Although numerous habits make up the structure of a happy retiree, financial habits play a large part in creating the fulfilling retirement you’ve always dreamed of and being able to fund your additional interests.
In this episode, Wes breaks down the five financial secrets of the happiest retirees based on research from his latest book, What The Happiest Retirees Know, and reveals how these patterns are fundamental to building wealth and living a comfortable retirement.
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Revisiting Five Financial Secrets Of The Happiest Retirees

Wes Moss is on a mission: help at least 1 million Americans of any age retire sooner and find joy along the way. A seasoned finance professional, best-selling author, broadcaster, and teacher, Wes has done extensive research on the habits of the happiest retirees. On this podcast, Wes shares key lifestyle and money habits you can implement now to prepare for a secure future while not depriving yourself of happiness in the present. In addition to leveraging his 20+ years of knowledge as an investment advisor, Wes brings in guests and specialists to teach you how to set and work towards your financial and lifestyle objectives. Refreshingly-free of mind-numbing financial jargon and unrealistic money goals, Retire Sooner with Wes Moss gives listeners the tools on how to retire sooner in the real world.

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On today’s episode, Wes welcomes Producer Mallory to the studio to tackle more questions from the hypothetical Retire Sooner conference. They analyze options for when to take Social Security, examine the idea of downsizing or relocating in retirement, review three habits that many happy retirees seem to incorporate into their lives, and discuss which tax considerations retirees might want to keep in mind when planning for the future.
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Answering Your Top Retirement Questions: Part 2

We live in a 21st-century world, and our brains haven’t quite caught up. They’re designed to look out for the Saber-toothed tiger, not a million dings and beeps from smartphones. It’s no surprise that anxiety is a massive problem in modern-day life.
But Dr. John Delony says anxiety isn’t necessarily a bad thing. It’s just an alarm system to keep us safe, and we can learn to tweak the settings.
John is a two-time bestselling author, holds two PhDs, spent over twenty years working in crisis response, and now hosts The Dr. John Delony Show on Dave Ramsey’s network.
John says that despite the good intentions of innovation, we’ve designed a world we just weren’t meant to live in. Trucks do the heavy lifting, air conditioners keep us cool, and algorithms decide what we experience. Our ancestors had to adjust to life’s challenges, and that’s what kept them healthy and connected. It’s easier to become overweight when you don’t have to move. And it’s harder to form a community when you can sit inside alone all day.
Many of us are less happy and more anxious, and John knows how to help change that. He helps people navigate tough decisions, improve their relationships, and accept that they are worthy of happiness. I know I could use some of that. And I’m pretty sure you could, too.
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Tweaking Your Anxiety Settings with Dr. John Delony

On today's episode, Wes is joined by Producer Mallory Boggs. They brainstorm the idea of holding a “Retire Sooner Conference” and answer some of the questions the attendees might ask the panel.
Using his retirement calculator, Wes explores what constitutes a solid retirement plan and how much inflation needs to be considered. Then, combining his Retire Sooner Team’s research with analysis from The Ramsey Network’sDr. John Delony about the burden of debt, Wes answers whether people should or should not pay off their mortgage at retirement age. Next, he runs through how people can plan for their savings to last the duration of retirement, emphasizing how critical it is to become a tomorrow investor. Finally, he suggests that saving alone is like pushing a manual mower, while investing is like riding a John Deere Lawn Tractor. Which one would you rather use to get the job done?
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Retire Sooner Conference Part One: Are You Pushing A Mower Or Riding A John Deere Lawn Tractor?

Edd and Cynthia Staton’s retirement plans were on track. Then, the 2008 Financial Crisis hit. Their careers disappeared, their home lost its value, and their savings plummeted. Realizing recovery was unlikely, they needed to come up with a Plan B.
And boy, did they ever.
In 2010, they moved to Cuenca, Ecuador. Don’t worry, they didn’t know where that was, either. But now they love it! They live in a 3,000-square-foot penthouse apartment, have a housekeeper, eat out frequently, never worry about health care costs, and walk to their favorite yoga studio.
And they aren’t the only ones. According to the Social Security Administration, the number of retirees drawing Social Security outside of the U.S. surged 40% between 2007 and 2017.
Edd and Cynthia are now seen as expat experts in retirement, traveling, and health and wellness. They’ve authored three Amazon #1 best-selling books, are regularly featured in major media, and run their own online program called Retirement Reimagined!
They believe the key to finding retirement happiness is not having to worry about money. As that becomes more challenging in the U.S., they may be saying hello to a lot more expat neighbors.
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Financial Freedom For Expats with Edd and Cynthia Staton

On today’s show, Wes is joined by Producer Mallory to elaborate on the pitfalls of fleeing the market during turbulent times. They comment on the shell shock of the Covid-19 lockdowns back in 2020 and how tempting it was for fearful investors to yank their money out of the market. Wes empathizes with the temptation but explains that letting the dog chase the tail rather than trusting in a balanced, diversified portfolio can have disastrous ramifications. Wes reveals that time in the market typically beats timing the market, and participation usually trumps perfection.
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Revisiting Five Financial Secrets Of The Happiest Retirees

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