Retirement: Caution…Timing is Everything 

In 1599, William Shakespeare first used the phrase, “timing is everything”, in his play, Julius Caesar. 

While I don’t have proof to this point, given Shakespeare’s many references to Biblical truths, it wouldn’t surprise me if he had Ecclesiastes in mind. There we’re told in chapter 3, verse 1:  


“There is a time for everything, and a season for every activity under the heavens: 

a time to be born and time to die, a time to plant and a time to uproot,  

a time to kill and a time to heal, a time to tear down and a time to build,  

a time to weep and a time to laugh, a time to mourn and a time to dance, 

a time to scatter stones and a time to gather them, a time to embrace and a time to refrain from embracing, 

a time to search and a time to give up, a time to keep and a time to throw away,  

a time to tear and a time to mend, a time to be silent, and a time to speak, 

a time to love and a time to hate, a time for war and a time for peace.” 


Solomon, after a lifetime of experiences, with the wisdom endowed upon him from God, speaks to the meaning of human life in Ecclesiastes. This passage about time serves to remind us about the breadth and depth of our lives. 

Somewhat contrasting to this famous adage of “timing is everything,” is a quote from poet Anthony Liccione, “They say, timing is everything. But then they say, there is never a perfect time for anything.”   

For me, I’ve found both facets of that quote to be true. I’ve seen procrastination for execution develop in the quest for perfection, but, particularly when communicating with others, “timing is everything” to be a fundamental truth. 

As you consider retirement—with the crux of its purpose not being aimed at luxury and leisure, but as a change in capacity and focus—I’d like to emphasize your critical consideration around timing. As we’ve all learned, once words are said, they can’t be ‘un-said,’ and managing others’ (and your own) expectations is a necessary part of the process.

Considerations Before Your Big ‘Announcement’

While I’m sure there are others, here are four cautions I encourage you to consider before you “announce” retirement timing. 

  1. People make assumptions. First up, consider how your decisions and actions affect other people’s perception of you. If you are in a corporate role, for example, and announce in June you’re retiring at the end of the year, you are now a “lame duck” in people’s minds. Regardless of their behavior, it’s in their minds and will affect their decisions. That may be ok, and even necessary, for the transition you’re desiring, but just know that people’s perceptions of you are constantly flexing, and this information may not shift them in the direction you’d like. 
  1. Financial ramifications. Closely aligned with #1 is this point. At my former employer, bonuses were paid for past performance, and equity awards were given for future potential. The second word was out that someone was leaving, equity awards were not a reality. Now that may vary at every organization, but I would play out the “lame duck” scenario fully for your employment situation before you announce a retirement date. Also, know when decisions and triggers are in play – – for example, if you leave before bonuses are paid, the adage of “must be present to win” is probably applied. Health insurance is another consideration – – if you’re employed on the first of the month, your health insurance will be in place for the entire month. If you leave on the 30th of the preceding month, you won’t be eligible for the next month’s insurance. More could be said here, but hopefully I’ve painted enough of a picture for you to carefully think through the financial angles present. 
  1. Circumstances could change. We’ve probably all made decisions in life…and then something changes…and we wish we could get a “do over”. 🙂 I’d take the bet for each of your lives that something will happen in your life to cause you to rethink your decisions. Rather than fight it, just accept it and build it into your decision process. Think through different scenarios (health, finances, family, etc) and play out the possibilities. Pick a time and use that timing as your decision filter for those scenarios. You’ll start to see some consistencies in how you see things and get a comfort level for a decision point. 
  1. You could change your mind. Simple, but true. You probably will. And that’s ok! 🙂 Allow yourself some time for your planning and decision to settle in a bit. For most people, this is a significant life decision, so allow yourself the time and space to bounce around for a while. Our minds are constantly at work, even when we’re asleep, so factoring in enough time for this allowance is critical. 

Confirming His Timing is Time Well Spent

The last caution and filter for you to consider is found in God’s word with Proverbs 16:9 which says, “In their hearts humans plan their course, but the Lord establishes their steps.” Amidst everything I’ve outlined above, each of us needs to be yielding to the Holy Spirit daily to direct our steps. Asking for His direction, as I pointed out last week, is essential. Confirming timing is His timing, and not our own, is time well spent. Blessings!   


Dave Sparkman currently serves as the volunteer Crossroads Career board chair and local ministry leader. He is also the founder and managing director of Spark Your Culture, a corporate culture consulting firm. Prior to that he worked at UnitedHealth Group, a Fortune #5 public company, serving in the role of Chief Culture Officer. His unemployment experience came from the implosion of Arthur Andersen, where he served as the West Region Managing Partner, People.

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