“I never look back, darling. It distracts from the now.” – Edna, The Incredibles (2004)

There’s an old saying: “Experience is something you don’t have until after you need it.” When it comes to leaving the military—or transitioning between careers—it’s a brutal reminder that you never know everything you need to know until after you need to know it.

Fortunately, we come from a checklist-driven culture, where there seems to be a list for everything. And there are for transition, too. A lot of them. There’s one for retirement. There’s one for basic separation. There’s one for outprocessing. There’s one for moving. There’s one for turning in all your issue gear. There’s even one for whatever transition assistance you receive.

A list for you. A list for me. Everyone gets a list.


When you string all those lists together, they appear—at least on the surface—to be fairly comprehensive. It’s an illusion. Those lists are designed to clear you off the books, to ensure that when you finally have a DD-214 in hand, you don’t still owe something to your rich uncle, have access to some classified program when you shouldn’t, or maintain possession of some piece of property that doesn’t rightfully belong to you. As a result, there are gaps between those lists, often significant ones.

Unless you had a great mentor by your side throughout the entire process, you’re never going to know everything you need to know to make a seamless transition. You’re going to miss a lot of those gaps. And the more gaps you miss, the more challenging your post-transition experience.

Ideally, you want to find a mentor who has endured the transition process within the past five years. Someone who still has the scar tissue from the experience and is painfully aware of those gaps. Take them to lunch. Spend quality time with them. Ask a lot of questions. Invest in your own transition through them.

Years after making my own crossing, I look back on my own mentoring as nothing less than pure, unadulterated luck. My mentor came to me, stood in front of my desk, and told me to start taking notes. He walked me through the entire process and provided ample warning of the gaps along the way. He told me to put down the Motrin and start documenting the aches and pains of 30 years of military service. That experience and his advice fundamentally changed the calculus of my transition and helped to ease the culture shock of what followed.


Nothing will prepare you for what comes after transition. A good mentor can get you onto solid ground again, but each path that follows is unique to the individual. We all have different interests; we all have our own ways of doing things. But there are a few things you can do to ensure that when you start out on your path, you’ll find what you’re looking for.

1. Set your goals.

This might seem obvious, but more veterans separate without a clear path forward than you might think. Take the time to think through where you want to be in six months, a year, and five years after transition. The more detailed your vision, the better appreciation you will have for the work needed to reach your destination.

2. Buckle up.

Transitioning back into the civilian world will be an experience. Some people do better than others, but everyone struggles in some respect to adapt. Expect a few bumps. Try to stay focused on the long game.

3. Embrace your inner Gumby.

If you learn one thing from your time in uniform, it’s the necessity of flexibility. That skill will prove invaluable after you throw your boots over the wire. Don’t satisfice. Don’t cling to a job that isn’t a good fit for you. Don’t settle for a location you don’t like. Be agile, be adaptive, be Gumby.

4. Find yourself.

Take pride in your service but remember that it’s just one part of who you are. Transition will inevitably affect your identity. Many veterans who struggle after transition do so because their entire identity is wrapped up in their military service. Don’t look back, look forward. The best years are still to come.

5. Find your tribe.

One of the hardest parts of transition is the loss of team and togetherness that you probably took for granted in the military. Join a good veteran service organization like Team RWB or the VFW. These organizations can be an anchor for you as you begin to establish your identity out of uniform.

6. Find your allies.

You’re going to meet a lot of people who genuinely feel indebted to your service and want to help you as you settle into your new life. Let them help you. Build a network of support. Make friends, spend time getting to know them. Find a new team of battle buddies.

7. Find your mission.

We tend to be a purpose-driven clan. We need a “why” to drive us to new heights. Find that mission. One that inspires you, one that touches your values, one that matters to you. Then give it everything you’ve got.

8. Hit the ground running.

You’ve got a work ethic. Lean into it. Be all you can be when everyone else is still catching a few extra minutes of sleep. Hitting the ground running is nothing new to you. And you’ve got a gear that no one on the outside has likely ever seen. Show them how it works.

9. Make a difference.

Wherever you go, whatever you do, you want to bring value. You want to be someone that others respect and admire as a leader who makes a positive contribution each and every day. You want to be able to look yourself in the mirror every day and like the person who looks back at you. Make a difference like no one else can.

10. Be a mentor.

Share your success with others. Tell your story. Help the next generation achieve the same good fortune that’s come your way. Invest the time to mentor those who follow in your footsteps. Pay it forward.

A few years after my own retirement, I was asked to speak to a group of transitioning service members about, of all things, how to communicate effectively on the outside. As I stood before the group and looked at them all, I saw myself looking back. You just don’t know what you don’t know. So, for the next two hours, we didn’t talk about effective communication. We talked about the future. We talked about their concerns. We talked about how to maneuver the outside world successfully.

And… I was never invited back to speak again.



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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 senior 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 former 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.