Retirement for the Second Time

For the past several weeks I have eluded to “major” changes in 2019. Now that I have officially submitted my resignation, I can finally announce my retirement … for the second time.

My family doesn’t quite believe me. They just roll their eyes, nod their heads, and assume I will return to the classroom in a few months time. I can understand their skepticism. This is, after all, is my historical pattern.

The first time I retired was in 2014. That wasn’t my original plan. I had several logical reasons for retiring the following year: 2015 had a nice ring to it … it marked ten years of teaching … and fifty-five was a respectable retirement age.

However, I couldn’t ignore the persistent inner nudge.

But what will I do? I asked.

Write a quiet voice whispered.

But what will I write?

You will soon discover that answer for yourself. But first, you need to retire.

Talk about a leap of faith: so many unanswered questions!

As an Enneagram 6, I crave security. I need validation that my decision is right. I desire a healthy degree of certainty that all will work out. This scenario offered none of that.

While I did retire from the classroom, I never fully left school. I led two groups to Europe (in 2015 and 2017) … I became a member of the Board of Directors … and I returned to the classroom in 2016.

As my family noted: I don’t retire well.

But here’s the thing, I’ve learned some valuable lessons over these four years. I know the potential pitfalls of “a life of leisure” and I am better equipped to handle them. I am mentally and physically ready to fully embrace retirement for the second time:

  • The first time I retired, I struggled to find my purpose. For over a decade my purpose was to teach high school English. Once I had the freedom to do what I want when I want… I floundered. I thought I had to accomplish magnanimousย things (like cure cancer) to live a purpose-filled life. And nothing I did measured up.
    • Now I realize self-care is as purposeful as serving others. Taking a walk through the neighborhood and reflecting on life’s blessings is a noble event. Reading a book in the middle of the day, resonating with the characters and learning a bit more about the human condition is a worthwhile task. Learning a new skill – like yoga or making pie crust – keeps my mind in shape.
  • The first time I retired, I didn’t know if we would make it financially. Yes, I knew how to pinch pennies and cut out frivolous expenses, but would I regret the loss of income? And then all guilt. If it weren’t for the sacrifices of my parents, I could never afford early retirement. Did I really deserve it?
    • Now I know finances will be fine. We are not rich by any stretch of the imagination, but we can live a lifestyle that brings us joy. While I still struggle with the guilt, I’m learning that Mom and Dad would want us to have financial peace. And we, in turn, are trying to pay it forward to our own children.
  • The first time I retired, I had no idea what to write. And I mistakingly thought exploration was a waste of time.ย  I thought I needed a viable idea, publish quickly and become a best-selling author. Otherwise, retirement was a failure.
    • Now I realize writing is far more about the process and far less about the results. I’ve met some wonderful new writer friends who support and encourage my efforts.ย They help me grow in ways I never imagined. While I did publish three books (and have plans for several more) – I now know the true benefit of writing is connecting with others. Even if it just a single person through a simple blog post.
  • The first time I retired, I feared the opinion of others: She is only fifty-four years old, Why should she retire and live a life of luxury? I reasoned sixty was a far more acceptable retirement age; sixty-five was even better.
    • Now I realize personal peace of mind is what counts – not the opinion of others. I gave 100% of myself to raising my children. I gave 100% of myself to teaching students. And I do not regret a single minute. But it’s now okay to give some time back to me. I have enough hobbies and interests to keep me occupied for decades. Boredom is not one of my retirement fears. And I am truly blessed to have the time and the money to follow these interests with abandon.
  • The first time I retired, I feared losing all friendships. Most of my relationships outside the family existed at school. Once I left school, I feared being alone. As an ISTJ, I can easily squirrel away in my nook for days at a time. I didn’t trust myself to venture outside those four walls.
    • Now I know I have solid friendships. I have a few close friends who like me for me. They don’t care if I teach or not. They don’t care if I publish a book or not. We simply enjoy one another’s company. While I am still content to spend time in my nook, I am also mindful of pursuing relationships that bring joy to my life.
  • The first time I retired, I thought my kids were too busy with lives of their own. We would connect for the holidays, but I wouldn’t see them much otherwise. I didn’t want to be in their way.
    • Now I know what a fool I was. The grandchildren enjoy time with their Mimi. And my grown children have become great friends. Within the next six months. all of them will be living out-of-state and several hundred miles away. I do not want an academic schedule to dictate when I can or can’t visit. I will relish the opportunity to “take off” when they need me – or when I need to see them.

