The Transition to Retirement — Smiling All the Way



When Donna asked me if I’d like to contribute a guest post for her Retirement Reflection Sunday Series, I was pleased, but I had to check with her whether I’d be the right fit because I don’t qualify as “retired.” I’m 55 and still working – retirement is like an alluring siren beckoning to me from afar – probably ten years away at my latest count. I must say that I’ve considered retirement on and off over the last few years, especially when I was stuck in a job I hated and could see no future with.

The term I use to describe where I’m at now is “Transitioning to Retirement.” I reached this stage by pulling myself up by the bootstraps a few years ago and asking myself the hard questions about what I wanted to do and what the future held for us. There’s just my husband and me nowadays. Both our children are grown and flown and self-sufficient. We aren’t supporting them anymore – but we still like to eat regularly!


A few years ago, I was sitting in a job where I was feeling under-appreciated and underpaid. I knew I needed to do something, but the question was “what?” I’d been there for eight years. I was 52, and I was scared to leave because I saw myself as too old to be considered by any new potential employers. I slogged away four days a week feeling miserable and I could feel the unhappiness pervading the rest of my life. I wasn’t fun to be around and it was made worse because my husband had returned to full-time study and I was our breadwinner.

To escape from that job, I had the magic “retirement” word floating around in my head. The temptation was there just to pull the plug and leave the 9 -5 daily grind behind. I could head into a lovely sunset of late morning sleep-ins and a lifelong twilight of endless leisure…… sheer bliss! Then reality raised its not too pretty head and I realized that we would actually need to be able to fund the next 30-40 years of no longer being gainfully employed and that would be a major issue with no income from work.


The trouble for Midlifers like me is that most of us aren’t independently wealthy and we don’t have the financial reserves to quit work in our 50’s and start living a life of unending ease. (I know there are some lucky souls who can do that and I envy them beyond words!) But for us, when I looked at our savings and started calculating how long they’d last for, the answer wasn’t very inspiring. We’re debt-free, but we still needed to eat and pay those pesky bills that rolled in with relentless regularity. What happens when the savings are gone and there are a couple of decades still left to live?

The idea of spending my twilight years living under a bridge in a sleeping bag and eating cat food was not hugely appealing. So, for this Midlifer, retirement wasn’t an immediate option. It lies in the future tantalizingly beckoning me, but unfortunately, it really wasn’t an option available to me at 52 with a mature-aged student husband.


For us, the secret is to transition into that glorious time of retirement. For me to stay on the work treadmill meant being brave enough to leave that miserable job and putting myself out there to look for something more suitable. I needed to find a job I liked and one that fitted in with the lifestyle I wanted to achieve. It meant finding a job that was part-time, so I could enjoy some of those retirement delights without losing my income in its entirety.

The amazing thing I found was that I am still very employable. I didn’t get the first job I applied for – it only took a month or so of serious job seeking to find one where I’m so much happier. Where I work now, I feel appreciated. I feel like I’m making a difference. I’m actually paid what I’m worth, and I know I give them value for the pay cheque I earn each fortnight.


Almost three years have passed since I put in my resignation and moved on. My husband finished his studies and we both now work part-time in jobs we enjoy. We have the flexibility to fit in some hobbies. I have a little volunteer position. I blog three times a week. My husband works from home, and we fill our week without any trouble at all. It’s not a rush and it’s not living from vacation to vacation. We won’t be retiring with millions in the bank, but that’s not what’s important to us.

We want to be living life now – transitioning and preparing for retirement. We want to be ready for the time when we won’t be going to work anymore. I can already think of dozens of extra things I could fill my spare time with if I had more available. That pipedream of retirement is still there – we’re just sliding towards it with a smile on our faces rather than a weary acceptance of our lot in life.

