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The Single Most Important Question to Ask Yourself Before Retiring!

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The other night I had dinner at my favorite sushi place (Sagami’s in Collinswood, NJ) with a good friend.  He’s over 50, and we discussed the topic of retirement.  He described vacillating between getting an RV (and a dog) to travel the country versus continuing to work.  After a few minutes of the pros and cons, I asked him one of my favorite contemplating-retirement questions. “Do you think you are retiring TO something or FROM something?”

There was a temporary silence as he contemplated the question.  Then he answered, “I’m not quite sure.”  Quite frankly, I heard enough in those words to form my thoughts about his readiness to retire.

The breakdown.

It is very important to understand the difference and importance of the question.  Retiring “to” something is very different than retiring “from” something.  If someone says to me: “I’m just done with work.  I dislike my boss, colleagues, company, travel, etc.,” that tells me they are retiring from something.  They are beaten down and often, just out of gas.

Now, if someone says to me: “I’m ready for that next phase. I want to travel, take up gardening, spend time with my grandkids, volunteer more,” that tells me they are retiring to something.  That person has things they want to do to fulfill their life.  These people are turning to a new chapter and getting energy in doing so.

The exercise.

First, make sure you heavily consider all aspects of retirement, such as are you financially able to do so?  Then (and only then), I recommend the following exercise to determine the appropriate outcome.

Take a minute and close your eyes. (Hey, at least wait until you finish reading this blog!)  I know it sounds cheesy, but this may be the most important decision of your life.  Take a few deep breaths.  Relax and ask yourself these questions:  “Am I retiring to something greater than work?  Do I have other interests to fill my day?  Are there things I want to accomplish outside of my business?  Are there things that I know will bring great joy and satisfaction into my life that I can’t accomplish because of the constraints of my job?”

Now open your eyes and write down your answers.  Look at them very closely and even review it with your spouse, closest friend, or a family member.  Take their responses to heart.  Put that piece of paper on your nightstand and leave it there for a week.  Have it be the first and last thing you read each day. After the week is up, ask yourself if you are getting energized by reading it.  You’ll know very quickly if the time has come to give your two week notice.

Now close your eyes again and ask yourself the second set of questions:  “Are you retiring from something?  Are you running away from a draining work environment? Are you not excited by your work?” Perhaps your answer is much like my friend’s, who wasn’t sure.  Maybe you are just antsy and need a change.  Therefore, retirement seems like the logical progression.

Related: Take the “Savings Assessment Test”

If you find yourself identifying more with this second set of answers, you may want to pause before retiring.  You might just be in the wrong line of work.  Perhaps you are simply getting envious watching others around you retire.  Remember, retiring when you aren’t ready doesn’t always lead to happiness.  After writing down your reasons, I suggest talking to those same people close to you. Then determine what you really want.  The answer may land you at retirement, but it also might land you at wanting a new challenge in the working world.

So which is it?  

The retirement decision is a heavy one. Certainly, do not take it lightly.  There are many things to consider from a financial, family, and logistical standpoint.  Before anything else, mentally determine what your motivations are before you make this big decision.

To be honest, I think this line of questioning can be helpful in many life decisions.  When it comes to retirement though, the stakes are elevated.  You want to make sure you’re doing it for the right reasons (before you buy that RV to travel the world)!

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