One of the most frequently asked questions I get when traveling around the country speaking to people about retirement is, “When should I retire?”  Because very few of the audiences I speak to are Jewish, they don’t get the irony of my response, which starts, “Well, there are these four questions.” They lean forward, waiting for what will come next. Meanwhile, I’m saying to myself, “Get it—four questions—get it?” Of course, they don’t.

But in fact, there are four questions that drive the when-to-retire decision.  We identified them about a decade ago, and they have stood the test of time. No one has said, “Wait, you forgot one.” Nor have they said, “No, that one’s not really important.”

Here they are, the four questions.  If you are not yet retired, ask these of yourself, and when the answer to all four is “yes,” it’s time.

Question 1: “Do I have enough?” 

Of course, this is the money question and typically the one people focus on most.  Sure, it’s important, but so are the others.

Question 2: “Have I had enough?” 

Said another way, am I no longer excited about going to work?  Although toward the end of a long career, the answer to this one is frequently, “Yes,” many say they still love what they are doing and jump out of bed in the morning ready to go to work.  They should keep working.



Question 3: “Will I have enough to do?” 

Another way to ask this question is, “Do I have a written, holistic retirement life plan?” More about that in a future post.

When we first learned of these questions, there were only these first three.  As we studied retirement in more depth and interviewed hundreds of retirees as research for our book, we decided there needed to be a fourth question.

Question 4: “Does my spouse or partner want me home 24/7?” 

When I share this question, I typically get a snicker from the seminar participants, many of whom are attending with a partner. But it is no joking matter. We have been surprised how few couples have really had the “crucial conversations” (another future post) to help them get aligned on their retirement plans.  And not being on the same page can cause problems.

So those are the four questions. OK, they’re not “the” four questions. But they certainly serve the purpose of helping answer, “When should I retire?”