Lessons Learned after Transitioning from the Army to Software Engineering


Posting up with Le and our mutual platoon sergeant in Kandahar Airfield, Afghanistan. Note how my glasses are both large and awesome.

At the time of this writing, I’ve only been a software engineer for 6 months, but one of the unique aspects of my career is that I transitioned from the Army to where I am now.  Only earlier this year, I was a Signal (communications) officer for an AH-64 brigade.  This year has been amazing for me with lots of positive changes including a new baby (initials SQL) with my wife, a position at an awesome company, and a move to San Francisco. I thought it might be worth documenting the challenges I faced in the hopes that the insight might be useful to some of my friends still in the Army (especially those that might be looking to become software engineers themselves), and otherwise my own lessons are likely to apply in any transition from any career to a different field.


The short answer behind why I left the Army in the most concise explanation possible is that the Army as a whole had no incentive to place any type of value on my labor beyond the baseline expectations associated with my rank. Conversely, the free market competes for labor and places appropriate values to employees that can create more value for the company than what they’re being paid. For me, this becomes quite fortuitous when I can find work doing something that I very much enjoy doing, and standing from my perspective now, it’s easy to say that I made the right decision. Here are some of the lessons that I learned:


People like comfort zones

Obviously. But this could not have been more palpable than when I left the Army. Ironically, the hardest thing I ever had to do while in the Army was get out. I never had to go out of my way for so many things, fill out so much paperwork, get so many signatures, attend so many briefings, and concurrently deal with finding a new job and figure out how to get there. Even after I managed to get a job offer from the company I wanted to work for, I still had to attend mandatory classes from the Army about how to find a job and fill out a résumé. I joked with some of my friends that some people probably stayed in the Army out of pure laziness, but I wouldn’t be surprised if this was the reality for some. Having said that and even though I was reasonably confident that I could find a job when I left, getting out was still a pretty scary thing. In fact, the only reason I had any confidence that I’d be able to leave the Army and hang on the same level as the infamous San Franciscan software engineers was because I was able to talk to one person, Mark McBride, who had made a very similar transition years before me and convinced me over an hour long phone call that it was all within reach. However, any fears in the back of my mind were all nullified. After leaving Fort Hood, I drove for a few days to a new city and started work right away without incident.

Software Companies are Awesome

I’ve only been with two software companies so far. One was an internship at iRobot for a few weeks during one of my summers in college, and the other is at my current company, Hearsay Social. I can’t speak for all software companies, but when I contrast their benefits specifically to the Army, it’s safe to say that a myriad of pluses exist. In San Francisco at least, these include competitive salaries, free lunches, flexible hours, flexible vacation times, no dress code, extremely intelligent and cool people, non-mandatory-and-also-fun company events, worthwhile and satisfying work, snacks, drinks, tons of learning, and a nice office. To be fair to the Army and really any other government organization, most of those wouldn’t be too feasible if the taxpayers caught wind of what their money was going toward. Chase Seibert also wrote an interesting post about the culture involved with startups.

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Coffee setup over at ThoughtBot’s San Francisco office.

You Only Need to Find a Job Once

Another somewhat common discussion I’ve had with some friends is this idea that a large amount of up-front investing needs to occur in order to make one’s self marketable. While this is true, I think there are diminishing returns to that concept. I’ve heard it said, well if I stay in the Army for three more years, then I’ll be really marketable to a company because of my command experience. Even if this is true, the same companies that you might find a fit with in three years would probably hire you now. And in 3 years time, you’ll have built 3 years of a reputation somewhere. Wild. Another issue with this logic is that you may in fact be more marketable to many many companies, but the reality is that you can only work for one company at a time, and you only need to find a company you want to work with when you’re unemployed, which is hopefully only a very tiny duration of your life. My experience was that it took me about one week to find the company that I ended up working for. The interview process took much longer, but contact had been initiated in only 1 week of job hunting. In one week, however, I’d also applied to dozens of places. Even if I’d gotten job offers from several more of those companies or if I’d continued searching after I had my offer from Hearsay, there’s not too many other things that would have enticed me to another direction. Even now, I’m free to continue searching for another job if I wanted, but clearly, I don’t want to because I’m enjoying my current work.

