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Two years ago I left the military with a bit of IT experience and basically no civilian tech resume to speak of. I started at the bottom doing tier-one IT support: password resets, ticket queues, the whole thing. It was humbling, but I kept my head down and paid attention to how the infrastructure around me actually worked. After about eight months I moved into a network operations role, which gave me real exposure to traffic analysis, firewall rules, and incident escalations. That was when I saw where I wanted to go. Security engineering.
From there I spent my evenings and weekends on training. I mean late nights after full shifts, working through courses on platforms I paid for out of pocket, grinding through labs, building a home setup so I could practice hands-on. I picked up certifications along the way and kept a running list of projects I could point to. Not because they were impressive, but because they were evidence I was moving in a clear direction. I found the job posting on a job board while I was still in the network operations role, and I almost talked myself out of applying. The requirements listed experience I didn't fully have yet. I applied anyway.
The interview process ran three rounds. The first was a general conversation about my background, the second got technical, and the third felt more like a culture and judgment assessment. In each one I was completely straight about where my hands-on security experience was thin. I didn't dress it up or dodge the questions. I told them exactly what I knew, what I was still learning, and what my plan was for closing those gaps. They offered me $95,000 for a hybrid, full-time security engineer position. I accepted without hesitation. I think the honesty landed as well as the certifications did. They could see the trajectory clearly, and apparently that was enough.
Changing careers from software sales into product design was brutal by the numbers: 14 months, more than 200 applications, 205 rejections, 6 interviews, and in the end a single design offer, a product design internship at Braze in New York. I want to be honest about what that felt like before I get to the part where it works out.
I spent the first few months convinced I just needed a better portfolio. So I enrolled in a bootcamp, rebuilt my case studies from scratch, and watched endless teardowns of apps I'd never used. I was still working a software sales job through all of it, which meant most of my design work happened after 9 PM or on weekends. I applied through job boards obsessively: LinkedIn, Wellfound, Handshake, company career pages, refreshing confirmation emails like they meant something. Most of the time they meant an automated rejection two weeks later, or nothing at all. I kept a spreadsheet. Watching it climb past 100 applications and then past 150 without a single interview response made me question everything about the pivot. My portfolio, my bootcamp, my timing, whether product design was even the right move.
The six interviews I did get felt enormous, partly because they were so rare. I over-prepared for every one. Researching the company's product in detail, practicing design critiques out loud, writing down questions I actually wanted answered. The Braze process was thorough. Hybrid, New York-based, and the internship paid 60,000 USD annualized. None of that was guaranteed to go my way, and I knew it. I treated each round like it was my only shot, because statistically it basically was.
There's no clever hack here. I built a portfolio through a bootcamp, kept applying through a wall of rejection, and stayed consistent when the payoff wasn't visible yet. If you're mid-career-change and the rejections are piling up, this is what the unglamorous middle actually looks like. And it does end.
211Applications
6Interviews
14 monthsSearch length
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