BWF’s Keith Whitcomb Describes the Challenges of Civilian Life After a Long Military Career

By Keith Whitcomb at Bob Woodruff Foundation

I retired in 2017 from the US Army after serving over 32 years. The transition from my military career to civilian life is ongoing. The journey started when I took my mother to the recruiting station. I was only 17 at the time. I remember a quick series of events— my mother signing my paperwork, a judge ending my probation, and then being sent off to basic training as a teenager. Over 32 years later I faced the daunting challenge of joining the civilian workforce. I had often been warned about this by leaders who had retired before me. Somehow, they survived, and I knew I was going to have to face the transition one day.

I did the usual things we were advised to do to prepare for the transition. I acquired a degree or two, some certifications, and went through the Transition Assistance Program. I created resumes, updated my LinkedIn profile, and started networking. I went to FourBlock toward the end of my military career to give me the best possible edge in transitioning.

The time had finally come. I was facing retirement, going through a divorce, and was trying to regain some semblance of sanity while identifying what my next steps would be. While on transition leave, I became a licensed insurance agent in the State of Washington. That career was short-lived and I resigned the next day. I just couldn’t do it. I realized I needed a purpose to put my time and effort against as I’d done for so many years. I also needed a paycheck.

Everyone has their own story when it comes to their transition from military to civilian life. On one particular day, I remember going to the Post Exchange (PX). I had about three weeks left on transition leave and met with an amazing friend who introduced me to one of his friends. Ahh, the power of networking. Two weeks later I was working with the National Veterans Intermediary to help veterans throughout the country through a national network supported by the Bob Woodruff Foundation.

The rest is history. Here I am, supporting my fellow service members, as I’ve been doing my whole life. I’m still working to support those who have selflessly served this country. The bottom line is that this new career gives me a purpose to pour my time, effort, and skill into.

Over the last four years, and after talking with my friends who have transitioned, I continue to build upon a few points that are top of mind when considering transitioning:


  • Find something that gives you a purpose. You want to work in a role that truly resonates with you and makes you happy if possible. Be realistic and find something that aligns with your passions. It may not be the first job you find after you’re out but keep looking. Retention rates, along with your happiness, are generally higher when you do what you want to do.


  • Adjusting one’s operational tempo. It was important to understand that I had to reduce my operational tempo (OPTEMPO) in some cases and some folks I worked with had to speed up a bit. I realized that time works differently out of the service and I’m still adjusting to that. In my current environment, I don’t have to be “ON” 100% of the time as I was in uniform as a senior leader. Work ebbs and flows, and that mindset continues to be an adjustment for me.


  • I had to learn to speak civilian American, to use fewer acronyms, and learn a new business lexicon to figure out some clear synonyms for military terms.


  • Adjusting my state of mind. Transitioning from the military, in my case at least, is mostly learning to adjust to a different mindset. I must continuously try to understand the “why” of it all, what constitutes quality work, the difference between “I need this soon” in the military vs. “I need this soon” in the civilian world. There is a overall difference that I’m realizing. I’m constantly examining different realities of both worlds, and different realities between different sectors. It is all eye-opening for sure!


  • I’m never leaving my tribe! The Department of Defense is a small subset of the American people, and a part of that is my Army tribe. While I’m not in uniform, I’m still serving my tribe that includes those still in uniform, veterans, and their families. I’m a “Soldier for Life”, and still serving with the Bob Woodruff Foundation to help support my tribe and the sacrifices they’ve made for our country.


  • The only constant in life is change. I continue to embrace this concept as I drive change in my life as I look forward to succeeding in my new profession and provide for my family’s future.


I’m still growing and trying to understand what is most important for myself and my family. It has been quite a journey and I continue to remake myself every day in this “new” life I’ve found outside of military service.


Keith R. Whitcomb is a retired Command Sergeant Major and served in the U.S. Army for 32 years. He is currently the Director of Development Operations at BWF.