Dying to Retire Podcast

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Podcast by Douglas

Dying to Retire Podcast

Doug is a retired federal employee, conservative, and Marine Corps veteran (1980s) with over 40 years in the workforce — blue-collar work, corporate life, and federal service — before walking away on his own terms. On Dying to Retire, he talks straight — no HR-speak, no toxic positivity, no polish — about what retirement actually looks like: the money, the identity shift, the marriage dynamics, and the reality of building a new life abroad. Doug is currently in the final stages of building his own retirement home outside Antigua, Guatemala, and shares the real numbers and real headaches as they happen. Think of it as a seat at the firepit — a cigar, a beer, and no-shit conversation between guys who have earned the right to talk straight. Questions or comments? Email me: dyingtoretirepodcast@gmail.com Follow me on X: https://x.com/Dying2Retire YouTube: https://www.youtube.com/@DyingToRetirePodcast

Latest episodes

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03 September 2026

#051: Insurance Bureaucracy Nightmares, FERS Supplement Cliff, and the Death of Accountability

In this episode, Doug gives us an update on why he’s stuck in Maryland instead of setting up Casa Douglas in Guatemala. He details the absolute nightmare of dealing with bank and insurance bureaucracy — from insurance and mortgage companies taking weeks to cross-check paperwork for a main line repair to waiting nearly a month for an adjuster to look at a leaking sunroof.

He drops a practical tip for anyone working through Guatemala residency, breaking down how doing your own state-side apostille work can save you over $1,000 to put toward your home.

He then tackles federal retirement math and explains the FERS Special Retirement Supplement "cliff" at age 62 — why it disappears whether you claim Social Security or not.

Doug wraps up with a raw perspective calling out modern society's total collapse of personal accountability — taking aim at the academic fraud scandal surrounding fake Cambridge professor Jason Arday, the media excuses in high-profile violent crime cases, and a lighthearted rant about why men will never loan out their shoes.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com Follow me on X: https://x.com/Dying2Retire YouTube: https://www.youtube.com/@DyingToRetirePodcast

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18 August 2026

#050: The Great Guatemala Box Tetris, Buddy Checks, and Medicare "Free" Healthcare Bullshit

In this episode, Doug gives us the real deal on shipping boxes to Guatemala — playing Tetris with beach towels, childhood afghans, and his wife's mysterious collection of cleaning supplies that apparently don't exist at the Walmart down there. He shares a volcano eruption update from Fuego and calls out the Facebook warriors who wanted Mother Nature to reschedule her eruption around their vacation plans.

From there it's a heart-to-heart about the importance of "buddy checks" among Boomers and Gen Xers — those sign-of-life calls that matter more as we age, inspired by a missed episode from another podcaster and a touching story about his dad's third cousin.

Doug then breaks down the Medicare "free healthcare" myth with numbers, explaining why it costs him $400-500 a month on top of his federal pension plan, and why younger generations' "Boomer privilege" complaints are full of shit. He takes it back with a Boomer Bitchin' segment from the vault comparing travel costs then versus now, and wraps with some choice words on Flock cameras — how they're being used by gangs in Guatemala to track police movements while we're still debating them up here.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com

Follow me on X: https://x.com/Dying2Retire

YouTube: https://www.youtube.com/@DyingToRetirePodcast

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11 August 2026

#049: Insurance Checks, Right-to-Repair, and Fuego Erupting Next Door

In this episode, Doug gives an update from the Casa Douglas front — the appliance walkthrough mess, the never-ending "two weeks" countdown, and the insurance check disaster back in Maryland that has him rethinking whether just to pay off the mortgage for good. He takes his car-buying video one step further, laying out why he thinks American automakers are setting themselves up for trouble overseas once buyers realize what "right to repair" actually means.

From there it's a real talk about retirement being a withdrawal exercise, not an addition one, before he gets into a Boomer Bitchin' segment on earning your retirement and not owing anybody an apology for it. He closes out with some choice words on NYC's government-run grocery store plan, a DEI scandal out of Cambridge, and a live update on Volcán de Fuego erupting right next to Casa Douglas as he prepares to fly back down.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com

Follow me on X: https://x.com/Dying2Retire

YouTube: https://www.youtube.com/@DyingToRetirePodcast

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28 July 2026

#048: Dude, Where's My Car, Breaking Rico's Rules, and the Telemundo Double Standard

In this episode, I dig into car shopping ahead of our move to Guatemala — comparing gas, EV, and plug-in hybrid maintenance, and calling out the double standard in how the government treats Chinese car data tracking.

I also review two expat guidebooks by Rico Unchained and share why retirement is the time to stop putting things off, plus an unfiltered look at how Spanish-language media and misinformation shape Latino political views.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com

Follow me on X: https://x.com/Dying2Retire

YouTube: https://www.youtube.com/@DyingToRetirePodcast

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21 July 2026

#047: Casa Douglas Four-Phase Plan, Get Off the X, Maid Backlash, and Joe Legal vs. Jose Illegal

In this episode, I give an update on retiring to Guatemala — the four-phase plan for furnishing Casa Douglas, and why State Department travel warnings after the Santiago Atitlán unrest matter for anyone living or traveling there. I also dig into the backlash from a video about hiring household help, my take on traditional gender roles in retirement, and the widening gap between America's legal taxpayers and its cash-based economy.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com

Follow me on X: https://x.com/Dying2Retire

YouTube: https://www.youtube.com/@DyingToRetirePodcast

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30 June 2026

#046: The Casa Douglas TP Rule, Media Narratives, Front-Line Karma, and Second-Rate Standards

In this episode, we look at how divisive identity politics crash head-first into the real world. I share a story about my brother-in-law getting a dose of workplace karma as a new manager, and draw on my thirty years of management experience to contrast today's manufactured divisions with the unshakeable bonds forged in the 1980s military.

True solidarity isn't based on skin color or checklists—it’s about competence and carrying your own weight. We close with a stark reality check: when you prioritize checkboxes over capability, things break. You simply cannot run a first-rate country with second-rate standards.

Questions or comments? Email me at dyingtoretirepodcast@gmail.com

Follow me on X: https://x.com/Dying2Retire

YouTube: https://www.youtube.com/@DyingToRetirePodcast

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