By Christina Plumley
In January, I left Active Duty after 10 years in the Army. Like many transitioning junior officers, I intended to use the GI Bill for graduate school. I leveraged a variety of veteran transition programs, made plans and checklists, and thought I had everything planned out. But life isn’t so cut and dry. When unexpected doors opened, I changed my plans.
If you’re at a transition point in your life, I hope the five lessons shared here provide an additional perspective to many of the tried and true transition pathways. At the end of the day, there are limitless possibilities, which can be daunting, but also liberating. If you’re itching to pursue something different, your transition out of the military is your chance. Take advantage of this opportunity to pivot with so many resources at your fingertips.
Lesson One: “Yes, and…”
This famous exercise centers on two improv partners. As one person adds something new to the scene, the next partner responds with “yes, and…” The partners support each other’s ideas, rather than saying “no, but” and closing doors.
When I prepared to take off the uniform, I did this exercise. I grew up as an Army brat and have spent my whole adult life in uniform, so my world was very military-centered. What helped me was the book “Designing Your Life” by Bill Burnett and Dave Evans, written by two Stanford professors who taught a class about applying design thinking to life design. The thought-provoking exercises in it challenged my assumptions and pushed me when designing potential career paths.
What if you did “yes, and” while planning your transition? We are our greatest critic. Our internal dialogue confirming doubts and fears can naturally echo thoughts of “well no, because…” But what if you considered the possibility of “yes, and?” Think beyond what you already know.
In improv, your success depends on being fully present in the moment. During your transition, it is equally important to pause and reflect on what a clean slate truly offers. A starting point could be to reflect on what you value, what’s non-negotiable in this next chapter, where will you find community, what interests do you want to pursue, and what impact do you want to have. What you see others doing outside of the military might not be the right fit for you. You owe it to yourself to think beyond the familiar.
Lesson Two: Make a Plan But Stay Flexible
I was so keen on applying to full-time MBA programs that I decided I wanted to try a unique Career Skills Program (CSP) internship—to gain exposure to a new world before starting my MBA. I considered interning on Broadway to learn the business side of theater. I pursued an internship with a NYC charitable organization. When that didn’t pan out, I ventured into the startup ecosystem because this was the one time I could try the risky startup life and have the safety net of an Army paycheck.
Whether you can leverage CSP or not, seek out ways to explore a professional pursuit you’re interested in before fully investing time, money, and opportunity cost. This does not have to be an internship. Here you can get creative. It could look like auditing a class at a local college in a field (or degree) you’re interested in. Job shadowing, volunteering, starting a side hustle, joining a community of interest, and reading books are also possible options.
After many informational interviews, coaching sessions, and reflection, I decided to pursue a career in water tech. I cold emailed five water startups and one responded that week. Two calls later, I made arrangements to relocate to northern California to intern at Lumo, a pre-seed precision irrigation tech startup helping growers save water.
What was supposed to be a pit stop en route to a full-time MBA became my end goal. I found an incredible team, a meaningful mission, and a cutting-edge product set to revolutionize agriculture technology. When I found out my dream school offered an executive MBA program and my company would support me, I knew what I wanted to do. I completely pivoted.
Lesson Three: Veterans Can Thrive in Early-Stage Startups
In my four months interning at Lumo, I quickly learned of the many similarities between the military and early-stage startups. Veterans are used to working in dynamic environments that require adaptation. Both in the military and in startups, guidance along the lines of “figure it out” is commonplace. In the military, there are a lot of challenges that regulations and funding can’t quickly address, so you have to creatively problem-solve and make more work with less. Similarly, startups also often require creative solutions. No matter what, you get things done. That’s the entrepreneurial mindset.
In the military, you probably jumped around different jobs, organizations, and ranks, which was completely normal. To succeed, you had to overcome a steep learning curve. Right when you got the hang of things, you moved. All of that was great preparation for early-stage startups because everyone is wearing multiple hats and helping where needed. The nature of a growing company mirrors many military units.