Pensions aren’t really a valid incentive

To be clear, I’m quite happy for my friends when they’re in the Army and loving it. There are not many other places where you can find a job as an infantryman or get paid to fly an attack helicopter. But from my perspective, it’s very unfortunate when I hear one my friends say that they’ve decided to stay in the Army because of the time they’ve already completed thus far and are thus that much closer to a pension. To them I say: pull out Microsoft Excel, and run a simulation with Army pay plus a retirement pension against an average free market salary in your career field with conservative estimates. Monetarily, the private sector generally wins. Otherwise, it’s hard to price years of your life, especially if you compare years of your life enjoyed vs. years of life not enjoyed.

Unemployment Numbers. Meh.

Another scary statistic heard over and over that can deter any desire to shift career is the country’s unemployment numbers. But of course, now that I’m with a successful company, I’m reminded on a weekly basis that Hey! We’re hiring! Tell your friends! We have more positions than we can fill!. Again, the basic concept of an employee is not that he or she simply fills a position. The important part is that the employee creates more value for the company than what he or she is paid. With that in mind, there’s theoretically no reason why any able-bodied individual wouldn’t be able to meet that standard and get hired and no reason why a company couldn’t continuously grow in a truly free market. Another way I look at these numbers is to see the inverse; an 8% unemployment rate means a 92% employment rate. So a laborer needs to have enough skills to fit into the pool of people encapsulated in the 92nd percentile.

I’ve Learned a Ton at my New Job

When I say I’ve learned a ton, I’m not really referring to life lessons. I’m mostly referring to programming. I’ve been coding for 6 months for usually around 6-8 hours per day of coding (at least) in an environment in which every bit of my work gets peer reviewed by other people who are smarter than me in at least a few different aspects (if not all). In an office of around 30 engineers, every single one of them has at one point or another directly invested in my growth as a programmer and taken the time to teach me something. If I’d stayed in the Army, I probably could have gotten a Master’s degree in Computer Science, but I’m guessing that what I’m learning by doing actual work that other companies are willing to pay for trumps what I could have learned at a university. I’m also fairly confident I’ve learned way more here than I did in years of school. One way I explained it to my wife is to imagine a school and how much your motivation would change if literally every single piece of information you learned immediately translated into added value for your life, and you could learn new things at any rate you wanted (this is how I reflected on things after seeing an incredibly excited 11 year old kid at a vim meetup I went to).

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Super excited kid presenting at a programmer meetup

Recruiting Firms Aren’t That Awesome

To those transitioning out of the Army, the standard approach to getting out usually involves linking up with a recruiting firm. Their sales pitch: “We take the top 20% of officers and NCO’s and help them find a job, and we make money from a percentage of your first year’s salary.” Translation: “We help the people that don’t need help in the first place and then make money from a percentage of their first year’s salary.” Their market is to translate generic management and leadership skills acquired in the Army and apply it to people-intensive organizations. I found that for a technical role, I was far better on my own, and they absolutely would not have been a necessity otherwise. I don’t mean to knock these companies since they can be a free service to the job-seeker, but the take-away for me is that taking the path less traveled can often lead to great fruition.


While it wasn’t entirely difficult finding a match with a good company, it wasn’t entirely easy either. I wouldn’t want to speak to the perspective of my employer on my own worth, but I did make every effort to make myself a worthy candidate prior to interviewing. I had created a number of web applications in an effort to create standalone, automated projects that could potentially generate revenue. I probably spent more time than I should have coding on the side and trying to create things that required way more time, energy, and probably money than I was capable of putting forth. I also started work on a semi-autonomous blimp that I’ve still yet to finish. I also regularly attended the Austin Python Meetup Group which was three hours of driving total round trip. This was all while working a full-time job with a wife and one baby. I probably wouldn’t recommend the same approach to anyone else, but I’ve definitely learned that temporary sacrifice can bring long term gain (I feel like I’m on the gain side of things at this point).

See Also

Akshay Shah, one of my co-workers also has an interesting story transitioning from the medical field to software.

  • Lone Wolf

    That 11 year old kid is awesome

  • Dad

    I’m proud of you!

  • your colleague

    YAY but you forgot to mention the role drudge played in your journey.

  • TopsyKretts

    Thank you for this article. I was in the South African Army for 8 years as an Infantryman, of which I spent 7 years studying.

    I eventually got tired of the….stupidity and lack of ambition. The Infantry being the most notorious for this. I was rapidly approaching the “10 year” mark, which is the virtual line where one becomes a “lifer” and sticks it out for the pension.

    So I took the plunge and left to go into software development. Quite thrust out of my comfort zone it was. But 4 years later and I am very happy with my decision. I miss blowing shit up, for sure, but I enjoy not being brain-dead even more.

    I can relate so much to your article (minus the family), so it was good to hear it from someone else too.