone looking to break into IT or expand their technical skills.
As someone who is currently thinking about my next step outside of the military, this has been a really big help. I never really understood how I could transition from my job to the outside, but this really helped me understand the leadership aspect of what will translate. I am working towards my certificates and degree right now and this just gives me a leg up for the future!
Answer A Few Questions, Get A Real Answer
No email required. This won't cover everything, the Playbook's decision tree does that, but it'll point you in a real direction right now.
Military & Veterans (for active duty, guard, reserve & veterans)
Breaking Into IT (for people who want to break into IT/Cybersecurity)
Nobody Tells You How Hard This Is. Here's Where To Start.
Whether it's military leadership or years in a different field, your real experience doesn't show up on paper the way tech recruiters expect. "Get into IT" isn't a plan either, it's several different careers with different entry bars and paychecks. Pick a side below and see what actually fits.
IT Support / Help Desk
Reset passwords, fix hardware and software, resolve tickets.
- Help Desk Technician
- Desktop Support
- IT Support Specialist
Systems Administrator
Manage servers, Active Directory, and uptime.
- Systems Administrator
- IT Administrator
- Infrastructure Technician
Cloud Support / Admin
Provision and monitor cloud resources.
- Cloud Support Engineer
- Cloud Administrator
- Cloud Support Specialist
Networking
Configure and troubleshoot routers, switches, and connectivity.
- Network Administrator
- Network Engineer
- Junior Network Engineer
Still not sure which one fits? The Playbook has a full decision tree. Get the Playbook →
How It All Connects
IT and cybersecurity aren't one job, they're webs of specialties. See how the pieces actually fit together, in plain English.
Domains
IT Support / Help Desk
The first people you call when something's broken. They fix everyday tech problems for employees.
- Help Desk Technician
- Desktop Support
- Tier 1 Support Analyst
Systems Administration
They keep servers, accounts, and company systems running day to day, behind the scenes.
- Systems Administrator
- Infrastructure Technician
- IT Administrator
Networking
They build and fix the connections, wired and wireless, that let every device actually talk to each other.
- NOC Analyst
- Network Administrator
- Network Engineer
Cloud Support / Admin
Same job as a Systems Administrator, but the servers live on the internet, AWS or Azure, instead of in a closet down the hall.
- Cloud Support Engineer
- Cloud Administrator
- Junior Cloud Engineer
Database Administration
They organize and protect a company's data so nothing gets lost, corrupted, or stolen.
- Database Administrator
- Data Administrator
- Junior DBA
Career Development
Not a job, it's how you keep leveling up once you're in: certs, training, and staying connected to people further ahead.
- Certifications
- Training
- Peer Communities
- Self Study
Want the decision tree instead of the map? Get the Playbook →
Your Clearance Is Worth Real Money
Sponsoring a clearance costs an employer real time and real money. If you hold one, or you're eligible for one, it's one of the most valuable lines on your resume. Here's roughly what it's worth.
Confidential
Modest premium, most common in admin and support roles.
Secret
The most common veteran clearance. Saves an employer 3–6 months of investigation time.
Top Secret
Saves an employer 6–18 months of investigation time.
Highest-Tier Cleared
Smallest candidate pool, strongest premium. Entry-level cleared IT professionals average about $82K in their first two years.
Figures reflect aggregated market data and vary by role, employer, and location. Your clearance loses value the longer you go without a cleared job after separation, most levels allow reactivation within a two-year window.
The Biggest Cleared Job Hubs
D.C./Northern Virginia is the largest by far, the highest concentration of cleared roles in the country. The rest are strong regional hubs built around specific bases and commands. If you can relocate, these are where the most cleared postings actually are.
Want the full cleared job board list and search strategy? Get the Playbook →
I built this because nobody handed me a map.
13 years as a Combat Engineer. No CS degree, no tech background, just certs, a clearance, and a lot of trial and error. I wrote this so the next person has an actual map instead of guessing.
Whether you're coming from the military or a completely different career, the actual process of breaking into IT looks more similar than you'd think. This site is built for both.
I walked out of my interview convinced I'd blown it. Got the offer anyway. You're usually a worse judge of your own performance than you think.