Obviously, I entered retirement the first time with several misconceptions. This time, however, I think I am going into this third act with a little more wisdom, a clearer direction, and a relaxed spirit.

For those of you who have already navigated these waters… what retirement lessons have you learned that might help me transition into this new lifestyle?


  • Suzanne

    Molly, you will wonder how on earth you had time to work and accomplish the things you did. I suppose I do things at a slower enjoyable pace, instead of racing around like a mad woman. There are so many options to fill in your time. I have just started a voluntary job as a Guide at a Historical house/gardens, well, I am in training for the next six weeks. So much to read and retain. We shall see if I pass muster! Enjoy the next stage in your life, I am reluctant to mention that “r” word ๐Ÿ™‚

    • Molly Totoro

      Suzanne… I have a feeling you are right. As it is now, I struggle to find time to teach my two classes ๐Ÿ™‚ I’m trying to enjoy these final months of school, though. Teaching has been a rewarding career and I want to fully appreciate these final days.

  • Michele

    Congratulations. You will find plenty of things to do and when you understand your purpose you will never be bored. I also retired early- too early in fact to be able to get my pension, but it has worked out fine. I found other things I love to do, including writing.

    • Molly Totoro

      Writing (or at least journaling) will be a large part of my life, Michele! I also hope to catch up on all those scrapbooks I have squirreled away in the closet. And I’d like to do some travel … and read the shelves of books that have patiently waited for me to make the time. I think I need to redefine my definition of “purpose” ๐Ÿ™‚

  • Leanne

    Molly this was such a great post – it really covers a lot of what’s been going on in my head for the last few years. I was all set to retire when I quit my job back in 2015 but there were a lot of questions in my head (many similar to your list!) Getting a job that only takes up 2 days a week has been a great compromise for me but there is still that little voice saying how nice it would be to not jump through the hoops of others and to not have to deal with the ongoing crazy stuff I face at work each week. I’ll probably keep going for a while longer, but I’d love to be able to write a post like this one in the not too distant future. Congrats on your second retirement!
    Thanks for linking up with us at MLSTL and I’ve shared on my SM ๐Ÿ™‚

    • Molly Totoro

      Oh Leanne… I hope your day comes soon! I have only taught 1-2 classes a week for the past two years. Truly, not a burden and easily managed. But the time is right to release the responsibility once and for all. It’s a little scary, but I’m going to put my word of the year into practice: Confidence ๐Ÿ™‚

  • Kay

    Molly, congratulations on your second retirement. I guess I’m retired, though I have avoided saying that. I just say that I don’t work right now. Honestly though, I’m not going back into the workplace again or very likely not. So, what do I do? Well, I volunteer at two different libraries. I travel with my husband when he takes off from his job. We don’t have to arrange two schedules and we spend some time in New Mexico. He is actually able to work from there a bit and so we can even spend a little longer. I have time to do my walking when I want to – on my schedule. I do understand your thoughts of being a bit guilty about not working, but I think I’ve gotten over that. I’m able to take care of the little details of our life without issues and my husband appreciates that. And, of course, there is time for reading and blogging. I think it will be lovely for you to be able to spend time with your children and grandchildren and, yes, you’ll be able to do that at your leisure or quickly if you are needed. You know, many authors didn’t really start writing a lot until their later years. ๐Ÿ˜‰

    • Molly Totoro

      “I don’t work right now” … I like that. Although I have a feeling that’s not quite an accurate statement for you. Anyone who volunteers at two libraries and leads multiple book discussions and maintains an active blog is “working” ๐Ÿ™‚

      I have only been to New Mexico once… but I hear it is a great spot for creatives to rejuvenate. I may have to travel there sometime in the near future. Where do you typically stay?

      • Kay

        We go to the Ruidoso area, which is in the southern part of New Mexico. I think most people think of Taos and Santa Fe, but there are mountains in the southern region as well. The picture in the header of my blog is from Ruidoso.

        • Molly Totoro

          I’ve never heard of this area but will definitely jot it down as a possible place to visit when my husband retires. We hope to do lots of travel, both domestically and overseas. I think New Mexico might be a nice winter spot (especially if we have another winter like this one!)

  • Jan

    I love this post Molly, as someone who writes in the retirement space I totally get what you are saying and I think it is great that you are now heading into retirement with a much firmer plan and greater understanding of what it all means. It is such a personal journey despite the mainstream view of retirement being all about finances – important yes but only a part of the pie. Happy second time around and I am pinning this.

