Retirement Challenges

We all know how exciting and scary retirement can be. These retirement poems about challenges poke fun at changes from work life to retirement that most people will encounter. When we are in our working life we fantasize about what retirement will be like but when retirement hits, some of us miss the structure that working brought us. Of course, retirement is a happy time for most, but it does come with some challenges. Enjoy and share these retirement poems that talk about some of those issues but with a humorous twist.
By Julie Hebert - Updated July 26, 2024

Retirement Poems    |   Retirement Challenges



  1. A Challenge In Retirement?
    Poet: C. A. Lynch


    Who would think a challenge in retirement you would see
    You can be happy and free!
    You have all day to do what you want
    You no longer have to be a confidant.

    So why worry about challenges ahead
    Be thankful each day you are not dead.
    You no longer have the challenge of what do I wear
    You don't even have to smile, you can be a bear.

    Challenges of bosses, and traffic jams
    You now only have to worry about phone scams.
    And the weather is no longer a problem
    You can stay in all day and sit on your bottom.

    The challenges of retirement are few you see
    You can sit and drink lots of coffee
    But don't sit to long as you will get fat
    Get out that exercise mat.

    Challenges are behind you now
    You are retiring, oh wow!
    Congratulations on retirement
    You no longer have work confinements!



  2. Retirement Sorrows
    Poet: Julie Hebert


    Retirement is not for the faint of heart,
    Once started it doesn't end.
    It hits you all at once you know,
    No more days off, it never ends.

    Calling in sick is no longer a thing,
    When you are sick you have to suck it up.
    Your retirement doesn't go on hold,
    Just because you need a checkup.

    Booking vacations won't be the same,
    No approvals are needed anymore.
    The excitement and hoping for a break in the year,
    Now seems so much more like a chore.

    Don't get me started on the money difference,
    You won't have any, that is the truth.
    The days of splurging and vacationing aboard,
    Are now memories from your youth.

    But wait, don't you worry, there are good things to come.
    Retirement never ends.
    That in itself is a wonderful thing,
    You have all the time in the world for family and friends!


  3. Retirement never ends. That in itself is a wonderful thing
    Funny Retirement Poems


  4. Retirement Is Not An Issue
    Poet: B. R. Clement


    I remember when you use to say
    "I can't wait for retirement day!"
    Now the day has finally arrived
    And you are acting like you can't survive.

    You will love just you wait and see
    You won't even miss me.
    You will find plenty to do
    You may even learn something new.

    So travel down this retirement road
    It will not be a heavy load
    Once you are out of here
    You will lose all your fears.

    Soon you will be telling me
    Retirement is so busy
    I can't believe that you even fret
    Like retiring is making you upset.

    Move forward with a smile on your face
    We all wish we were in your place.
    Happy days are ahead for you
    Retirement is not an issue!


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