I used to fly in business class, now I'm crawling in the grass

November 9, 2021

May 9, 2019 was a Thursday. An unremarkable workday.

However, May 9 wasn't just another Thursday. It was on that day that I knowingly put my signature on documents that would throw me into a world I knew almost nothing about and change my life in ways I had yet to fully understand.

Fast forward to September. It’s 5 AM, and my face is on the ground—I’m gasping for air, sweaty, knees weak, arms heavy. Glasses in the gravel, scratched already. I’ve only had three hours of sleep, but this doesn’t dissuade my tormentors. They bark unrelentingly at me and the dozens of other unwitting “victims” because we have a lot to do and not much time to do it—in fact, we’re already behind. I scramble to my feet and grab my weapon. Pawing for my fallen frames, I put them on as I hastily get a headcount of my squad.

"Twelve… thirteen… fourteen...OK, we’re good." I snap to the position of attention, salute, and shout as loudly as my belabored breathing can allow, "THIRD SQUAD. ALL FIFTEEN TRAINEES PRESENT AND ACCOUNTED FOR, DRILL SERGEANT!”

Surely, I wasn’t in Kansas anymore (actually, I was in the neighboring state of Oklahoma). I was at US Army Basic Combat Training—more commonly and endearingly known as boot camp. And over the next 10 weeks, I'd be subjected to inhaling tear gas, having machine guns fired over me, sleeping in the rain, and rucking for dozens of miles with 45 lbs on my back…as well as a few push-ups here and there.

About six months later—three of which was spent at officer school in Fort Benning, Georgia—I would receive my first salute as a newly commissioned officer of the US Army. And three days after that, I was in my midtown Manhattan office waiting for IT to retrieve the last backup on my laptop. And just like that, I was back.

The ways whys are wise

At an age when many of my peers were completing their MBAs, settling down into their first home, or posting photos of their newborns on social media, I decided to join the Army National Guard—a choice that someone typically ten years my junior would be making. And appropriately so, I’ve been asking myself “why” for the better part of the past decade.

Why do this if you’ve never even heard of someone embarking upon this path in the same manner?

Why do this if you aren’t in debt and there aren’t any other clear benefits?

Why do this if it could potentially stunt the growth of your professional career and strain personal relationships and subject them to long, intermittent periods of absence and general uncertainty?

Why do this if it means putting your health, safety, and possibly your very mortality at risk?

From a “purely logical” point of view, these were all valid questions and were echoed by the few people I confided in. These were questions that I would ask myself every time the urge to join would inexplicably, yet inevitably, resurface year after year.
 

Nevertheless, the dream persisted

Part of me hoped that the allure of the Army would eventually fade away over time, and I’d look back on it as a drawn-out daydream—that I would simply continue chasing the more understandable goals (and, of course, the complimentary airline seat upgrades, hotel rewards, and credit card points from my frequent travels). Yet, another part of me just wasn’t convinced, despite all signs of reason pointing towards the proven paths to plenty, safety, and comfort. That other part of me didn’t want to let my dreams just be dreams.

So while I was at home in California as 2018 came to a close, I gave myself an ultimatum. I would either 1) go talk to a recruiter and begin the enlistment process as soon as I got back to New York in the new year, or 2) I would bury the idea of joining the Army once and for all and move on with my life. So, I set aside all the internal conversations, debates, and "conclusions" made over the years and asked myself a brutally basic question:

If I don't do it, would I be proud to share the story of this part of my life?

And when I distilled that question down even further, I realized what I should’ve been asking myself all along is: why not?

Why not challenge my status quo and pursue experiences and take the roads less traveled? I had traveled to over 30 countries, climbed mountains in Patagonia, backpacked solo in Southeast Asia, gone shark-cage diving and bungee jumping in South Africa. I had even ventured into the streets when Hurricane Sandy hit New York just to see what it was like. I have a penchant for adventure, why not continue having the opportunity for unique journeys for as long as and however I could?

Why not seek purpose in earning the right to wear the uniform and being a leader in the greatest fighting force the world has ever seen? I knew that the privilege of serving as an Army officer and leading Soldiers of the United States Army would be a source of immense personal pride and purpose that I wanted to carry for the rest of my life. I have the capacity and conscientiousness for servant leadership, why not apply my strengths in an organization that is fervently focused on developing their leaders’ ability to provide purpose, direction, and motivation?

