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What Does Retirement Look Like?

Putting your finger on exactly what retirement will look like can be difficult. Often, people get blindsided when unexpected events derail their plans. Understanding the four specific stages of retirement can help you thrive and flourish, even in the midst of life’s curveballs. Seeing retirement as a journey instead of a destination can be a powerful mental model.

Here is the problem: Retirement isn’t an event but rather a new phase of life that has distinct stages that can be planned for. Each stage of retirement will bring new opportunities and challenges, both financially and emotionally. If you don’t become aware and plan for these various stages your retirement can be upended and you can be blind-sided.


Do you remember the movie, Remember the Titans? It’s one of our family’s favorites and very well could be one of the best football movies of all time. The story is set in 1971 at TC Williams High School in Alexandria, Virginia. 

One of the main characters, Gerry Bertier, is an All-American football player who tragically gets in a car accident and becomes paralyzed. He was blind-sided. (In a story for another day, he goes on to become a Paralympian and become an inspiration to many.)

Just like Gerry Bertier was tragically injured and and his life derailed, many retirees have their retirement dreams derailed or even shattered.

Here are some examples of being blind-sided in retirement:

  • You lose 20% or more of your retirement investments right before you retire so you have to work longer or retire on less.
  • You learn that you claimed your Social Security incorrectly and it cost you more than $100,000. (See my free training on Social Security).
  • You take too much out of your investments early in retirement and run out of money.
  • You are unable to take vacations and travel because you don’t think you have the money.
  • You have a major health challenge and you become a burden on your children and don’t know how to pay for it.
  • Once you pass away, your spouse lives in poverty because proper planning wasn’t put in place.
  • You spend your whole life uniting your family, only to have the assets you leave behind divide your family members through legal battles.

Though life can be very unpredictable, retirement planning can help you avoid many of the reasons retirees are blind-sided. 


The journey of retirement can be divided into four phases. As you understand each stage, it can reduce your chance of being “surprised” during your retirement years. That isn’t to say that life won’t happen and throw you curveballs, but at least you can prepare for them. 

Each of these stages can be different years in length but for simplicity can be broken down into decades.


As you approach retirement and see it on the horizon, it becomes much more of a focus and concern. Retirement can be an exciting stage of life but “Am I ready?” or “Will I be o.k.?” can be a common questions you ask yourself. The closer you get to the big day, the excitement and anxiety builds. Most people recognize that retirement is much more complex than they realized and they need answers.

Common questions and thoughts in the pre-retirement stage:

  • How much money do I have in my investment accounts?
  • Should I save more?
  • How much will I have when I retire?
  • How much will my Social Security be?
  • Do my current financial professionals have the skill set to help me prepare for retirement and then help me during retirement?
  • Do I need a financial advisor to help me?
  • When will I retire?
  • How much can I live on?
  • If I retire early, how will I pay for health insurance?
  • How will I replace my income


This stage of retirement begins as you transition into retirement and continues as long as your health and desires allow you to stay active. As you begin retirement, you begin your Social Security, turn on pensions you may have, and draw from assets that you’ve saved for retirement. We call this the preservation and distribution phase.

This can potentially be the most exciting decade of your life as you have more freedom than ever before. Think about it, no job, no boss, sleeping in if you want, and no 9-5. You get to travel, spend time with grandchildren, and take on hobbies you may have never had time for. You may even choose to give back in the form of a charitable cause or start a part-time business on your terms. It’s vital that you seize these years of feeling good and make a financial plan that supports your vision.

Common questions and thoughts in the early-retirement stage:

  • Where do I want to go?
  • What will I do with my time?
  • How can I maintain my health?
  • How can I travel and see the world?
  • How do I create experiences and memories?
  • What new hobbies will I pick up?
  • How will I give back to my community?
  • Do I want to work part-time or start a small business?


Middle retirement begins as you want to go places but you start getting a little tired. As a friend of mine said this week, “the used car just starts to wear down.” In this stage, you’ve settled into your retirement groove but you feel yourself slowing down. This phase of retirement can be amazing but is often less active than the go-go years.


Last time I checked, there was only way to get into this life and only one way to get out. Eventually, our bodies start to wear down. The no-go years are characterized by the fact that you want to go places but just aren’t able to. This period can bring its share of financial and emotional challenges, especially when health declines. Having a plan in place that can pay for health expenses such as nursing care or assisted living can be vital to your peace of mind.


Understanding exactly what retirement will look like before you experience it can be difficult. By understanding and planning for the four phases of retirement, you can limit the risk that you’ll be blindsided when unexpected events occur. During the work and save years, put retirement plans in place to transition successfully into retirement. After you retire, take advantage of the go-go years, when you want to enjoy your retirement freedom and you can! Recognize that the slow-go years will come, when you’ll choose not to be as active. Lastly, prepare and plan for the no-go years, when your health eventually declines.


Do you have a plan to transition into retirement? Do you understand it? Are you confident in your plan? Learn more about how we help our clients replace their paycheck income, manage their investments, and minimize retirement taxes. Do you have questions about when to take Social Security and how to maximize your benefit? Take our free online Social Security Masterclass.