Military Retirement Podcast

#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

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Military Retirement PodcastBy w/ John McConnell and Victor De La Flor

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