Why not consider the possibility of pursuing both a professional career and a military one? I would be able to lead an additiona career in the Army because as a National Guardsman, I would attend drills locally one weekend per month and an annual training lasting 2-3 weeks per year (also rank-specific trainings required at the federal level). Theoretically, the time commitment wouldn't be too different than my standard work/PTO cadence. For my civilian career, I am fortunate enough to work at an organization that provides excellent benefits to its employees, including generous leave of absence and sabbatical programs that make it possible for me to pursue my personal commitments without worrying about my job. Not to mention, I had built a strong relationship over the years with my project’s leadership, teammates, and clients, and they were extremely supportive, if not enthusiastic, of my new endeavor. Since my organization genuinely believes in the benefits of investing in its employees and the strengths that servicemembers offer, why not take advantage of their offer and come back a stronger and more resilient professional?
 

And when I made the unassumingly simple switch from asking “why not?” instead of “why?” I changed the trajectory of my life.

As it turns out, the genuine responses to "why not?" were much more loud and convincing than the contrived responses to "why?" I knew that I would regret not joining the Army more than I might regret joining (knock on wood). And with that, I met with a recruiter o January 4, 2019 and eventually swore my oath of enlistment on May 9. The rest, as they say, is history.
 

Dual-core processing a dual-purpose life

I am just beginning my next step into my journey of two lives. Many have surmised that these two worlds have very little overlap and that adjusting between them would be difficult. However, I've found that there can be many parallels drawn between the two, and—in fact—there are plenty of strengths and lessons that I can draw from each side to complement and supplement my growth in the other.

So what can I say has changed? How am I different?

I am more confident and energized. I was honest with myself about what I wanted, committed myself to that goal, and applied myself fully to excelling in my new identity—achieving top physical fitness test scores in my platoon at boot camp and receiving recognition by the brigade commander for my performance on troop leading evaluations at officer training certainly helped to reinforce my confidence in my ability to succeed in this completely new environment. I set a bold, personal goal out for myself and crushed it—hard to beat that feeling. And going forward, I will be able to leverage this as precedence to have confidence in myself for other significant life choices that I will inevitably be confronted with. Though this might've been a rather unconventional life choice, when it comes to questions of personal conviction and self-identity, social convention should be an insignificant deciding factor. As the saying goes, you only live once.

I am more disciplined and engaged. By minimizing distractions and sticking to srict timelines, the Army is able to turn new recruits into combat-ready soldiers in 10 weeks and enlisted soldiers into commissioned officers in 14 weeks. I brought that same energy to my goals in the civilian world, and it’s amazing how much can be achieved in 24 hours with proper planning and rigorous focus on the task at hand. With dedication to set priorities, I can keep progressing forward step-by-step and ensure that I am making the most of my time and energy. If I can change my life in just 6 months, imagine what I can do with a year and more!

I am more convinced of the power of effective leadership. Throughout training, peers were rotated into positions of command from squad (10-15 people) to company (120-160 people) levels to give us opportunities to develop our leadership skills. The very success of the respective groups in their ability to accomplish set goals were often directly tied to how effective the leader was. Those that lacked empathy, confidence, or direction were more likely to fail. But the teams that had leaders that understood their team's needs, their commander's intent, and their own capabilities were the ones that would be most motivated and perform the best—a clear reminder that individual success is meaningless, if not impossible, without the success of the team. There is no doubt that many of the same leadership principles that apply in the military world can also apply in the corporate world, and I aim to further exercise and develop the lessons I learn from the Army to the teams I manage at my job.

I am more humble and open-minded. Most of the people I met at Army training come from a very different world than the ones I've met as an urban professional. It can be very easy to get lost in the concerns, complexities, and sometimes craziness of our own particular way of life, and I never thought to question some of the priorities that I held—or was always taught to hold. But after spending months enduring shared moments of joy, pain, failure, and triumph (and no shortage of ridiculousness) alongside a disparate group of people from all walks of life—many of whom were just teenagers—I was able to take a step out of the routine mindsets of climbing corporate ladders and comparing bonus sizes and re-examine what is important in life, what we should be thankful for, and what keeps us going.
 

Soldiering on

Looking ahead, there are still many unknowns. I do not know exactly what this uncharted path will have in store for me. I do not know the full extent of the challenges of balancing the futures of my civilian and military lives. However, I do know that I am excited to continue with this new choose-your-own adventure-esque chapter of my life and to keep growing, learning, and making the most of these new experiences. I know that I am better off for finally betting on myself.

So next time you have to make a big life decision, make sure to also ask yourself, "why not?" It might be the most important question you can ask.


About the author
Timothy Kao is a Risk & Financial Advisory manager for Deloitte & Touche LLP.

The information, views, and opinions expressed in this publication are those of the author and do not reflect the official policy or position of any employer, company, the National Guard Bureau, Department of the Army, Department of Defense, or the U.S. Government.