Before You Take the Retirement Leap – 10 Questions to Consider

We have a very dear friend who is six months to a year away from making the leap into retirement.  He has worked long, hard hours to make sure that he and his wife will be financially ready.  In his mind, I think he envisions retirement as just “stopping.”  But at the Voyage, we’ve learned that there is a lot more to consider:

  1. Do you have a plan?  You are about to enter your own “second act.”  Think of this as an opportunity to start over…to redesign your life to be any way you wish it could be!  An architect friend of ours recently published the book, “Life-A-Tecture: Build an Experience-Driven Life.”  It’s a great read, full of timely advice and lots of motivation.
  2. Do you really want to be just ‘done’?  Perhaps you want to consult, teach or work part-time.  Is there a different way to continue with only the best parts of your current job?
  3. What are you curious about? What is it that will get you up in the morning?  Do you have a passion, something you wish you could do, something you’ve always wanted to try or learn?  You know how when you are so busy with working and the day-to-day grind that you never have the time to xxx (fill in the blank here).  Well, you are about to get that time, so give it some thought!
  4. What is your hobby or interest?  Now is the time to start considering what you need to pursue that hobby.  Are there art classes nearby?  Do you need to finally purchase that kayak?
  5. Is there an opportunity for you to give back?  If you are like us, you have led a very blessed working career and have a lifetime of experience.  Now may be the time for you to volunteer, participate in a professional organization or give back to your community.
  6. Do you have a sense of adventure?  I’m pretty certain that no one who enters retirement does so thinking, “I know…I think I’ll sit here in my recliner in front of the TV every day until they haul my sorry behind away.”  You need to develop a sense of giddy freedom!
  7. How will you maintain your circle of friends?  This is a big one.  Because a primary source of our contacts come from a work environment, you need to keep and expand your relationships with intentionality.  We’ve found that professional organizations, clubs, coffee groups and even social media have been critical in keeping us from ever feeling lonely.
  8. Do you plan to travel?  There are lots of issues to consider with traveling, including destinations, traveling styles, and the ins-and-outs of traveling together. Time to start dreaming, discussing and planning!
  9. For those of you who are married, are you ready to be together 24/7?  This is a huge thing to consider!  It was probably the steepest learning curve we had when we started the Encore Voyage.  In “Life-A-Tecture” our friend has made this his #1 Rule:  “Marry the right person.  If you have not married the right person, you have got problems.  That person should be the love of your life and your best friend.” We have found his advice to be spot on, and share even more hints in Retirement Togetherness – 10 Steps for 24/7 Success.
  10. What are your DREAMS and GOALS?  Because you see, Retirement is NOT an END!  It is just a beginning of a new adventure.  A new Voyage, if you will.  To be really successful in retirement, you need to have some new and bigger plans for the future!

So how about it.  If you could give one piece of advice to someone who is about to retire, what (non-financial)  advice would that be?  I’m anxious to hear the things I’ve missed!






14 thoughts on “Before You Take the Retirement Leap – 10 Questions to Consider

  1. patwdoyle11

    Since I love lists, you know I love your ten questions. Another one I’d add into the dream and goals section is… do you know what is really important to you… your values? Not the values you “think you should have” but the values that you really live by. One of the things I’ve had to do in early retirement is really “Know Thyself”! Part of retirement for me was figuring out to replace what work provided me… and since I was a workaholic, work provided me a lot. You’ve captured the circle of friends – work provides so many of us with most of our daily connections with humanity! Work also was my source of scheduling…and since I’m a rule-based, list-based, schedule driven girl – this was a huge replacement need. Work was also my source of identity and status. So It’s not just about will you travel or volunteer, it’s also do you know who are you without work? A big question for many!

    Liked by 2 people

  2. Donna

    I love how you have set up this list as ‘questions’ rather than ‘suggestions’. As every individual’s retirement picture is unique, I believe that questions are the best tool to help people reflect, plan and figure out what will work best for them. Thanks for sharing this, Lynn.

    Liked by 1 person

  3. Liesbet

    These certainly are some great questions to ask yourself before retirement, and, to be honest, at any time in your life. I can answer “yes” to all of your “yes and no” questions, but… I am too young to retire. That being said, I have always tried to live my life to the fullest and know 100% how to answer all of your questions. Looking at it this way, retirement sounds very exciting to me! Bonus points for having lived with my husband 24/7 since the day we met. Yeah… that’s another story. 🙂

    Liked by 2 people

  4. amoralegria

    Good advice. I had some of it figured out at the time of my retirement, but at that time I thought I might like to earn a little extra working part-time. Since then, I’ve definitely decided NOT to do that! I make my own “work” with my blog and ancestry research!

    Liked by 1 person


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