I started in IT in 2008 at $14 an hour. Since then I’ve more than quadrupled my income, earned 14 certifications and a Master’s degree, and worked my way from Level 1 tech to security leadership.
I’m not that smart. I’m just driven, and I figured out how the system works.
This guide is what I figured out along the way, written down to help the next person up. It’s for the family computer wizard, the help-desk tech who wants to be a sysadmin, and anyone who knows IT, cloud, AI, and security are the future but can’t see the path from here to there.
What’s Inside
- Why listen to me? From $14/hour to security leadership, and what actually made the difference.
- How much do I need to learn? Six IT career paths, the roles in each, and the certs that move the needle.
- The Big Math Problem. Turn “I want my CCNA” into real study hours, a budget, and an exam date on the calendar.
- The 3 Pillars. How certifications, education, and experience stack up to get you hired.
- Motivation, technical aptitude, and social skills. The parts nobody teaches you in IT.
- Learn your weaknesses. An honest look at what’s holding you back.
- Your action plan. Everything in one place, ready to put on the bathroom mirror.
Plus two printables: a Certification Study Plan Worksheet and a Certification Goal Calendar.
This is for you if…
- You have the curiosity and drive, but not the roadmap
- You’re tired of watching less talented people get promoted
- You’re willing to invest time, money, and effort in yourself
- You want a repeatable system from someone who’s done it
This isn’t for you if…
- You want a get-rich-quick scheme
- You won’t study outside work hours
- You think one cert will change your life overnight
- You’re not willing to fail and try again
About Me
I’m a Lead Security Engineer and CISSP with over 18 years in IT. I’ve been a Level 1 tech, a Linux sysadmin, a security engineer, a Director of ITSM, and an IT Security Manager. Everything in this guide is something I’ve actually done. More about me.