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Planning for the Many Phases of Your Retirement Journey

Cypress Wealth Services

January 2024

Retirement is a momentous life transition where you shift from the workforce to your golden years, with the journey looking slightly different for each person. Some common experiences include grappling with a changing sense of identity and purpose once your career ends. Some recent retirees or those nearing retirement often find themselves questioning the meaning and purpose (*1) of their lives post-career.

However, the retirement experience goes beyond the quest for purpose. It’s a complex transition that can vary depending on the timing of your retirement, which can unfold gradually, similar to the chapters in a book. Each chapter brings its own challenges, moments of joy, and pivotal decisions. The entire retirement journey can be classified into five distinct stages, each bringing unique emotions and expectations. Read on for insights into each phase and how you can best prepare.

Chapter 1: Your 50s

At this stage of life, retirement becomes less like a far-off dream and more like a forthcoming reality. You begin to seriously think about when you can retire and how to take the right steps to retire comfortably. 

During your 50s, you will likely launch your kids into adulthood and experience your highest earning years, which gives you more to work with. But that extra money you aren’t used to having can result in “lifestyle creep,” where your expenses grow along with your pay raises (*2). These increased expenses may not always be nonessential either, as you might become responsible for increased housing costs, education expenses, healthcare costs, and even eldercare costs.

Despite these financial strains, the inflow of new money into retirement accounts must not cease; your retirement plan assets should not be drawn down through loans or withdrawn too early. Rather, these should be the years where you maximize your retirement plan contributions. If you are over 50, you can make catch-up contributions to beef up your nest egg.

Chapter 2: Your Early 60s

You are so close, you can almost taste it. Now you are starting to think about the many details that make up the process of retiring and the financial and lifestyle decisions involved.

If you find yourself in this phase, it’s time to get realistic about the near future. Do you know what you will do next? How will you make it a reality? For example, will you be able to keep up with your current expenses while on a fixed income? Be sure to test out different budgets to make sure your finances are set. Do you want to volunteer or start an encore career? Start mapping out the details now. If you do not have a set plan for the next chapter of life, a phased retirement may give you more of an opportunity to figure it out.

Usually, this is the time to dial down risk in your portfolio. Market downturns have a greater impact on your long-term success as you don’t have the same time to recover. This is what is called sequence of negative return risk. You should speak with an advisor to make sure you have the correct mix of investments (*3) that will provide cash flow in the short term and growth in the long term. You also can’t afford to be too conservative as lower growth will be eroded by the rising cost of living.

Chapter 3: Retired Life Begins

The first year or so of retirement is akin to a “honeymoon phase.” You have the time and perhaps the money to pursue all kinds of dreams, so the key is not to spend wildly. Lifestyle creep also affects new retirees, and free time often means more chances to spend money.

When it comes to your investments, your portfolio looks very different than it did when you were in your 20s and 30s. Bond funds and fixed income may make up a larger portion of your investments. Your focus is on generating cash flow to live on and preserving what you’ve worked so hard to save. However, you should still have exposure to the stock market. If you retire at age 65, there is a good chance you have a 30-plus-year retirement ahead of you. As such, you should keep exposure to stock funds for their growth potential.

Up until now, you’ve probably received healthcare coverage from your employer. When you retire, it’s a new ball game. Medicare eligibility begins at age 65. You have plenty of choices for your Medicare plan, such as original Medicare coverage, prescription drug plans, and supplemental insurance. Your premium costs will depend on your coverage choice and your income. Medicare can be complicated and overwhelming, so if you are in this chapter, start researching now (*4) to make informed choices.

Chapter 4: Mid 60s Through Late 70s

This is the chapter where restlessness can begin to set in. If you didn’t make concrete lifestyle plans before retiring, you might get bored with your all-leisure, all-the-time lifestyle and decide to volunteer or work on your own terms, health permitting.

It’s also the time when people begin to worry about how their retirement savings is growing smaller. You may want to adjust your retirement income strategy (*5) or see if new streams of income can be arranged.

Chapter 5: 80s and Beyond

The last chapter of retirement is one frequently characterized by the sharing of legacies and life lessons, a new perspective on the process of living and aging, and deeper engagement (or reengagement) with children and grandchildren. This is also the time when you should think about your financial legacy and review or update your estate plan so that when you leave this world, things are in good order and your wishes are followed.

A Partner to Help With Every Phase

In every stage of life, having a seasoned financial professional by your side is a valuable asset. Whether you’re navigating the challenges of early career financial planning, seeking a comfortable retirement, or considering wealth transfer strategies, partnering with an experienced advisor can make a big difference in how quickly you reach your financial goals.

At Cypress Wealth Services, our commitment is to deliver professional support, comprehensive education, and knowledgeable guidance tailored to each client's unique needs. If you’re ready to explore your financial options and create a plan that spans every life phase, we invite you to schedule a no-obligation introductory meeting by reaching out to us at 866.888.6563 or contact one of our offices today.


About Cypress Wealth Services

Cypress Wealth Services is an independent RIA firm providing financial planning and investment management to high-net-worth individuals, families, business owners, and institutions. Cypress Wealth Services comprises professionals with diverse backgrounds and extensive experience and qualifications. Cypress Wealth Services serves a broad range of client needs using their knowledge and experience to act as a foundation for their client service process. The firm uses The Second Growth, which focuses on efficiently protecting, growing, and transferring the wealth and legacy a person has already built to their loved ones. With financial advisors in California, Alaska, Arizona, and Georgia, the firm serves clients across the country with Wealth Management Services, Fiduciary Services, 401(k) Design and Management, Investment Reporting Services, Financial and Retirement Planning, and more. For more information, visit or call 760.834.7250.