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Are You Ready for Day One of Retirement?

Are You Ready for Day One of Retirement?

August 20, 2025

 “Day One of Retirement” actually begins five to ten years before Day One. And probably really thinking about it, probably fifteen years - when you’re thinking about retirement. There are some serious questions to answer before that transition into that phase of life. Some of them are financial – I find a lot of them are actually more “lifestyle”.

A couple of questions on the financial side we're going to address, or you want to address, is, “How much is enough? Do I have enough?”  And, “Will it always be enough?” to maintain the lifestyle that you want, to achieve the goals that are important to you. Those are really important questions that you definitely want to address. Car replacements, travel, long-term health care planning, education, or legacy-type ideas or planning for future generations, or organizations that are important to you that you want to support financially. Those all come under the financial discussions or questions. So, I think you reach a point before Day One where you know you have enough money or resources to sleep at night.

Some questions to think about, in addition to the financial side of things… 

  • What are you retiring from and to?
  • What do you know about retirement? 
  • Who do you know that’s done a really good job in retirement? 
  • Who do you know who hasn’t done a great job in retirement? 
  • What are some of your images or vision of your personal retirement?
  • What are you called to do in retirement? 
  • What does it look like to live a vibrant life to the very end?
  • What will you do with your time?
  • Who will you spend it with? 
  • Who and what truly brings you joy and contentment in life?

The first year or two of this transition phase, and again, you can call it retirement, work optional - whatever you want to call it - it is going to be extremely different, and if you really haven’t thought much about what your day-to-day looks like, it can be even more challenging.

I would say, give yourself a lot of grace and a lot of patience, and know that some of the things you’re gonna do, you’re not going to enjoy doing. It's kind of a trial-and-error phase. Consider it a long sabbatical in this next phase of life. I think coming back to one of the key questions that I mentioned is to think about who and what brings you that joy and contentment. And what does it look like to truly live a vibrant life to the very end?