Meet Leanne:
Hi, I’m Leanne. My blog is Cresting The Hill. This is where I write about how great midlife is. I’m a huge fan of the empty nest, and I love where I am in life at this moment in time. I share the lessons I’ve learned and my journey towards this point – because I want everyone to find the happiness that I’m experiencing. I’d love you to visit and leave a comment – let’s get to know each other because connection is what it’s all about!

From Retirement Reflections:

Thank you to Leanne for providing such an open, honest and thought-provoking post. I love how she has so effectively modeled making a much desired job change, regardless of age. Stay tuned next Sunday for ‘Retire From Work But Not From Life — The Art of Positive Aging’ by Sue from Sizzling Toward Sixty. Once again, you won’t want to miss it!

67 Replies to “The Transition to Retirement — Smiling All the Way”

    1. Hi, Leanne – Thank you again for writing such an inspiring guest post. I learn something new from it each time that I read it. I am still in BC, so will be able to chime in to all comments. Wishing you many Retirement Reflection visitors to your site!

    1. Hi, Sue – I fully agree with your comments. Believing in ourselves and having the strength to make necessary changes is such an important message. Thanks for stopping by!

  1. Thanks for hosting Leanne, Donna!
    Leanne, I’m so happy that you found a job you enjoy going to each day. I’ll be 52 next month and so grateful to have a full-time job that I enjoy going to each day, and one that provides great health insurance and other benefits. Will I retire anytime soon? Probably not, but I can write in my free time without money worries. Thanks for visiting!

    1. Hi, Jill – I love seeing the interconnections among readers. I agree that having free time to do what we love is most important. Thanks so much for sharing this.

  2. Wonderful (and inspirational) story! People need to be happy at work (I worked in human resources — happy employees make a company successful) and I’m glad you found the courage to move on. I worked well into my 60s and then transitioned to part time for a year or two and loved the transition. It worked for me and I’ve never missed the full time job (which I loved). Retirement is full of fears — health, money running out before you do, etc., but you can’t do anything about it. I love the concept of starting early! Cheers!
    Kate recently posted…Random 5 for June 25 – Anniversaries, changes, fireworks, crazy people, hydrangeasMy Profile

    1. Hi, Kate – I agree that Leanne’s story is very inspiring! I also loved hearing more about your own transition into retirement. Thanks for stopping by.

    2. Hi Kate – it’s nice to meet another transitioner – and it obviously worked for you too. I think the whole concept of retirement sits more easily on us if we haven’t stepped straight out of full time work into no work at all without preparing ourselves. Doing it gradually makes it a bit easier (IMHO!)
      Leanne | crestingthehill recently posted…CREATING OUR LEGACY IN MIDLIFEMy Profile

    1. Hi, Jennifer – Leanne’s story is a wonderful illustration of the pay-offs that we can gain by facing our fears and taking charge of our lives. Thanks for visiting. I look forward to visiting your site too!

  3. I’m glad and amazed that you were able to find a new job so quickly! For many of us, looking for work at midlife is pretty discouraging. I, too, look forward to a future retirement of friends, grandchildren and blogging. Thanks for your uplifting post!

    1. Hi, Linda – I agree that it is impressive that Leanne was able to find a job that she loved so quickly in midlife. Even more impressive, and incredibly inspiring, was Leanne’s honest, brave and positive determination to take charge of her own life. Thanks for stopping by. I look am off to check out your website now.

      1. Linda I had two other goes at replying to your comment and they both disappeared (weird) so I’m trying by replying under Donna’s instead. I think the secret to finding work in your 50’s is to work in a field where maturity is a desirable quality (I’m in a specialist medical practice and patients appreciate an older person rather than a cute young thing dealing with their sensitive issues) The biggest thing is to be confident in your worth and your skills and it will win employers over if they’re looking for quality and reliability.
        Leanne | recently posted…I GET TO DECIDE WHO I AMMy Profile

    2. Hi Linda – I was more surprised than anyone about how easily I moved into a new job. I think the area I work in (specialist medical/dental reception) lends itself to mature women – we are able to cope with the pressure of patients needs and they trust us more than young girls. It’s a tough employment world out there, but if you present with confidence then employers are often willing to take you on. That doesn’t mean that I’m not looking forward to retirement though!
      Leanne | recently posted…I GET TO DECIDE WHO I AMMy Profile

