Putting An End To Living With Retirement Regrets

It’s no secret that my retirement planning didn’t work out the way I wanted to. That’s the whole point of this blog. I’m dealing with continuing to live my retirement life NOT according to my lifelong plan.

What was my retirement lifelong plan?

My retirement planning was a two-parter. The first part was to retire young by selling everything and downsizing to a smaller abode and living off my investments plus work part time. That part came true 100% in 2001. The second part was to sell everything again, buy a low cost condo in Florida and invest all my money wisely and retire young with absolutely no working at a job whatsoever. I was in the process of doing this in 2014 when we found out DH was not as healthy as he was supposed to be. I thought that by marrying a younger man than myself (six years younger, to be exact) I’d have someone young and fresh to take care of ME in my old age. That part of my retirement planning didn’t work out either.

So, I had to backtrack, sell the condo and move back into the downsized home. It’s at this point (2016) that my retirement stalled. I had absolutely no idea what to do after this point, except retreat and lay low. DH’s health became the Number One priority. I also had to make a financial adjustment to the fact that I wasn’t living in a $180,000 Florida condo with $500,000 in the bank. I was living in a $500,000 home with only $180,000 in the bank. Instead of living on $50,000 a year, I was going to have to learn how to live on $25,000.

You can line up all your dominoes in a row. But it can turn out to be meaningless.

You might think the natural solution here is to sell the $500K home and move. But that’s not so easy. DH now has serious health issues and can NOT move away from his medical team. Also, I’ve been twice burned on real estate. I lost $100,000 after a ten year ownership of a Newport, RI beach house. And I just about broke even selling the Florida condo. That’s two real estate strikes against me. I have no intention of making it three. I think a massive move right now would probably kill DH. I don’t think he could handle the stress. Plus, it only costs us $816 a month to live here. I don’t think we could find any other place else to live as cheaply as we do right here.

Now starts all my midnight financial regrets and angst. Why did I spend so much money? Why did I take so many vacations? Why did I buy so many new cars? Why did I give my kids so much money to buy their own condos and pay off their own student loans? Why did I buy and trade in perfectly good RVs for different models? Why did I spend so much money period? Why? Why? Why?

Why didn’t I know what was going to happen to me? Why didn’t I plan better for the future? These last few years have been nothing but regrets for me. It’s time for me now to brush off my regrets. What was done was done. I made the best decisions I could, at the time, based on the information I had on hand. At that time! What I learned from my new situation, however, in the end, made me a much better person.

Go figure?

I have a much better relationship with my adult children than I ever did before. I see them regularly, am included in many family functions and my grandchildren run to hug me when they see me. I’m more involved in my community. Instead of running away, I’m staying put. I’m embracing the surroundings that have always been here but I kept searching for it somewhere else.

I seem to be managing my money better. I’m more mindful of my financial situation. I feel as if I have finally mastered my money at age 68 than at any other time in my life. I have no qualms cancelling things or going without in order to keep me flush and in the black.

Maybe this was the retirement I was destined for all along? I did dream and imagine myself living in a mortgage free home, free of debt and RVing coast to coast in as many National and State parks as possible. The end goal was when ‘Assisted Living’ or a nursing home rang my doorbell, the goal was to sell and afford an end-of-life lifestyle.

There’s a quote reference I like from Margaret Manning of Sixty And Me on How To Live Without Regret After 50: Don’t get stuck in self-defeating thought loops . Acknowledge what happened and move on. There is a quote that I love from the movie Slumdog Millionaire: “Everything will be OK in the end – and if it’s not OK, it’s not the end.”

I think everything is OK now. I didn’t last week. But today I do. I had to get some toxic things and some toxic people out of my life before I could move forward. I also had to spend a lot of time just thinking. When I came to realize that if nothing had ever happened to me, I’d still would have wound up exactly where I am today. That was a true eye opener.

Lao Tsu said: ‘If you are depressed you are living in the past; if you are anxious you are living in the future; if you are at peace you are living in the present.’ I’m at total peace right now. Everything is fine. We’re living well. Bills are getting paid on time. We have a nice roof over our head, food on the table, friends and family to love and love us back. Thinking about numbers was causing me grief. My life is NOT about numbers. It’s about having ‘enough’. And that is exactly what we have: enough.

