Blow This Popsicle Stand: What Is the Best Decade of Your Life to Leave the Military?

superman with giant popsicle ready to blow this popsicle stand

Is there ever a perfect time to leave the military? For you, yes. There is a perfect moment in your active-duty life when you know it is time to blow this popsicle stand.

Then you look at the economy. It seems like people are getting laid off out there. Or you get picked up for a cool assignment and the military seems like a great idea again. Or your working spouse lets you know this is their dream job and their forever home. Or someone who likes you asks, What kind of job are you looking for?

And you look out there at the civilian world and realize you don’t have a clue.

If you’ve had any such thoughts, you may feel your cool confidence about the perfect timing melt away.

As the transition master coach for’s Veteran Employment Project, I’ve helped more than 13,000 veterans and spouses learn skills and strategies to find their next high-impact job. I can assure you that every decade of your career changes the opportunities you have when getting out.

Timing matters. What career issues should you consider before leaving the military in each decade of your life?

Get Out in Your Very Early 20s

If you leave the military in your very early 20s, it may signal to employers: Bold career experiment gone mysteriously wrong.

You don’t have to tell them how it went wrong. As long as you did not commit a felony — or actually blow any popsicle stands — you are fine. Employers know people try a lot of career options in their 20s that may or may not work out.

RESOURCE: This time, try something a little better suited to you. A good place to get one-on-one coaching in your state is with the Department of Labor’s American Job Centers. They offer training referrals, career counseling, resume services, job listings and a deep knowledge of the needs of local employers.

MASTER CLASS: Also, check out our FREE master class for young enlisted to learn a lot of strategies.

Get Out in Your Late 20s

Although your late 20s are the same decade as your early 20s, it looks different to employers. Getting out now means you probably enlisted more than once, completed your training for your military job, and received some experience. Many of you have led or managed other people in these jobs. Employers like that.

Some of your military peers may claim you’re not qualified to do anything on the outside. They’re wrong. Defense companies, for example, have veteran hiring programs aimed at you; plus many junior officer recruiters are hunting you down on LinkedIn.

RESOURCE: Use your Post-9/11 GI Benefits to help you find your dream career. A bachelor’s degree in a STEM field, a master’s in an in-demand profession, or an MBA from a bricks and mortar school in your target location can be a great next step.

MASTER CLASS: You can find solid strategies in our FREE Master Class for Junior Officers (which is also good for enlisted who have or plan to get a degree.)

Get Out in Your 30s

In some ways, your 30s can be the hardest decade to leave the military. Leaving now can mean one of three things to employers:

A) You gave up on the job. Getting out in your 30s can mean you have no interest in the next part of the job, that waiting for retirement is not worth it to you, or that you weighed the benefits of military life against the cost to your family and realized it isn’t worth it.

B) The job gave up on you. Getting out in your 30s can mean you didn’t make rank, you got passed over, they closed your rate, or your knees can’t take one more ruck.

C) You were enticed away by something fabulous. Getting out in your 30s can mean you or your spouse found a fabulous career opportunity. If you are in a sought-after field, civilian recruiters may dangle an offer that can’t be refused.

RESOURCE: Look into a DoD Skillbridge Internship. You have so many military-specific skills, retooling with a Dod Skillbridge partner while you are still getting paid by the military can make all the difference in your 30s.

Use your Skillbridge time to get certified with an organization like Transition Overwatch or Workshops for Warriors. If you are a college grad, land an internship with Hiring Our Heroes Corporate Fellows. Or get more help and more time to define your job prospects with Allegiant Giving’s Skillbridge program.

MASTER CLASS: We have two FREE master classes specifically for people in their 30s: Mid-level with Experience and Mid-career with Bachelor’s Degree or higher.

Get Out in Your 40s

If you leave the military in your 40s, that usually means you are a senior leader — enlisted or officer — who is retiring with 20+ years of experience. In your early 40s, there’s still time for a significant second career.

The biggest challenge may simply be to describe your work in a way that civilians understand.

RESOURCE: Our Veteran Employment Project video library is full of free 60-minute master classes that can help give you insight to describe your experiences the right way.

Also, consider a professional coach like me to work on your resume with you. Without the right resume, you may miss opportunities in the civilian world.

MASTER CLASS: You are likely trying to transition into a management position with high stakes and little room to maneuver. Check out our specific recommendations in our FREE master class for senior leaders and shave months off your job hunt.

Get Out in Your 50s or 60s

If you are getting out of the military in your 50s or 60s, you are likely at a very senior level. Civilian employers keep a close eye on how much runway you have left.

This can be tricky, but at this stage, it’s often worth it to stay in the military. If you are stationed overseas, consider staying for one more tour so you can get stateside. It’s hard to transition from an overseas location.

Your “twilight tour” — the last job you take in the military before retirement — is another thing to consider. If that job does not move you to the state where you want to retire or add to the knowledge, skills and abilities that would attract an employer, it might be better to get out sooner. Remaining in that twilight tour for three years can burn up your career runway.

RESOURCE: Check the retirement calculator. If you’re staying only to maximize your retirement pay, you may sacrifice financial gains of a civilian job plus retirement pay. Also check out USAA’s National Guard and Reserve Calculator.

MASTER CLASS: When you leave the military in your 50s, you should take our FREE Senior Leader master class. Also check out our master class about Finding Defense Jobs.

No matter when you choose to get out, the years you serve in the military can be a solid base of your career. Make the most of your gains by carefully considering the perfect time for you to move to your next high-impact career.

Jacey Eckhart is's transition master coach. She is a certified professional career coach and military sociologist who helps military members get their first civilian job by offering career-level Master Classes through our Veteran Employment Project and on her website Reach her at

Find Your Next Job Fast

Transitioning military, veterans and spouses may be qualified for the job, but they are missing the secrets of civilian hiring. Find out everything you need to know with our FREE master class series including our next class You can view previous classes in our video library. Questions for Jacey? Visit our Facebook page.

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