3 questions Service members should ask before transitioning to the civilian workforce 

By Jessica Ruttenber

“And then I hit transition, and then it was retirement.  I kept asking myself, what do you wanna do, what do you wanna do and then I switched it to Who Do You Want to Be?”  RET Navy SEAL Dan Luna

According to the Department of Veterans Affairs approximately 200,000 men and women annually leave U.S. military service. For many veterans, finding a job is an important and often stressful part of the transition to civilian life. A PEW Research center study showed that almost half of veterans leave their first post-military job within the first year, and another 21% left before year two.

Originally, I began this article as a sort of top ten list on the upcoming anniversary of my military retirement but honestly you can do an internet search and find numerous articles that give great advice. Instead I would like to share the recurring theme I found in numerous conversations with my peers transitioning behind me. I found three factors, that if not properly balanced, can earn a transitioning member a ticket to ride the struggle bus.

3 factors that need alignment when considering a post military civilian job; money, purpose, and lifestyle.

Ask yourself the following questions:

How much money do you need to support your current or desired standard of living?

As you might have done your homework you will know that a considerable part of your income in the service such as your Basic Housing Allowance was not taxed so you actually have to make more than when you left service to break even unless you can augment your income with alternative sources of income such as investments or military retirement. You can use this calculator here to estimate your own needs.

What will give you purpose?

This is your why, not what you do.  What motivates you? Often veterans feel out of place, a little lost or disheartened when entering the workforce. It can be difficult to find a career that will fill the camaraderie and purpose that serving your country did. Without addressing this basic question as you transition, you may leave constantly trying to fill a void. What are you passionate about?

What kind of lifestyle do you desire?

For example, you can certainly make a lot of money but find yourself commuting an hour each way every day or constantly on trips that lead to missing important events such as an anniversary or holiday with those you love. In that case I would say you are a good candidate to burn out and would likely to change jobs at the next opportunity.

Or maybe you have found purpose giving back by working for a nonprofit or becoming a public-school teacher but will likely not be able to afford your current standard or living or put away more money towards your kids’ college fund.  What adjustments are you willing to make?

What I have found is it is difficult to achieve all three right out of the gate especially if you are uncertain. After countless interviews with multiple companies I found I could achieve two but not three.

Here is how I answer these questions.


Being an Air Force pilot made me an ideal candidate for the airlines, allowing me to maintain my current standard of living. After missing countless birthdays, anniversaries and holidays in the military with my three children and spouse I desired a better lifestyle and opted not to fly.  Eventually I would be able to compete for a more desirable airline schedule but that would take years and my kids will only be this little once.  It is natural to gravitate to the familiar in a time of uncertainty. Being a pilot was who I was. Not who I am now. I saw some of my friends reach out of fear of pivoting in a different direction and went with the familiar that did not necessarily align with their lifestyle.


Now this was the trickiest one for me because I was and still am a passionate advocate removing barriers for Service members. I wanted to work for a nonprofit like the Service Women Action Network in Washington DC but found that most nonprofits could only pay a tiny fraction of what I could have made in the airlines. That might have worked given my retirement pay but the DC area is one of the most expensive in the country. Even combined it would not cover my rent.

Life Style:

After watching a few friends crash and burn in this department I decided flexibility for my family was a priority and with this I started looking for jobs with small commutes or virtual options that met my desired income. I didn’t want to work 12-hour days or anything that resembled shift work. I think it is a safe assumption that if you served you have already had you fill of that.

So where did I land? After a 6-month search that started while I was active duty I accepted a position at Amazon Web Services (AWS).  AWS more than fulfilled both the income and lifestyle my family needed. AWS lets me work virtually for the majority of the time.  However, despite being intellectually stimulated working in a fast-paced tech environment it didn’t completely fill my desire for purpose.  Was I about to over index on income and lifestyle and find myself less than satisfied a year down the road? Instead I eventually filled this need with volunteer work. I even started my own nonprofit that gives scholarships to the under served looking to break into the aviation community. Additionally, I started small passion projects at work outside my job description to help increase the low numbers of women in tech.

When considering a job during your transition ask yourself the three questions about income, purpose, and lifestyle.  In what order are they important to you? What are you willing to start doing or stop doing to achieve your goals? I wish you a smooth and successful transition into civilian life and thank you for your service.

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