The incredible thing about early-stage startups is that you help build the organization from the ground up. You have much more frequent engagement with the founding team than you would in an established company. Your level of impact on culture and process can be substantial. And you’ll stick around to see that early vision come to fruition. The chance to help build something new and see it through—that was a thrilling revelation for me.
What I originally thought was a risky endeavor that I couldn’t commit to turned out to be the exact opposite. This discovery started with the leap of faith to first try it out.
Lesson Four: Leadership Experience Doesn’t Necessarily Translate to a Leadership Role
I was in a leadership position for much of the last 13 years. It was a new experience to be an individual contributor. And it makes 100% sense. While my resume spoke to leadership experience, I was at Lumo to learn. This change served me well once I started my full-time role. Because I “cut my teeth” working so closely with our product as an intern, I was that much more informed when later coordinating company-wide operations.
At an early-stage startup, everyone is empowered and expected to have leadership traits because there are so many tasks that need to get done with a limited headcount. You’re expected to take initiative, be proactive in anticipating challenges, provide feedback to improve the product and company, and make decisions with limited guidance. At a minimum, you must be disciplined with your time and diligent in your work.
Leadership is an action, not a title. You’ll see that when working in a flat organization where leadership is more about how you carry yourself rather than having subordinates. Rest assured, your leadership experience will make itself evident. Take advantage of the time to really learn the ins and outs of the company without direct reports. You aren’t taking a step back by starting at a company in a non-leadership role. You are accelerating your growth potential by building a stable foundation first.
Lesson Five: Interviewing and Negotiating Requires Preparation
I imagine both interviewing and negotiating compensation are uncomfortable for everyone, but probably more so for veterans. Everyone else has already had a few reps. But do not shy away from the preparation required to advocate for yourself. This starts with a proper professional resume.
You absolutely must quantify the impact of your military accomplishments and make it easy to understand. The way military evaluation bullets are framed does not cut it. The burden of responsibility is on you to communicate what you achieved to a civilian. A good resume is the first step to bridging the understanding gap that your prospective employer may have about your military career.
Next is the way you explain your major accomplishments. While negotiating my full-time offer, I referenced many of the attributes under lesson three to show the relevance of my Army experience, which was corroborated by my recent performance as an intern. That helped transform what began as an entry-level job placement into a middle-management role. While I performed well during the internship, it was not until I brought up my years of operations experience that the conversation shifted. Had I not prepared adequately and led with that explanation, I would have missed a huge opportunity.
The reality is that working hard does not differentiate you as a veteran. To be successful, everyone is hardworking. What helps set you apart is professional maturity, your experience as a leader (which is different from management), your ability to learn quickly, handle stress, take initiative, make decisions, plan, and follow-through. Many of the things we considered a normal day in the uniform are pretty impressive if you can properly translate what you did.
In conclusion, through reflection, preparation, and leveraging CSP, I eventually found myself at an early-stage agriculture tech startup working operations and pursuing an executive MBA. My path to Lumo was filled with the unexpected. Two years ago I never could have anticipated where I am today. The beauty of pivoting is that life inevitably takes you in a new direction. While the unknown is scary, you will land on your feet. Remember that your first job out is not necessarily your forever job, which means that there’s less pressure associated with it. Put in the work to figure out what you really want to do, not what others think you “should” do. In doing so, the better your chances are to find a fulfilling place to land.
Christina Plumley is a U.S. Army veteran who served as a Civil Affairs Officer until January 2024. She served operationally in the 2nd Cavalry Regiment and 1st Special Forces Command with two deployments to Southeast Asia. She now works at Lumo, an agriculture tech startup, and is a Wharton MBA candidate. Her work has been published in the Civil Affairs Association’s Eunomia Journal and the Center for Excellence – Disaster Management’s Liaison Journal. If interested, check out these veteran transition programs: The Commit Foundation, Tuck Next Step, Special Operations Transition Foundation, Donovan and Bank Foundation
