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From the Military into Software Engineering (5/5): Context

How This Went for Me

In the span of two years, I pivoted from field artillery to intelligence to cyber security to development. I spend all of my nights and weekends learning, coding, and studying, to catch up to where I could have been if I had made different choices years ago.

I decided to leave the Army in early 2017 because of the poor quality of the people-are-replaceable-parts assignment process: being the least-senior of the candidate group, the wisdom of Human Resources Command was to place me in a “powerpoint-clicking” (their words) position for a year to allow my more-senior colleagues the chance to hit their gates for promotion. No thanks. Of course, in the Army, nothing matters more than promotion timelines. More than once, I was instructed to time marriage and children around key career events. Next slide.

To the surprise of that same HRC representative, my resignation was accepted almost exactly six months before my exit date, which started a hustle. Most of the hustle was silly hoops the Army makes soldiers jump through to keep us from ending up homeless and unemployed, or at least provide plausible deniability.

At that point, I knew I wanted to work in tech, but had only a cyber security background. The six months prior had been a 24-7 ramp-up period, coding day and night, learning linux, python, powershell, and pen testing. I didn’t find the security training I had done (ie OSCP) to be very rewarding, and was looking to pivot out into development. I had intense impostor syndrome, and didn’t know where to start.

Five months out, I took over day-to-day operations on an Army-owned OpenStack cluster, which was both very challenging and very fun. I was working 16-18 hour days through the weekend to improve uptime, and in the process discovered my new target career path. I took a shot at becoming a remote contractor on that same deployment, but it stalled in bureaucracy.

About the same time, I joined a military transition program just starting up in Silicon Valley. It was an opportunity I couldn’t have dreamed of only a few months before, but I felt shoehorned into a role and location that I knew, in my gut, I wasn’t interested in. I ignored my instincts and went out anyway, while still on active duty.

I worked at the company for two months - it was a deluge of new information and a new way of working. It was probably among the best startup experiences possible - small enough to still have lunch with the founder, big enough to know its raison d’etre, and all but guaranteed to succeed. The people were uniformly talented, interesting, and incredibly welcoming to veterans. The company, with only ~300 full-time employees, hired on a half-dozen transitioning veterans in the span of a few months. The founder got his start in tech as an Army contractor in the 90’s, and showed a kinship with us that was unusual for Silicon Valley.

While there, I discovered that the veterans’ network in the valley is small but strong. Word was that there are only ~1000 veterans employed by tech companies in the San Francisco area.

However, my impostor syndrome had only gotten worse as I realized how complacent with my own technical skills I had become in the Army. I was restless, anxious about my future, and not happy in San Francisco.

I had been hired on as a data analyst. That was the most-technical role offered in that round of veteran fellowships, but I was looking to pivot to engineering. Like most military officers, I had a great manager’s resume with sparse technical experience. Generously, one of the startup’s chief engineers gave me the benefit of the doubt and made me an offer of full-time employment in a better role, after working with him for only 9 days. Looking back, I’m still in awe. I accepted it from the taxi as I left to return to home station for final-out.

A month later, after transition leave, I called him to decline the offer. This was not an easy decision to make. Months before, my girlfriend had moved from Arizona to DC on my account, anticipating an Army relocation, and I couldn’t then bail on her to go back over to San Francisco.

I accepted an earlier offer from a big tech company in the DC area and started two weeks later. After almost a year, I am already far more confident and capable.