Head and the Heart Reading: Redefining the “R” Word – Retirement

By Bruce Thompson on July 11, 2025

Let’s stop asking, “When are you going to retire?” and start asking, “How do you want to spend the financial freedom you’ve earned?”

In Short:

Confusion around retirement today often stems from a mismatch between an outdated definition and modern realities. People want more than just an end to work—they want a meaningful next chapter. And that takes reflection, planning, and often, a redefinition of what “retirement” really means.

In last quarter’s letter, we introduced Maslow’s hierarchy of needs as a lens for thinking about what’s required—both financially and emotionally—to experience fulfillment and purpose in life. Many view retirement as a sort of finish line when these things might finally come into focus. But in today’s world, the very concept of retirement feels increasingly unclear—even problematic.

The traditional model of retirement was built for a different era: stop working at 65, collect a pension, and enjoy leisure. At that time, life expectancy was shorter, work was typically more physically demanding, and retirement was supported by predictable income from Social Security and pensions. After World War II, policy encouraged older workers to step aside for the younger generation. Later, the financial services industry—along with Madison Avenue—marketed the dream of retirement along with IRAs and 401(k)s.

But that dream doesn’t always align with modern realities. Today, people are living 20–30 years beyond traditional retirement age. According to a recent Goldman Sachs study, the average 70-year-old now has the same cognitive ability as a 53-year-old had just 25 years ago. Financial independence is no longer the only goal; people are asking deeper questions about purpose, connection, and impact.

Unfortunately, cultural messaging hasn’t caught up. Society continues to romanticize retirement as a permanent vacation—golf, travel, and endless relaxation. Yet many retirees discover that too much leisure can lead to boredom, and that they still crave growth, contribution, and connection. This disconnect often creates quiet tension: “Shouldn’t I be enjoying this?”

In today’s more knowledge-based economy, work may be a source of identity, structure, community, and meaning. Leaving a career can feel less like freedom and more like a loss of self. Even those who’ve achieved financial independence may feel directionless or underutilized.

Unlike generations past, there’s no longer a clear script. Some retire early, some retire multiple times, and many “unretire” to pursue second careers, part-time work, or passion projects. With no one-size-fits-all model, retirement today is more of a design challenge than a destination.

That’s why it’s never too early—or too late—to consider the “soft side” of retirement: the emotional, social, and purposeful aspects of life after full-time work.

For some thoughtful summer reading, we recommend the blog of the Modern Elder Academy (MEA). Founded by Silicon Valley veteran Chip Conley, MEA helps people reimagine retirement as a time of continued growth, contribution, and meaning—a chance to share the wisdom we’ve earned.

In one piece, Why Retirement Confuses Knowledge Workers, Conley challenges the outdated, industrial-era idea of retirement—especially for those whose value increases with age. Unlike physical laborers whose bodies may wear down, knowledge workers often grow stronger in insight, empathy, and judgment. So, the question becomes: How do we offer what we still have to give?

MEA offers online workshops and in-person retreats at its Baja, California campus, helping people navigate life transitions, explore purpose, and design their next chapter with intention.

Another thought-provoking article, Finding Purpose in Purpose by Andrea Deskin, explores how the pressure to find a grand, post-retirement “purpose” can become its own trap. “The current retirement playbook,” she writes, “goes something like this: first, you leave your job. And then—immediately—you’re supposed to find your purpose. Because if you don’t, it’s implied your life will be totally unfulfilled.”

Deskin encourages a gentler, more organic approach: focus on small, meaningful actions. “Think of yourself as someone planting seeds in the world. A kind smile to a stranger. A homemade meal shared with love. A moment of real attention. You’ll grow. You’ll feel joy.”

Words matter and, for many, “retirement” has become the “R word”—failing to describe the possibilities this phase of life can offer. A recent AI-assisted brainstorm suggested fresh alternatives: Post-Career Life, Second Act, Financial Freedom Years, Downshifting Phase, and Life Unplugged.

We leave you with this question: What would you call this chapter of life?

We’d love to hear your thoughts.

As always, your Lexington Wealth financial advisor is here to support you. We understand that effective investment and financial planning goes beyond the numbers. Planning for financial independence is also about attaining confidence and freedom from worry — and saving you irreplaceable time — that allow you to live with purpose and on your own terms.