Plan for Four Retirements Rather Than One

By Jennifer Osgood
President
Wagner Wealth Management

For many Americans, especially those entering retirement with substantial assets, retirement is not a single event but a multi-decade journey that evolves over time. Lifespans continue to lengthen, with many retirees now planning for 25 to 30 years of post-career living. This expanded timeline means your financial life will likely pass through several distinct stages, each with different priorities, expenses, and risks.

These different stages are often referred to as the Four Retirements. Understanding them can help you anticipate the changes ahead and create a strategy that supports your lifestyle, protects your wealth, and keeps you in control.

The Honeymoon Phase
Freedom and Exploration

The first years of retirement often resemble an extended vacation. This is a time marked by travel, hobbies, philanthropy, and the enjoyment of long-planned pursuits. Financially, this stage can feel quite comfortable. Income begins shifting from paychecks to portfolio withdrawals, Social Security, or pension benefits. Because household spending tends to increase early in retirement, today’s affluent retirees often feel financial independence while recognizing that withdrawals need to be managed carefully.

With longer life expectancies and healthier early-retirement years, this phase is the ideal time to reinforce the foundation of your financial plan. Strategies such as tax-efficient withdrawals, stress-testing retirement income, and revisiting asset allocation can help ensure your resources last through the decades ahead.
This is also a prime phase to confirm contingency plans. Establishing long-term care strategies, evaluating life insurance needs, and reviewing estate documents early can help shield you from potential reductions in resources later in life.

The Big Decision Phase
Lifestyles and Long-Term Choices

As retirees settle into their new routines, the second phase brings more free time and more consequential decisions. Complete disengagement from the workforce becomes real, and income is now driven mainly by retirement accounts, Social Security, and investment income. For many, this is the first time living on a structured, predictable income rather than earned wages.

This stage often triggers key lifestyle questions:

• Should we stay in our current home or relocate to a more desirable location?
• Would downsizing simplify life and reduce long-term expenses?
• Is now the right time to purchase a new vehicle, second home, or family vacation property?
• How much travel or discretionary spending is sustainable over the next decade?

Financial choices also become more complex. Retirees may consider converting a portion of their assets into guaranteed income through annuities, evaluating Medicare supplement plans, or timing withdrawals to minimize taxes. Required Minimum Distribution (RMD) rules, Roth conversion strategies, and charitable giving can all play pivotal roles during this period.

This is also the phase when an estate plan should be formalized, if it is not already in place. Wealth transfer goals, philanthropic intentions, trusts, and legacy planning take center stage.

The Navigating Longevity Phase
Health, Housing, and Support Systems

In the third retirement stage, health management becomes more prominent. Even healthy retirees find that appointments, preventive care, and wellness routines begin to shape their daily lives. National data continues to show that healthcare spending increases significantly after age 65, particularly for affluent retirees who prioritize high-quality care and specialized medical services.

Lifestyle complexity can also increase. Home maintenance, transportation, and everyday tasks may require more support. Some retirees begin exploring aging-in-place modifications, part-time assistance, or local services that enhance daily living.

This is an essential time to ensure that legal and financial documents are up to date and actionable—before cognitive or physical limitations arise. Key items include:

• Healthcare proxies
• Powers of attorney
• Updated wills and trusts
• Clear instructions regarding advanced medical care

Establishing these plans while communication remains clear gives you control and protects your family from unnecessary stress.

The Solo Journey Phase
Changing Needs and Family Dynamics

The final phase of retirement often brings significant transitions. A major health event, loss of a spouse or partner, or a sudden change in mobility can reshape day-to-day life. For many, this stage involves navigating practical and emotional challenges, often with increased reliance on adult children or caregivers.

Family dynamics may shift as well. Adult children may express concerns about driving, home safety, or the ability to live independently. While these moments can be difficult, the burden is eased significantly when plans have been established in advance.

A well-structured estate plan, long-term care strategy, updated power of attorney, and clear guidance on personal preferences can help avoid conflict and ensure that decisions align with your values and wishes.

Plan Early, Review Often

Although each phase of retirement is unique, one principle remains constant: the need for ongoing evaluation and proactive planning. Retirement is not static, and your financial strategy shouldn’t be either.

A comprehensive retirement plan helps ensure that each phase remains as seamless and fulfilling as possible. Regular reviews with a trusted wealth advisor allow you to adapt to changing markets, health needs, and personal priorities.

With thoughtful preparation, the Four Retirements can become four rewarding chapters in a life well lived.

Jennifer Osgood is the president of Wagner Wealth Management, which has offices in Greenville, Anderson, and Oconee counties. Call them at 864-236-4706 or visit www.wagnerwealthmanagement.com to learn more about our firm.

Securities offered through Arkadios Capital. Member FINRA/SIPC. Advisory services through Wagner Wealth Management Advisors, LLC. Arkadios Capital and Wagner Wealth Management Advisors, LLC, are not affiliated through any ownership.