Mike MilliganFounder and CEO, 1.oak Financial · Founder and CEO, 1.oak Financial

The Emotional Side of Retirement Planning

16 Mar 2026 · 1 min

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In this brief monologue, Mike Milligan highlights loneliness as a hidden but serious retirement risk, especially for baby boomers. He cites recent analysis showing that today’s boomers experience higher loneliness levels than previous generations at comparable ages, even after adjusting for health and demographics. He points out that boomers are more likely to age alone, have weaker family connections, and face a breakdown of traditional community structures. Milligan stresses that loneliness is not just an uncomfortable feeling—it harms health and reduces longevity. Consequently, he argues that retirement planning should begin with building a community, ensuring that retirees have a sense of belonging and purpose.

Chapters

Let's talk about loneliness, the unforeseen retirement risk. This is one that I see even with people who have called into the show and we've said, and we build financial plans for, people will continue to work because they feel like they're part of a community. A recent analysis confirms that baby boomers are experiencing higher levels of loneliness from previous generations at similar life stages, even after accounting for health and demographic factors. Boomers today are more likely to age alone, have fewer closer family ties, and experience a breakdown of traditional community structures. That's why loneliness is just not an uncomfortable feeling. It negatively impacts your health and your longevity. That's why we start in building the vision for retirement. We actually start with community.