Matt Driskill, Military Leadership Circle

Transitions by nature are disruptive. They alter our routines and the status quo with which we have grown comfortable. They force adaptation, sometimes immediate, to a new reality. Leaving active duty military service is such a transition and one that began for me in August after 17 years of service in the Navy.

Serving in the military had been my childhood dream. My childhood heroes were never athletes or pop culture celebrities, but instead, the military and political leaders who had dedicated, risked, and sometimes sacrificed their lives to a cause greater than their own selfish ambitions, the idea of America. They hadn’t simply lived through history but had changed our history.

I sought to share in their legacy, doing my part in upholding that proud tradition. I followed their example, pursuing a career as a Naval Flight Officer (NFO) after ROTC in college. Though I incurred an eight-year commitment as an NFO, I set out with an open mind about the length of my service after that term.

Time for transition

My work has and always will be more than a job; it’s a deeply personal calling in life that must align with my values, priorities, and God-given abilities. It must sustain my family while acting as a means to improve my community and my country. If the Navy provided challenging roles with the opportunity for personal/professional growth and mission impact while still balancing family priorities, then I would continue to serve. Once it did not, then I would quickly know my professional calling was ready to take a different direction.

Unfortunately, that moment for me came after the 17-year mark, less than three years from minimum eligibility for retirement, when I could receive a pension for life. The Bureau of Naval Personnel (BUPERS) had given me only one job choice, which was really no choice at all. The job they offered failed to leverage any of the highly specialized skills or work I’d done the past three years, provided no transferable value to a post Navy career transition, would take me away from my family for a year, and frankly, it just wasn’t interesting.

The Navy valued a temporary organizational need and they wanted me to fill it at great cost to my family and future career options, just for the gratification of a small, but immediate pension. I found it hard to wrap my head around the idea that my Navy career would end that way, but in my heart, I knew my priorities no longer aligned with the Navy’s — it was time to begin the transition.

Testing the waters

In a matter of days, we went from thinking about what would have likely been my last job in the Navy to what “we” wanted to do with the rest of our lives. I say “we” because in our family career planning is a team sport, where my wife plays an integral role and consideration for her and my young children is of utmost importance. Some military members begin their transition knowing they want to enter a profession directly correlated to their military role. I chose to take a risk and do something very different.

Initially, I cast a wide net by listening to and talking with everyone, including people and other vets in industries or with firms that I didn’t believe I had any genuine interest in pursuing. Even though I sensed no calling to certain career paths well established by other naval aviators due to their direct correlation to military roles, I needed to reach a reasoned conclusion as to “why” I was saying “no” to those careers and know that it wasn’t due to any emotional or even gut response. I had a strong desire to pursue a certain path, but I begin with an open, investigative process.

Veterans like me have had a very pre-determined, or at best a limited set of career options while in the military. Going through a process of investigating what career opportunities are really available, what they provide, and doing the heavy mental lifting to think through why they are/are not worth pursuing has been a very important aspect of the transition for me so far.

As my wife and I went through this process, we began to have clarity about the biggest factor in our transition. First, we realized the need to leave the local community around our base in Patuxent River, MD to pursue a more diverse set of career options elsewhere. While jobs existed in abundance there, they naturally consisted almost exclusively of government jobs or defense contractors serving that particular base.

Though staying in Maryland had huge appeal due to the love for our community there — our co-workers, neighborhood, schools, and church — we knew those careers were not our next professional calling. Perhaps those roles could be a future calling. But the thought of thriving professionally and accomplishing the mission as a divergent thinker set in an excessively bureaucratic environment built around conformity seemed exhausting to me.

Looking for maximum opportunity

We didn’t know immediately where we would move, but we knew it had to be a place of profound and diverse career opportunity, where I could apply my current expertise, even as an entrepreneur working for myself if desired, while also learning new skills. We needed a place where skills mattered more than any one company or industry because they could be applied across industries and roles. That would yield an unknown number of career paths, without rigid timelines or artificial ceilings.

To us, those factors all combined to yield one thing: maximum opportunity. And if there was one word which began to drive our decision making it was the word “opportunity.” We began to hunger for professional opportunities that simply had not been afforded to us so far. To us, no greater opportunity existed than in the greater New York City area. We could live with the uncertainty and potential failure that could accompany a career risk, but we couldn’t live without taking a risk to pursue an opportunity. We weren’t wired that way.

In the very short time, we have been in the suburbs of Connecticut, our transition has consisted of getting settled in an unfamiliar place, fulfilling pre-existing commitments such as a part-time national security fellowship in DC and an advisory role with a nonprofit foundation holding its major fundraiser, as well as exploring new career opportunities. We believed being settled and actively pursuing relationships to help us form a community of friends and navigate my career path would be the best formula for personal and professional career goals in our new home. So far, this has proven true.

While I interview for a number of more defined roles at different firms in New York City and Connecticut, we’ve pursued a number of career opportunities as we explore the transition — whether it’s starting our own LLC to provide consulting for various clients I knew through my naval career and other business interests or applying for paid fellowships centered around areas of interest where I seek to become more influential and impactful professionally.

Lessons learned and shared

No amount of time or preparation while on the inside of the military fully prepares you for life on the outside, but there are some brief lessons I’ve learned these last few months which may speak to the vet on the verge of their own transition or those in the midst of one.

  1. Let go and move on. The military — it’s culture, processes and language — may be all that we know and love from our years of service. However, as we transition to begin the career search in earnest, we should remember them fondly as something which shaped us and made us the leaders we are today, but let go of our attachment to them.
  2. Know your value proposition in the private sector. The answer is built around three key questions: What are the critical skills/expertise which you possess or do exceptionally well or what can you be good at if given the chance to learn? How will that skill add value to a business in the private sector? What is someone willing to pay you for that skill/expertise?
  3. Know your own story and tell the best version of it. Your military service makes you unique. It’s given you a set of life experiences, skills, and character attributes that are uncommon, yet highly sought after. Tell your best story to include what’s made you who you are today and why that will add value to a business’s bottom line and equally important, it’s culture.
  4. Dare greatly and risk something. You just spent years in the military risking everything at times for those brothers and sisters in uniform serving beside you, for the ideals of the country you love, for your family and friends at home, and for people you don’t even know in places you may have trouble pronouncing. Don’t artificially constrain yourself by changing that mindset when it comes to pursuing your career transition.

America needs leaders like us in the boardroom, the schoolhouse, and the halls of Congress just as much as it does on the battlefield. Both our nation’s security and prosperity depend on it.    

Matt Driskill is a former Flight Officer for the U.S. Navy and is the founder of the Military Leadership Circle.

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