Retirement decisions, should I or shouldn’t I?


retirement signRemember when you started working? Retirement seemed like a long way off, kind of like a child’s version of when Christmas is coming or a trip to Disney World.

It seemed like you would be working a long, long time. Suddenly you are approaching “that” age. Where did the time go?

One day you are hot stuff and the next you start thinking about what you want to do when you retire. Travel? Spend time with family? Volunteer? Start a company? Write a blog?

Will I be better off if I wait a few more years?

Or should I go now?

Many of my friends who have not already retired are struggling with the timing. Working longer may give you better benefits.

Working longer gives you less time to do what you want to do.

Your days are numbered. We all have an expiration date on our heads. Working longer does not extend it. You will have less time in retirement.

Created by John Wagner for Shoebox division of Hallmark Cards

Created by John Wagner for Shoebox division of Hallmark Cards

Retirement should be fun. We’ve waited for it our whole life and now it’s here along with saggy skin and wrinkles!

Not too long ago, I was in this conversation at a party. The discussion was getting intense when I dropped my “your days are numbered” comment. Trust me I was the life of the party. I haven’t been invited back. (If you invite me I promise I won’t say it!)

Sometimes the decision isn’t hard. You know what you want to do and what you can afford to live on so it’s easy. Or maybe you won the lottery! That works just fine.

Then there are all the rest of us who wonder if we will outlive our money. Visions of those terrible nursing homes haunt our dreams. Could we really live in a car? (Note to self: Stop watching 60 Minutes!)

We don’t worry enough to stop buying shoes or having lunch with friends. It’s just a nagging in the back of our head that rears itself at ugly times. Like when we open up the tax bill.

There is nothing like a big tax bill to make you recalculate your needs. In my head I can hear the lady in my GPS saying, “Recalculating” in a very disapproving tone.

You may think about returning that last pair of shoes but don’t worry. Somehow you will justify the purchase and keep them.

At some point you make the decision. Sometimes you can feel when it’s right. For me it was easy. My company was going through some tough changes and I had to downsize my department so why not me? It worked out great for both me and one of my employees who was able to move up.

Sometimes the itch to do something else gets overwhelming. The job gets tedious or mundane or not interesting anymore. Those are all good signs.

Can’t stand the thought of being at home? You can work part-time or volunteer for a cause you believe in.

I am amazed at how little free time I have. There are many interesting things that I can participate in. I don’t know how I found the time to hold down a full-time job.

I have enjoyed my retirement and laugh when I think about how hard the decision was for me. That’s why I tell my friends, “Jump in! The water is warm!”

Besides $$, what else is affecting (or affected) your decision and what wonderful things are you doing?

retirement cartoon

“And to think we were worried about how he’d handle retirement.” Courtesy of the Saturday Evening Post

32 thoughts on “Retirement decisions, should I or shouldn’t I?

  1. In two years, I plan to retire. I’ve often joked that I have the cardboard box and the bridge we’ll live under once that day happens. But I think we’ll do fine and I look forward to spending more time just writing … and having fun. Kate, I’m glad your decision worked out well for you and for another employee where you worked. 🙂


    • A surprise to me was how much money I spent as a result of working — lunches, clothes, gas, stuff. It took a while but my hyped up shopping gene has settled down considerably. Now I worry that I’ll stay healthy. If you get stuck, we have a nice tool shed…..


      • Decisions, decisions. A nice tool shed in (NJ? Pennsylvania?) … or a cardboard box under a bridge in sunny Fla? Thank you for the offer, Kate.

        Some of my working expenses will be drastically reduced when I retire. The only place I’ve managed to cut back on now is bringing my own lunch. My downfall is Barnes and Noble – books, movies and lattes. 😉


  2. CH retired at 56 in 2007 and I quit working part-time at Hallmark card stores in 2001.. don’t think I can say I retired.. 😀 Our biggest worry about retirement was doing it early enough. We couldn’t wait. CH was burned out and so was I. We both wanted to retire early enough that we could enjoy it without health issues. We all work hard for retirement and we were SO ready! We haven’t looked back. CH isn’t remotely interested in working anywhere but his shop out in the garage and in the flower beds and I am not interested in working either. We stay busy with family, do day trips and overnights in St. Louis, head to Florida in the winter for a couple of weeks and maybe once in the summer, visit wineries with friends, we volunteer at a local shelter and let the cats and kittens get some exercise in the playroom, and we run errands. What is it with errands when we get older.. who knew there was so much errand/running around stuff to do?


    • Bravo! Some people wait too long and then they can’t do the things they want to because of health issues. I’ve always thought that we should retire first and then go to work after age 45 or so just to be sure we enjoyed it. We have never worried about nothing to do. In fact, we think (but don’t worry) about all we want to do yet.


