From combat to coding: Former Army Ranger explains how to break into tech after the military
You will have to learn a new language.
This is it. After five short years, my time in the Army has come to an end. Beyond lies ambiguity and probable career turbulence. Military service is often defined as altruistic in nature; we join to fulfill a higher purpose. It seemed fitting to spew my subjective thoughts onto a Google doc in a last-ditch effort to further cement my legacy as the selfless leader servant that I was bred to be. Or maybe I just wanted the clout. I’ll let you be the judge. All jokes aside, what follows is an honest account of my journey transitioning from the Army into the civilian world. The goal here is not to spotlight me, but rather to educate and inform others that may be in my shoes staring down the same crossroads as I did just 12 short months ago.
To cover my background, I was commissioned as a military intelligence officer (branch detail infantry) out of a non-brand midwest ROTC college in the spring of 2016. Like nearly all of my peers, I consumed all content involving Dick Winters, any and all leadership books (Black Hearts, anyone?), and prophesied about one day joining the Ranger Regiment, earning a Green Beret, and taking the fabled Long Walk, in that order. This was obviously before I had any concept of what kind of witchcraft would be needed to enable this kind of timeline. I will mention that I did not spend my career starter loan on the tan Tacoma and full-sleeve tats. Like the typical hardo-wannabe, I attended Ranger and Airborne shortly after the basic infantry course and moved on to my first duty station. Pretty standard career path after that; Platoon Leader, Assistant S3, etc. Then, I attended Ranger Assessment and Selection, passed, and moved on to the 75th Ranger Regiment as an intelligence officer and deployed twice to Afghanistan.
The highlight of my career is undoubtedly my time with the Regiment. The people I met there are, quite frankly, legendary. The hardest part about the transition is leaving the people, culture, and mission behind. So, why leave? Why abandon this well-trodden path of self-fulfillment and adventure? Well, something strange happened in between my deployments. I started to feel unfulfilled. But how? How could I feel this way surrounded by the Army’s best? I started to mentally forecast what my Army career would look like if I stayed in. I could probably project a timeline with ~80% accuracy just based on the first five years of time in service alone, and guess what? The certainty scared me. I realized that I had no desire to lock my rails into tracks and take my hands off the wheel. I realized that I wanted uncertainty, that feeling of being the captain of my own ship, charting my course towards whatever the hell I wanted.
But enough talk about me. What I would like to do is reflect on the lessons I’ve learned so far during my transition process and be so bold as to insist on words of advice. At the time of this writing, I’ve concluded a Career Skills Program (CSP) internship at a tech company in Seattle, Washington, and have interviewed with Facebook, Apple, Amazon, Netflix, Google (FAANG) and startups of various growth stages. Additionally, I participated in an education program called BreakLine which tutors veterans on navigating through the turbulent career pivot into tech and subsequently advocates for full-time employment on their behalf. The observations I share likely apply to all career paths post-military but some are skewed towards the tech field.
- First and foremost, working in true ambiguity is hard. Like, really freaking hard – it is not comfortable! Nobody is going to hold your hand. You have to decide every single day what you are going to do to add value to the organization. Your manager isn’t going to check in on you daily and help clean up your mess. There is no portal or share-drive to access where you can reference last year’s training event PowerPoint, change the dates, then march off to your Initial Planning Review and regurgitate it all to the S3/XO/BC. You truly learn the meaning of being creative and thinking outside the box. But at the same time, it’s exciting, so embrace it. It is definitely a “you vs. you” feeling. Best advice here is to get used to being uncomfortable: adopt a new hobby, research creative thinking, explore previously foreign ideas etc. You will grow exponentially by pushing yourself outside your safe space.
- Absence of some freedoms is a freedom in itself. When was the last time you had to worry about a resume or a cover letter in the military? How about stressing over what health insurance plan or provider to choose? Deciding what school your kids will attend? Picking out what to wear for work? Obviously, these are somewhat trivial things and do not apply uniformly across the broad spectrum of military occupations. The military dictates most of your life: when and where you will eat, how you will complete your work, how you will dress, who moves your belongings and when, your physical appearance, where and how you will receive medical attention etc. Upon exit, you will experience that you will be responsible for making personal decisions that you may not have had to think about before.