I write everything on this site and in the Playbook myself. No ghostwriter, no agency, no AI dumping generic advice and slapping my name on it. If something here doesn't work for you, that's on me, not a template.
Pick up what you need, when you need it.
The Discord
Best for: Anyone who wants real answers from people already doing this, before spending a dollar on anything.
- Talk to people working toward their first IT job right now, no matter your background
- Career discussions and networking with people actually in it, not theorizing about it
- Real support
- Free info and answers you'd otherwise pay for elsewhere
- Someone else stuck on the same cert, the same rejection, the same 2 AM doubt, you're not doing this alone
- Ask questions before you spend a dollar on anything
The Playbook
Best for: People who want to build their own roadmap and work it at their own pace.
The real transition, not just the resume, the actual table of contents so you know exactly what you're getting:
- Who wrote this & my actual transition timeline
- The transition nobody talks about: healthcare, TSP, identity, fear
- Choosing your lane
- Degree vs. no degree: a real decision framework
- The cert path that actually works
- Building your first stack: skill breakdowns by lane
- Resume that gets interviews
- LinkedIn & networking
- Clearance advantage: real salary numbers
- SkillBridge: should you fight for it?
- Job search system
- Interview preparation
- Your first 90 days
- VA disability, benefits & transition planning
1-on-1 Calls
Best for: People who want a personalized strategy and faster progress than figuring it out solo.
Leave with a clear career target, a certification roadmap, resume priorities, and a personalized action plan. A direct session with me, not a generic template.
- Includes The Playbook if you're military or a veteran
- 60 minute session
- Custom roadmap built around your background and goals
- Resume and LinkedIn review included
- Direct answers to your actual questions, not a script
- Cert path clarity, so you're not guessing what to study next
- Real talk on what's realistic for your timeline
Your First Stack Mentorship Program
Twelve one-on-one sessions built around your actual roadmap, not a generic course.
Best for: People who want real, ongoing support instead of figuring it out alone, whether that's certs, resume, LinkedIn, or the job search itself.
01 How It's Paced
No fixed weekly calendar. Someone starting from zero might take five or six months to work through everything. Someone who already has a cert in progress might move faster. Either way, you get my full attention until we're done, not a countdown clock.
02 Support Between Sessions
Not just scheduled calls. You get Discord support the whole way through, with a 24 hour response window on weekdays. Questions, stuck points, a second opinion before you hit submit on an application, that's covered too.
03 Job Application Support
When you're ready to apply, I'll personally recommend you for roles where I can, real doors opened, not just advice from the sideline.
04 Once You're Through
You don't get cut off. You move into The Command Post, a private space in the Discord just for people who've completed the mentorship, where alumni stay connected, help each other, and get first access to anything new I build.
05 What I Can't Promise
I can't guarantee you a job. Nobody honestly can, and anyone who tells you otherwise is selling you something. What I can guarantee is a real roadmap, a rebuilt resume and LinkedIn, real interview practice, and someone actually in your corner, not a PDF you skim once and forget.
06 Your Part In This
I can't take your CompTIA test for you, and I can't study for you. That part's on you. Failing an exam is normal, it happens to a lot of people, myself included. What matters is you get back up, re-engage, and keep going. I'll be right there when you do.
Here's exactly what happens, session by session.
- IT Track: targets real entry-level roles, IT Support, Junior Systems Administrator, Junior Network Engineer, Cloud Support Tech
- Cybersecurity Track: built primarily around landing a SOC Analyst role, with ISSO as a realistic target if you already have the right military or IA background
- Military and Veteran Track: for military members and veterans overall, whether you already worked IT, signal, intel, or cyber in uniform or not, where your background actually points gets sorted out together in the roadmap during session one
Check-ins happen as needed, daily during interview prep, lighter during heads-down cert weeks.
- We talk 1-on-1 first, free, no pressure
- We'll talk through your background, goals, and whether the timing's right
- You decide if this is the right path for you
- If it's not the right fit, I'll tell you straight
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Your next mission starts here.
Grab the free checklist built for military members and veterans breaking into IT, and get moving today.