    • Molly Totoro

      Thank you so much, Jan! I know I sometimes focus too much on the money and lose track of life’s intangibles. While I enjoy the luxuries and conveniences money can buy, I also know I can live a minimalist lifestyle with no regret. I’m looking forward to using the right side of my brain a bit more and delve into creative pursuites while relishing the simple pleasures of life.

  • Debbie

    Hi Molly, your experiences are so interesting and you really seem to have given this a lot of thought! I love seeing your thought processes and wish you well. Reading a book while lying in a hammock in the middle of a work day is a great feeling!! #mlstl

    • Molly Totoro

      Oh my, Debbie… I need to put “reading in a hammock in the middle of a work day” on my bucket list. That sounds divine!!

  • Molly Stevens

    I retired twice, too, and I know others who have done so. In my case, I put in my resignation but couldnโ€™t go through with it. I was miserable after I announced my retirement. I ended up negotiating a job share with another nurse and kept working for one more year part-time. After that I was ready to fully retire though still had reservations. It was rough the first couple of months – I had a very hard time feeling comfortable with my new found freedom. I was lonely (my husband is still working). I have done much better since the holidays are over, and have settled in to a better balance of socializing, helping with grandchildren, pursuing my creative endeavors. I pressured myself big time as soon as I retired. It was like I transferred work stress to my retirement. I canโ€™t say I donโ€™t still do that, but Iโ€™m getting much better at cutting myself some slack. And I have a job interview tomorrow – a per diem job as a nurse working for the public health department. I didnโ€™t seek the opportunity but I think it might be a nice option for a very limited amount of work. I figure it will help pay for my blogging/writing expenses. Weโ€™ll see how it goes and if I decide to do it or not. Good luck to you as you enter your second retirement with a better frame of mind, Molly.

    • Molly Totoro

      Molly… I’m hearing of more and more people like myself who retired more than once. It’s good to know I am not alone ๐Ÿ™‚

      Your new opportunity sounds nearly perfect: a chance to keep your hand in the workplace (and providing a bit of extra income) while still maintaining a relatively stress-free lifestyle. I look forward to hearing how it works out for you.

      • Molly Stevens

        I did the job interview, Molly, and as I left the building I knew I was not ready or willing to take a job – even one that was as perfect and flexible as this one was. It was liberating! I am so happy to know that Iโ€™m not going to be working! Iโ€™m retired and Iโ€™m free!

        • Molly Totoro

          Retired and Free … doesn’t that sound wonderful, Molly!
          While this school year offers a relatively easy schedule and the students are fun, I still resent going into school each morning. I KNOW this is a sign that I am ready to move on – and it is indeed liberating ๐Ÿ™‚

  • Nancy Dobbins

    Hi Molly, So glad to connect from MLSTL…loved your post. I just retired from teaching almost 27 years this past September and I was afraid after having such “purpose” all those years I would flounder in retirement. I’m glad to say quite the opposite has been true. The blog has been a great outlet for all of those anxieties and feelings as well as keeping me busy. And I LOVE the community of mid-life bloggers that I have met since I started my blog in September – and so many of them participate in MLSTL. Shared to SM.
    Can’t wait to read more!

    • Molly Totoro

      Nancy… thank you SO much for stopping by!
      I am so grateful I found the #mlstl community too. It is nice to read how others are navigating this new phase of life. I think that might be one reason why I am more excited to retire this go around… I know what great opportunities lie on the other side ๐Ÿ™‚

  • Agnes

    Love, Love, Love this article, Molly!!

    Our generation struggles with the traditional definition of retirement and, hopefully, ours will be the generation that redefines it completely. Redefine by, perhaps, not defining it. For most of us, visions of rocking chairs on porches holds little allure. As you found out, retirement for Molly needs to be created by Molly. I’m so excited for this next chapter in your life and will enjoy seeing how your definition of retirement unfolds!

    • Molly Totoro

      Agnes… while I didn’t realize I held onto these old definitions, I think you may be right. Perhaps I have struggled with retirement because I’ve associated it with being put out to pasture. What an erroneous image! And with the help of the internet and such accepting online spaces like #mlstl, I feel my connection with the outside world will only increase.

  • Pat

    Molly, I love your format of “the first time” and “now I know”. As I read the individual points, I was shocked at how many I too had, and still am working through. Clarifying my purpose (still a work in progress), worrying about the finances (we will be fine, but every downturn in the market creates a pang of worry!), continuing to work on building/ maintaining friendships, still worrying about what others think. I’m telling you this because I do know all these things, but it still takes focus to continue to work them through. To find satisfaction in the self-care, the exploration of interests, and the investment in relationships. The less stress, the freedom to choose, and the ability to create the life I’ve always wanted — retirement is definitely worth it.

