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David E. Winslow of Brewer served in the U.S. Air Force and Maine Air National Guard. He has served in various community service organizations including Down East Big Brothers, Kiwanis, and Maine Air Guard Charity (MAINEiacs Charity).
I first enlisted in the U.S. Air Force in 1965 and served until 1969. Thanks to the GI Bill, I was able to attend Husson University and earn my four-year degree in 1973. After graduation, I reenlisted in the Maine Air National Guard, returning to my former career field in communications.
In 1981, I was selected for a full-time recruiter position with the 101st Air Refueling Wing in Bangor. Ten years later, I transitioned to the Security Forces and retired in 1994 after a total of 27 years of military service.
Military life wasn’t always easy. There were times I thought seriously about leaving, but I’m glad I stayed the course. The long-term rewards have far outweighed the challenges. While I’m not wealthy, my monthly Social Security and military retirement checks are deposited automatically, providing steady financial security.
After retiring, I continued to work. At 78, I’m still employed part-time in a job I enjoy with Charter Vans, a company based in Ohio. I shuttle military applicants between Bangor and the Military Entrance Processing Station in Portland. The best part of the job is talking with these young men and women about what military service can mean for their futures.
I tell them to take their time with big decisions like marriage, especially in the early years when pay is modest and training takes up most of their focus. I also remind them of the benefits that make military service unique: housing allowances, education opportunities, steady pay, and health care that would be out of reach for many civilians.
Even for those who serve just one enlistment, the military provides top-tier training, discipline and experience that employers value. For those who make it a career, the rewards multiply. After 20 years, most service members are still young enough to start a second career while collecting a pension of around $2,000 a month or more, depending on rank. Add in Social Security, a civilian paycheck, and — when the time comes — health coverage through Medicare and Tricare for Life, and you’ve built real financial stability.
Personally, I haven’t paid a medical bill since 1995. That’s not an exaggeration — just one more reason I’m thankful I stayed in uniform. Between Tricare and the VA system, I’ve received excellent care without the financial worry that so many face today.
A 20-year military career isn’t always fun or easy. But few careers offer the same sense of purpose, camaraderie, and long-term security.
Given the uncertainty and high cost of living today, I believe military service remains one of the best opportunities available for young people in Maine — and across the country — to build a strong foundation for their future.
