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

🎧 Summary

In this heartfelt and wide-ranging conversation, John and Victor open up about parenting, military service, veteran homelessness, emotional resilience, and their shared desire to give back. They reflect on guiding their children toward meaningful paths like the Naval Academy, critique homelessness policy, explore what they’d do with $200 million, and advocate for veteran skill-building and community mentorship. The episode also features discussions around policy changes from the VA, especially related to sleep apnea, and wraps with an exciting announcement: their co-authored book “Bottom Line Up Front: What You Need to Know Before You Leave the Military” is now available for pre-order on Amazon.

⏱️ Key Timestamps

00:00 – Naval Academy visit & inspiring the next generation

03:00 – Reflections on youth, opportunity, and American privilege

06:30 – The importance of direction and leadership

10:00 – VA awards $800M in grants for homeless veterans

13:00 – On mindset shifts and meaningful help for the homeless

17:00 – Skilled trades as a pathway for veterans

21:00 – If I won the lottery: serving others over self

24:00 – Documentary idea: following vets pre and post-retirement

32:00 – Recap & reflection on powerful episode with Eric Domani

36:00 – Vulnerability, emotional growth, and stoicism

43:00 – Meeting Medal of Honor recipient Robert M. Modrzejewski

50:00 – On the politicization of military service and media bias

58:00 – Social media fatigue and information overload

1:03:00 – VA changes to sleep apnea rating & rental assistance rules

1:14:00 – VA loan rates, refinancing, and international relocation

1:23:00 – 📚 Book Announcement: Bottom Line Up Front now on Amazon

1:30:00 – Upcoming goals and continued mission to help fellow veterans

📘 Mentioned in This Episode

Book: Bottom Line Up Front: What You Need to Know Before You Leave the Military

📖 Available on Amazon: https://amzn.to/4jUiPky

Eric Domani Podcast Episode: A must-listen story of resilience and reinvention - https://www.youtube.com/watch?v=5jed1RhqlQ0

VA Sleep Apnea Changes: https://www.vetlawoffice.com/blog/understanding-upcoming-changes-in-va-sleep-apnea-rating-criteria on CFR 38 Update

Policy Tracker: RegInfo.gov – VA Rule Changes

💬 Join the Conversation

🎥 YouTube: ⁨@thegreenlogbook⁩ ⁨@militaryretirementpodcast⁩

📘 Facebook Group: Military Retirement Group: https://www.facebook.com/groups/981767756191573

📧 Email: info@militaryretirementpodcast.com | thegreenlogbook@gmail.com

Military Retirement topics, Homelessness, College education, standards of conduct in the Navy and the Army.