After 3 years of retirement, I’m learning money isn’t enough – here’s what actually made retirement feel fulfilling

Photo of David Beren
By David Beren Updated Published

Key Points

  • A retired tech entrepreneur who achieved financial independence 3.5 years ago found that wealth and leisure don’t automatically eliminate mental health challenges, requiring therapy to process identity loss and find meaning beyond business success.

  • Early retirees benefit most from prioritizing authentic relationships with people who knew them before wealth, spending quality time with family, and contributing to their community rather than pursuing status symbols.

  • A recent study identified one single habit that doubled Americans’ retirement savings and moved retirement from dream, to reality. Read more here.

After 3 years of retirement, I’m learning money isn’t enough – here’s what actually made retirement feel fulfilling

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One of the many things that people learn after retirement is that it’s not all sunshine and rainbows. Whether you retire early or exactly at 67 years old, there is no guarantee that the moment you retire, all of your stresses will simply lift from your shoulders.

This is precisely the scenario one Redditor posting in r/fatFIRE is learning firsthand, having retired over three and a half years ago. This narrative aligns with the 2026 CenterWell Fulfillment Index, which reveals that early retirees often experience a significant “fulfillment dip” within their first five years as they realize financial security is only a fraction of the retirement equation. Having been retired, there is some pretty clear thinking about what is most important in life, and, surprise, it isn’t always about the money.

Early Retirement Observations

Having retired around 3.5 years ago and living as a member of the fatFIRE club for the last 2.5 years, this Redditor should be living the good life. Making his money through a successful tech startup, this Redditor believes he is in a unique position to talk about some of the most important things he is noticing, including mental health, community, and family.

Mental Health and the 2026 Perspective

After working on a startup for more than 9 years, this Redditor decided enough was enough and saw the writing on the wall. Initially, there was a belief that there would be an immediate sense of relief. However, as noted in the 2026 Retirement Confidence Survey, even high-net-worth individuals are facing “Post-FIRE Financial Anxiety” due to rising healthcare costs and macroeconomic shifts. This Redditor found that a year after walking away, they still did not feel renewed.

As a result, they found a therapist to process a mix of feelings. Finding a professional to help navigate the void left by a high-stakes career is increasingly common for the modern retiree, emphasizing that success in business does not automatically translate to finding meaning in life afterward.

Sense of Community

Having retired, it’s not always easy to stay friends with co-founders or colleagues. To help navigate these new waters, the Redditor turned to reinforcing their existing friendships while building new ones. What he realized is that the people he values most are the ones who knew him before the money. Some of their closest friends are teachers or doctors in rural communities with far lower salaries. He discovered that trying to fill an internal void with luxury items like sports cars or expensive watches would only be misinterpreted by the people he values most. The big takeaway is that it’s invigorating for him to spend time with the “normal” people in his life.

Grounded by Family and Functional Longevity

The best part of this Redditor’s story is jumping in headfirst with family. In 2026, the trend of Functional Longevity suggests that social connection and intergenerational mentorship are the most valuable amenities wealth can buy. He values the extra time spent with his kids, using it as an opportunity for self-growth rather than just “relaxing.”

This includes focusing on how to avoid overparenting and ensuring his children understand the privilege they have. He wants to raise his children to appreciate money enough to pass it on while being involved in charitable giving, ensuring that less fortunate people also have an opportunity to improve their lives.

Editor’s Note: This article was updated on May 13, 2026, to include new data from the 2026 CenterWell Fulfillment Index and the Retirement Confidence Survey. These updates pivot the content from a standard social media reaction to a broader analysis of modern retirement trends, specifically addressing post-FIRE financial anxiety and the rise of functional longevity as a primary goal for high-net-worth retirees.

Photo of David Beren
About the Author David Beren →

David Beren has been a Flywheel Publishing contributor since 2022. Writing for 24/7 Wall St. since 2023, David loves to write about topics of all shapes and sizes. As a technology expert, David focuses heavily on consumer electronics brands, automobiles, and general technology. He has previously written for LifeWire, formerly About.com. As a part-time freelance writer, David’s “day job” has been working on and leading social media for multiple Fortune 100 brands. David loves the flexibility of this field and its ability to reach customers exactly where they like to spend their time. Additionally, David previously published his own blog, TmoNews.com, which reached 3 million readers in its first year. In addition to freelance and social media work, David loves to spend time with his family and children and relive the glory days of video game consoles by playing any retro game console he can get his hands on.

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