How to know when you are ready to retire

Today, I am sharing an excerpt from my most recent book, “Retirement is Underrated.” This chapter attempts to help you know when you are ready to finally make that difficult decision to break away from the workplace. Previous chapters have discussed in some detail each of the items included in the checklist. If you are interested in reading more, you can find the book on Amazon here (

Overcoming the fears and anxiety of making that fateful decision

OK, now that you have a good handle on your financial situation, better understand your health insurance options, and feel you can transition to the “retired life,” what is keeping you from pulling the trigger and making that final decision? What is still holding you back?

Everyone has a different excuse for waiting to retire. For some, they want to finalize health items (such as a knee replacement). Others want to build just a bit more financial buffer. Still others want to ensure that they have everything at work in place before they go. Practical reasons hold back some, such as: “I’ll just wait until after bonuses are paid” or “I need to stay until after my daughter’s wedding.” I remember working with one man in the past that was still working as supervisor on a night shift. He was over 70 years old and I remember asking him why he still worked. His answer was, “There is so much drama around here, I just want to hang around to see what happens.” 

Let me offer a bit of courage or encouragement as you ponder the “when” question. Think of the 7 items below as your “to do” list. When you can check all of these boxes, you are ready:

Checkbox Checked with solid fillYour finances are in order – You have estimated your income and ongoing expenses and have confidence that you have adequate buffer to remain solvent throughout retirement. 
Checkbox Checked with solid fillYou know how you will approach health insurance – For those retiring before age 65, this means developing a plan to bridge that period until 65. This could be in the form of COBRA, Affordable Care plans, or private plans.
Checkbox Checked with solid fillYou are ready to make the emotional shift – You understand that your identity is not in your work, but in your character. You have a vision for retirement and have spoken to others about their experience and approach to retirement.
Checkbox Checked with solid fillYou have a plan for remaining physically active – You understand the need to have regular interaction with your physician and have plans for a lifestyle that involves activity.
Checkbox Checked with solid fillYou have identified a social network of other individuals – You and your spouse are ready for more day-to-day interaction. You have plans for staying in contact and re-acquainting with others to remain socially active.
Checkbox Checked with solid fillYou have assessed your need for part-time work – You have decided if you will work in retirement, what it will be, and how many hours per week you think is appropriate.
Checkbox Checked with solid fillYou have developed a plan for the first 90 days of retirement that will help your transition – You have a plan for how you will fill your time, what activities are important, and who will be in your social circle that cover the first 3 months of retirement.

If you can check each box, you are well prepared to make the move. Certainly, there is the feeling that, once you commit to retirement, there is no going back. That is true to some extent, but that should not inhibit your decision provided you have planned well.

In my own experience, the decision to retire was not all that difficult. I was able to check all the boxes for preparedness, but I do recall continuing to work for some time after I could have made the move. I used to say when others asked how much longer I planned to work, “I’m one bad day away from retirement.” Knowing that you can and are ready provides a significant sense of relief and confidence. Just knowing that you can make that decision any day provides an entirely different perspective as you make that drive to the office or worksite each day. 

I heard another retirement story just this week about an individual that delayed retiring. It seems this individual finally made the decision after a couple years of handwringing. His last day of work was on a Friday and his coworkers celebrated him with cake, punch, and a party. By Sunday, he had died. It seems he had a massive heart attack that he could not survive. The individual telling me this story, his coworker, said his death had a huge impact on others in that department. Many of his coworkers used his death as motivation to retire as soon as they were able. The man telling me this story ultimately retired the day after his 55th birthday. He said he never had a day in the 26 years since that he regretted retiring at that age.

Here is the bottom line… If you are ready financially, emotionally, and physically to retire, you have to ask yourself, “What is to be gained if I work one more day?” Maybe today is the day to make that decision and begin that important next chapter of your life.

In the next section of this book, we will look at “What’s next? Now that I’m retired, what do I do and how do I maintain the lifestyle I want?”

Best wishes to you as you contemplate this serious and life-changing decision.

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