Retirement by Proxy

Most people we consult about preparing for retirement are not actually retired. Their advice is often based on financial and actuarial models that project how much money we will need, and life expectancy assumptions that estimate the likelihood we won’t outlive our savings.

While financial stability is an essential part of the retirement equation, it is not the only one. Along with money, we need emotional maturity, a sense of purpose, and the energy to embrace this new phase of life.

We are not fully equipped to truly understand retirement until around age 50. Wait—shouldn’t we start saving much earlier? Of course! But something significant begins to shift at 50: we realize that life ahead of us is shorter than what we’ve already lived. Although increased longevity may challenge this perspective, the thought remains a powerful and useful prompt.

The retirement experience is deeply personal, and we start preparing for it by living it by proxy. Since we can’t experience retirement firsthand until we reach it, we attempt to pre-experience it by learning from those who have. Speaking with retirees provides valuable insights into the emotional, financial, and lifestyle changes they face. While the guidance of younger advisors may be spot on financially, it is incomplete.

Retirees who have secured financial stability warn that wealth does not guarantee fulfillment. Other factors, such as health, meaningful work, social connections, and having a purpose play an equally critical role. As my friend Chuck put it:

"Retirement is a poorly sketched dream." — CDO, 87 (18 years in retirement)

Let’s debunk the myth that retirement is a single event. It is not. Financial planning software requires a date to calculate projections, but retirement is a transitional phase, and we must prepare for it as such. Unlike youth, which involves self-discovery supported by parents, schools, and society, retirement is largely an internal journey, a phase in which a battle between our rational minds and our irrational emotions takes place within the ever-growing limits of the body. As we age, physical changes become more pronounced, affecting not only mobility and stamina but also how we process information and manage emotions.

Focusing solely on the financial aspects of retirement creates an illusion of security which is misleading when preparing for the complexity of this stage of life.

Understanding the difference between our expectations of retirement and experiencing it is important. Expectations are often filled with idealized visions of leisure, travel, and the freedom to pursue hobbies. Retirement by contrast is not an idealized vision, but an effort to adapt our day-to-day to a new routine, finding purpose beyond work, and navigating challenges such as health issues or financial constraints. The emotional and psychological transitions are significant and often underestimated.

In essence, the theoretical discussion of retirement and the actual experience of it are worlds apart. One is built on hopes and assumptions; the other unfolds slowly as a multifaceted reality.

The First Obstacle: Loss of Purpose.

Work provides more than a paycheck—it offers structure, relationships, a sense of contribution, and even ego-boosting moments through decision-making and influence. Retirement often brings an unexpected void. When work stops, so does much of what gives us purpose. While not everyone derives purpose from their work, most have at least a defined role within it. Those who retire prematurely frequently seek new employment, only to discover limited opportunities for meaningful or well-paid work. What they miss most isn’t the job itself, but the sense of contribution it provides.

Many initially seek happiness in leisure activities like golf or travel, but these rarely sustain fulfillment beyond the first few years. As Ralph Waldo Emerson aptly noted:

"The purpose of life is not to be happy. It is to be useful, to be honorable, to be compassionate, to have it make some difference that you have lived and lived well."

Happiness, therefore, is not an end in itself but a consequence of meaningful engagement with life. How do we keep that engagement alive in our later years?

The Paradox of Work and Retirement

While retirement is often seen as freedom from work, work itself provides immense rewards: structure, relationships, and a sense of accomplishment. Many people find work unfulfilling because they are engaged in tasks that align with someone else’s purpose rather than their own. This lack of personal alignment leaves them at risk of losing the joy and strength that comes from working toward their own purpose in their retirement years.

Retiring by Proxy: A Balanced Approach

Relying solely on financial security can create an incomplete picture of what retirement looks like. We should try to incorporate the retirement advice of those who are retired and ask deeper questions: Who do I want to become? How do I want to engage with the world? What skills bring me joy, and how can I use them in this next phase of life?

Rather than retiring "by proxy," let’s start now intentionally exploring our own retirement. By searching, experimenting, and preparing for a meaningful and purpose-driven life we can ensure the 20 to 30 years in retirement are not just lived, but truly fulfilling.

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