10 Questions to Ask Yourself Before You Transition

Army colonel discussing jobs.

Preparing yourself to separate from your military career involves a job search and addressing all the aspects of your military life that will now need to adjust or be repositioned for your life out of uniform.

As noted by CareerOneStop, “Although military life is full of assignment changes and moves, there is a certain stability in knowing that you are employed, you have support and a paycheck. However, leaving the military and looking for a civilian job will probably bring about the most change and uncertainty you have had to deal with in quite a while.”

Awareness typically helps individuals dealing with stress, and the more information and insight you can have about your transition, the more prepared you will feel to embark on your life as a civilian again.

Here are 10 questions to ask yourself before you transition:

How Much Do I Need to Earn?

This is not the same as, “How much would I like to earn?” or, “What do I think I’m worth?” Get a realistic baseline of your expenses, needs and spending habits to accurately decide what you’ll need for income. Look realistically at the parts of your budget that could be shored up if necessary, such as entertainment and vacations, and the expenses that are necessary to work, such as child care and transportation.

Where Do I Want to Live?

Depending on the type of work you will seek and the income you need, geography could play an important factor. Certain regions of the U.S. have higher per-capita income and the cost-of-living matches. Certain jobs pay higher in higher income areas, but you might not be happy living there, and visa versa. A good look at incomes by geography is helpful when considering where you’ll live after leaving your last duty station.

What Kind of People Do I Work Well With?

When you think over your military career, who did you get along with the best? This is an important question when considering the environment where you’ll be most happy. If you are most comfortable around strong-willed, commanding individuals, you might choose to seek a company or industry that leverages those personalities to drive results.

Do I Want to Lead or Follow?

Years ago, in a Transition Assistance Program training session I facilitated in Colorado, a soldier stopped me midsentence and said, “You know, not everyone who leaves the military still wants to be a leader.”

What a great point. As you get ready to separate from your roles and responsibilities in uniform, consider whether you are at a point in your career when you are still attracted to high visibility, high responsibility leadership or whether you are ready to have a career that allows you to leave work behind at the end of every day. Neither is right or wrong.

What Makes Me Happiest?

Consider the types of projects, initiatives, work and missions you’ve been the happiest at: What were you doing? Who were you with? What were the desired outcomes? How did you meet expectations? What about it made you happy? Then try to map that to civilian careers, which could possess the same ingredients with a different job title.

What Would I Hate to Do All Day?

For one of my clients, the idea of sitting all day behind a desk, in front of a computer, makes him shudder. For him, being outdoors and creating something with his hands is more meaningful and fulfilling. What kind of work or environment would you hate to work in? Write that down.

Who Is My Support System?

Who will you lean on for advice, guidance, mentoring and emotional support as you transition? As early as possible, start to prepare these people in ways they will be called upon to help.

What Tools Do I Have?

You likely never needed a resume while on active duty, but do you have one handy? Have you invested the time and effort to craft meaningful online profiles? Do you have a list of your networking contacts from the military and civilian sectors? Take inventory of the tools you have readily available.

What Tools Am I Missing?

If you don’t have a resume, cover letter, business card, professional wardrobe, list of contacts, social media profile or other job search tools, then list out what you need and prioritize how you will acquire them. Your online profiles will be easier to produce if you have a resume, for instance, so those two might go together. You might hold off buying a career wardrobe until you land a first job.

How Will I Measure Success in My Career?

What are your ultimate goals? Do you work to live or live to work? When will you believe you are confident in your career direction? Set the goals and expectations now, before you’re fully immersed in your career transition, to have a strategic advantage.

Arming yourself with information is key to a successful transition to the civilian sector. Continue to make lists, assign yourself tasks and complete those tasks in a timely manner to ensure you have the right approach and attitude for your next career.

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