#85 🎙️ Retired Life, Real Talk: 22 Years, 4 Deployments, and Finding Purpose After the Army | Guest: Winway Bertley
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#85 🎙️ Retired Life, Real Talk: 22 Years, 4 Deployments, and Finding Purpose After the Army | Guest: Winway Bertley
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Welcome back to the Military Retirement Podcast — the show by veterans, for veterans. Today, John is joined by Winway Bertley, a U.S. Army retiree with 22 years and 8 days of service, to talk about life during and after the military.
In this episode:
🇺🇸 Infantry Roots to Logistics Leadership: The journey through Army life
🚁 Four Deployments, 54 Months Overseas: The emotional toll of 16-month deployments and missing key life events
🧳 Transition After Deployment: Adjusting from combat to family life
🛡️ Veteran Benefits 101: Starting VA disability claims early and preparing medical records
🐾 New Passions: Why Winway is pursuing a dream in wildlife conservation instead of staying in logistics
🏡 Post-Retirement Jobs: Working at CIF and embracing a low-stress civilian life
💬 Real Talk About Friendships: Rebuilding a social network post-service
✈️ The Importance of Decompression and Vacations: Finally taking that first real vacation after two decades of service
📚 Resources for Retirees: TSP matching, military hotels, and taking advantage of your veteran benefitsTo all the brave men and women out there still protecting our freedom 🇺🇸 🫡 Thank you for your service!
Timestamps:
0:00 - Intro
0:40 - Winway’s background: Infantry to Logistics
2:00 - Why Army deployments were so long
4:00 - R&R experiences in Qatar
9:00 - Reconnecting with family after deployments
12:00 - Being present for major family milestones
17:00 - Life immediately after retiring: first civilian job at CIF
23:00 - Transitioning out of the "always on" military mindset
29:00 - Building a second career and choosing happiness
32:00 - Wildlife conservation goals after the Army
36:00 - VA Disability claims: tips and hard lessons
45:00 - Finding purpose after military retirement
53:00 - The importance of preparing financially for retirement
1:00:00 - Dealing with the weirdness of civilian friendships
1:10:00 - Taking your first real vacation after retirement
1:20:00 - Final advice for transitioning service members
Resources Mentioned:
Book: Bottom Line Up Front: What You Need to Know Before You Leave the Military
https://amzn.to/4jUiPky
Facebook Group: Military Retirement Group
https://www.facebook.com/groups/981767756191573
Military Retirement Podcast on YouTube
https://youtube.com/@militaryretirementpodcast
The Green Logbook on YouTube
https://youtube.com/@thegreenlogbook
some links may result in commissions for the site