  3. I’m happy you’re enjoying the retired life. My father took an early out at 56, he’s now 76 and he has loved every minute of it. He says he never has enough time. 🙂
    As for me, unless I win the lottery, I’ll be working until I’m eligible for Medicare because I can’t get health insurance unless I’m on a group policy. Oh well, luckily I enjoy my job. 🙂
    Great post, Kate!


    • Kudos to your Dad. My brother retired at 64 and is now 84 and still enjoying it. As long as you have your health what’s not to enjoy. I can never find my brother because he has so many activities. He is my idol. I worked until I was eligible for Medicare so I get it. For me social security was another year away but I didn’t have to wait for that.


    • You have a very interesting job. Always something different and lots of interesting people. I think that you have a nice life too. Sometimes I worry and to be honest it’s easier with a partner but I spent most of my life without one.


    • I still find a lot of things to do. I write, take classes, exercise more regularly, meet with friends, working on a family cookbook, house projects. There are a lot of things I don’t like to do in the summer because I want to be outside so I do those in the winter. I do get annoyed when the weather locks me in for a day or two but I felt like that when I worked too.


  4. What I see most often when a friend retires is that he or she is so accustomed to living on the hamster wheel that he or she doesn’t know how to slow down and savor life. While doing stuff can be fulfilling, I believe that retirement’s blessing is to do what you want when you want– not to do as much as you can as if you’re still working every day. The joy of retirement, imho, is in the pauses.


    • So true. Back in the old days when a man retired, he died within a short time because his job was his whole identity (and he couldn’t stand his wife all day). Times have changed but there is an adjustment. For me I transitioned out working part time for 6 months. That was perfect. I just love pauses.


  5. One of the things I like about pet sitting is that I can just do less of it, and only cats, as retirement looms. Do the pet sitting I want for some extra income…don’t do what I don’t want. Sounds like heaven to me!


    • One woman I exercise with was a downsized vet tech. She started a pet sitting business and is doing well. She also took two jobs cleaning houses which all filled her $$ requirement for now but she can do either or neither and control the volume of work she does. I think that is perfect.


      • Yup, the control of the volume of work seems like retirement to me. Enough for a little extra spending money, and fun visits with kitties, but time for other stuff for a change.


  6. I guess everyone needs to make the decision based on what is best for them. If someone doesn’t have enough money saved, then certainly they must continue to work. But, if they are worried about not having enough to do… oh my! There is plenty to do… just not enough time! Life is too short and, like you said, we all have an expiration date. My husband retired two years before I did. When I could no longer stand watching him have all the fun, I decided I needed to go too. I haven’t looked back.


    • Yes my husband retired several years before me and when I left for work while he was still drinking coffee and reading the papers on our porch I knew something was wrong with this picture. I loved my job but I didn’t want to overstay my usefulness. There weren’t any new initiatives going on anymore so it was time.


  7. I checked out my estimated SS payments and added them to what I think I may have saved by retirement time..whew/ If I can make it till then…woohoo.


  8. This is a delightful treatise Kate on the best reasons to quit while you’re ahead. The world is full of unseen, untried adventures and even if I just decide to start my day at noon, it’s o.k. Yes, I would invite my friends “Jump in. The water’s warm!” And you are absolutely right through this whole awesome post – but if you come to visit, please don’t remind me my days are numbered. 🙂


  9. Hmm . . . let’s see, what have we done for fun?

    Water aerobics, biking, walking, wandering the beach, meditating, art festivals, outdoor concerts, gallery openings and receptions, ping pong, shuffleboard, eating pizza, baking homemade bread, savoring chocolate, clearing clutter, pizza & game nights, organizing the garage, donating stuff to Goodwill, reading, donating books to the library, assisting with the library’s book sale, attending plays, trying out vegan recipes, eliminating processed foods from our diet, bowling, hosting happy hours, mini-reunions (aunt and uncle from VT, cousin and spouse from New England, my sister’s family), sorting through letters my dad wrote from Korea, organizing writings from my maternal grandfather and grandmother, finishing mom’s autobiography, organizing letters from my paternal grandfather, blogging, reorganizing my office, resurrecting my slow cooker, updating our gratitude jar, blog meet ups, etc.


      • Great RX ~> “take one margarita and call me in the morning.” 😎

        When we moved to FL, we didn’t plan to retire. We just planned to take a short sabbatical before getting jobs. Our sabbatical has now lasted for 5 1/2 years and neither of us has missed working. Not a single day.

        If the “right job” came along, we might apply. I did apply for one job here ~ as education coordinator for the local CSA. The farm didn’t fill the position that go round ~ which worked for me. 😎


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