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Seize control of your destiny in retirement

David May by David May
October 6, 2026
Seize control of your destiny in retirement

Courtesy photo.

Retirement from the military — whether you served part-time or full-time — is a major milestone. Truthfully, it can feel just as daunting as it is exciting. It’s a massive life transition, but it’s also a blank page and a rare opportunity to completely seize control of your own destiny.

Ultimately, it is up to you to make sure your next chapter complements your service and takes you to a better place.

The engine room: establishing your planning factors

Let’s start in the engine room with some standard military planning. Before you dive into the unknown, you need to establish your planning factors by asking yourself a few critical questions:

  • Timeline: How soon am I actually retiring?
  • The pension: Am I eligible for a pension right away, or will I be experiencing the “gray area” until I reach age 60?
  • Employment: Do I have a civilian job, a job waiting for me, or is it finally time to look for something completely new?
  • Finances: What does my overall financial situation look like right now?
  • Benefits: Have I talked to my County Veterans Service Officer (CVSO) about VA disability?
  • Documentation: Do I have physical and digital copies of all my important records?

That is a lot to think about, which is why an ideal amount of lead time is about two years. Believe me, it goes by incredibly fast, and the answers to these questions won’t arrive overnight. Take some time to get organized with your spouse and dedicate a regular block of time to forecasting these items.

This is also the perfect moment to start checking in with your personal and professional networks. Let the right people know about your upcoming plans; you’ll be surprised how often opportunities pop up simply because you let your network know you were looking.

Operations: owning your moment

Now, let’s move over to the operations section. The day is finally arriving, and you have a once-in-a-lifetime chance to decide exactly how you leave the service.

Think carefully about your ceremony planning. This isn’t just about tradition; it’s a profound opportunity to thank your family and friends. This is likely the only time they will all gather in one room to hear a complete rundown of your military accomplishments and to hear your remarks about how vital their support was to your success.

Whenever I would walk on stage to retire someone, I always gave them the same advice right before we stepped out: Take a deep breath, relax, smile and enjoy. This is your moment. Own it.

Future operations: finding your balance

How does a disciplined, organized, motivated and self-driven military retiree find true happiness in civilian retirement?

  • Put up the guard rails: If you are headed back into the civilian workforce — or focusing solely on the civilian job you already have — it might be time to establish some serious work-life balance. The heavy sacrifices you made during your service might not be necessary now. Take advantage of this new freedom to ensure you are fully experiencing life with your family and friends.
  • Keep a connection: It is an incredible feeling to maintain a bond with the military community. It binds us together with a shared sense of familiarity and pride. There are numerous veteran service organizations to consider. A fantastic option available in every state is Employer Support of the Guard and Reserve (ESGR), a volunteer-based organization always looking for new retirees to join the mission.
  • Look after your fitness: Without a recurring PT test, it’s easy to let things slide. Take a new look at physical activities you genuinely enjoy and stick to them consistently. You’ve got a lot to live for!
  • Give yourself some grace: Every retiree I’ve talked to has felt unmoored for some period of time after leaving the military. Be prepared for some ups and downs, and give it some time.

You served honorably, sacrificed a lot along the way, and now it’s your time to take control of your fate and enjoy the next chapter of your life on your terms.

For more information about VetJobs or these columns, contact dmay@vetjobs.org.

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Tags: David Mayfeaturedmilitary retirementmilitary retirement advicemilitary transitionretirementTransition
David May

David May

Maj Gen (ret) David May, PhD, is the Vice President of Military Partnerships for VetJobs, a non-profit organization that provides no-cost employment support to all military affiliated job seekers. He can be reached at dmay@vetjobs.org.

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