Anyone else a little tired of hearing about ‘retirement?’ It can feel like this vague, far-off finish line that we're told to obsess over for decades. But here's the thing: when you look at the research, a surprising number of people who are retired—or about to retire—are anxious. They've got regrets. Some of those regrets are financial. But many have nothing to do with money at all. So if we're going to spend years working toward retirement, we should probably make sure we're aiming for one we'll actually enjoy. Joel has known Wes Moss for a long time. They worked at the same radio station for well over a decade. He's still there because, believe it or not, terrestrial radio is still alive and well. His show, Money Matters, has helped countless listeners make smarter decisions about their money, their investments, and, yes, their retirement. Wes has a new book out that challenges a lot of conventional thinking about what makes retirement successful, and today we're diving into the financial and non-financial choices that can help you avoid the regrets so many retirees have. Today we discuss:

• Why his new research updates his earlier work on happiest retirees rather than replacing it entirely.
• Fear around retirement is often amplified by nonstop media coverage.
• Wes says more money alone does not erase anxiety, even for people with $3 million or more.
• Wes defines happiness in a more Aristotelian way, focusing on fulfillment and purpose rather than pure pleasure.
• He introduces “money green zones” for investable assets, income, and years left on a mortgage, arguing that happiness rises when retirees land in those ranges.
• A major theme is core pursuits, which Wes describes as hobbies on steroids. The happy retiree group tends to have 5 or more, and they spend about 20 hours a week on them versus about 13 for less happy retirees.
• Wes warns that purpose does not just appear in retirement. It has to be built intentionally well before leaving work.
• They talk about the “friendship recession” and how it gets harder to make close friends with every decade, making community a key retirement asset.
• The conversation also covers the emotional power of being able to say you could retire now, even if you choose not to. Wes says that confidence correlates with a 21% jump in happiness.
• On the financial side, Wes explains why a retirement plan, safe assets, and a flexible withdrawal strategy can reduce fear and improve spending confidence.
• They discuss Social Security timing, with Wes leaning toward using it sooner if doing so helps someone retire a year or two earlier and live better.
• How much of a remaining mortgage leads to higher levels of happiness
• And much more!

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