More advice: If your regrets feel overwhelming, take steps to reengage with the world. Join an exercise class, establish a daily ritual of walking in the park, take up dancing. Whatever you do – do something! As you develop your body and mind, you will build up the energy to face your regrets without fear.

cindi watercolor.jpg
Get back into the world! I started a watercolor class and got my picture in the local paper. Yay! For me!

Finally, remember to give yourself a break. Not everything needs to be rationalized and sorted through. Sometimes the best way to deal with regrets is just to smile at our foolishness and move on. You’re human, so don’t expect yourself to be anything else.

I was a very foolish girl. But I’m a much smarter retiree.

Live well and prosper, my friend. Live well and prosper.



  1. I’m glad you shared your story with the rest of us. The more we know about others’ lives, the easier it is to figure out our own.
    I have that quote — “Everything will be OK in the end – and if it’s not OK, it’s not the end.” — on my fridge, and I know it has helped me.
    I am almost 50, but I’ve been trying to plan for a retirement that sounds similar to your own for quite some time; scaling back to part time, living off the house equity, and then quitting work altogether. But then life happens. And not always in a bad way. I recently discovered that my skill set and experience has set me up nicely for a second career. Suddenly I’m passionate about it; I’ve even gone back to university (part time).

    It is very unfortunate that your hubby’s health declined, and I wish him comfort. All the best to you as well, and I hope you will continue to write online.


    • Hi McSpell. I’ve been blogging since 2007. I won’t be leaving the platform anytime soon but I am expanding in social media. I’d like to blog in the very near future working on it!
      Thanks for your comment. I appreciate your thoughts and sharing. Best of luck to you!!


  2. Your life adventure has been fun to follow. Your upbringing did not prepare for what retirement was going to bring. You have had to learn by trial and error. Somewhere though, you learned how to research so that your decision have increasingly been based on planning and thought. Also, you try to learn from your mistakes. That is part of your charm. Learning to be satisfied with what you have and what you can do is a lesson we all try to follow. Comparing ourselves to anybody else just does not work. Trying to find that state of grace in this turmoil of life is hard. We cannot hope to keep that grace, but those few moments of contentment are precious.

    Take care and enjoy, Sue


    • Hi Sue. Thanks for your keen observations. Life is indeed trial and error. We’re all learning by the seat of our pants. 🙂 Thank you also for your comment.


  3. Cindi,

    I so admire your honesty. It helps all of us take a deeper look at our own lives. I’ve never made much, if anything, on any house I sold. I always bought high and sold low which is exactly why I don’t invest in stocks. I have my share of regrets about financial decisions in the past. There was a time that I spent obscene amounts of money on handbags. I look back on it now and only wish I had all of that money in my savings.

    I spend a lot of hours configuring and editing my budget. I’m divorced and live on my own so things can get financially precarious sometimes. Or at least it can feel that way. But I’m grateful for everything I have and for all of the people in my life. In that regard, I feel like a millionaire.

    You and your DH have a wonderful life, a beautiful home in a perfect location, children and grandchildren that love you, the ability to travel and see nooks and crannies of this country that most of us will never get to experience, financial stability, a happy marriage, excellent medical care and so much more. You’re a talented artist and blogger, too. Keep embracing the joy of your retirement and please continue to share all of your thoughts, fears and ideas with us because I assure you, we’re all going through similar things in our own lives, too.

    Warmest regards,


    • Hi Lisa. I hear you on those handbags! They are expensive. Luckily my oldest daughter worked for Kate Spade in nYC for 11 years. I’ve got 15 or so of Kate’s handbags and I am NEVER going to give them up I change them out seasonally and I don’t care if they are out of style. I love them! To me, they are irreplaceable.
      Not too many writers concern themselves about people like us. They write for the successful masses, if there really are people like that. I think most people today are like you and I. We’re the forgotten ones. No matter. I’ll bring attention to us. We’re all figuring it out basically together.
      Thanks for the kind words about my family and my life. My husband keeps telling me we’re doing AOK. I’m just a worry wart because I read too many financial books. See above.
      Thanks again for your comment.


  4. Cindi

    What an excellent post. DH and I were talking about my being so anxious. Now if I could only live in the present!

    Just realized how much you look like my oldest sister.

    Best wishes from Best Bun.


