Throwing Your Boots over the Wire: How to Know When the Time Is Right for You

Military Transition

A staff sgt. swears the oath of re-enlistment. (Photo Credit: U.S. Army photo by Paolo Bovo)

Early on in my career, I knew that my time in uniform would be short. Not long after arriving at Fort Campbell, Kentucky, I contacted the headhunter firm Cameron-Brooks, and began planning for life after the military. I attended the seminars, read the books, and discussed the future. I completed work on my master’s degree, focusing on a career in industry where I could put my education to work. In the summer of 1990, I was determined to “throw my boots over the wire.”

Then came the phone call that changed it all. “Report to Sherman Army Airfield. You’re deploying to Saudi Arabia.” Six months later, I changed my mind. I made my decision on a deserted stretch of Highway 8 near As Salman, Iraq, on the last day of February in 1991. It was a much easier decision than I had anticipated, and in the closing hours of Operation Desert Storm, I knew that I was committing to a career in the United States Army.

Take a mental Inventory of Your Military Career

We all face that decision point in our careers, often more than once. Some face it early, others later, and some not until it’s forced upon them. When I made my choice, I sketched out a mental checklist that I used to assess my own “career cutoff point.” Over the years, I revisited the items on that list at roughly five-year increments, until finally committing to my own exit strategy. My list grew from years of being mentored by more senior and seasoned leaders, and from watching and learning others, often people who had overstayed their usefulness in uniform.

The checklist isn’t really complicated, and although it’s changed somewhat over the years, the intent remained consistent.

  1. Am I still having fun? Few careers are as much fun as the military. I mean that seriously. The day it stops being fun is the day that it’s time to reconsider your options. Yes, you’ll have good days and bad days, but when the bad days outnumber the good, it’s probably decision time.
  2. Is it a job? The Navy’s best marketing campaign sums this point up quite well: It’s not just a job, it’s an adventure. When it becomes a job, it’s time to stop and consider your options. And you’ll know the difference. It’s no longer exciting, not even remotely interesting. You’re just going to work to slog along in the same mud you do every other day.
  3. Am I making a difference? One of the most rewarding feelings is the knowledge that the profession is better off with you in uniform. Some people have a greater influence out of uniform, while others don’t make a difference at all. The minute you are no longer making a difference, you should take a professional pause and ponder your contribution. If you’re just part of the machine, your passion might be elsewhere.
  4. Do I still care about people? The less you care about the people around you, the more likely that it’s time to move on. If it’s about you, and only you, you’re in the wrong profession.
  5. Do I watch the clock? Are you a clock watcher? Do you arrive later and later every day, take longer and longer lunch breaks, and keep a close eye on the clock to know when to “cut slingload?” These are indicators that you’re not all in  – signs that it’s time to punch out for good.
  6. Can I deploy? Some people can’t deploy. I get that. But I always took great pride in my deployability, to the extreme of pulling out 13 stitches with a Swiss Army knife in the Sherman Army Airfield latrine so a flight surgeon would clear me to get on a plane. We have a great influence on our ability to deploy, and we share great stories of leaders who deploy again after being grievously injured. If they can do it and you won’t, that’s another indicator.
  7. Am I toxic? Do you hate everyone you work with? Does everyone you work with hate you? Do you poison the well every time you drink from it? Have you gone straight from skeptic to cynic and not passed “Go?” Do everyone a favor and find a new career.
  8. Do I live the Army Values (or the values of my branch)? Don’t be that  guy. The day you can no longer uphold the values of your profession is the day you need to walk away. There’s nothing worse than knowing (or not knowing) that the people around you think you’re a cretin. They see what you do, and they talk about it. We all make mistakes, just don’t wear yours on your sleeve like a badge of honor.
  9. Is my family happy? Few things impact your career as much as your family. If they’re happy, it’s a lot easier for you to be happy. If they’re not happy, then you need to do some soul-searching. Communication is the key to every happy family. Listen to them and listen closely.
  10. Can I still laugh? Ever know someone who only laughed when something bad happened to someone else? You don’t want to be that guy, either. If you can answer “yes” to the first question, then this one is a close second. Don’t take yourself too seriously and you’ll go far. Learn to laugh, to live, and to enjoy the little things. When you stop laughing, start packing. You’ll be doing everyone a favor.

Eventually, we all make that fateful decision. Some sooner, some later. When the time comes, we all know when to go. When that time comes for you, do it the right way, do it on your terms. You’ll be happier and so will everyone around you.

Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a non-resident fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.