When to Start Your Military Transition, and How to Make the Most of It

Military Transition

Should you stay, or should you go? It’s a question everyone asks at various points in their career, and one with specific importance for service members. The military transition process involves numerous factors – from finding a job to navigation of the VA system.

ClearanceJobs recently discussed the importance of lifelong learning with Steve Leonard – aka, Doctrine Man. Leonard is a retired Army colonel and the program director for the Master of Science program in Business and Organizational Leadership at the University of Kansas. He’s also the creator of the popular Doctrine Man, a humorous military cartoon that blossomed into an online brand with nearly 200,000 followers. You can listen to that earlier conversation on why lifelong learning is so critical. In our follow-up conversation, Leonard discusses his own military transition, and the important considerations for every service member.

“The lesson that I took from my own transition…was that you never know everything that you need to know to make a successful transition until after you transition” notes Leonard. Another fatal flaw is attempting to go through the process alone. Because the process is personal, the one-size-fits-most approach of standardized training is not going to tell you what you need to know.

Transition Tip #1: Find a Mentor

“You kind of have to find those areas that are important for you, and then find a coach or mentor to help you in the process,” said Leonard. “You don’t take on the VA without a coach or mentor.”

Whether it’s navigating the process of applying for VA benefits or healthcare, finding a contract or civilian job, or relocating to a military friendly state – when it comes to almost any aspect of the transition process, you can find individuals within your military network who have faced the same questions before. If you don’t have them, be proactive in reaching out to find those who can help.

“If you want to get a job in the GS system, don’t wait until you’re retired, or you’re sitting in the ACAP system,” advises Leonard. “Find someone who’s done it. Find someone who understands the process.

Transition Tip #2: Have a Plan

“I went through executive ACAP, and you could have drawn a line and split the class in two half of the people wanted to start t-shirt businesses, the other half wanted to start crossfit gyms,” said Leonard. “No one knew what they were going to do, and they were all within months of transition.”

If you’re planning to start your own business, you should have a business plan, know the tax laws, and be prepared for the financial and administrative aspects of running a business, notes Leonard. And the earlier you do that, the better. Don’t count on the transition program to give you all of the information you need to know.

“We tend to look at things as, you’ve served x number of years, the military’s going to take care of you on the way out,” said Leonard. “That may be true to some extent. But don’t expect them to hold your hand all the way through transition.”

Transition Tip #3: Take jobs that push you out of your comfort zone

The skills that help you with your post-military career may be skills you acquire from unexpected assignments. That’s why lifelong learning and a successful transition go hand-in-hand. If you’ve focused on making the best of every job along the way, you’re more likely to have both skills and a network of mentors to assist you navigating that post-military career.

For Leonard, one of those assignments was running a strategic communications office – despite not being a public affairs officer or having a communications background. It was a job he didn’t want- but one that turned out to be invaluable for helping him navigate his worth and role after the military.

“That was a job that helped me learn about branding, marketing, and my own professional value outside of the bounds of what I was doing,” said Leonard. For many service members toward the end of their career, the temptation may be to take the easy job that allows more down time versus the challenging job that requires more effort. But if you’re looking to keep gaining value from your career all the way to the finish, that’s the wrong approach.

“Maybe handing out towels at the gym for the last year you’re in the military isn’t what you need to do,” notes Leonard.

When it comes to seeking out new positions and tackling unwelcome assignments, the approach you take directly relates to what you’ll get out of every position – and how it will help you in your overall career.

“I believed all along that if I focused on making a difference, things would work out,” said Leonard. “And generally, that proves to be true. There’s a silver lining in every cloud, you just have to find it. Even the worst assignment will play out, but you have to find a way to make it work for you.”

Lindy Kyzer is the editor of ClearanceJobs.com. She loves the NISPPAC, social media, and the U.S. military. Have a conference, tip, or story idea to share? Email lindy.kyzer@clearancejobs.com. Interested in writing for ClearanceJobs.com? Learn more here.