When Steven Upshaw retired from the U.S. military in 2021 after 25 years of service, he wasn’t sure what was next. What he did know was this: he still had the drive to serve, solve problems, and continuously grow.
What he didn’t expect? That within just a few years, he’d be working as a Cloud Security Architect, leading defensive strategies in one of the most in-demand fields in tech — cyber security. And a huge part of that journey, he says, was TryHackMe.
“Never in a million years did I think I’d be where I am today. I started learning with TryHackMe, and it became my springboard into the industry.”
Discovering Cyber security… and TryHackMe
Steven's journey into cyber didn’t begin in a classroom or at a traditional bootcamp, it began while finishing his MBA. With just a few electives left to complete, he chose cyber security on a whim. That decision would change everything.
He initially explored other platforms, but found the steep entry barrier frustrating.
“Other platforms made me hack just to get in, it was too much for someone just starting. TryHackMe, on the other hand, was clear, structured, and hands-on.”
From his first login, TryHackMe’s gamified rooms, engaging learning paths, and real-world labs captured his attention and kept it.
The Power of Community and Consistency
It wasn’t just the content that hooked Steven it was the community.
“Some days, I didn’t feel like logging on. But people in the TryHackMe Discord and on LinkedIn kept cheering me on. That kind of support? It’s rare.”
Steven soon became known in the community for his dedication, logging in every day and working through challenges for over 1,500 days straight. He completed every room on the platform (except one!) and spent hours helping others, often encouraging newcomers to start with the fundamentals and take their time.
“Be consistent. Be patient. Learn one thing a day it adds up. You don’t need to rush.”
Breaking Into Cyber With Confidence
After taking a break post-retirement, Steven re-entered the job market — and TryHackMe was instrumental in helping him stand out.
“In every interview, they’d ask how I stay relevant. I’d talk about TryHackMe — and they knew exactly what it was. That practical experience made all the difference.”
Steven didn’t just land one job offer — he received multiple, all within a few interviews. His skills, shaped by TryHackMe’s platform, helped him transition straight into mid-level cyber security roles, including Cloud Security Engineer and Cloud Security Architect.
“TryHackMe bridged the gap between theory and practice. That’s what hiring managers want — people who can apply what they know.”
Advice for Future Cyber Professionals
Now, Steven uses his time to help others find their footing in cyber security. His advice?
- Start with the fundamentals – Learn how computers talk, how networks function, and how to use tools like Linux and Python.
- Be consistent – It’s not about speed, it’s about steady progress.
- Use platforms like TryHackMe to get practical, hands-on skills that go beyond textbook theory.
“Everyone wants to jump ahead to six-figure salaries, but if you skip steps, you’ll struggle in interviews. Take your time. You’ll get there.”
A Thank You to the TryHackMe Team
Steven’s closing words were for the community and team that helped him grow:
“When I started using TryHackMe back in 2020, there were about 100,000 users. Now the platform has exploded and it’s no surprise. You’ve built something amazing. Thank you for helping people like me turn a dream into reality.”
Feeling inspired by Steven's story? That’s great! We have many other success stories from users who have either switched or progressed in their careers thanks to TryHackMe.
So get ready to take the leap and check out our guided learning paths!
Carah Els