    • Hi Best Bun. I like being an older sister! Bet your sister is beautiful! LOL.
      Thanks for your kind words and your comment. When I am anxious I Iisten to ‘sleep’ music on Spotify. It takes me around a half hour of listening before I can calm down but so worth it. Try it. Especially with headphones or ear plugs. The music is lulling. Good luck.


  5. I really like this post CindI , you make many excellent points. I’m glad you’re not kicking yourself with wouda couda shouda. No one knows what awaits them in the future. Even the best planning could go amuck. There’s a saying in Spanish that I think I’ve told you before but I will repeat it which says “ que me quiten lo bailado “ loosely translated it means that the experiences you’ve had cannot be taken away from you.

    I often think of this when I think of my own money mismanagements, and to be honest I don’t know that I would do anything differently. Nothing helping my kids out, not to traveling so much, not to enjoy the life that I have with my husband. Life is too short to live with regrets.

    Like you, I probably could’ve done a lot of things differently. But I cannot turn back the clock. I also want to continue to travel, and enjoy the good health that my husband and I currently have since we don’t know what the future holds.

    So we will continue doing that, we will be more frugal in the future with needs versus wants, with all except travel. We will figure it out somehow. I don’t worry about it anymore.

    Having worked as a social worker for so many years and seeing so many elderly, I do not want to go into my old old age without these wonderful memories that we are making. This post was excellent and very on point.


    • Thanks Teri. I learned from my mom’s early death that we have to live our lives NOW. Not in the future. My mother found out she had terminal cancer three weeks after she retired! And on her first trip/vacation at age 58!!!! Not good!
      I think you and your husband are having a blast. Your family is beautiful and your vacations superb!!! Good job!
      I’m with you: we will figure it out. That’s what it is all about.
      Thanks Terri for your comment. 🙂


  6. I love your blog because you are so real and fresh air compared to most other blogs I read. When I am having a crappy day at work, and if I am able to get a lunch break, I come read your blog! Thanks!


    • Hi Cindy. Thank you for your compliment Cindy. I hope you don’t have too many bad days BUT I hope you read my blog as often as possible. 🙂 Glad I can cheer you up.


  7. Hi Cindi, I so agree that this is one of your best blog entries. Oh so much of what you said hit home for me. Since January my main focus was to help my son with his health crisis and in the last thirty days I have been watching his two year old 25 days for them to move. I basically feel like a fish out of water since I let all of my creative endeavors go and everything at home. I had bought all of the materials to redo my lawn and all of this is sitting in my garage having to wait till the fall. Last week I had six hours to work on my landscaping and garden then hired a neighborhood teen to water everything while I helped my son. I missed my bed and slept nine hours my first night home. I paid my bills, unloaded the third loaded car at the Goodwill and shopped at Market 32. They had fantastic mark down on hormone free meat to clear out for an order coming in today. Imagine prime hormone free pork tenderloins for $2.25 a pound, cube steak $1.75 lb and boneless prime pork chops for $1.75 a pound! I walked out of there with all the basics for a month for $38! Including 2 -dozen eggs @ 49 cents each and .99 cents Cracker Barrel sharp cheese -their bonus buys for spending $15. Total savings $32.
    My son had sent me home a Nature Promise sixteen pound turkey last week and I Cooked that and smothered Salisbury steak, brown rice, roasted carrots, cornbread, candy cane and rocky road brownies all in my convection oven.
    Opening my mail I found added to my savings $22 dollar refund from Ct, $25.69 and $47.21 from my rewards. They go into 2.4% money market account. I direct deposit my pensions into this account so anything left over after paying my bills earns this. I just started scheduling my payments to pay the outstanding payments the day before their due to maximize the interest. All of this adds up! June and July I have my house and life insurance, property taxesSincerely, Lara

    Liked by 1 person

    • Thanks Lara. Looks like you’ve had your hands full. Hope you son’s move went well. Take care and get yourself back together again as easy as you can.
      I got some good deals this week on cut up chicken parts: only $1.49 a pound! I bought two packs and made up 4 freezer bags with 2 thighs, 2 legs and 2 breasts each. That’s about all we would eat per meal. My freezer is close to bursting! LOL!
      You have some really good money saving things go your way. Brava!
      Thanks so much for sharing.
      Always welcome your comments. 🙂


  8. Love, love, love the quotes. I’ll be writing them down, and referencing them. I hope not to have any reqrets in retirement. BUT, I most want to live in the moment. The right.now. Releasing regrets is GREAT for the soul. xoxox


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