  4. This sounds a great way to transition into retirement. I kind of jumped off a cliff because my job disappeared – but I didn’t sink, I swam, so it can work both ways. I was lucky, because I was over 55 and so I qualified for early retirement (by 2 weeks! Thanks Mum and Dad for planning that right). I still think I’d like to have had the chance to prepare first though.
    Anabel Marsh recently posted…Budapest: the BelvarósMy Profile

    1. Hi, Anabel – As I read more and more retiree’s (and near-retiree’s) stories, I love that there are so many different paths to retirement that work out well. I had to give two years notice before leaving my position. It seemed frustrating then, but really gave me the gift of time to prepare. I’m glad to hear that even without much notice, you thrived. That speaks strongly to your character. I look forward to your upcoming guest post!

    2. I thought mine might be a cliff leap too Anabel – but fortunately there was a ledge waiting – because there’s no early retirement to qualify for at 52! Going into the whole retirement thing gradually is a rather nice way to go – but ultimately it’s all about your attitude and willingness to fill your time productively isn’t it?
      Leanne | crestingthehill recently posted…CREATING OUR LEGACY IN MIDLIFEMy Profile

  5. A very inspiring story, Leanne. Kudos to you for moving on from the toxic job, for supporting your husband in his academic pursuit, and for getting another job that you like in relative short order. That you can work part-time now is the cherry on top of that “fulfillment sundae.” Well done!

    1. Hi, Marty – There you were in my spam folder again. Somehow it’s only you — and I’ve done everything that I can think of to remedy this!
      Thanks for taking a break from all things move related and commenting on Leanne’s post. I agree that it is a very inspiring story. I hope that all is well for you and Gorgeous.

    2. What a lovely comment Marty – my husband may not agree with me winning any awards for being completely supportive of him suddenly becoming a student again (I kept asking him why he couldn’t have decided to do it at 18 instead of 50+) but we muddled through and he’s really happy working in his new field. It’s nice to be out of the tunnel and enjoying our transition.
      Leanne | crestingthehill recently posted…CREATING OUR LEGACY IN MIDLIFEMy Profile

  6. The quote referenced at the beginning is so true. After fretting about repatriating I found living in my home 🏡 state of Ohio is like living in a new country. The level of appreciation found after leaving the last job and moving here exceeded expectations expectations. There are a list of things to do way beyond the time we have left to do them (and that includes being pretty selective).

    1. Hi John – I love that quote – it’s been a pretty good summation of how I’ve started looking at life over the last few years. I used to count the days until it was time for a break – now holidays are an added bonus. I’m glad things worked out well for you too. Isn’t it lovely looking back and seeing how far we’ve come?
      Leanne | crestingthehill recently posted…CREATING OUR LEGACY IN MIDLIFEMy Profile

  7. I totally agree about that list, John. Richard and I are trying to cram in major items from our bucket lists….while still trying to enjoy some relaxation and balance. I am so glad to hear that all is going well for you in Ohio. Keep in touch!

  8. Overcoming fear – planning and knowing your direction – all great moves and happy that everything worked for the better. I am fortunate that I am still able to work full time at 64 and, at least for now, enjoy my job. I have time to dream and plan.
    Alana recently posted…Roses 2017My Profile

    1. Hi, Alana – I absolutely LOVED the dreaming and planning pre-retirement stage. Thanks so much for stopping by and commenting.

    1. Hi, Dee – Thank you for your kind words. I agree that Leanne’s post is well worth the read! I look forward to your upcoming post. Hope that you are enjoying your summer.

  9. I adore your expressions, Ally. ‘Bounce in your Pounce.’ I’ll have to remember that! Thanks for stopping by to visit Leanne here. Hope your renovations are going well!