- You will have to learn a new language. This may be a humbling experience for some of you, it certainly was for me. The jargon of investment banking, management consulting, project/program management, and tech all vary between organizations. Tribal knowledge plays a hand in this and you will have to be resilient and make yourself vulnerable enough to ask “dumb” questions. There is little you can do to prepare for this besides reading books, listening to podcasts, and immersing yourself in the culture of corporate America. I would recommend “The Personal MBA” by Josh Kaufman and a daily dose of the Wall Street Journal Daily Tech Brief. Additionally, connect and network your ass off with people in the fields that are interesting to you. The more people you speak with, the faster your new language proficiency will become. Humility is key here.
- You will have to assimilate back into “the real world”. Regardless of how little time you devoted to the military, you will have to readjust to being a civilian again. I was recently described as “too direct” when expressing my reluctance to accept something I did not want. In another instance, one of my emails was dubbed “passive aggressive.” I had to be conscious of the language I used around the office since I was not a soldier anymore. These anecdotes represent slight differences between military servicemembers and their civilian counterparts. I would like to point out that I am not inherently passive aggressive, overly direct, or foul-mouthed. I was just unused to a different type of environment. Be aware of this — you don’t want to be labeled as an uncoachable veteran who substitutes their time in service as a cutout for personality.
- Learn a technical skill while in the military. One of the main principles in the Army is that everything is tailored to be understood and utilized by the lowest common denominator. In this case, the LCD is an 18 year old private (in most cases). I am not slandering the lower enlisted, just pointing out that literally everything is explained with the KISS concept (Keep It Stupid Simple). If you are leaving the service as a junior officer, you likely possess invaluable people and project management skills. Tech employers, however, care much more about your match to the actual job description and if you are proficient with technical skills. Can you query databases using SQL? Can you COUNTUNIQUEIFS across multiple sheets in Excel? How’s your formula knowledge? What is your understanding of UX/UI? Do you know what Pandas are and how to manipulate them to tell a story? Today’s managers are becoming better programmers and programmers are becoming better managers. Tech is all about automating jobs and functions using artificial intelligence and machine learning. Sure, you can learn through osmosis at your next job but why not flatten the learning curve now? You’ll be all the better for it, and you can apply those skills to your current role in the military and blow everyone away with your INDEX(MATCH) wizardry.
- Have someone look at your resume. If you share a similar background to mine and are getting out of the military, your resume will likely be stacked with soft skills. “I led, developed, mentored 40 Soldiers and maintained $100 bajillion worth of equipment”. Sound familiar? News flash: employers don’t actually know what any of that means. Most civilians don’t know the difference between Green Berets and Navy Seals let alone what an Assistant S2 does. Normalize your employment titles so a civilian recruiter can read it (i.e. S1 = Chief of Human Resources). Do NOT use military jargon, talk about the number of insurgents you “removed from the battlefield”, or fabricate information. Follow a simple but proven results-based format: Drove X process, improving efficiency from Y to Z. Is it sustained? How much reach did it have? At the same time, don’t let your imposter syndrome keep you from making yourself sound like a rockstar. Don’t ever self select out of a process or job candidacy. Have a bias towards yes.
- Learn how to communicate to your chain of command that you are getting out. Fortunately, I had the best chain of command a junior officer could ask for. My battalion commander was literally a hero. I had no issues communicating my intentions to resign my commission. It is sad to say that I am an anomaly in this case. Many service members are subject to downright guilt trips at times. My best advice is to come into your commander’s office with a solid primary and secondary plan of action ready. Make the plans airtight and remember that you decided to go into that office for a specific reason in the first place. Be able to coherently articulate that reason in a way that doesn’t slander the organization or the Army. I found one of the best responses to the “why do you want to get out?” question during a physical training session with the regimental commander while deployed. He asked me what my five year plans were and I told him I was in the process of transitioning out. He did not object, become offended, or protest. He simply asked me what made me decide on it. I think at that point I was so gassed that I didn’t answer right away. He replied to my silence with, “Hey man you gotta do what you gotta do. If it’s the right thing for you then you gotta do it.” What a perfect answer. One possible way to phrase it: “It’s just the right thing for me/my family to do right now”. It’s blunt yet non-combative and will (hopefully) leave little room for scrutiny. Another great way to navigate this conversation is to explain that you have other passions and goals that you want to achieve. “I had an amazing experience in the military that I would not trade for anything. At this point in my life I am ready to move on and take on other challenges and pursue other passions.” Simple, concise, and to the point.
