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Our Military Retirement Journey Begins

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Our Military Retirement Journey Begins

We are ten months out from military retirement–a milestone after 23 years of marriage. We are in the early stages, and it already resembles the typical rollercoaster ride when preparing for a Permanent Change of Station (PCS), the military term for relocation or a deployment. I thought it would help to journal our experience as we navigate this process, sharing all the ups and downs.


Our retirement story starts with some background. My husband’s previous assignment was in Belgium. We planned to retire there and maybe settle in Europe. In September of 2022, we completed the Executive Transition Assistance Program (TAP) in Naples, Italy–a course that helps prepare for civilian life. We gained resources like the Managing Your Transition Timeline and felt ready. What we learned after the TAP class is that my husband would likely have to do 10 days of Temporary Duty (TDY, a short-term assignment) to Norfolk, VA, to sign retirement documents. The admin team in Belgium was not equipped to handle everything. He consulted his detailer, a career mentor, and we chose to extend his service for one final assignment in the U.S. and not risk a messy retirement from overseas.


That assignment brought us to Vandenberg Space Force Base. He picked Vandenberg for its opportunities and mild weather. In December of 2024, we attended a Benefits Delivery at Discharge (BDD) class at the Education Center, learning how to claim veteran benefits based on his medical record before retirement. This class provided tips and tools for each stage. Vandenberg’s opportunities excited him – NASA and SpaceX operate here and offer SkillBridge, a program that allows service members to intern with companies within a certain timeframe after retirement. With his Naval Postgraduate School background in space systems, this was a shot at a dream job. In February, he contacted SkillBridge reps for both companies.


Pursuing SkillBridge, he submitted his retirement request in June but encountered some hurdles. Issues accessing the system caused problems, and then the system that tracks his achievements needed to be updated. After resolving that problem, the next hurdle was that his admin team in Denver lacked the authority to approve his request. He is working through this issue.


At the same time, he requested a SkillBridge start in December. His request was denied. We learned from the denial that Navy regulations limit him to participate in SkillBridge only 90 days before retirement, due to his rank. This forced us to cancel terminal leave, which is not possible if you elect to use SkillBridge. He recalculated and rescheduled leave days and Permissive Temporary Duty (PTDY, authorized time for transition, like finding a home). He will resubmit for a March SkillBridge start, aligning with his June 1, 2026, retirement.


Military boots to civilian work shoes – Photos by Rikki Winters

Since TAP in 2022, programs have evolved. We have been approved for an updated TAP in San Diego next month to learn the latest. The uncertainty–admin delays, SkillBridge limits–has us reevaluating. I joke that my husband can work for me and help me with my business when he retires. He counters for tax-free tips only. I know it wouldn’t be satisfying work for him. We are exploring all paths.


I was hoping that the transition would be a smoother sail. We still have to schedule the education or business track following TAP. Military or not, what’s your experience with big life transitions? Fellow community members, what are you or did you experience with your transition? Do you have any tips?


Originally published on LinkedIn on July 14, 2025. [Read it here]

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