  10. I’ve always heard that it’s harder to find a job the older you get, but I don’t buy that. I actually found it REALLY hard in my 20s to find a job. I didn’t have the experience to compete with older people for the same roles. It took me a year and a half of constant searching to find a job…and the whole time I was in a position that made me miserable. I’m a freelance writer now but if I ever had to go salary again, I’d only take a job I could do from home. No more office for me…I can’t take being around people all day!
    Stephanie Faris recently posted…Mystery Monday: PolybiusMy Profile

    1. You make a good point, Stephanie. I was responsible for much hiring in my previous positions. I found that nothing replaced experienced. Thanks for stopping by and visiting Leanne’s post!

    2. I’m glad you can see how valued we ‘mature’ ladies are Stephanie – it’s all in the mindset isn’t it? If you know your worth then you are attractive to an employer. I haven’t figured out how to work from home yet (and seeing my husband already does, that may be a good thing!) Part-time work is my saviour I think – a little bit of both worlds until that magic retirement age comes along.
      Leanne | recently posted…I GET TO DECIDE WHO I AMMy Profile

  11. Leanne, this is such a great example of taking the risk and having faith that a better, more fulfilling job is out there, even at midlife! When I retired from my day job in parks and rec after 32 years, I had already started teaching as a part-time lecturer, so part of the retirement formula was to teach the allowable 15 units a year. I ask why I didn’t do this sooner, but could not because the experiences I share with my students is what helps define their education. The key to retirement (or semi-retirement) is keeping meaningful work or hobbies. It’s not always about the finances, but about what we will do with all that free-time!

    1. You hit the nail on the head, Terri. I believe that ‘meaning’ and ‘purpose’ are important ingredients to a smooth transition to retirement…or semi-retirement. Thanks for sharing this.

    2. You are so right Terri – all those years of work we have behind us really do set us up for finding something meaningful to do as we head towards retirement. Experience is key and also working somewhere you feel you are valued and hopefully with a reasonable pay cheque (I hate being paid rubbish money!) and then shifting gradually into that blissful land of coffee, reading, blogging and retirement!
      Leanne | recently posted…I GET TO DECIDE WHO I AMMy Profile

  12. I am starting to realize that “traditional” transitions into retirement aren’t the norm anymore at all. Working until age 65, pensions, etc. are a thing of the past. Many people are retiring early (either by plan or not), or working until much later. Some work part time, some retire, then start their own businesses. It sounds like you are on a great path, Leanne. You and you husband are designing the retirement that you want. Good for you, and especially good for you for having the courage to leave a soul-sucking job. Life is way too short to remain in a job that is hateful. Work doesn’t always have to be fun, but it should be fulfilling.
    Janis recently posted…GratiTuesday: A Cuppa GratitudeMy Profile

    1. You are so right Janis! I think we all have different paths to retirement but the days of working in the same job for 40 years and retiring with a pension seem to be behind most of us. Now we have the option of changing jobs if we hate where we are, and if we’ve been wise with our earnings, by the time our 50’s come around we can often cut back a bit and have some time to ourselves without having to wait to the magic 65 when we suddenly have nothing to do and not much money to do it with!
      Leanne | recently posted…I GET TO DECIDE WHO I AMMy Profile

    2. Well said, Janis! My reaction was the same as your’s but I wouldn’t have expressed it as well.

      Leanne – kudos to you for your bravery and belief that a better job was out there that would provide you with the fit you needed!
      Joanne Sisco recently posted…Row, Row, Row Your BoatMy Profile

  13. Hi, Janis – It definitely is no longer our ‘Grandparents’ Retirement’. The retirement landscape has shifted significantly and most of us are left to create our own map. That’s one thing that I love most about this little corner of the blogosphere. It’s great to share our experiences and learn from each other. I agree that Leanne has modeled courage and is on a great path. I look forward to catching up soon!