- You are not owed anything in the civilian world. You won’t get the job you applied for based solely on the fact you are a veteran, regardless of special operations experience or not. This is admittedly a pill I had to swallow. After all, I was a full blown ‘war hero’ to civilian hiring managers: Infantry Officer, Ranger Tab, Ranger Regiment as a junior officer, two deployments, top evals; overall shining career. No recruiter would pass up on that, right? Right?! Wrong. Remember the technical skills I mentioned before? Those bring tangible value. Not saying that your experiences won’t, but an employer — tech or not — is not going to care how many missions you went out on or how many trillions of dollars of inventory you were “responsible” for. They are going to care about the bottom line: what value do you bring to the company? Do you have potential to learn and grow and net the company more profit than the payroll expense they dish out on you annually? Are you a good fit for the culture and mission? I’ll share an anecdote. I expressed my interest in a role to a hiring manager and she told me she would let me know when the job posting would open up. A week later I found out that the offer for that position had already gone out and had been accepted. And I took that personally. I was upset! How could she not consider me first? I was a vet with multiple deployments, dammit! My sponsor looked at me and nonchalantly said, “What are you on about? She doesn’t owe you shit” and went back to work. I was taken aback. He was so right, she does not owe me anything. I am not owed anything. You are not owed anything. You have to earn your keep out there and work hard to get what you want out of your transition and civilian career.
- You will lose some lucrative perks. You are not going to enjoy the same tax benefits that you do now. Your income will be subject to state (barring a few exceptions) and federal taxes. Your income will no longer be split between taxable and non-taxable portions. It’s all going to be taxable. No more of those deployment tax perks. You will lose access to an inexpensive healthcare plan and that premium 401k with an exceptionally low expense ratio. The take home salaries of a servicemember making 80k and a civilian making the same amount will differ. Familial circumstances may dictate this to be a significant consideration.
- Your transition is what you make of it. To be clear, at the time of this writing, I have yet to accept an offer of full time employment in my target role or company — yet I feel little stress associated with this. It has been three months of continuous hustling, networking, interviewing, and emotional ebbing and flowing. Despite this, I feel confident that my experience with the internship, BreakLine, networking, and interviewing will yield results as long as I don’t quit. I believe the aforementioned experiences were absolutely instrumental in a successful transition and I implore you to take advantage of every single opportunity you have. Army transition assistance alone is insufficient. Do all you can to secure the time and resources needed to ensure a smooth exit. Acquiring a job outside of the military is a lengthy process with numerous screening calls, multiple interview rounds, case studies, compensation negotiation etc. Sometimes this can take 6-9 months! Companies want to absolutely ensure that they are adding value through the additional headcount. After all, it is a for-profit organization and every employee needs to add value to justify their employment. I would recommend allocating six months to ensure a successful transition. Treat it like a full time job. Connect with folks on LinkedIn via Zoom calls, have your resume reviewed multiple times, and take the time to educate yourself. You’ve got to hustle!
- Side note: I believe that the military should make CSP/SkillBridge or some sort of internship a more accessible part of the transition process. Right now, it is not. The CSP packet requires your O3/O5/O6 approval. This is systematically flawed as it puts transitioning Soldiers at the mercy of their commanders’ subjective perceptions of minimal manning requirements in the CO/S3/S4 spaces. The application for these opportunities should be a simple DA 4187 much like the process towards applying to attend Special Forces Assessment and Selection. “Hey Sir, here is what I am planning to do” vs. “Hey Sir, can you please allow me to do this thing I have planned?” I highly recommend pursuing this option as it will greatly help you with your transition success.
I hope this brief essay does justice to the great people who took the time and effort to ensure my success during my transition. In the end, that is what the military is all about — looking out for one another. I would only ask that those that are coming to terms with their own transition would take note of their struggles. Write down your thoughts and pass them on to others. Your time and your word are the simplest and often times the most profound acts of altruism. It is your sincere duty to look out for your fellow veterans on their journey out of service and beyond.
Alex Proskurnya is a former intelligence officer with two deployments with the 75th Ranger Regiment. He recently transitioned out of military service and is now working for a tech company in Austin, Texas. He is passionate about giving back to the SOF community, traveling, and all-you-can-drink beers at Scruffy Murphy’s.
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