Season 4 Episode 163: Navigating the Ups and Downs of Military Transition with Chris Dreisbach

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We are excited to welcome back Chris Dreisbach for his fifth appearance on the Lessons Learned for Vets podcast. Chris retired in 2020 as a Senior Master Sergeant for the United States Air Force. Now in his sixth role since his retirement, Chris continues to share the lessons he’s learned along his path. 

Chris reflects on his previous roles and discusses the challenges he experienced. In his first role as a maintenance manager, Chris assumed the job would be similar to his military experience in aircraft maintenance. In reality, the job required long hours to fulfill the production goals of a 24/7 facility. Chris lasted 3 months before moving into a remote, entry-level data analyst role. While in this position, Chris took his time to find a better fit in the warehouse industry. Utilizing his experience in quality assurance and interest in safety programs, Chris found a role that better suited his background. While working as a Safety and Training Manager, Chris took on more responsibilities hoping to get promoted but instead his company took advantage of his work ethic and continued to stretch him thin without additional compensation. Chris realized that he needed to shift his military mentality if he was going to find success in the civilian sector.

Chris remarks that this is the longest he’s ever lived in one place, and he finds himself getting antsy – almost like he’s ready for new orders. The military transition is a process, and it may take years to feel settled into a new rhythm. 

After applying the lessons that he learned in his previous jobs, Chris is finding success in his current role working remotely for a tech company. His scheduled hours work well for his desired work-life balance, and he no longer tries to take on additional responsibilities. Like many other veterans, Chris’ networking skills led him to this role. He reminds others that networking doesn’t have to be deliberate – for him, his opportunity came organically from a conversation that occurred months prior. In the 4 years since his retirement, Chris has learned to find ways to authentically connect with others. 

As an avid listener to the podcast, Chris credits the information he learned from the episodes with Misty Moreno, Keith Cassant and Sarah Bumgardner to help him change his mindset to better function in the civilian sector. Keith says he was fully prepared to be unprepared for retirement. Due to unforeseen circumstances, Chris was unprepared to leave the military when he did. Thankfully by the time he retired, he and his wife had learned how to be financially responsible and had been living within their means. Looking back, he realizes that he had a solid foundation to retire even if at the time, he perceived himself as being unprepared. It’s important to take an honest look at finances and expectations with your family before separation or retirement. It’s also equally important to make wise financial decisions before exiting the military. 

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Connect with Chris at https://www.linkedin.com/in/christopher-dreisbach/

Download the AAFMAA transition timeline at

The Lessons Learned for Vets Podcast is sponsored by Seek Now and their Drive Academy. Seek Now is the property inspection industry's leading business and they created Drive Academy DoD SkillBridge and CSP internships to teach transitioning military service members and veterans skills that prepare them for lucrative and rewarding careers in the property inspection and insurance industries. You can learn more and apply today at www.internwithdrive.com.