    1. Hi, Debbie – It’s wonderful seeing all of the interweavings and connections in the blogging world. I agree that Leanne has a very insightful blog.
      Love your new logo — it is very effective!

  14. The quote on the top is so true and fitting! I really respect and appreciate people who take their “fate in their own hands” as we say in Dutch, and change the unhappy situation they are in. It takes some courage, flexibility and belief in yourself, but the end result, as proven by Leanne, is so worthwhile. So many people complain about situations and circumstances, not realizing, or desiring that they can actually change it, be in charge and improve their lives. Why aim to be happy at a retirement age if we can be happy now? Sometimes, you have to do with less financial wealth if you want to be free, but there are ways around that! 🙂
    Liesbet recently posted…Three Day Vacation in Budapest, HungaryMy Profile

    1. Hi, Liesbet – I agree that Leanne’s story gives a great example of taking charge of your own life. Your post also effectively illustrates courage, flexibility and belief in yourself to live life to the fullest at any age. I am so glad that you have also agreed to guest host!

    2. Liesbet – you so totally understand what I’ve come to learn. It’s not all about money and waiting until that ‘magical’ time when you think you’ll have enough of everything to be allowed to stop and be happy. I certainly wasn’t prepared to wait another 15 years before I was allowed to enjoy my life! Taking a risk and believing in yourself is the key isn’t it?
      Leanne | recently posted…TURNING OFF THE NEED TO MICRO-MANAGEMy Profile

  15. I’m going to retire in two months and your post made me happy, Leanne. I wish I could transition to a part-time position because I think it would be easier for me to handle emotionally and financially, but I have not been able to secure anything that suits me at the moment. So I’m taking leave from my Monday – Friday well paid job that is very stressful and consuming to take a break. Maybe later I’ll have the urge to work again but I’m going into retirement cold turkey, inspired by positive people like you! I know it will be an adjustment, and I believe my interests and penchant for staying busy will make me say what I’ve heard so many retirees say, “How did I ever find time to work?”

    1. Hi, Molly – Thank you so much for commenting. We all come to retirement from different routes and for different reasons. All of these stories are very meaningful to me. One of the biggest things that helped me in my own retirement transition was reading the words of others, and interacting with them through their blogs. I look forward to following your site and reading how your transition goes for you. My bet is that you will (very) quickly say, ‘How did I ever have time to work”!

    2. Molly I have a sneaking suspicion that you will find yourself filling your days and wondering how you can fit everything in! I also think you’ll find yourself doing something part-time (even in a voluntary capacity) because you have so much to offer and people see that and want your skills. I’m sorry about the cold turkey part of it, but also a little envious of all that time you’ll have to do whatever you like!
      Leanne | recently posted…TURNING OFF THE NEED TO MICRO-MANAGEMy Profile

  16. Leanne, the point that really jumped out for me is how important it is to live your life in the best way possible in the present rather than focusing only the past or the future. There are many routes toward retirement, including not retiring at all!

    Dr Sock recently posted…Finding my Housework MusclesMy Profile

    1. That is so true, Jude. What’s right for one person at one point in time, may not work for another person at the same point. Different retirement options work best for different people…including, as you say, not retiring at all. Thanks for stopping by and sharing this.

    2. I couldn’t agree more – some people are still working in their 80’s because they love what they do. I’m not sure that will be me, but at the same time, this should be a stage of life where we get to work a little more on our own terms. Slaving away at something you hate because the carrot at the end of the stick is all you can see is really sad (IMHO) – I want to live my life now – not in 10+ years time.
      Leanne | recently posted…TURNING OFF THE NEED TO MICRO-MANAGEMy Profile

  17. Hi Leanne,
    I’m sorry I’m so late in responding to your post. I’m one of those people who retired fully after burning out badly, and can’t figure out how to fit in everything I want to do. At least that’s my story some days. Other days I have no clue what I’m doing.

    I think your approach makes great sense. Kudos to you for coming up with a plan that let’s you continue to earn an income while being happy and transitioning to retirement activities.

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