    • Molly Totoro

      I feel like the only comment I can make here is “ditto” ๐Ÿ™‚
      What you have said completely summarizes all I feel.

      I do think learning about the Enneagram – and the fact that as a six I will worry (it’s what we do) – has helped me put life in better perspective. Yes, I may have times when I feel a lack of purpose or a dip in finances… but feelings are not reliable. Life is good. We will be okay. It is time to relax a bit and enjoy the blessings.

  • Sue from Sizzling Towards 60 & Beyond

    Hi Molly what an inspiring post. I retired at 57 at it has taken about 4 years for me to come to terms with it. You have written what I wish I had known when I retired and have only learned over the last few years. Retirement is such a huge change not only to our lifestyle but also to our mental health. I found it very difficult to settle rather than just taking time out to be kind to myself, instead of feeling like I had to keep looking for something to fill in my days. Congratulations on your second retirement and reading your post tells me you are ready and raring to go! Have a great day and thank you for supporting #MLSTL. Sharing on social media. xx

    • Molly Totoro

      Yes, Sue… I spent far too much time trying to fill my days. Don’t we retire to have a little breathing room?!
      It’s nice to know I am not alone with these struggles. And knowing others deal with these same issues gives me confidence that I will find a retirement rhythm that will suit my personality and allow me to enjoy a more relaxed lifestyle.

  • Bethany @ Happily Loco

    It is hard to leave a teaching career, because in teaching, the career IS a purpose, a mission. After I left the classroom, I found that a lot of little things can constitute a “purpose” as well. My paying job is no longer my mission, so I am free to focus on myself, my family, and my friends…as well as hobbies such as writing! I wish you the best in your journey! Enjoy!


    • Molly Totoro

      Yes, Bethany… you are SO right. Teaching is not only a vocation, but it is also a mission and a calling. That’s a lot to “give up” in retirement. I think I am ready to embrace another lifestyle though. One that is not so all-encompassing and allows me the freedom to care for and accept me.

    • Molly Totoro

      I think my husband plans to work until he’s 65 (about five more years). I’m praying for good health so we can make good on our travel plans. But I know life can throw a few curve balls. Caring for sick loved ones can be a full-time job ๐Ÿ™

  • Jennifer

    Early retirement can be a double-edged sword. For me, it was an opportunity to be the primary caregiver for my mother. But now that she’s passed I’ve gone back to work at 57 because I do miss the social aspect of working. While I love my blogging friends, chatting online is certainly different than chatting in person.

    • Molly Totoro

      What a blessing that you were able to give full-time care to your mother.
      While I know the social aspects of retirement life can be difficult for some to navigate, that is not a concern for me ๐Ÿ™‚ If anything, I need to monitor how much time I spend alone. It is quite easy for me to become a hermit. At this point, I am content with my social life of just a few close friends. I’m glad you were able to remedy that void by returning to the workforce.

  • Christina Daggett

    My husband was 52, and I wasn’t quite 50, when he retired, and I gave up teaching preschool to become perpetual travelers. We’ve never regretted our decision for a minute. Now we just want to share our experiences with others, and show them how this lifestyle can work for them. Enjoy your retirement Molly, and thanks for another great post.

    • Molly Totoro

      What a FABULOUS lifestyle, Christina! And quite frankly, one I would love to emulate – at least to some degree. One of my retirement bucket list items is to visit a few key places (Paris, London, New York City, Italy) and live there for about three months. I want to experience the place as a native and really immerse myself in the culture. Should that come to pass… I too would like to share the experience with others. You are literally living the dream. Thank you so much for stopping by – and I look forward to following your future travel adventures ๐Ÿ™‚

  • Bonnie Aldinger

    I’m hoping to retire someday, and I’m assuming that it’ll be AWESOME because I have so many things I love to do that I’ll have more time to do once I’m not being a workaholic trying to keep up with a job that I fell into but am not entirely trained for – but there’s a good lesson here about maybe not just assuming it’s all going to be great but rather coming up with realistic plans to make it go the way I think it will. Thanks!

    • Molly Totoro

      Bonnie… I must admit I was shocked retirement did not come naturally. After all… how much does one need to prepare to sit back and relax? (turns out… one does need to prepare). I made assumptions that did not work for me. However… I feel better equipped to handle those challenges this time around ๐Ÿ™‚

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: